Making Tiny Choices Each Day

With homage to a Cherokee legend of the black wolf and the white wolf

White wolf and dark wolf at The Wolf Heart Ranch in Southern California

We often think about big goals—to take the company public, to get a C-suite title, to keynote at the leading industry conference. These are important. They are big sweeping visions that shape the direction of our lives and careers. Yet equally important to these touchstone goals are the tiny choices we make every single day.

This past weekend I had the privilege of spending time with wolves at a spiritual retreat. My teacher had brought us to visit his non-profit organization—The Wolf Connection— focused on empowering at-risk youth and rescuing wolfdogs. Watching and feeling the energy of these majestic creatures helped me deeply experience of each minute in their presence. It helped to balance out both the big questions as well as stay in the moment and become aware of the tiny choices we make each day. 

Which Wolf Will Win? 

There’s a Native American legend, I believe that it’s Cherokee, which I’ve heard multiple times and am now retelling with creative license. 

A grandmother is talking with her granddaughter. The conversation is happening outside under a blanket of stars by the light of a flickering campfire. The grandmother tells the girl: “There is a continual fight happening inside me. It is a fierce fight between two wolves. One is the black wolf. She is arrogance, shame, envy, perfectionism, and over-confidence. There is also a white wolf. She is joy, love, compassion, forgiveness, wonder, and humility. The two wolves continue to fight inside me. The same fight is happening inside you and within every single person.” 

The girl listens thoughtful then asks her grandmother, “Which wolf will win?” 

You may have heard a version of this story where the grandmother replies, “The one you feed.” 

I’ve heard a different ending to the story. Perhaps it’s from the Cherokee world, perhaps it’s from my re-claiming or appropriation as I can’t find the source. Or perhaps it’s a dreaming up of my own answer. 

The grandmother replies, “If you feed them right, they both win. If you only feed the white wolf, the black one goes into hiding. She is suppressed, pushed down, and ignored. She will jump up and bite to get the attention she deserves. But if you acknowledge the black wolf, she is happy. Both wolves can co-exist together. Both wolves are needed. Feeding and caring for both acknowledges that there doesn’t need to be a fight or an internal struggle for your attention. Without that exhausting battle it’s easier to listen to the voice of deeper knowing. It’s easier to make choices.” 

Feed the Wolf with Tiny Choices Each Day

One mistake I often make is to think in terms of black or white. I’ll succeed in my goal of talking to 10 people each week or writing 1000 words each day. I’ll hit a big milestone of success when I reach a certain title or financial milestone. If I don’t achieve them within a certain expected timeframe, then I’ll have failed.

Our world doesn’t exist in black or white and these are false dichotomies. There are so many more nuances, shades of gray, and complexities in both the modern working world and in our lives. We live in ambiguous times when it’s not as simple as feeding the black wolf or the white wolf. 

Instead, we feed both wolves. We will continue to have the self-critical voices, the fear, the frustration, and the irritation of living in a world where the cat throws up on your pants when you’re rushing out the door late for a crucial appointment. There will never be a perfectly enlightened state where this darkness completely goes away. Yes there’s times where this fear drives hustle, commitment, and the ability to push through and get shit done. And this fear can lead to success. Personally, it’s helped me for many decades of my life, leading me to a lucrative career in technology. 

At the same time, we feed the white wolf by choosing joy, gratitude, and turning towards people around us. We keep making things and staying in flow each day. 

The daily practice is staying aware of both the black wolf and the white wolf. Of noticing your patterns and making tiny choices each day that feed the different wolves: 

• Perhaps today is the day to choose rest and vegging out with Netflix

• Or the day to step on that gas pedal and finally finish the report

• Or simply to put on pants with buttons and leave the house for brief moment

• Or to stop for a moment and smell that delicious coffee aroma and revel in the first warm sip

The big goals are truly important. And it’s also the tiny steps and choices you make every single day that keep you moving on and going forward. 

