When Your Work is Your Only Identity

Photo by Damien TUPINIER on Unsplash

Many high-achieving professionals in tech at some point in their career find that their work has become their identity. In certain years, this can be a really good thing. Having the drive and capacity to pour all your energy into a professional endeavor is what powers innovation from both startups and larger tech companies. Yet, the danger zone of this is when life feels imbalanced. This imbalance happens when your work is your only identity and when things aren’t going well, especially in times of transition or stress. As we approach the one-year mark of the pandemic, we’ve seen the additional stressors caused by isolation and co-sharing work/life spaces with roommates, partners, or children. This year has triggered many leaders in tech to seek some change from their existing patterns of behavior. 

The first “work” that we encounter in life is being a student. We go to Kindergarten and happily receive gold stars for individual achievement, and as a class we add marbles to a reward jar for collective good behavior. Our identities start to be shaped by how well we succeed at the work of school. This outside-in reward system continues with grades, making the honor roll, and receiving awards through the school and university system. Our habits are formed and parts of our identity become tied to the external successes we collect. 

There’s a wonderment in starting your first job and getting paid real money in exchange for a service you provide or a product you’ve made. This feels even more momentous when you go beyond babysitting or campus jobs and you get that first paycheck from a company. It’s an economic exchange of value—the company gives you money in return for a service. Yet in Silicon Valley, it feels more than that exchange. We put more value on what we do at work and who we are at work. We often talk about our teams being our family. We spend long hours working together and these interactions continue outside of work as our roommates, social circles, and vacation buddies are often our coworkers. 

We are born into some identities. Each of us is somebody’s son or daughter. We all inherit a racial and socioeconomic identity. As we become adults, we choose our next identities and these are shaped by how we choose to spend our time. For many years I’ve spent hours in the ocean practicing my paddling and wave catching. As the hours and years add up, I’ve settled into my identity as a surfer, even though I’m still not very good at it. Hours spent doing activities cements these activities into our identity. There’s been periods of my life where I’ve worked 70–80 hour weeks at startups and design firms. The more I worked, the more that work became my identity. For CEOs and founders, their company is their baby. They are the public-facing brand of the company, tightening the loop between work and identity. 

Having your work be your identity isn’t a bad thing. This drive can lead to huge professional and financial success. Yet frequently I hear leaders in tech wanting more balance, especially through the stress of this last pandemic year. There’s two particular triggers that I see repeatedly:

1. Feelings of stress, overwhelm, constant busyness but never feeling that you’re making any progress

2. A negative event. This could be negative feedback, not getting promoted fast enough, or being put on a performance plan and getting fired from a job.

In both of these triggers, leaders have had the hardest time recovering and stepping back into their own success when their work had been a sole part of their identity. 

Three strategies to mitigate work being your sole identity and develop multifaceted identities outside of work: 

1. Know what you want from this job

Your job is not your family. There is no unconditional love or support that continues over long periods of time. If you work in corporate, you work for a business whose main purpose is to make money or create some impact in the world. As long as you contribute to the business purpose, you have a job. There may be periods of vacation or health leaves, but these tend to be short-term with the understanding that it’s a temporary situation until you return to productive work. You create your own community with relationships & friendships that you form, however, you’re ultimately working for a business. 

Within the context of this job, understand what you want to gain from it. In addition to the financial compensation, it could be:

• Understanding how to get to the initial MVP (minimum viable product) for a net new product or service

• Building the culture & process of a company

• Learning the skills to manage a team

• Finessing your leadership to inspire a team of other leaders

• Experiencing an IPO

• Building deep relationships with cross-functional partners

Keep your personal goals in mind. These will last beyond your stint with this one company and help to develop an identity that outlasts the job. 

2. Develop identities outside of work

Creating a multi-faceted identity helps to buffer for stress or disappointments that arise from work. While it took four or five years for my patterns to shift, becoming a mom was my first step away from workaholism and spending countless hours in design work, with my identity tied to being a design leader and continually seeking to prove design’s value at each new job. Identities can come from: 

• Parenting, whether to human babies or pets

• Circle of friends, loosely clustered around the activities you do together or conversations that form the heart of the friendship

• Communities formed around a variety of purposes from volunteering at the food bank to political causes to mentorship or learning circles

• Activities from physical or fantasy sports to crafts or other creative endeavors

• Fandoms, whether in gaming or other forms of media entertainment

There’s no judgement about which of these identities is more valuable in a society, instead, seek to try on and develop many multifaceted identities so that work doesn’t become the sole identity. 

3. Understand your values

Through understanding what you want from this job and experimenting with a variety of identities, start to form a solid picture of what matters most to you from the inside-out. This can be in the form of values or understanding your strengths, or knowing the mission/purpose behind this period of your life. 

Bottom-Line

There’s periods of your life when work is your main identity. And there’s times of uncertainty or negative feedback at work when developing a multifaceted identity beyond work will help you move through the challenge. Three strategies to break out of this identity trap include knowing what you want from the job, developing identities outside of work, and deeply understanding your values. 

Leading Design Festival 2021 - Day 2 Live Sketch Notes

Taking inspiration from Scott Berkun and also Zsofi Lang’s official sketchnotes, I’m live sketching Day 2. Unfortunately I missed Jane Austin’s first talk.
Phew… it’s also the first time I’m doing sketchnotes with an apple pencil on my ipad.

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Leading From the Middle, Lessons From The IC Track

by D. Keith Robinson — Lead Product Designer, Atlassian

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Design Leadership For Imposters

by Temi Adeniyi — UX Lead, Shopify

How to Thrive as a Female Leader in the Male World of Tech

Photo by Randy Tarampi on Unsplash

“Don’t be silly all women have imposter syndrome.”

A male coach had offered to help one of my clients with her imposter syndrome and when she told him that she thought her problem was possibly the opposite, he cut her off with those words. 

This story made my blood boil. I’ve long had issue with the term imposter syndrome. I wrote in From Imposter Syndrome to Pioneer Syndrome:

Perhaps imposter syndrome isn’t a bad thing. If you’re feeling a little bit intimidated and out of your element, it’s likely a sign that you’re playing in the big leagues. You don’t want to be the smartest, most accomplished person in the room. That means you know exactly how to do your job, and that’s boring. There’s plenty more growth opportunities to be the small fish in the big pond and learn from all the smart, inspiring people around you. Perhaps imposter syndrome could be a good thing because then you’re in the right room and ready to be stretched.

This past week, I’ve been leading two separate female leadership groups and also spoke at a Clubhouse fireside chat on “How Women Advance in Tech Leadership.” The shared stories and experiences reminded me that we continue to exist in a corporate world where both conscious and unconscious bias towards women happens every single day. It’s the system of the world we live in. My context is as an Asian woman in tech where my ethnicity happens to be in the majority, unlike other people of color, or immigrants for whom English is a second language. Sexism in the workplace is of bigger personal context than race. So many of these stories are even more devastating for black or LatinX women who have to sort out both racism and sexism, but that is not my story. (If you’re curious, I try to sort out some race thoughts in My Asian Privilege).

My client had shared her story as a response to this Harvard Business Review (HBR) article Stop Telling Women They Have Imposter Syndrome by Ruchika Tulshyan and Jodi-Ann Burey This article was the first bridge for me between imposter syndrome and systemic bias against women and people of color. When starting a new job, especially for high achievers who have excelled and reached for the next tier job in their successful career progression, it’s entirely normal to feel that you might not belong, that you’re scared, and intimidated and worried that you might not perform well. We all feel this. When I worked at Facebook, after a period of time when I built trust and relationships with people, every single person, male or female, has confessed that they’ve felt imposter syndrome. Yet its women and people of color who continue to experience this throughout their career. The HBR article explains:

As white men progress, their feelings of doubt usually abate as their work and intelligence are validated over time. They’re able to find role models who are like them, and rarely (if ever) do others question their competence, contributions, or leadership style. Women experience the opposite. Rarely are we invited to a women’s career development conference where a session on “overcoming imposter syndrome” is not on the agenda.

Yes, there’s so much more that companies and leaders can do in these years after #MeToo and #BlackLivesMatter, and as leaders we must continue to push for these changes. However, today, we still have to live our lives within this system and continue to thrive as female leaders in tech. 

These three points are frequent themes that I touch upon to help my female, people of color, and immigrant clients advance in their careers and companies. 

1. Understand That Bias is part of the System

You’re not crazy. Yes, that gaslighting incident did happen. You weren’t imagining it. And it’s not your fault. Countless women and people of color have experienced this. You are not alone. You don’t need to be fixed when someone else calls you aggressive, emotional, non-confident, or too quiet. 

As a designer, I’m responsible for coming up with design solutions within the constraints of an entire system. At Facebook, we had to design within an existing system. Newsfeed was a great place to showcase new products we wanted to promote. There’s an existing notifications and navigation system. Creating new video formats needed to live within the existing single app that was Facebook. Every design decision fits within the constraints of a greater system. 

Similarly, we all live within constraints of a larger system. In tech, most positions of power are occupied by white males. Bias, whether conscious or unconscious, exists. In this societal system of race and gender, some of us have the drive and energy to file discrimination lawsuits, organize movements to change the system, participate in protests, or simply share our stories widely. Others of us may not have this same energy. We’re too exhausted, and are barely surviving our full-time jobs and identity as a female leader. That’s OK. Know that we are all doing the best we can within this biased system. You have permission to acknowledge the system. 

2. Know Your Unique Leadership Strengths

Within this system, know that there is an existing language of leadership style and with a pre-existing western bias. It’s a bias towards confidence, being extroverted, and claiming the space to express your opinion. While this system exists, you must also take the time to understand your unique leadership strengths. 

Every leader is different. You were born with a particular personality and strengths. Over the years you have refined and developed additional values based on the experience of your life. This experience has been shaped by your gender, race, and cultural identity among other things. You can continue to build upon this foundation of strength and values by trying on different leadership traits and habits. Experiment with them. Try to see what traits feel like an evolution of your uniqueness. 

3. Build Relationships

Relationships matter. We spend a lot of time in our professional life, even if it’s currently over video-conference. Thrive as a female leader by creating relationships one at a time. Over the years, this support system will prove invaluable. I frequently advise my clients to follow these three paths to build relationships:

• Find your people. Find the people who make you feel the most safe and comfortable, who give you a sense of belonging. It might be people who speak your same native language or come from similar racial and cultural backgrounds. It might be other women. It might be other people who went through orientation with you, or a buddy that’s assigned to you. It’s OK if these people change over time. And as you spend more time with people at work and from past workplaces, start to cultivate and build this network of your people. If these people don’t exist within your current workplace, seek out online groups. I’ve found both Moms in Tech and Elpha to be invaluable female networks.

• Find your allies. Look around for people who are peers or more senior to you. See if these people could help be mentors or sponsors. Watch how people show up in meetings to see if they might be sympathetic. These are your allies. Start confiding in them and asking for help. There are good people in every company. I know many white male allies would love to help and leverage their privilege to raise up others.

• Build trust with your key partners. There are key people you must work with to get your job done—your boss, key collaborators, key reviewers of your work, your team, and your reports. Open up and share your stories about your particular perspective. Starting by sharing often invites the other person to listen, and in turn also share.

Bonus: For Allies

In our Clubhouse conversation, a male ally raised his hand and asked how he could help. He wasn’t a VP with a titled position of power and he wanted to know how he could support his female colleagues from where he was. We shared some ideas:

• Amplify the voices that are less heard. Ask to hear opinions from quieter people in the room. If you hear a female colleague get interrupted or talked over, say something: “Can we go back to Jean’s point? I’d like to hear more from her.” If you hear a male colleague take credit for someone else’s idea, state: “David, you added some interesting points to Ellie’s road map suggestions…”

• Point out any examples of conscious or unconscious bias you see. You can do so in a gentle 1–1 conversation with a colleague: “I noticed in yesterday’s meeting that you called upon more of the men to ask questions than the women. I’m curious if you were aware of that behavior.” Or if you’re lucky enough to be in a company that encourages this conversation, you can point it out as it happens in a bigger group. When I’ve been in interview debriefs or conversations comparing performance review ratings for a variety of people, I’ve asked the question: “Would we use those same words to describe Donna if she were male?”

• I’ve been in some large meetings where my idea was re-stated by a male colleague and the room gave him credit. My anger and shame (“Why didn’t I say something in the moment?”) have been mitigated by allies messaging me or talking to me afterwards and letting me know that they heard me, they saw what happened. So even if you don’t feel like you can to say something in the moment, always reach out later.

Bottom-Line

We exist within a male-dominated world of tech. I’ve heard the stories from countless women and people of color and experienced it myself many times. To thrive as a female leader understand that you’re not alone in this system, know your unique strengths, and continue the work to build relationships and community. There’s a lot of allies out there. We can all do better. 

Rest Time is Training Time

Photo by Derek Liang on Unsplash

I used to work out regularly with a personal trainer, Cam. This was when we still had in-person gyms and the camaraderie of sweating and grunting together. I got a personal trainer to keep me more accountable and to help me with the mechanics of strength training. As I aged, I wanted to build functional muscle strength in my entire body and particularly get stronger in my upper body to build up paddle power for surfing. I didn’t care how much I lifted or achieving personal record (PR) numbers. Or so I thought. It turns out that I’m pretty competitive, even when the numbers largely don’t matter. In our first weeks together, Cam pointed out how obsessed I was with getting my form right and trying to lift heavier weights, also noticing: “You don’t like to rest at all, do you?”

He told me that I needed rest time between the sets of heavy weights doing squats, deadlifts, and bench presses. He taught me that my body needed 1–3 minutes rest between sets so that the muscles could recover and recharge. Ever the skeptic, I didn’t really believe him and fought him for many weeks. Rest time to me, is synonymous with laziness. If we only had 30 minutes to train together, we better be making the maximum use of each minute, and sitting around chatting for 1–3 minutes between sets wasn’t going to cut it. I needed to be productive with every minute of my training. 

Over the months and years of working together, I begrudgingly realized that Cam was right. Cam was always right. I noticed that using rest time made me stronger. When I worked out alone, without the patience to wait between sets, I couldn’t lift as much. When I restrained myself to wait beyond a minute and stopped whining to Cam that it was time to get going, I would inevitably break a personal record that day. 

I’m a skeptic and a rebel. My first instinct is to challenge and push back (and occasionally whine). Yet, I am always willing to give things a try. Inevitably my head and heart would break through the hard shell of skepticism, until I finally accepted and internalized that rest time is for training. 

Last year, in a coach training intensive, I listened to lessons from another coach, Matt Chavlovich, a 2x Ironman and pro soccer player. He shared a number of lessons, and the main one that stood out to me was:

Rest day is a training day.

In training for his Ironmans, he had to build in the rest days. He had to make sure he took the rest days, knowing that muscles grow when they’re not in constant motion. Like me, he was driven to keep training. His need to force himself to rest resonated with my insight fighting my own go-go-go drive when training with Cam. 

Rest Time and Creativity

The design process has a rhythm of divergence and convergence. When starting off a new project, there is a curiosity and openness to anything that can happen. Brainstorming new ideas and possibilities is a divergent process to generate many new ideas. Then at some point, there needs to be a narrowing, a prioritization, and a selection of which ideas to move forward with. This is the convergence. Underlying this design process is having the patience to wait and trust that the ideas will come, and they will hit you when you least expect it. 

Have you ever had the experience of going to sleep wrestling with a thorny problem and then after a night of restful sleep, suddenly waking up to see a brilliant solution? What about having a moment of inspiration in the shower or while taking a walk through the park? Rest time in creativity, similar to rest time in training, allows your brain to process the ideas in a different mode and then eventually spit out something non-linear, different, and potentially brilliant. Rest time generates different thinking that can lead to inspired breakthroughs. 

Allowing yourself to rest and not constantly push forward requires patience and the ability to take the long view. It requires integrating the data and facts around the issue or design problem you’re working with and letting your intuition continue to process while you’re not actively focused on it. Trust that divergence and convergence will work. Trust the process. And rest time is a crucial part of the creative process. 

Rest Time and Ease

I love to surf and often fall back into a performative mode where I want to paddle out at the fiercest, biggest breaks and both 1. make it out to the lineup, and 2. powerfully catch and ride the biggest set wave down the line. I can be laser focused on continuing to single-mindedly take stroke after stroke to make it through the battering whitewash. I can be no-nonsense and fixate on timing the next set to make sure that I select the best possible wave to take off on. 

A couple of weekends ago, I met up with a dear friend in Santa Cruz. We hadn’t spent as much time together since Covid, and in addition to the pandemic, he had also recently become a new dad. It was Superbowl Sunday and not many people were out in the water. The waves were uncharacteristically small that day, especially rare as the Northern California winter tends to have massive, giant waves. I switched out my usual shortboard to borrow one of my friend’s longboards. We bobbed together in the water, basking in the warm California sunshine. On these giant logs, any wave was catchable so we would lazily paddle for the little bumps and have long, pleasant, knee-high rides all the way to shore. In between, we kept up a long conversation, catching up on kids, partners, how we handled the pandemic, and updating each other on our mutual passion for personal growth. 

Longboarding is rest time. This session reminded me of the ease, pleasure, and camaraderie of surfing without the pressure of performance and wave counts. A week or so ago, I was chatting with a semi-professional young female surfer. She was a shortboarder who grew up riding big waves on Ocean Beach. Yet sometimes she would get into a rut. She would keep messing up and not be able to catch waves in her competition heats. She was stuck in the pressure of performative mode and unable to get out of her head. Her coach gave her a technique—get on a longboard for a week and go catch long, effortless rides. After that restful, slow change of pace, she got back on her shortboard. She’d broken the performative pattern with this ease of longboarding, which always cleared her rut. 

Bottom-Line

We can be so overly focused on the hard edge of training. We want to be successful, to perform, to hit our best record, and to win. It’s important to realize that rest time is training time. Rest time provides balance whether it’s for creativity, greater ease, or to make us more performant.

Be the Leader to Create More Leaders

Photo by Ian Parker on Unsplash

The term “leader” can be problematic. Some of us hear the word a lot but we don’t necessarily know what it means. As a leadership coach, I help people find their strengths and unique voice to perform better at work, develop stronger relationships, and amplify their growth + impact at the organization. Yet I also hear from many people that they’re not leaders because:

• I don’t manage people. I’m not the boss.

• I do manage people, but I’m not good at it.

• I don’t have the skills or training to be a good leader.

One of the most important parts of leadership is the relationships you cultivate. The most important one being the relationship with yourself. In context of relationships, leadership is:

1. The self awareness to know what lights you up. This is an ever-changing cauldron of ingredients that includes your values, what you’re good at, your long term purpose, and what gives you energy. Always start with this piece of knowing what lights you up.

2. If you manage a team, know what lights up each one of your people. And do whatever it takes, balanced against the business needs, to empower them to spend the most time on what lights them up.

3. In a corporation, there is an even bigger group of people who you don’t manage. Steven Covey talks about our Circle of Concern, things we care about over which we have little or no control, and our Circle of Influence, the things we do have some control over. Regardless of your role, there are key people within your Circle of Influence. These include your manager, your peers, partners, and collaborators who you work with frequently. For these people in your tight Circle of Influence, know what lights them up.

If you’re not sure what lights you up or what constitutes a good leader, think about the bosses you’ve had in your life. Which one of them was a fantastic boss? What part of their leadership would you like to incorporate into yours? 

It may be more common to remember bad bosses. Can you think of all your terrible, micromanaging bosses and the things you hated about them? What parts of their leadership do you want to stay away from? You can use these examples from your life, and more importantly, your reaction to these bosses to define your leadership values and what lights you up. 

One of the best bosses I ever had gave me two pieces of leadership advice:
1. Hire people smarter than you and who think differently than you. 
2. Create more leaders around you to work yourself out of a job.

You want a smart, diverse team to be able to see your way around problems and find innovative, creative solutions. You want to work yourself out of a job so that you develop your team and create other leaders. This allows you to go on vacation without worries, remove yourself from being the bottleneck, and also start succession planning. Working yourself out of a job eventually opens up enough space for you to find different activities and scope that light you up and then… you’re on the path of working yourself into a new job. 

There are two key ways to start creating more leaders: Delegation and Asking for Help. 

Delegation

We often become leaders because we get very good at accomplishing things, whether it’s executing on projects/processes, working with people, or contributing to the organization at some larger level. Over time, as highly performant people, we get to a stage where if we hold on to every single thing, we get overwhelmed and overworked—there is always more work to do. Yes, there is the process of prioritization which we all try to do. And sometimes there is still too much very important work to get done. 

This is where delegation comes in. 

As a leader, you know what lights you up and you know what lights up the people around you. Be a matchmaker and stop doing the things that don’t light you up. Instead, give them to the people who want more opportunity, especially if it lines up with what lights them up. 

It’s hard to delegate. You have to give up your control and your one right way of doing things. And it’s this process of letting go, of eliminating the certainty of doing it yourself, that provides autonomy and creates more leaders. You can put in guardrails. You can help the person with defining the goals/outcomes and teach them how you’ve done the thing. However, give them some autonomy to do it in their own way and provide both the support to let them succeed and the space to let them make mistakes and learn. 

Part of the leadership process is to SEE/DO/TEACH. You first observe someone else doing it, or do your own third party research to figure out an unknown thing. Next you do it yourself. Figure out what works for you, learn from your mistakes and from others around you. Finally, teach it to someone else. See what resonates for them and what confuses them. Try telling them another way until it clicks. Watch them as they do it themselves, and provide the support they ask for. SEE/DO/TEACH cements the continuous learning process. 

Asking for Help

For many people who follow the servant leadership philosophy and who exist to support their teams and others around them, asking for help can be difficult. Yet, can you think of the last couple of times when someone asked you for help and you were so excited and eager to say YES because the help was easy for you to do, it was something that lights you up, and it genuinely felt good to help someone else?

 Asking someone else for help is offering them a gift. 

If you know what lights them up, you will always strengthen the relationship. Asking for help shows your vulnerability, acknowledges their expertise, and overall builds more trust in the relationship. 

Leaders can stop doing everything themselves and create more leaders around them by asking for help. 

Bottom-Line

We may not always think of ourselves as a leader, and that’s OK. We can continue to do the work to become more of a leader both personally and professionally. Start delegating and asking for help to be the leader who creates more leaders. 

Bounce Back from Burnout

Photo by Joshua Reddekopp on Unsplash

Exhausted. Overwhelmed. Continually stressed. Running on fumes. Maxed out. That sinking feeling in the pit of your stomach starting on Sunday afternoon, knowing that your work is piling up for Monday and the week to come.

These feelings aren’t uncommon. We all can have off-days or off-weeks—those occasional periods of stress or pushing to meeting a high-pressure deadline. We may be dealing with family stress, grief, or illnesses. The slippery slope towards burnout is when these feelings start to become the norm; when they persist over weeks, months, or years. It’s not healthy for humans to be in this chronic state of stress—we make more mistakes, our performance suffers, and eventually we hit a wall and burst.

Bouncing back from burnout is much easier if we catch ourselves heading down this slippery slope before hitting that maxed-out point.

Putting a name to swirly concepts can lead to insight. Naming things can uncover enough uncomfortable truths to provoke behavior change. I recently listened to a brilliant podcast where Brene Brown interviews Simon Sinek on his latest work, The Infinite Game.

From his book blurb, Simon Sinek summarizes:

In finite games, like football or chess, the players are known, the rules are fixed, and the endpoint is clear. The winners and losers are easily identified.

In infinite games, like business or politics or life itself, the players come and go, the rules are changeable, and there is no defined endpoint. There are no winners or losers in an infinite game; there is only ahead and behind.

So how does this relate to burnout?

Burnout in tech most often happens when you’re working for a fast-paced corporation or startup with high expectations, short deadlines, and a continual need to scale & grow. Most companies, and the people who work there, are playing a finite game.

Performance Reviews

Performance reviews are a prime example of a finite game. There are a clear set of winners (e.g. the top 20% of people reviewed) and losers (e.g. the bottom 10% of people reviewed) along with the gradients of people in between. At larger companies, performance is often stack-ranked and on a curve. This means that even if the majority of people have been model employees doing highly impactful work, only the top 20% will be rewarded. It’s a zero-sum game that only a minority of people can truly win, whether it’s with money or a promotion.

Anecdotally, performance reviews and their associated rankings, are one of the leading sources of stress for employees. There is resentment if you’ve been working around the clock, and don’t get the limited number of available recognition or reward slots. There is jealousy of your teammate’s achievements because of this win-or-lose system. And there is resentment from the misalignment when you think that you’re doing a lot better than your review shows. Burnout is caused by this finite game of performance reviews and thwarted expectations.

A different perspective, one that helps prevent burnout, is to treat performance reviews as an infinite game. This job, and this six month or yearly review, is simply one moment in a career that spans multiple decades. Focus on the feedback you’re receiving in the review. Focus on the learning and skills that you’ve gained or can gain on the job. This starts to transform your mindset into playing an infinite game rather than the scarcity mindset of competing with your teammates for a limited number of prizes. Read more on how to approach Winning at Performance Reviews.

Short-term vs Long-term Thinking

Finite games, by their definition, have a clear end-point and are focused on the short-term. Performance review cycles are every six months or every year. They are built for showing immediate value to shareholders or investors for short-term financial gain. There’s many benefits to short-term thinking. We get more affirmation faster. Setting and hitting short-term metrics or goals makes us feel good. We love getting gold stars and checking items off a list. We get dopamine hits from that and want to go keep going back for more. This cycle sets up a hamster wheel of continual striving, and pushing for more in a go-go-go corporate lifestyle. This deadly cycle leads to exhaustion, overwhelm, and burnout. Many of us treat our work as short sprints, but can end up trapped in marathon working years without rest.

Infinite games focus on long-term thinking. You will eventually leave this job. It’s one job of many in a decades-long career. Imagine that you’re the guest of honor at your farewell party. Your boss, key partners, and colleagues are gathered to celebrate your tenure at this job. Consider:

• When you look around the people at this farewell party, who do you truly care about?

• What are they toasting or thanking you for?

• Is it achievements that you’ve completed (finite game) or how you’ve showed up at work (infinite game)?

• What have you learned in this tenure?

• What matters the most about this job for you?

• How far away in the future is this farewell party? 6 months? 1 year? 6 years?

When you consider this future visualization of your farewell party, think about how your day-to-day actions matter. How are you contributing to your slide towards burnout? What might you experiment with changing to both help with your feelings of stress and overwhelm AND also ensure that you achieve what matters most to you about this job?

Connect Your Career to Your Why

Dreaming about being the guest of honor at your farewell party starts to activate what really matters about your job. Finding either your Why¹ or the vision of where you want to go, what Simon Sinek calls your Just Cause¹ in his book, helps connect you to what matters in the infinite game of your life.

To help with bouncing back from burnout, consider the meaning of your job, or why you work there. If you have the luxury, think about your deeper Why of how you seek meaning in your life. There’s many places where Simon Sinek talks about Start With Why including this one.

Simon Sinek shares his why from the podcast’s transcript:

To inspire people to do the things that inspire them, so that each of us can change our world for the better.

When I worked in corporate, I felt that I was continually on the edge of burnout. I reveled in feeling needed and important, which meant that I spent a lot of hours working. I was in meetings for most of the day, sometimes double- or triple-booked and would spend precious nights catching up and finishing the “real work” I needed to do. I felt stressed, continually behind, and tried to compensate by multi-tasking and pushing through harder. I never stopped to think about a bigger Why or the meaning behind the work I was doing. And I ultimately ended up leaving corporate because it started to feel hollow and meaningless.

Now I run my own business, a combination of leadership coaching, teaching, and product consulting work. After many months of pondering, I came up with this Why:

Boundless self-exploration to get lost and co-create maps with others.

I love what I currently do because I get to go deep into the world of personal growth and improvement. I can take my own journey and then serve as as guide for others around me, whether they’re clients, partners, friends, or acquaintances. I continue to practice mental fitness against my need for control and perfectionism by deliberately stating the intent to get lost as part of my Why.

The ultimate way to bounce back from burnout is to connect your career to your deeper why. The stress and overwhelm may always come up in some parts of your work life, AND it’s easy to handle if you’re clear about the purpose of your work.

Bottom-Line

We all experience periods of stress, overwhelm, and despondence. These can be early warning signs of burnout. Learn to identify these early and bounce back from burnout by using Simon Sinek’s framing of finite vs infinite games. Move beyond the limitations of short-term performance reviews (finite games) to thinking long-term and starting to connect your career with what matters to you in this infinite game of life.

¹Disclaimer: I’m a little confused about the difference between Simon Sinek’s definition of Why vs Just Cause, and I feel slightly mollified that Brene Brown also suffers from the same confusion in her podcast. In this article I’m mainly focused on the Why.

The Trap of Certainty

Photo by Mike Erskine on Unsplash

I tend to be a person who is sure of things. I’m certain of many things— what people I like to be around, what I like to eat, where I like to travel, and what I want to do with my time. I am the queen of certainty. This certainty has served me well and led me to success. I live in the United States, in San Francisco, and have worked in technology in Silicon Valley for most of my professional life. We are a culture that values visions, plans, decisive action, and consistent follow through. But at what cost?

My colleague and friend, David Taylor-Klaus, asked this question earlier this week:

“Where are you trapped by your certainty?”

This question stopped me cold. I’d always valued my certainty and decisiveness above all else. And yet when I think back on my own life, I could bring to mind many stories where I was trapped by my certainty.

The “Finding A Major” Story

I was good at math and science in high school. I was also fascinated with how things work. I enjoyed problem solving. When I entered Stanford as a starry-eyed freshman, I was enamoured with the myth of California and Silicon Valley. It seemed that the clear path forward was to become a computer science major. I went straight to work, jumping through the hoops of basic classes and prerequisites; and diving into C++, LISP, operating systems, and artificial intelligence. Along the way, a rebel side of me insisted that I take other classes that fascinated me, including psychology, philosophy, and ethics on top of the required reading of Great Works. Math and computer science classes became really hard. It felt like I was going through the motions and spending countless all-nighters to barely scrape by and complete the assignments. It felt rote, a bit life-less and soul-ess. And yet I persevered. I kept working hard. I was certain computer science was my path.

After slogging through a couple of years of this certainty, I had had enough. I realized how much more I enjoyed learning about the Turing Test, participating in psychological experiments with grad students, debating ethics & morality, and appreciating the history of the first computer interfaces. I was lucky enough to discover human-computer interaction as a early precursor to the new discipline of product design. It let me blend my love of analytical problem solving with the beautiful complexity of understanding humans. I found a unique role translating between the two systems.

My certainty about computer science led me to some great things—the ability to understanding coding down to the metal and to wondrous applications in creating gaming systems and programming robots. But for a couple of years, that certainty closed off the possibility that I might find something else to love better.

The “I’m not good at sports” Story
Having a tiger mom growing up, succeeding at school mattered a lot. Early in primary school, I realized that I wasn’t the best at hand / eye coordination or physical stamina. In gym, I was often the last kid picked to be on a team. I could never run a 12 minute mile. The only blemish in my straight A high school record was getting a B for P.E. I still remember being outraged at both failing to hit the physical benchmark as well as failing to correctly answer some obscure question about points gained for certain plays in American football. I was certain that I was not good at sports or anything physical.

For years I avoided doing anything physical. This changed when in college, I spontaneously took my first 7-day backpacking trip with 4 other women. I don’t think I’d ever even been on a hike before that week. With my heavy pack, we trekked through the backcountry in Death Valley, Zion, and Joshua Tree, setting up camp where-ever we wanted and sleeping under the stars. Then some years later, I discovered surfing, and then snowboarding. These were individual sports where I didn’t need to run or have the best hand-eye coordination. Instead, they let me build on my adrenaline-junkie urge for speed and the ability to keep persevering through the strength of waves and power-covered mountains.

My certainty about not being good at sports led me to spend all my energy towards academic excellence. For many years, it trapped me within the space of the mind. It closed me off to the possibility of finding physical activities that brought me energy and joy.

Strong beliefs, loosely held

Working in tech for decades, I can think of many instances where I was convinced that a design solution was going to work well for certain groups of people. And in many of those cases, I was right. I also remember the sinking feeling of failure when I went all-in for a product solution that I was certain was the correct one; a product solution that I had fought for and gotten research to back me up, that I had sold through many executive reviews, and yet… when we had people use it, it was clear that there were many things wrong with my solution. I’ve learned over the years to adopt the principle of strong beliefs, loosely held. That we can have hypotheses around people’s problems and how we might provide solutions to these problems. But these are not facts steeped in 100% certainty. As time passes, we run experiments to test the validity of these hypothesis and remain open to the possibility that new data can, and will change these hypothesis.

Certainty is a good thing. It’s valuable to know a direction, and to have beliefs and strong desires in both a professional and a personal setting. The warning of “the trap of certainty” is to have us move forward toward that goal, but never forgetting that we have the freedom to change our minds.

1.Be all-in to the certainty
Keep moving through the process and days knowing that the work you’re doing levels up to a bigger cause and purpose. Whatever it is that you’re certain about, commit to it. Go all-in.

At the same time as complex humans, we can hold on to paradox and ask ourselves the following questions:

2. Where might I be wrong? Who could help me with a different perspective?
It’s always valuable to be aware that this certainty is not 100%. Holding it as a hypothesis opens up the possibility that I might be wrong. Anticipating and thinking through these areas without being paralyzed with indecision helps to create a counter-balance to the certainty. Surrounding yourself with people who have a different perspective also serves as this invaluable counter-balance. In lieu of having these strong partners, you can use Edward de Bono’s Six Thinking Hats to actively question the certainty by donning different modes of thinking ranging from the yellow hat of optimism to the red hat of intuition to the black hat of being the devil’s advocate.

3. Am I approaching this from scarcity or from abundance?
As you focus on the thing you’re certain about, notice the emotion associated with the passion. Is it driven from a negative emotion that might be a scarcity mindset? For example:

• Fear of looking stupid or losing credibility

• Shame at not being skillful enough at sports / math / drawing / presenting

• Jealousy around other people’s success

These are all negative emotions around a scarcity mindset. Instead, try to re-frame the thing of certainty to a statement of abundance.

• Empathy around how this proposed product could help people’s lives in particular ways

• Curiosity or determination that practice could lead to more skills

• Desire for your own success

4. Will this certainty hold over time?
Sometimes in the heat of the moment, the certainty feels so strong and powerful that you feel it must be 100% right. Give yourself a container to evaluate how this certainty will hold over time. For example:

• Before accepting or rejecting a job offer, think about it at least overnight and hopefully over a period of days.

• When in a professional or personal relationship with conflict, note how your feelings for the other person changes over days, weeks, months or years.

5. Permission to change my mind
One of my clients knew that her current corporate job which was filled with meaning and social good wasn’t the right long-term path for her. It was giving her financial stability, yet she yearned to start her own business. She was certain that entrepreneurship was her future path. We explored many options together ranging from getting an MBA, to starting research on her product idea, to finding potential partners to talk to, to how to create an MVP (minimal viable product) version of her idea. She ran experiments around all these paths. Yet the biggest freedom from her certainty was the insight that “It’s OK if I change my mind.” It’s great to be all-in to a certain passion, and know that it’s completely OK to change your mind later on.

Bottom-Line

Certainty is a wonderful thing in our problem-solving, forward-focused culture of getting things done. Yet it can become a rigid taskmaster that closes off possibilities and traps us within its structure. Avoid the trap of certainty with the mantra of strong beliefs, loosely held.

Winning at Performance Reviews

Photo by Jason Dent on Unsplash

One of the most stressful and time-intensive periods of my Facebook tenure was the performance review cycles that happened every 6 months. I’d spent decades working at startups and design firms with erratic approaches to giving feedback; so despite the mental impact, I remain grateful for a formal, if flawed system of performance reviews.

Performance reviews are inherently nerve-wracking. In theory, you should be aligned with your manager and already have a good sense of how you’re doing. This should happen through regular feedback and 1-on-1 conversations. Yet in practice, even the best managers and organizations get distracted with the thousands of urgent requests that take precedence over long-term people development. Most people I’ve worked with and coached still get blind-sighted with the feedback and ratings they receive.

Sometimes we put on an armor and pretend not to care or we retaliate by criticizing the process. But we all really care. And it’s OK to care. Most people reading this are going to be growth-minded high performers who are used to succeeding and achieving throughout their lives and careers. This performative culture is the norm in technology and especially so in Silicon Valley. We are all human. And being human, it’s important for us to have recognition, security, and the external validation that we’re doing OK.

We may also vaguely feel that there’s something wrong with us for caring so much about a performance review, especially if it’s a negative one. Or perhaps you’ve received a glowing performance review yet can’t let yourself trust that wealth of positivity––instead you flip to the growth areas and keep pushing to improve and make yourself better. We do this because we care. And it’s OK to care.

It’s important to keep in mind that performance reviews are for the company’s benefit. Similar to going through a school system, with a large enough company, there’s a curve or a distribution for how many people are in the top 10%, next 10%, average and so on. By definition, the majority of employees will be average and get a Meets All Expectations rating. This is innately hard for us to understand because we like to believe that we are all above expectations. But that’s not how the company works. It’s hard to feel that Meets All is a good rating. For high achievers who are used to having been the best throughout their lives, it feels mediocre, like getting a C in school. But if you’re working for a world class, top tier company, the comparison pool is of the highest caliber. Comparisons can be healthy if they push you to learn and improve, without hating on yourself (see my article Want to Dream Bigger? Start with Envy). But sometimes you may not want to keep pushing or striving because it’s putting you on the edge of burnout.

There’s another perspective to consider. What if you frame the performance review as being selfishly for you and your growth? I’ve used this three-question framework both within tech companies and also with clients that I support. This framework is the key to truly winning at performance reviews.

1. Why do I work here?

Ask yourself why you work at the company. I’ve heard a variety of reasons including:

• It’s a name-brand top-tier company / Their clients are the top name brands

• I want to impact people’s lives at scale

• I value the mission of the company

• It pays well and I need the money to finance other parts of my life

• I’m simply grateful to have a job that pays me and is the start of a career

You might share these reasons or have your own. It’s important to be clear with yourself why you work there. It’s what will get you through the long hours, the difficult feedback, the conflicts with other people, and remind you of the purpose of your professional life.

Many people know this when they apply for a job and decide to accept the job. Yet this can often be forgotten after months or years and taken over by an overwhelming need to be conditionally successful or happy. For example, telling yourself “I’ll be happy when…”

• … I get that raise or bonus

• … I get promoted to the next level

• … I start managing managers

• … I make partner

• … I make it to the C-suite

The challenge with tying happiness to a future event is that we so often move the goalposts once a goal is achieved. This leaves us perpetually unhappy or malcontent in the present, and continuing to strive for an unknown future goal.

Instead, try to get in touch with the original why, the purpose for working at the job. And then consider this next question.

2. What do I want to learn?

Beyond the money, title, and prestige, think about what skills you want to learn or opportunities you can explore at the job. I was recently chatting with a product manager who was considering switching to a more hands-on, craft-oriented role either as a designer or as an engineer. Rather than have to leave her current job, I coached her to have a conversation with the engineering director, leading to a plan for her to work with a mentor and be responsible for a small part of the code base.

At larger companies, there’s often the opportunity to show impact at the company-level by contributing to initiatives such as recruiting, diversity & inclusion resource groups, or working with interns. You could find opportunities to share your expertise through teaching, speaking or writing.

Within your current job responsibilities, consider what do you want to learn and get better at. Many designers I’ve worked with will pick an area of craft to focus on for 6 months or a year. This could include learning to code, becoming a master prototyper, creating vision videos, or aspects of physical graphic design.

I was able to spend a lot of time at Facebook coaching women across the company, working on diversity efforts within the design organization, as well as broadening our pipeline to seek out more diverse interns and university hires. All of these skills helped me to switch careers into leadership coaching.

3. What have I done?

Finally, take a hard look at what you’ve done through this performance evaluation period so that you can self-assess for what matters to you, not the company. You figure out what matters to you based on why you work here and what you want to learn.

Get into the habit of setting your own growth goals for the period and sharing them with your manager. Also, at the end of each week, capture what you’ve done and what you’ve learned. All too often, we forget all these details when it’s three or four months later and it’s now time to write a self review.

These are some ideas of what you could capture for each week’s progress. They’re written distinctly from a product perspective, but can help as a starting point:

• Work or project tasks completed; This could be numerical such as number of design iterations, or number of bugs closed

• Processes you’ve initiated

• People you’ve helped, whether it’s colleagues or end-customers

• Skills learned

• Meetings that were collaborative

• Times that you were in a state of flow, and what you were doing

• Milestones such as features or product releases and major research or design initiatives

• Celebrations, including moments you were proud of and also praise from others

Over time, you’ll have a history of your weeks and months. In looking back, you can pull out what feels like success for you. This lets you discover what matters to you in addition to what matters to the company.

Bottom-Line

Performance reviews are stressful times where you yearn for external recognition, feedback and reward. As humans, we want to know where we stand and how we’re doing from other people. To truly win at performance reviews, start asking yourself this three-question framework to gain more insight into what success looks like for your personal standards, and not simply the company’s expectations.

How to Expand Your Leadership Lens

Photo by Matthew Ansley on Unsplash

When we get negative feedback at work, there can be a first moment of resistance, a recoil against the feedback:

• “That’s not me. That’s not who I am.”

• “I can’t lead like that.”

• “It doesn’t feel authentic.”

• “I don’t have the [confidence/wisdom/courage/voice/xxx] to be like that.”

Through the years, I’ve worked with many people who have been seeking that perfect leadership style, aura, or presence. In the corporate world, where we’re used to seeing specific descriptions of performance metrics, job expectations, and clear behaviors to attain, it can be really frustrating to get feedback that our leadership style isn’t right. It’s hard to take action on that feedback. Even without that feedback, we can feel that everyone else around us has this mysterious leadership quality that we are lacking.

Let me tell you a secret—there’s no magic secret to leadership.

Leadership is not one-size-fits-all. Leadership is not set in stone. It continually evolves as we move through our different contexts and experiences. It changes as we work with leaders we admire and leaders we dislike—we choose which traits to emulate or discard. How you show up as a leader is similar to the product development process or scientific method: you experiment with a number of different leadership lenses, and you vary them depending on situation & context. Keep the ones that work for you; discard the ones that don’t.

Power and Attractiveness

This Harvard Business Review article on How to Develop Your Leadership Style defines leadership style as “what you do, how often, and when.” They proceed to analyze the markers commonly associated with leadership in the workplace and break them down into 2 categories — power and attractiveness. The power markers are the prototypically masculine traits of confidence and competence, and can also be associated with arrogance and abrasiveness. In comparison, the attractiveness markers are more prototypically feminine including approachability, agreeableness, and also submissiveness.

My leadership has tended to land closer to power than attractiveness. It’s been the most consistent way I’ve expressed myself in a professional setting. However, the most experienced leaders don’t land in one or the other category. They practice range—the ability to switch their leadership lens from power to attractiveness depending on context.

When I first managed teams, I was in my mid 20s. I was simultaneously insecure and ambitious. I adopted a command-and-control style of leadership that was predominantly in the power range. I used this one-dimensional leadership when interacting upwards to my bosses and downwards to the people who reported to me. The only times I exhibited attractiveness markers was to my peers as we struggled through first-time management together. As I transitioned into design firms I discovered that this power style of leadership was crucial in my expert Creative Director role to pitch our brilliant innovations to clients. It wasn’t until I left these environments and moved into startups and then later Facebook that I learned to build more relationships and consensus to ship products at scale using the lens of attractiveness.

A common mistake new managers make is to adopt attractiveness markers while managing up—classic “kissing up”— and power markers while managing down to their team. Yet the most successful leaders in fast-paced tech companies with autonomous employees do the opposite—show your competence by using power markers upwards and demonstrate servant leadership by using attractiveness markers when working with your team.

Experiment with range in your leadership lens by identifying behaviors, phrases, or emotions of power and attractiveness that feel natural to you. For example, because I was seeking to stretch my range into more attractiveness markers, I would try:

• Never being the first person to speak or ask questions in a room. Instead, I started with listening. From there, I would summarize the positions and build upon them with questions for others. I’d often start with the phase: “I’m curious about…”

• I noticed that I interrupted others a lot. As a woman in tech, this had been my coping mechanism to jump in to get a word in the conversation. Instead, I yielded to others, and amplified voices of other women and minorities. If two of us jumped in at the same time, I would make an intentional choice to defer or speak depending on how vocal the other person was.

• I sought to build trust and relationships with new colleagues via 1–1s, walks, and coffee chats to better understand where they were coming from before diving into work discussions.

Try making your own cheat-sheet of behaviors to try. The most important thing is to be aware of power vs attractiveness and experiment with when to play up or play down each marker.

1–1 and Groups

A separate lens on leadership is to examine how you typically show up in 1–1 meetings versus groups. We tend to be the most comfortable in a 1–1 situation and given that there are only 2 people in the conversation, we have more ability to direct the content, the emotional resonance, and the overall rhythm. Some things to notice in a 1–1 dynamic:

• Are you more comfortable listening or speaking?

• How do you show up when the other person is higher power vs lower power?

• What do you like best about your 1–1 presence? What would you like to change about it?

Now, take these same questions and apply them to a group format. It’s best to pick a 6–8 person mid-size group where there’s the group size is intimate enough that you can shift between participation and consumption.

Experiment with shifting your typical behaviors in 1–1 and apply them to a group setting, or vice versa. Notice the impact on yourself, and on others around you. Ask for feedback.

Professional and Personal

One last lens to play with is to look at how you show up in your professional life vs your personal life. We’ve been talking a lot about work leadership, yet you also play a leadership role in many personal contexts—as a parent, a friend, a sibling, a romantic partner, or a son or daughter. Your leadership can simply be how you describe yourself or how others describe you in these roles. For example, while I show up as strong, direct, courageous and compassionate in a professional setting, as a parent I’m more silly, playful and directive. As a romantic partner, I am more deferential and flexible, yet also demanding. As a friend, I can be crass and competitive.

Think about how you show up in all your personal contexts and experiment with how you might add one of those flavors to a professional context. What would it look like if you added more play or humor to a work meeting? At best you may find some new range to play with professionally, and at worst, you’ve shown a different, more vulnerable aspect of you to colleagues. Vulnerability always builds trust.

Bottom-Line

You already have a way that you lead professionally. It’s a mixture of your personality (who you are) and the behaviors, phrases, and ways that you show up at work. And, every single day, you can choose to experiment with different leadership lenses. Try some new ones on, and keep the ones that you like. Your leadership will continually change, so be intentional about the lenses you pick.

Transitions are Tough

Photo by Joshua Sukoff on Unsplash

It’s the first work week of 2021 and for some of us it’s a rough transition time back from a period of holiday celebrations followed by rest and relaxation. Transitions are tricky. Our bodies and minds get into particular rhythms of being—what we eat, when we wake up and go to sleep, and the movement patterns of being free from a desk+computer— and it’s hard to change these habits.

Another transition is the hope of leaving the chaos of 2020 behind and approaching the new year of 2021. Yet many of us are also sick of that phrase “the new normal,” realize that we’re still in a challenging fight with COVID-19 and vaccination, AND can also appreciate the psychological clean slate of a fresh year. Being able to appreciate paradox and still function is a familiar state. We’ve all lived it through 2020.

Transitions refers to the messy space between two things. Right now I’m dealing with two transitions: 1. being in the space between 2020 and 2021 and 2. starting up work again after a 2 week break. I’ve been using the following strategies to dealing with transition:

1. What do you want to grieve and put behind from the past?

Joseph Campbell’s work on mythology talks about the hero’s journey, a template for a protagonist that departs home to adventure out in the world before returning a changed person. On the adventure, our heroine meets many people and has different “chapters” of adventure, learning from each one. Playing homage to the hero’s journey, we can look at each transition period as closing the chapter to the past and opening up a chapter to what’s next. A heroine can’t fully move on until she’s properly grieved and put to rest things that have happened in the past.

For me, in transitioning from 2020, I want to leave behind the anxiety around planning of events, trips, visits in a volatile and unknown public health crisis. I have a controller saboteur and can be a type A planner. I find comfort in having a road map of certainty for my year. When that wasn’t able to happen, I’ve reluctantly found a certain freedom in being spontaneous and flexible. At the same time, I grieve all the trips I haven’t been able to take and all the people I haven’t been able to see in 2020. The biggest grief is not going home to Thailand to see my mom and extended family.

2. What do you want to honor and take into the future?

Continuing with the hero’s journey, it’s also important to identity what heroine tools you want to honor and to take with you onto the next part of the journey.

From 2020, I want to keep my flexibility and ability to keep on moving with a plan B, plan C, plan D, or even to wake up each day with no plan and see what feels right. I want to keep the freedom of unplanned free time at home to play games, watch movies, do puzzles, bake and connect with my homebody girls who are delighted that I’m not pulling them out into new adventures.

At the end of December, I had a celebration-filled week with my daughter’s birthday, my birthday, and Christmas. That family time was followed by an introspective 5 days alone at a yoga and meditation retreat. I went inwards and found deep relaxation as well as a renewed creativity for my business & life. From that downtime, I want to honor the white space I gave myself to be silent, to think, to do nothing… all of which spurred more energy and creativity. I want to take this white space into the busy bustle of this packed work week and back-to-back Zoom calls, and onwards to a sustained white space practice for the year.

3. Transitions are Tough

The final non-strategy is simply acknowledging that transitions are tough. This happens when you’re the one driving the transition—quitting a job, leaving a relationship, moving to a new apartment or city—and is even harder when the transition is unwillingly happening to you.

Transitions are tough when they’re for these big examples, and they’re also tough for little things such as adjusting to an hour time change from daylight savings or transitioning back to work after a break.

Some of the darkest months of my life happened after my kids’ dad moved out of our family home. I knew all the right things to do and I was disciplined enough to do them: exercise with my trainer, eat properly, get enough sleep and supporting medication to help me sleep, continued visits to both a psychiatrist to prescribe anti-depressants and a psychologist for talk therapy, plus surrounding myself with a tight circle of loving friends and others who had been on the same journey. About 8 weeks into this transition, I remember wailing to my therapist:

“I’m doing all the right things. And it still feels terrible.”

Yes. Because transitions are tough.

And yet time passes. You get up and keep going through each day. You crawl into bed each night and hope for rest. You know that this too will pass. And when it passes, you’ll have learned from this challenging time of transition.

Bottom-Line

As we transition from 2020 to 2021, and back into the work week, think about what aspects of the hero’s journey we want to grieve or take into the future with us. And ultimately remember that transitions are tough, but they always eventually end.

Creating Your 2021 North Star

North Star framework of leadership

2020 was not what anyone expected. It’s a historic year that will be remembered through our lifetime. Moving into the new year of 2021 is a quirk of human calendars, and yet there’s something magical about passing the milestone and getting a fresh start.

We’re all familiar with New Year’s Resolutions and how they typically end in a dumpster fire by the end of January. Yet without dreaming and wishing for something different, we end up stuck in default modes, repeating old patterns, and continuing to tread the well-worn grooves of our lives.

This article outlines about a leadership framework revolving around your one word intention to define your 2021 north star. I’ll also share mine as an example. If you want additional support to create yours, my colleague Jim Herman and I are leading a 4-week group program that begins on January 12.

Last year, I wrote about Defining your 2020 North Star. My word for the year was Grow. It was fitting as I needed to grow more patience and learn to surrender to uncertainty. In a New Year's ritual, my girls and I went to the beach. We lit incense and burned gold paper in memory of my father. We talked about our hopes for the year. We wrote down our intentions, and burned them.

2020 has been a hard year for all of us. I’m lucky to have gotten a early start on working from home in fall of 2019. I’m lucky to have a coaching business that’s pandemic-friendly, supporting people through their crises and helping them show up as stronger leaders. I’m lucky that my two daughters, in 4th and 7th grades, are good independent learners, able to cope with Zoom school while distance socializing with friends. And, it was hard to cope with our first global pandemic, thrive in isolation, and grapple with my place and role in racism. Grow was the right word for the year.

Setting your North Star is not establishing rigid goals that you must accomplish by the end of the year. It’s not a typical New Year’s resolution to lose 10 pounds, find your life partner, run your first 5K or get that promotion at work. These are all outcomes. For successful, driven people, you’ll reach these outputs at some point in time. What’s important is to ask yourself if these are the internally-driven outputs you truly want. Or are they externally-driven outputs, deemed important by your parents, your successful friends, or society — the “shoulds”?

A North Star is a directional setting that guides you to the right behaviors and choices to achieve focus, fulfillment, and success through the year. It can involve outcomes and goals, yet the key is to hold these lightly. One of my colleagues, Erin Baker, asks people to dream about 2021 by considering a “wouldn’t it be awesome if _______________” list. Rather than a rigid goal, this awesome list comes from a place of dreaming and giving ourselves permissions to desire big things. The key to this list is to remain unattached to the goal. We’ll do all we can to reach it, and if it doesn’t happen, it’s OK. A North Star is directional and not prescriptive.

Looking forward into 2021, I offer up a two-part strategy to set your North Star.

Part 1: One Word Intention

When working at Facebook, one trait that was consistent among the strongest designers was something we called intentionality. Like all the best concepts, it is both a paradox and a mix of mind and heart.

The digital products we designed all existed to serve a purpose and solve problems for some group of people. A designer may work on a brand new concept for a product (e.g. Facebook Dating), a feature to add to an existing product (e.g. the ability to Save videos), or a small UI element such as navigation or call-to-action buttons. Having intentionality means that the designer could see the purpose and why behind the design solution, regardless of the size of the problem. The designer knows how the solution will directly impact the people using it. And after the solution is executed, there is self-awareness to evaluate if the design hit its intention. Part of the creative process is trying many different things, many of which will fail. Yet they’re all part of the process. In evaluating product designers, intentionality refers to having the foresight to know what feelings and outcome you want to achieve with the product, and the self-awareness to discern if you hit it or not.

A one word intention for 2021 helps to focus attention on what YOU need more of. What would you like to be the theme of your year and the why behind it. It’s not a specific as a goal. It’s a feeling, an emotion, and energy and foundation upon which you can build your goals.

One of my clients had a tough 2020. She joined a startup as a design leader and realized that the leadership and company values didn’t match hers, despite their strong mission and interesting product space. She spent the first half of the year second-guessing her decision to join the startup, and dealing with her demanding self-critic. This fall, she found a new job with leadership that matched her values. She was energized and rejuvenated,and still found herself grappling with imposter syndrome, wanting to come in strong and prove herself. Her word for 2021 is “enough,” to remind herself that she is enough. That her biggest barrier to success is her own self doubts and self-critic.

As you think about what your one word may be for 2021, consider these questions:

• What do you need more of in 2021?

• Who do you want to be?

• Is there something you want to focus on that you’d forget about if you didn’t call it out?

As part of the divergent, exploratory process of design thinking, you could write down a list of 50+ words that appeal to you. Go as broad as possible. Afterwords, circle the ones that continue to resonate the most. Think about these words for a couple days and perhaps one or two will bubble up.

If you’d like a little more direction, check out Susannah Conway’s free 5-day program to Find Your Word. I haven’t personally done this program, but have experienced Susannah’s killer workbook to Unravel Your Year 2021.

A more visual option is to dream & ideate your word via creating a vision board. Some tips and tools for creating a vision board include:

• Soul Collage video by J.J. Lassberg and introduced to me via Lyssa De Hart

• Vision Board — a Powerful Tool to Manifest Your Life Desires from Mindvalley, a coaching school that has a fantastic reputation.

• Quasi-science from Huffington Post about The Reason Vision Boards Work and How to Make One

You can see an example of my one-word intention and vision board below.

Part 2: Projects, People, Community

The leadership model for creating this North Star is divided into four parts. It starts with me in the middle, because leadership starts with me. This leadership is represented by your one-word intention for 2021.

The three points of the star show aspects of leadership both at work and at home, across projects, people, and community or organization.

Projects is the work that you produce on your own. It’s the craft of the things that you create, whether it’s sketches, designs, project plans, spreadsheets, slide decks, or emails. We all create things even if we don’t often think of ourselves as creators and makers. What projects are important to you in 2021, either at work and at home?

People refers to the relationships that you care about the most. This is a combination of relationships that you’ve chosen, and the ones that you have to work with in your current life. And it can often be the same tricky people! In your professional life, who are the people that are important to you? There’s some that may immediately come to mind — your boss, the team of people you manage, partners that you have to work with, or many other co-collaborators. Which of these people bring you joy and energy? And if some of these key relationships might be considered difficult people, what is your role in improving that relationship? When setting your 2021 north star, think about the 3 to 5 people who are important to you. How do you want the relationships with these people to be in 2021, and what can you do to help reach that outcome?

The last part of the leadership star is community. This is the broadest arc of the system that we live in. For many people working in corporate, the community may be the company you work for. It could be company-wide, or it could be for your organization or team within the company. Community could also be an organization you volunteer for. Community may also be a group of people that you want to serve, be it the neighbors on your block, your extended family, for a book club that you run. For 2021, is there a community that you want to focus on for your leadership? How do you want to shift the shape of that community this year?

I’ve outlined the four parts of the leadership north star. Leadership starts within with the one word intention to found you in the middle. Your leadership grows as you interact with the projects, people, and community around you.

As an example, I’m sharing what mine looks like for 2021.

My 2021 North Star

My “one word” intention for 2021 is white space. I’ve been able to build a sustainable business in 2020, yet oh-too-often, I’ve been too rigid, too serious, too driven, and too obsessed about hitting financial goals. As I move into year two of the business, I want more magic, more joy, more ease, and a greater sense of flow. White space captures that spirit and intention for me.

For my leadership, I have things that important to me across the axis of Projects, People and Community.

Projects

• Write & self-publish a business book, White Space to Lead, while working on a second book that is more of a personal memoir

• Continue to serve my 1–1 clients and creating new ones

• Make more art. Take more time to sketch and hand-draw meaningful quotes.

• Surf more

People

• Co-create programs with partners who make me laugh. A podcast called “Science and Magic” may be in the works.

• Give my tween girls the space to find their voices and make their own mistakes

• Continue to connect with dearest friends and family now that we’ve all made the time over Zoom

• Bring my girls to visit family in Bangkok this summer, even if it means quarantining for 2 weeks

Community

• This January, I’ve created a Facebook group, White Space to Lead. It’s a playspace for me, and for everyone who wants more creativity and magic in their lives. Together, we will hold each other accountable and fight against busy-ness and overwhelm. Friend me and message me on Facebook if you’re curious or jump in to join this free group.

Bottom-Line

This north star model is a framework that I use with my clients, and that I reapply for myself each year. I hope that it proves useful for you. If you would like additional support in creating your 2021 leadership north star , my colleague Jim Herman and I are leading a 4-week group program that begins on January 12.

Want to Dream Bigger? Start with Envy

Photo by Dietmar Becker on Unsplash

“What’s wrong with me?,” a client asked. He’d been toiling away at a management consulting job for many years but still hadn’t made partner. His friends, relatives, fellow alumni were all eminently successful — tech CEOs, non-profit Exec Directors, surgeons with their own practice, and tenured professors. It seemed like everyone else was doing well, while he was facing failure after failure.

We’re born into a society of comparisons. In school, we’re assigned letter grades to assess our performance. We’re broken into groups and assigned reading materials based on our level of skill. Everyone implicitly knows how they compare to everyone else. She’s funnier than I am. He’s more attractive than me. She’s got better taste than anyone else. He’s more social.

We apply to colleges that have an implicit ranking from Ivy Leagues to prestigious schools for specific programs to state schools to community colleges. There’s tiers of companies to work for, from world-class brand names to funded startups; from international to local reach; from mission-driven to advertising-driven; from high prestige to low prestige.

We all have envy. It’s a very human emotion and is born out of our wanting things that other people have. We want what’s commonly perceived of as “the best.” Yet many of us want to tamp down this emotion. We’re horrified at this ugliness in ourselves because we want to be happy for our best friend, for our boss, for our former colleague when they get wonderful opportunities in their lives. We beat ourselves up because we’re not supposed to feel envy. We’re supposed to be genuinely happy for the other person, otherwise we’re not a good friend, or not a good person. This is black and white binary thinking where there’s a right way and a wrong way. The reality is that we experience the whole range of emotions when we hear someone else’s good news. Think about the last time you heard about a good friend’s opportunity. Did it feel like this?

• Initial envy. Why couldn’t that be me?

• Happiness / support. Good for her, I’m happy she’s finally gotten what she’s wanted.

• Rationalization / envy. But she’s always had it lucky. She gets all the breaks.

• Self-judgement. What’s wrong with me? I should be happy for her. I am a good friend. I AM happy for her.

• Support / recognition. She deserves it. She’s been working really hard.

• Self-pity Why can’t I do that? Why can’t I be a bigger person and be happy?

Falling into this loop of negative emotions spirals us down into self-judgement and blame.

Instead, embrace the envy and use it as a path of self-knowledge to better understand your desires. Move away from picturing this absolute thinking of the dream job, the perfect romantic partner, or the fastest startup to reach textbook product/market fit. Know that the grass is always greener. Instead, explore the nuances as to why you’re feeling such a strong emotion . Let the envy be a signal that lets you dream bigger and be a breadcrumb to what you truly desire.

1. Re-set your context — there is no standard “dream job.”

We think that everyone else has the dream job, best boss, or perfect marriage. Yet all too often, in this culture of comparisons, wonderfully curated instagram posts, and practiced cocktail hour stories, people share a scrubbed, sanitized, and beautiful version of their life. They are sharing their “dream life,” one rose-tinted view of reality. Because it’ll take too much time to share all the details. Because it’s hard to be vulnerable and expose my giant mess of a life. Because we don’t want to be known as the Debbie Downer or the whiner who shares tales of woe.

This language, where we talk of a “dream job” sets up binary black or white thinking. No job is perfect. Every job has its good days and its bad ones. The coworkers may be fun and inspiring, but your boss doesn’t have your back. The company mission may be fulfilling and impactful, but the hours are long and demanding. You have full autonomy and budget from your boss, but you have resistant partners who don’t agree with your strategy. Every job has its ups and downs, so let’s drop the myth of the “dream job” or “perfect marriage.”

2. Find the kernel of insight within the envy

Feel into the envy and ask yourself, what’s triggering the feeling? Break it apart to see what desire you have hiding beneath the envy.

As you look deeper for insight, you might see things such as:

• She just got a new job at a healthcare company. She gets the chance to work on meaningful problems. Hmm… I’ve always wanted to solve problems in healthcare or government…

• He started teaching on-the-side. What a wonderful opportunity! I’d like to do that someday…

• A friend just bought a new RV/boat/house/car. Hmm… maybe I want that too.

• A family member just had a unique experience—vacation, new sport, new hobby… That sounds so cool, I’d like to do this as well.

• My colleague got promoted over me. This feels super hard as I wanted that promotion… What skills, behaviors, actions has she been doing that I need to practice more of?

From these tinges of desire, there’s the opportunity to dig deeper and see what the root of the desire is and what’s been holding you back. It might be fear. You might not want it enough. But starting to ask yourself the questions helps to flame and fuel the desire.

3. Give yourself permission to dream

Often we don’t dare to dream. Or we fear that our dreams are too big. We’ve all been burned before. It’s a familiar feeling of making mistakes which makes us feel like a failure. It’s familiar because when you’re new at something, mistakes are entirely normal and always a part of the learning process.

What’s important is to accept that the mistakes are part of the process and not a sign that the dream was too big, that we’re not good enough to strive for it. Don’t let the failure and comparison—everyone else is better at X than me— stop you from dreaming. Instead, listen to the whisper of desire within your envy and use it to refocus to find your dream.

Bottom-Line

Envy is a familiar, and all-too-human feeling. It’s OK to feel envy. Instead of beating yourself up over it, dig deeper to find the kernel of insight within the envy. Stop to ask questions of yourself. Seek to understand why you feel so strongly. Build upon this desire and give yourself permission to dream bigger.

Breaking Through Patterns

Beauty strips of trees along the 101 in Oregon

We all have our default-mode patterns of behavior. These are well-worn grooves for how we act. It’s built upon years of pattern-recognition and success. These patterns can serve us really well both for our success and as a coping mechanism to lean heavily on in times of crises. And, it’s important to clearly see and recognize the patterns. This leaves us with choice.

I was recently driving down the 101 in Oregon. We were struck by the natural beauty — swathes of green forests emerging through the misty shreds of fog. Then we entered a strange corridor. Looking down the freeway in tunnel vision, you could see an endless curtain of green trees lining both sides of the road. Yet when you looked closely, the trees were quite thin and through the gaps you could see wide expanses of clearcut logged stumps. My activist partner explained that these trees were “beauty strips” left by the logging companies for drivers to admire, leaving them free to chop down the forests behind this scanty curtain.

As we approach the end of 2020, it’s a good time to evaluate patterns of behaviors to see if they might be “beauty strips” covering up desolation and pain or if they are true forests.

Beauty Strip 1: Money & Security

I worked in technology for 22 years, most recently at Facebook. The big tech companies pay really well in a mixture of cash, bonus, and stock options. They are notorious for over-the-top perks to take care of employees from free food and drycleaning to all types of on-site services. Facebook HQ would take care of all your errands providing every service you might want—gym, dentist, doctor, barber, masseuse, and bank.

Beauty Strip 2: Impact of Work / Success

It felt great to be a Facebook employee. My Asian parents could finally explain to their relatives what their daughter did and proudly wield the Facebook brand (much stronger internationally than in the U.S. and Western Europe) as a status symbol. My teams were designing products that we hoped were improving the lives of billions of people around the world. As designers, we aspired to do our best work, working on the latest devices, prototyping the most innovative interactions, partnered with a prolific engineering team that would rapidly ship the designs, and with access to quick data & research to see how well the products did.

Beauty Strip 3: Wearing Someone Else’s Leadership Armor

Since my Stanford computer science days and stretching through decades in tech, I was often one of the few females in a sea of male colleagues. I’d grown up in a Thai-Chinese culture with a strict tiger mom and had learned to adhere to stringent standards of good girl behavior. As I started leading, I learned how to adopt patterns of dominance, aggression, and interruption to get my voice heard in design firms and while performing for our primarily male executive clients. It worked really well and got me to a lot of professional success

Seeing Behind the Beauty Strips

The devastation behind the beauty strips. Photo by Toben Dilworth

Yet all three of these were beauty strips for me.

Behind both the money & security and impact of work/success was an unrelenting workaholic grind that took a toll on my relationships and family. I loved being a designer and much of my identity was wrapped up in professional success. These trappings were the beauty strips that masked stress, anxiety, overwhelm, and continual busy-ness.

Wearing someone else’s leadership armor let me bring my passion and ideas to products, and also brought me professional success. Yet it masked my own leadership style that I felt wasn’t good enough. I wasn’t confident enough to flaunt the compassion, kindness, and empathy. Those all felt too feminine. It also didn’t feel good to be the difficult person, the challenger who would push myself and others to perform to ridiculously unrealistic expectations.

These were all beauty strips for me, but they could be full forests for other people. Some of my clients are working in corporate as their day job, to pay the bills and provide security for their families as they spend time on their passions—startups and small businesses that will take time to nurture. Money and security is the absolute right bet for this context of their lives.

Evaluating the Pattern

When looking at some of these patterns, it’s useful to ask a couple of questions to figure out if it’s a beauty strip or a full forest.

• How does it serve you?
  We’re all smart people who have made choices leading us to the current path. How does the pattern serve you? What benefits does money, success,or a particular leadership style provide for you? What does it feel like to get these benefits?

• Who else might it serve?
  The pattern may also serve as a proxy for others around you. It could be financial security for your family or a job that you’re doing with the mission of helping a certain group of people.

• Is this short-term or long-term?
  Some of us make the mistake of jumping into a pattern that was needed for the short-term. But we never take time out to re-evaluate it years later. Is it still relevant? Does it still serve our needs?

Exploring the negative emotion

Ultimately, we can evaluate the patterns to see what type of turmoil or negative emotions they cause within us. If there is long-term stress, anxiety, fatigue, or sleeplessness, pay attention to these negative emotions. These are often clues to the devastation behind the beauty strips that we choose to ignore. Start to peek between the trees to see if these negative emotions have been suppressed or ignored for a while.

Bottom-Line

We all have patterns in our lives. It’s the default mode of our daily behavior that we rely on. It subconsciously gets us through our days. Every once we in a while, we need to pause as we drive down the freeway to evaluate these patterns. Are they shallow beauty strips destroying our long-term fulfillment, or are they genuine lush forests of patterns that serve us well?

Finding White Space in 2020

Photo by Toben Dilworth

It’s been a year since I’ve gotten on an airplane, the longest period of time in my life when I haven’t traveled. I’d gone home to Thailand to attend a joyful family wedding and to spend time with my widowed mom. I got a brief taste of travel when I spent this past Thanksgiving week driving from San Francisco to Bend Oregon, and back again. It’s been the longest and farthest I’ve gone in the last year. It’s felt like a giant sigh of relief from the constriction of 2020 and my soul marinated in the white space.

White space in design is any section of a piece that is unused; or space around an object. If you look at a magazine layout, white space is the space between the words and pictures. It’s not something you typically pay a lot of attention to. We often focus on the content of the words and pictures. As designers, we’re told to “make it pop,” “make it bigger,” “make it stand out more” around the logo or button call to action. Yet the magic of white space is that it gives the content room to breathe. Rather than making the logo bigger, if you leave more white space around it, the logo will stand out more and feel bigger.

Being vs Doing

Similarly, in our lives, we often focus on all the things we need to do. We have long to-do lists, billable hours, milestones, OKRs (objectives/key results), SMART goals (specific/measurable/achievable/relevant/time-bound), and our own 3 or 5 year plans. I know this world too well, having spent 22 years working in technology across design firms, startups and large corporations. Self worth and success is based on all the things we do.

Yet the truly meaningful things in life are neither linear nor measurable. More things matter than what we do. In a company, we thrive in relationships with our colleagues, we move within a company culture, we identify with the meaning which our company adds to the world, and we feel a sense of belonging when our opinions are heard. These are all states of being. They’re based on our existence and are subconscious rather than the more active doing. The design process & creativity are states of being. The way that we “be” makes us better in our doing.

And white space enables this being.

What’s your default mode on this balance beam?

Finding White Space

I often find white space through the creativity of making things. Yet last week’s road trip made me realize that I also get my white space from other sources.

I find white space in adventure and travel. Historically that’s been on airplanes. My father worked for Thai Airways and I grew up on planes. They feel familiar and I’ve always had a fascination with the liminal space outside of place and time. You’re insulated in this metal capsule and have time to reflect. You can magically jump the international date line and gain an extra day. This last week, I found white space in driving on a road trip. There is freedom and openness in driving towards a destination, unconcerned about time or stops. I am free to explore the cuteness of feeding baby Alpacas, taste the world’s best salmon jerky, stop at a breathtaking viewpoint, or briefly admire bizarre dinosaur statues by the side of the road. I highly value adventure. Experiencing that value during the travel constraints of 2020 is a huge source of fresh air.

I find white space in nature. I’m a surfer. When I’m out of the water for more than a week, I get cranky. I need the ocean and outdoors. Each day this past week I’ve been dumbfounded by the beauty of the natural world whether it’s viewing Crater Lake covered in snow or hiking above the peaks of Smith Rock, the birthplace of American rock climbing. Water in nature moves me the most. Both the discovery of secret waterfalls as well as finding one of the most breath-taking coastal scenes I’ve ever encountered — Natural Bridges at Oregon’s Samuel Boardman State Scenic Corridor. My white space is being fully present, fully alive while walking over a treacherous crossing in solitude, my heart racing as I listen to the roiling waves below.

Crossing the Natural Bridges in coastal Oregon

I find white space in rituals and traditions. Last week was Thanksgiving in the United States. It’s normally a time to gather with family and friends over a sumptuous meal. It wasn’t possible this year, another casualty of the pandemic. Yet beyond the in-person connection and breaking of bread is the genuine sense of gratitude. We ate our Thanksgiving meal in a tiny house on the outskirts of Bend. We were thankful for each other, for family, and for countless other things that have happened this year. I connected remotely with many friends and family members. I don’t think this slowing down and break from a regular pattern would have happened without the white space created by 2020.

White Space is Freedom from Default Mode

Back in March at the start of it all, I wrote an article — COVID-19: the gift of time and space. There was a lot of naivete as I wrote it, failing to recognize that only the most elite of us had the freedom of time and space. Others are struggling to make ends meet, first responders fighting a war, or people simply too exhausted with the business of survival to think of anything else.

Today, it’s been eight months since the start of shelter-in-place. We’ve adjusted our lives and existed through the waves of fear and frustration. As we look back at 2020, this year has given us a gift, which is the freedom from default mode. Nothing was controllable — plans, health, safety, a contentious U.S. election — everything went out the window.

And through these eight months, we found glimpses of white space. White space is the absence of content & busy-ness. It’s the spaces inbetween. The emotions and creativity for what feeds your soul. As we’re trapped in our houses, some of us have more time. As we curtail the number of people we physically visit, we have more time to connect with friends & family from all around the world.

We can choose to be, and to have more white space, even within the chaos of 2020. And this can be the spirit of 2021.

The White Space Manifesto

• White space gives room to breathe

• White space is the path of ease and flow

• White space cures the need to hold busy-ness as a badge of honor

• White space is creativity

• White space gives us the wisdom for better performance

• Fiercely protect & nourish your white space!

Where might you consider adding more white space in your work and life?

The Cult of Busy

Photo by Karen Lau on Unsplash

“Hey, how are you?”

“Phew, so crazy busy. You?”

For many years, I held on to my busy-ness as a badge of honor. I would proudly brandish my calendar that’s packed with double- or triple-booked meetings as a mark of how important I was. Often when people stopped by my desk to talk to me, my snippy glare and body language let them know that I needed to get back to the urgent emails and pings on my laptop rather than take a couple of minutes to connect with a human.

I worked at design firms for 10 years. It was the perfect environment for my restless spirit. Projects were often 3–6 months long and focused on envisioning the future for all the world’s top technology companies. We all had shiny-object syndrome. Ooh, we get to work on a social gaming system! And now switch gears to design a videophone for deaf people! And now a mobile phone OS built around relationships! Woo-hoo, it’s a connected smart home! It was constant pings moving from shiny object to shiny object. I never had the chance to focus and go deep because we there was always something new to do—collaborate with talented designers, run sprints with clients, create more future-facing design concepts, and shoot day-in-the-life videos of happy people fiddling with their devices. The constant stimulation and motion meant that I was never bored. My shiny-object-obsessed spirit kept happily bouncing from project to project.

Until one day I had enough of the brutal work hours, the loneliness of being one of the few female creative directions in a misogynistic culture, and years of creating concepts but rarely shipping anything. I had lost my way. I felt like a kid who’d spent too long in a candy shop and was now suffering from a massive belly-ache and longing for healthy food. This led me to years working at startups and at Facebook where I could both conceptualize the product North Star as well do the long-term work to create an MVP (minimal viable product), and iteratively launch over months and years to hone the entire product system.

Busy-ness and restlessness are both distractions and and escape from dealing with discomfort. Negative feelings such as anxiety, boredom, fear, anger are all part of the discomfort. The path of fulfillment is working through these feelings, rather than running away from them to the next shiny thing.

The restless saboteur¹ is a limiting belief that has us continue to search for more excitement in the next shiny object, or immerse ourselves in constant busy-ness. These distractions mean that we are rarely at peace or content with the current activity. We often feel extreme impatience and a desire to move even faster. And frustration when others can’t keep up with us.

There’s also a strength within this feeling of busy-ness and restlessness. I’m an Enneagram 7, The Enthusiast with high energy and vitality for life. I’m creative, spontaneous and always seeking out new experiences. I was once described by a team member as having “x-ray vision and the energy of a 5 year old.”

The key to escaping the cult of busy-ness is to balance out the wisdom of the Enthusiast while mitigating the impatience, anxiety, and boredom that come with a fear of missing out of something better.

1. Acknowledge the Impatience

Negative feelings are uncomfortable and we shy away from them. Try acknowledging the feelings & emotions instead. If you don’t know what the emotion is, scan this list and pick out the top 3 that you might be feeling.

Table of negative emotions

You can try two techniques to acknowledge the emotion.

1. Take 5 deep breaths to reset your mind & body. See if you can feel the emotion, e.g. impatience anywhere in your body. For some people, it can be a tensing of the shoulders or jaws. Or others it’s a gripping sensation in the chest or stomach. Put your hand on that body part and and think of that body part while breathing. 2. Alternately journal about the emotion. Sit and write how impatient you are with the task ahead of you. Capture your anger with all the people who are moving too slowly and not dedicated to the project. Tear it up afterwards.

Run the experiment and see how you feel when you name and acknowledge the negative emotion.

2. Stop Multitasking

Multitasking is a myth. Nobody does this well. Rather than being able to simultaneously do 3 things at once, we actually do rapid context-switching between the 3 things. There’s a tax on our brain when we switch as we have to remember and refocus when we transition between the things.

One of my professors at Stanford, Clifford Nass, has done multiple research studies on the myth of multitasking. Listen to him in this 18-minute NPR clip or dig into his research of cognitive control in media multitaskers.

Of course this is easier said than done. Multitasking is what we do to survive and to feed our cult of busy. I am guilty of multitasking so many times in each day. The first step is awareness. Try to notice when you’re multitasking and choose a different path.

3. Pick your Level of Scale

I continue to be inspired by Charles and Ray Eames’ Powers of Ten 9-minute video. It starts with an ordinary lakeside picnic in Chicago before zooming out 10x every 10 seconds until you end at the black expanse of the universe. The voiceover reminds us:

“This emptiness is normal. The richness of our own neighborhood is the exception.”

We are in default-mode when we seamlessly fall back into busy-ness and multitasking. Instead, remind yourself to zoom out into a metaview and observe the situation from above. Figure out if you’re lost in the details of the trees and if it’s time to zoom above the forest. The best designers I’ve worked with have been able to deliberately shift their scales. They can focus on the minute details of a microinteraction or tiny UI element. They can also scale far up to see the business context and the user needs that are driving the product strategy. The trick is to be aware of what level of scale you’re at during any point in time. Then be deliberate about picking what level of scale you want to be at. You can choose to be in busy-mode for a short spurt of time to get some crucial things done. But don’t stay there simply for the sake of being busy. Be able to zoom out to the metaview and get a perspective of what scale you’d like to choose next.

4. Focus on Creation

One most effective antidotes I know to the feelings of busy and restlessness is to immerse in deep focus. For myself, and many of my clients, that focus comes from creation, the craft and joy of making something from nothing. Creation doesn’t have to be limited to a craft like painting, knitting, woodworking, or filmmaking. It doesn’t have to be good or perfect. In a professional sense all of the following activities allow for a focus on creation—writing a product specification, sketching out a workflow diagram, building a slide-deck, or recording a product demo. Notice which acts of creation let you disappear into ease and flow where you lose track of time. That feeling of restlessness wants to have you skim the surface of things and quickly move on to the next shiny object. Instead, focus on going deep into one creative act.

Bottom-Line

It’s too easy, especially as we hurtle towards the end of the year, to get caught up in the cult of busy. We can wear busy-ness as a badge of honor commensurate to our importance. Instead, harness this energy and enthusiasm by 1. acknowledging the negative emotions, 2. stopping multitasking, 3. picking your level of zoom, and 4. focusing on creation.

¹The concept of the restless saboteur is from Shirzad Chamine’s Positive Intelligence research

How to Recover Faster from Failure

Photo by Tom Crew on Unsplash

We have all experienced failure, catastrophic events, or instances where things did not go our way. These are all part of the uncontrollables of life and feel even more acute in 2020. These failures will never go away because life is uncontrollable, however, we can learn to live with them and to recover faster from negative events.

I look at Joe Biden as the epitome in recovering from failure. He’s had 77 years of life and some corresponding years of catastrophic events.

He’s struggled with stuttering since boyhood. While he’s not the most crisp and confident speaker—his stutter was noticeable last Friday evening as he spoke to the nation and told everyone to have hope, one day before the news outlets officially called the presidential race. His speaking style is all the more impressive for knowing what he’s overcome. In this Atlantic interview he discusses his lifelong strategies for taming the stutter including this lesson:

Biden says his father taught him about “shouldering burdens with grace.” Specifically, he told his son, “Never complain. Never explain.

Joe Biden understands grief. He’s faced unbelievable personal losses in his life. His wife and infant daughter were killed in a car crash leaving him with two toddler sons to raise solo. He kept on moving forward, serving his first term as senator and then eventually meeting Jill and building a blended family. Years later, his son Beau passed away from brain cancer at 46.

“By focusing on my sons, I found my redemption,” Joe said in a Yale commencement speech in 2015. “The incredible bond I have with my children is the gift I’m not sure I would have had, had I not been through what I went through.”

We celebrate him today for winning the presidency. Not everyone knows that this was his third try. He ran unsuccessfully in 1988, and then 2008 before becoming Obama’s VP. He epitomizes perseverance, recovery from failure, and continuing to try over and over again. It’s been 32 years since his first presidential run. This is a man who looks at the long-view.

I look to Joe Biden as a hopeful leader. He will be a president who intimately understands grief and suffering and is unafraid to shine in the strength of his emotions. Inspired by him, I’m sharing three lessons that I’ve learned on how to recover faster from failure:

Lesson One: Honor the Emotions

You’ve just received some negative information that’s hitting you like a punch in the gut. It might be health-related about a dear friend or family member. It might be a negative performance review, or news that you’ve been laid off or fired. It’s OK — we’ve all been there and we’ve all gone through this.

A common reaction is to go into shock and disbelief. We may have known that something like this is coming, either because a loved one has been ill for a long time or if we’ve gotten warning signs about our job. This may also be a complete surprise. Either way, disbelief is often the first emotion and it aligns well to the five stages of grief (denial, anger, bargaining, depression, acceptance).

Listen and experience the emotions that you’re going through. We often make the mistake of wanting to suppress anger, resentment, fear, or any negative emotion because they feel bad. It’s uncomfortable to marinate in the emotion and we want to put on a cheery positive outlook. Yet when we try to suppress the emotion, we often find ourselves thinking about it even more; leading to being trapped and wasting time in a vicious cycle. An alternative approach is to honor the emotion — you can try strategies like journaling about the feelings, venting to a confidant, or meditations that help work through the emotion.

Many years ago, I was fired from a dual job I held as General Manager (GM) of the San Francisco office and Head of Design for a digital innovation consultancy. It felt entirely unexpected. I’d just returned from a week-long vacation in Mexico and both my children were suffering from food poisoning as I took the call. The CEO decided to shut down the San Francisco office and let me and everyone else go. After hearing the news, I made the mistake of suppressing all my emotions and robotically going through the next several weeks of closing the office and laying off all the employees. When I finally slowed down to take a breath, all the negative emotions emerged—anger, resentment, self-hate, self-doubt, and guilt for letting down the team.

When you pay attention to your emotions, notice when they start to change. It might be within hours or days, or it might take weeks. Paying attention to the transition of emotion can be a guide that you’re ready to move forward.

It took time for me to sit with those emotions-of-failure before a new one emerged—relief that I was done with a job that felt impossible to do well despite my optimism and that took me away from my family so frequently. When I honored all the emotions, I was finally able to acknowledge the reality of how unhappy I was at my job.

In order to recover faster from failure, start with honoring your emotions and not suppressing them.

Lesson Two: Surrender to the Past

We rationally know that we cannot change the past, yet we spend so much time beating ourselves up for what’s happened. I’m super familiar with this:

• Self-recrimination: I should have spent more time being nice and building better relationships with the rest of the leadership team.

• Regret: How did I not see that it was impossible to do two jobs at once? Why did I even take that job? Why am I so ambitious and eager to say yes to more?

• Blame/victim-hood: Why didn’t they hire a business development lead for the San Francisco office? How can I succeed as GM without that?

• Guilt: I personally recruited everyone. What’s going to happen to all the people I had to lay off?

This can be an endless, self-repeating loop that only takes us on a downward spiral. Instead, surrender to the past and accept that the events unfolded exactly as they should have to set the stage for what happens next. There is a gift from knowing that the past experiences are now a part of your auto-biography and life experiences.

I’ve worked with many clients who have had challenging bosses, and been stuck in miserable jobs for many years. Eventually they are ready to move on. And when they’re not, they can accept their past choices with equanimity. They’ve learned some lessons:

• I know what type of leader I don’t ever want to be

• This is not a job I love, yet it pays well and I’m optimizing for that security right now.

• My boss was mostly absent, so I was given full autonomy over the team.

• I understand the culture and processes of [my current company] and when I start my own, it’s going to be nothing like that.

There may be things you regret in the past. And that’s OK. There is an acceptance to know that it can’t be changed. And there is discernment to know that you can use it to fuel what happens in the future. Limit the time you spend in self-recrimination, and surrender to the the past, both rationally and emotionally.

Lesson Three: Failure Fuels Introspection

If we change our relationship with failure, it helps us to recover from it faster. We go through most our lives in a complacent type of default mode. The days, weeks, and months pass by and we settle into the rhythm of the work days and the weekends. These points of failure, catastrophic events, or instances where things didn't go our way serve as a giant STOP sign to break us out of the patterns of default mode.

When we run into this wall of failure, stop and take a breath. First work through the emotions and truly surrendering to the past. This can take days, weeks, months, or years. At some point in time, you’ll be able to reflect on the failure and ask yourself what’s the gift of that failure. Take a look at the event, consider the learnings, and let it fuel what your next steps might be.

After I got fired from my dual job, I spent a lot of time thinking about what I valued in a job, what gives me energy, and what type of people I wanted to be around. With that introspection, I was more discerning about the next companies I talked to. The next job I accepted turned out to be one of the most fulfilling jobs of my career. It was the opportunity to be head of design at a series B funded startup. The parts that drew me in was the relationships with my key partners — the CEO and the head of product. I knew it was right when hours of the interview passed by and it felt like we were simply colleagues whiteboarding the future of the company together. The icing on the cake was that I also got the opportunity to drive culture and process, not for design, but for the entire company.

When we reframe our relationship with failure and call it out as a gift that fuels introspection, it shifts our frame of mind. Failing fast is simply part of the process.

Bottom Line

We will all continue to experience the uncontrollable events of life. We can choose to dwell in these failures and catastrophic events, or shift our mindset. Recover faster from failure by honoring emotions, surrendering to the past, and reframing that failure fuels introspection.

Emotional Leadership Through Uncertainty

Photo by Colton Duke on Unsplash

We often think of leadership as how we show up at work and inspire a team towards a common organization goal. Yet we can show up as leaders in all aspects of our lives. Emotional leadership is how we we work through our emotions — negative, positive and all the nuances in between — and continue to show up as leaders for everyone around us. It helps us understand stress & anxiety and better manage those emotions. It leverages our curiosity, enthusiasm, and confidence to inspire others.

Emotional leadership is especially needed as we navigate through uncertainty and complexity. This year of 2020 has been particularly challenging. We’re facing multiple global crises on an unimaginable level — COVID-19, Black Lives Matter, climate change affecting severe wildfires in the American west, and this week’s U.S. Presidential election. This is a year of change where all the best laid plans get thrust out the window. We need emotional leadership more than ever.

Emotional leadership model

Leadership Starts with Me

Emotional leadership is inside-out. It starts with understanding and naming the complex roller coaster of emotions that’s within each of us. We often numb ourselves to emotions. When we feel a negative emotion—the most common ones being anger, fear, sadness, loneliness— we often suppress it and try to mask these emotions with distractions. I’ve spent many hours doom-scrolling through news sources or social media. I also turn to desserts and sweets to make myself feel better. Most toxic, I’m sometimes unaware of my negativity and instead gripe or lash out at loved ones around me. We all have our familiar patterns of negativity and how we try to distract ourselves from them.

Instead, emotional leadership from the inside-out starts with naming the negative emotions and recognizing that they exist and can’t be suppressed. One way to work through them is to use Tara Brach’s RAIN (Recognize/Allow/Investigate/Nurture) method which includes a 20-minute guided meditation.

Emotional leadership recognizes that emotions are simply states of our being and that we cycle through as part of a normal process. I’ve felt intense fear and anxiety before stepping onto the stage for a keynote speech, and I often feel the emotion turning into excitement and confidence as I settle into the rhythm of the talk. I’ve had moments of intense joy as I watch my sleeping children which can then turn into immediate fear and wistfulness — When will I lose her to sulky teendom? Is she growing up too fast?

We can better manage our emotional leadership as we focus on three interactions with sources outside of ourselves.

Three Interactions

When this model is applied to the workplace, the three leadership interactions span Projects (individual contributor work that the leader does), People (the team(s) the leader manages), and Organization (the leader’s impact on the overall org). When pivoted towards emotional leadership, these three interactions become Projects, People, and Community. Each interaction can be targets of emotional leadership and also serve to fuel you.

1. Projects
   Creation—making things— is part of our human birthright. The art, carved spoon, or music that you produce doesn’t have to be “good.” Creation is the act of ingesting information, processing it and then producing a thing. The output could be words, a sketch, a photo or video, or simply a spoken idea put out into the world. The creation doesn’t need to be profound. It could be a meditative coloring page, baking cookies, or a simple chalk drawing on the pavement. The pure art of creation allows you to express and move emotions from the body into an external object. It triggers a less rational mindset that can focus difficult emotions, and is also a positive distraction. Getting into a state of flow around the creation is its own fuel.

2. People
   We crave and get energy from the connection of interacting with other people. Certain people are natural maximizers — being with them amplifies some of your emotions. Other people may be more difficult for you and sink you into emotional negativity. Choose which people you want to engage with to reflect your state of emotional leadership.

3. Community
   Larger than individual people is the community to which you belong. The community system of multiple people and their collective agreements is a place where emotional leadership can shine. We show up in a different way when we’re serving a community. Helping others is well-trodden path to mitigate personal difficult emotions. We serve as an emotional leader for the community when we model how we react to events in the world.

If these three interactions are ways to showcase our emotional leadership, three principles help with leading through the uncertainty.

Three Principles

1. Embrace Uncertainty

Uncertainty is a fact of life, especially demonstrated by everything happening around our first global pandemic. As humans, we crave certainty. We make plans and want to be able to follow-through on them. However, life and especially life in 2020 is uncertain. As I write this on November 5, two days after the U.S. elections, we don’t have a clear-cut answer for who won the Presidency. We face more unknowns and uncertainty. In the face of the unknown, you can choose a rational or an emotional coping mechanism:

• The rational mechanism is contingency planning for multiple options. Having a plan A, plan B, plan C, D, E, etc. This can be helpful as it provides alternatives when something prevents the first option from happening. However, it can be exhausting to create and manage all the options, especially if you need to sell them to the multiple others involved in the plan. Yet creating the options can provide a mental source of comfort.

• The emotional mechanism is surrendering to the uncertainty. This requires being able to hold two contradictory thoughts simultaneously in your mind—I am able to have a goal and a plan, and I’m equally OK if it doesn’t happen. There is a gift in both outcomes. Everything will be fine in both outcomes

Emotional leadership is learning to live with uncertainty. It’s being able to adapt to each context based on your current state of being.

2. Create White Space

White space is unstructured pieces of space and time in your life. It’s the blankness and openness in-between the scheduled, to-do items. Rather than packing the calendar with events for for each hour, week, weekend, or month , white space calls for having blank stretches of nothing. There is a structure with holding time for nothing in your calendar, and it takes discipline and flexibility to not fill it beforehand. Many of my clients create a half-day chunk in their weeks. I’ve seen that time used for self-care, personal reflection, or a time to plan out the next 3 months of the work roadmap. It’s valuable unstructured time to think & feel.

The other aspect of white space is letting go of self-imposed, fake deadlines. Sometimes we are so eager to get something done that we create an arbitrary deadline simply to make ourselves feel better. Instead, give yourself permission and space to not-decide or not-do something. The reflection time in the back of your head may get you to a better solution. Not forcing a deadline may get you to a better solution.

Emotional leadership is knowing what parts of your life and work could benefit from more white space.

3. Lead with Compassion

Finally emotional leadership thrives most with compassion. Compassion is a precursor to empathy and allows us to feel emotions, or passion, for the suffering of ourselves and others. Life is hard. Especially so in 2020 with these uncertain times. Emotional leadership starts with having compassion for ourselves. To call-out our own self-critic, and stop berating ourselves for not being enough. Having self-compassion makes it easier to feel for other people around us. Leading with compassion recognizes that we all are having a hard time with uncertainty, that we are all human and in this together.

Bottom-Line

I often use leadership models with corporate clients. In this uncertain week of the U.S. Presidential election, within this uncertain year of 2020, I needed to remind myself of how to practice emotional leadership through uncertainty. Leadership starts with me. It’s supported by the three interactions with Projects, People, and Community. Emotional leadership is lived through the three principles of Embrace Uncertainty, Create White Space, and Lead with Compassion.

This article is inspired by multiple leadership conversations with Jim Herman and builds off his leadership framework.

From Imposter Syndrome to Pioneer Syndrome

Photo by Ben Lowe on Unsplash

I work with a lot of high achievers, both from my previous life in tech companies as well as my current coaching clients. I also work with many women and people of color. Imposter syndrome is a familiar concept to many of us.

Imposter syndrome is described on wikipedia as:

a psychological pattern in which an individual doubts their skills, talents or accomplishments and has a persistent internalized fear of being exposed as a “fraud”.

Valerie Young in The Secret Thoughts of Successful Women: Why Capable People Suffer from the Impostor Syndrome and How to Thrive in Spite of It highlights a familiar internal monologue:

It’s only because they like me. I was in the right place at the right time. I just work harder than the others. I don’t deserve this. It’s just a matter of time before I am found out. Someone must have made a terrible mistake.

When I worked at Facebook, I was surrounded by unbelievably smart people, all world-class experts in their specialities. My first 90 days was a disaster. Everyone I met in my first 2 weeks intimidated me. I knew nothing about how Facebook advertising worked. It felt unbelievably complicated to learn about a product and the culture of a giant corporation. My ideas and suggestions were terrible. Everyone else, from the data scientist to the product manager knew a lot more about the design patterns than I did and had far better suggestions.

I made all the mistakes in my first 90 days. I wanted to prove myself quickly and ended up alienating my more experienced teammates. I rolled up my sleeves to dig into the product at the expense of getting to know my teams and cross-functional partners. I gave pointed suggestions rather than listening and learning at the design critiques. All of this was because I was suffering from imposter syndrome and felt that I had to work harder and do more because I didn’t belong and desperately needed to prove myself.

Fast forward and a couple of years and I was leading workshops for women leaders across the technical and sales teams as well as running monthly coaching sessions for senior female designers. In every session, we would talk about imposter syndrome. Through the years, imposter syndrome came up in every intimate 1–1 meeting that I had with designers or any cross-functional team member. We started having panels where some of the most successful people in the organization would share their imposter feelings. Across the board, everyone at Facebook had imposter syndrome.

This is unsurprising given that the company has a culture of high performance and achievement. While there’s not a lot of variance in titles—every designer from the recent college graduate to one with 15 years of experience has the same Product Designer title— everyone gets a performance rating every six months and compensation is directly tied to this rating.

I’ve seen four main beliefs of imposter syndrome:

1. Skills: I lack the skills to do this job. Everyone else is smarter and has better skills than me. I don’t know what I’m doing, so I simply must work harder to compensate.

2. Belonging: I don’t belong here. No one else understands this feeling. I feel alone. They all fit in and I’m the one that’s achingly different.

3. Achievement: My performance achievement matters most. What I do and accomplish is the number one goal. I must be superwoman and do everything. I don’t have time to be nice or build relationships.

4. Failure: I can’t make any mistakes. I can’t fail. Failing would expose my fraud for everyone to see.

Another Perspective — Pioneer Syndrome

Yet what if there’s another perspective? Perhaps imposter syndrome isn’t a bad thing. If you’re feeling a little bit intimidated and out of your element, it’s likely a sign that you’re playing in the big leagues. You don’t want to be the smartest, most accomplished person in the room. That means you know exactly how to do your job, and that’s boring. There’s plenty more growth opportunities to be the small fish in the big pond and learn from all the smart, inspiring people around you. Perhaps imposter syndrome could be a good thing because then you’re in the right room and ready to be stretched.

Instead of thinking that you have imposter syndrome, consider adopting *pioneer syndrome. These are the definitions of pioneer from dictionary.com:

• a person who is among the first to explore or settle a new country or area

• a person who is among the first to research and develop a new area of knowledge or activity

• a member of an infantry group preparing roads or terrain for the main body of troops

Imagine that you are blazing the way for others and are among the first to experience this new thing.

If we look at the four beliefs of pioneer syndrome:

1. Skills: I lack the skills to do this job. No one has done this before as it’s brand new, so I have as much to contribute as anyone else. We’re all figuring it out together.

2. Belonging: I don’t belong here. This is a brand new place where nobody has historically belonged. Together we can co-create what the norms and culture of this new place are. And if I’m not the very first pioneer, often pioneers travel or work together in groups. Working with someone else or finding a connection may be the best way to survive in a new place. Start reaching out to share stories & connect.

3. Achievement: My performance achievement matters most. Out in this new place, both what I do as well as who I am — how I show up and what relationships I form— will make me stronger.

4. Failure: This is a completely new context for pioneers. We’re going to make mistakes and learn quickly. We’ll experiment and iterate to find out the best way to fail fast.

Bottom-Line

Consider that not all aspects of imposter syndrome may be bad. That feeling of apprehension can mean that you’re playing on a bigger stage. Shift your perspective from imposter syndrome to pioneer syndrome which then allows for a different framing on skills, belonging, achievement, and failure.

*Full disclosure: I completely made up the term pioneer syndrome. There is no psychological basis in this at all.

How to Give a Remote Talk with No Slides

Photo by AbsolutVision on Unsplash

I have decades of experience giving keynotes, talks, leading workshops, and design sprints. I would always follow the same formula— sketch out an outline of the talk in rough blocks, translate the points into slides, design a gorgeous slide deck, and build out the slides while populating the talk content. I’d then rehearse the content, often running through the talk 20+ times until I was satisfied with the language and rhythm. I was going for the effortless knowing of the content that comes after intense memorization and internalizing the talking points. This approach served me well through many conferences. But it was time-consuming and exhausting. While I loved being onstage and giving the talk, I started to hate the weeks of preparation.

This carefully controlled and planned approach to talks was an accurate reflection of my former leadership style. It felt like I had to be perfect and the consummate professional. I liked to be confident, prepared, and meticulously detail-oriented. Which really meant that I was massively over-prepared and obsessively controlling every aspect of the experience. As you can imagine, this resulted in a lot of stress and the inevitable panic when something goes slightly off course, whether it’s a crashed laptop, A/V issues, or your co-presenter not showing up.

This past year, I’ve embraced a different path where I’m paying much more attention to connecting with the audience and our shared experience rather than the beautifully crafted story arc of my slides. This path is a different path of ease and flow where I embrace spontaneity and get excited by interruptions and deviations from the set course. Perfection has been replaced by planned messiness.

My personal transition came with learning and honing the craft of coaching. Each coaching conversation is a 3-part container where the coachee brings in a particular challenge, we end with co-created actions & experiments, and the magic happens in the free-form middle. The juicy, luscious middle is a meandering exploration of deep listening, powerful questions, embodiment, and ideation all wrapped up in a swirling soup of emotions. As a coach, I’m paying exquisite attention to the coachee’s words, body language, emotions, our interplay, and also the unnamable space of what wasn’t said. I’ve transitioned from being a designer of digital products to being a designer of human experiences.

“In improvisation, there are no mistakes.” —Miles Davis

After March 2020, when in-person events were cancelled and everything moved to zoom, I took the opportunity to revamp my rigorously planned approach to speaking. As I look back through my calendar, I’ve given 9 talks, 6 workshops, and run dozens of group coaching sessions since March. The first talk was the only one with slides.

This is what I’ve learned about how to craft a remote talk with no slides.

1. Know your audience

Before prepping the talk, have a clear understanding of who the audience is. Spend some time with the event organizers. Dig into more than the audience demographics, and seek a deeper understanding of why they’re interested in your talk and what the #1 takeaway for them would be. It could be something practical, e.g. they want to hone their design or leadership skills, or perhaps they simply want to be inspired, entertained, or distracted with a good laugh.

2. Have a clear intention

People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”― Maya Angelou

How would you like people to feel at the end of your talk? What emotion do you want them to leave with? If it’s a practical talk, you may want to leave them activated and motivated to try things out or perhaps hopeful that things could be different if they use these tools you share. You may want to leave people peeing in their pants laughing and seeing the humor in every situation. You may want to leave them falling in love with typography or appreciating the beauty of nature. Be intentional with how you want your people to feel.

3. Meet Your Audience Where They Are

When you start your talk, know the context of the day. Are there larger country- or world-level breaking news that has just happened, whether it’s the death of a leader, a natural disaster, the Nobel prize awards, or national elections? Your audience will implicitly bring in this context of the day, so it helps to reference the events.

Part of the magic of a remote talk with no slides is also being able to make it more interactive. We’ve all been in lectures where no matter how engaging the speaker, it’s tough to focus on a single voice for an extended period of time. As part of meeting the audience where they’re at, kickoff the talk with a series of questions to get everyone participating:

• If it’s a workshop with less than 12 people, you can ask everyone to share two words of emotion for how they’re feeling right now. Or make it contextual to your talk and ask them to share a one sentence challenge that they’re facing. This works well both in-person or remote.

• If it’s a larger group of 20+ or even 100s of people, ask a series of questions to gauge the mood of your audience. It only takes 3–5 minutes to get user feedback and learn more about your audience. These can vary from: “Who’s nervous right now?” to a post-lunch crowd of “Who needs coffee to work through this mid-afternoon slump?” and get more specific into demographics or shared experiences. e.g. “Raise your hand if you’ve built and launched a product” or “Raise your hand if you’ve ever been fired” (you might want to build up to this last one). 
  This is easier to do on zoom than in-person when you may not have a visual on the entire audience. On zoom, ask people to turn their cameras on (and you can scroll through the screens of little squares) or have them use emojis to respond to the questions.

4. Outline Your Points

More practically, if you don’t have a slide deck, you start with an outline or storyboard of the beginning / middle / end of your talk. You should have a sense of the ending intention & emotion. The beginning should have some of your intro, which should help answer the question — why am I here speaking about X today? Other common intros are sharing a story or anecdote.

Outline the middle in a series of bullet points. You can capture the 5 or 7 points you want to make. People will forget more than that.

Alternately, if writing an outline doesn’t work for you, try improv speaking. You can turn on your camera and record a selfie video of your trying this unscripted talk. Watch it afterwards and pull out the top points, or send it to a close friend for instantaneous feedback.

5. Collect Stories

We all have stories that we’ve told throughout our lives from memorable disasters, learning moments, or incidents of pure hilarity. Start collecting stories from your personal and work life. There’s different types of stories that could be useful:

• Life stories with a lesson or self-deprecating humor

• Case studies of work projects

• Stories of memorable people & interactions

• Lessons from elders or mentors

Think of these stories as tools in your toolbox that you can pull out at any point in time to sprinkle throughout your talk to make a point.

6. Pull the Audience in

One huge benefit of no-slides on zoom is that your video will be up and center allowing your audience to better connect with you. Throughout the talk, pull the audience in to interact with you. Figure out how you want the flow of the talk to run as you outline your points and consider if you’d like Q&A or feedback throughout the talk rather than at the end. Tips and tricks include:

• Asking the audience to share their key insight from the talk via chat

• Starting with a short poll

• Planting a friend in the audience to ask the first question. Typically after the first question is asked, then Q&A starts to flow

7. Breathe, Loosen Up, and Have Fun

Finally, try it out with the spirit of “Yes And” from improv. The first time you try something new is always the hardest. There’s a comfort in having slides as a plan to follow. Instead, think of the talk as a casual chat. Try to approach it with a spirit of curiosity and have fun.

Bottom-Line

Have you always been curious about giving an unscripted talk? Why not try it out for your next presentation during pandemic times? Much of this works especially well on zoom and has the bonus of being unexpected for the audience. I’m finding myself really loving this way of presenting and am looking forward to playing & adapting this style for in-person events… hopefully to come in 2021.

The Power of Play, Redux

Photo by Kei on Unsplash

I sat down to write this article and perhaps because I’ve been so prolific and similar themes keep re-emerging, realized that I’d previously written on The Power of Play. This creative concept keeps re-emerging.

One of the biggest self discoveries I’ve made this year is tuning in to the power of play. More specifically, I’ve integrated it better into my work life rather than solely being playful at home.

I’ve always tended to have a serious persona at work. Others view me as professional, competent, and sometimes outrageous / intense, whether in the ideas I shared or how I show up. I’ve been a professional design leader for 22 years so I would often run design sprints and lead brainstorm sessions. In those sessions, I’ve led people through playful exercises, including one time I had 100+ engineers play a speed-dating game to get to know your colleagues. And I deeply know and teach that mistakes are OK, brainstorming is about generating tons of bad ideas, and how to get the most creativity from everyone through a facilitation process. Yet my persona through all that was quite serious—I was the conductor of all the play and not actively being playful myself. As a female in tech, some of this was also wanting to present myself as someone to be taken seriously.

In contrast, I’m much goofier in my personal life. I’m playful, funny, and also outrageous. There’s still seriousness that’s tinged with a willingness to pack up and jump into any adventure. My father passed away less than two years ago, and recently as part of a coaching exercise, I did a reflection on a childhood photo and realized that I had his eyes. His eyes, and mine in the picture, sparkled with mischief, fun, and lightness. That realization helped me better access the rebel inside and a sense of play that’s slightly deviant.

In the Harry Potter series, in order to access The Marauder’s Map that magically shows the location of every person on the castle grounds, the wizard has to incant the following spell:

“I solemnly swear that I am up to no good.”

That saying, and the corresponding “Mischief managed” to erase the map have always resonated with me.

This year I’m embracing a more integrated life between work and home. I’m learning to bring the power of play into all aspects of my life. To be more open to spontaneity.

My muse in this endeavor is the fool from a tarot deck of cards. The fool is ready to bring in a beginners mind and ask the not-so-foolish questions. The fool is willing to laugh at herself and at life. The fool can dance on the edge of silliness and wisdom.

Fool, first card of the Major Arcana from Motherpeace Tarot deck

Life is hard enough. There’s so much more ease and flow when I embrace play.

These are three ways that have helped me integrate the power of play into my work and home lives.

1. Embrace a beginner’s mind

We often find ourselves jumping into a new situation or processing new information in one of two default modes, either:

• I’ve heard this concept / done this thing before. I know all about it. I got this.

• Yikes, this is completely brand new to me. I’m not sure what to do.

There’s stress and seriousness with both of these approaches. If you feel that you already know all about the existing situation or concept, there’s the danger that you tune out, assuming that you already know all the answers. One of my coaches frequently teaches and often reuses the same stories. His brilliant move is to ask the audience to listen to the story with a beginner’s mind, approaching it as if they’re hearing it for the first time. Even if it’s the 10th time you’ve heard something, the context will have shifted—you’re a different person today, and this day is different than before. Using this beginner’s mind opens up the brain to be welcoming of new possibilities and ideas rather than smugly closing down because you already know all about it.

On the other hand, there can be anxiety doing a new thing for the very first time. I often support clients through their anxiety in starting a new job. It’s natural to feel like you have to prove yourself and rapidly show impact by impeccably executing a 30/60/90 day plan. Yet you were hired to do this job for a reason. You’re a professional bringing in pre-existing experiences and knowledge, and more importantly bringing in a beginner’s mind to the new job. Slow down, take the time to ask a lot of questions, and invest in relationships. Embrace a beginner’s mind and know that your strength is the not-knowing.

2. Be Spontaneous

I have a controller saboteur that wants to perfectly plan out every activity, milestone, and year. While this planning can be useful in defining a goal and outlining what needs to happen, it’s often killjoy behavior. Part of the power of play comes from embracing the spontaneous. Creative ideas, either for defining the roadmap, generating new blue sky ideas, or in building better relationships often arise from the serendipitous unplanned moments.

As a design leader, I used to speak at lot of keynotes, typically for large design, technology and data conferences. It would take weeks to perfect my beautifully-crafted slides and I would have every detail of my keynotes memorized and rehearsed down to the minute. It meant that I practiced and learned to become a very good speaker, and it was exhausting. In contrast, I’ve given four talks over the last two months, and because people have become so zoom-fatigued and sick of listening to yet another slide-driven webinar, I’ve thrown away the slides and instead worked off a rough storyboard outline of what I want to say. It was terrifying the first time I did it, and like many things, became easier with practice. I was more playful, spontaneous, and the ease and flow of pulling together stories & teachings without formal slides helped me to better connect with the audience.

How might you look for the moments of spontaneity in your day? What could you do to open up the space for more serendipity to occur?

3. Laugh at Your Goof-ups

Finally, one inherent part of play is making mistakes. Batters in Major League Baseball are considered to be really good if they have a 300 batting average, which means that they hit one in three balls. The flip side is that they goof-up 2/3 of the time. Many video games are about experimenting with the controls to see how to move the character, often resulting in killing yourself many times before you figure it out.

It’s OK to make mistakes. We all do it. It’s the most humanizing when you’re able to laugh and point out your goof-ups. To be self-deprecating enough to laugh at yourself and voice what everyone else may be thinking or judging. Plus, it’s a lot more fun than being 100% serious all the time. `

Bottom-Line

While I’ve always been an advocate for play and know the value of play in creativity, I’ve often drawn hardlines between being playful at work vs playful at home. Yet some of the biggest power of play is integrating these two personas.