Update: A reader shared with me how the story of the black wolf and the white wolf reinforces bias with the “black is bad, white is good” narrative. I 100% agree and also personally realized that it was something I failed to realize would be a trigger when sharing this story. We all have unconscious bias. I’m leaving this story up because I believe that all the shades of gray of emotion are needed and it’s our choice in each moment. I reject thinking in black and white. 

Intentionally Observe the Wolves

We will make mistakes. Some days, it feels like we keep repeating the pattern of bad choices. We will feed one wolf and forget about the other. Or the two will wrestle for days as we feel stuck in unwinnable situations. This is the messyness of life. All you can do is observe the choices and notice which wolf has gotten more attention that minute, that hour, that day. 

Then with no additional judgement or self-criticism, simply decide what the next choice will be. If it’s made with intention, consider that there might never be a wrong choice. 

Bottom-Line

Being in the presence of these wild, free creatures reminds me that they live in the present. They are curious when they see humans enter their pen. But soon they get bored and wander away back to their napping or grooming. There is no past or future, only now. Taking inspiration from their energy helps to de-pressure the intensity and expectations of achieving long-term goals. Instead, it opens up space to make tiny choices each day. 

Shifting Fear to Excitement for Big Events

Photo by Tim Trad on Unsplash

Take a moment and think back to the last big event in your life. It might have been leading an important presentation, sharing big ideas on a conference stage, running a workshop, or holding space for a vision-setting planning session. It might have been making a toast at a wedding, or celebrating a milestone birthday.

For me, the anticipation and preparation for a big event involves the dual emotions of fear and excitement. They seem to feed into each other. I recently ran a four-day women’s leadership retreat and I could feel the familiar swirl:

• Will my co-leader and I disagree on the programming?

• What if nobody shows up?

• What if I get distracted and forget what to say?

• Will everyone laugh at what I present? Will it be a massive waste of time for them?

• What will go wrong with the logistics (weather/food/lodging)?

And at the same time, I could feel the excitement and sense of possibility:

• I love speaking, talking and teaching. This energizes me.

• I can’t wait to meet and learn from the other leaders attending. They are so cool!

• I’m thrilled to spend time away from the day-to-day and in an outdoor setting.

• It’s exciting to see what will unfold.

• There’s magic in the serendipity of bringing a like-minded group of people together in person.

All these emotions are present. All these thoughts run through our ruminating monkey-minds. We can let all these emotions be present, and simultaneously reframe them to aid our leadership.

Here are four strategies to help shift fear into excitement.

1. Recognize that emotions are in our control

Dr. Lisa Feldman Barrett is a neuroscientist and researcher who studies emotions. Her research argues that emotions aren’t simply something that happens to us, but a way for the brain to process the world, and tell you how to feel. In her 18 minute TED talk she explains:

“Emotions are guesses. They are guesses that your brain constructs in the moment where billions of brain cells are working together, and you have more control over those guesses than you might imagine that you do.”

The physical feelings of excitement & fear are not too dissimilar — heart pounding, butterflies in your stomach, maybe a tingle throughout your body. Dr. Barrett suggests that you can influence whether you’re feeling excitement or fear with a change in perspective… and lots of practice. Your brain can reframe these physical feelings and channel them from fear into excitement.

Let’s play with how.

2. Remember patterns of success from the past

Your brain remembers emotions from the past. Think back to other big events that have happened in your life, other times that you’ve been on stage, or led a meeting, or drove a vision workshop.

On the emotional side, focus on the highlight moments, the celebrations, and feelings of accomplishment. Remember what it felt like to complete that meeting or get a compliment on how you ran it. Paint a scene of the success. Relive how it made you feel.

On the intellectual side, take stock of the strategies that worked for you. Perhaps it was taking the time to rehearse the presentation multiple times, or to identify allies in the room. Perhaps there’s something that didn’t go well and you now want to adjust and experiment with for the future.

Visualize these emotional and intellectual patterns of success. The more you think about these, the stronger you reinforce these brain patterns.

3. Reframe uncertainty into possibility

Fear often comes from uncertainty. We can ruminate and anticipate all the possible things that could go wrong. Instead, think about the possibilities of what might go right at the big event. When we plan and anticipate good things, it can be even better than the actual experience. This New York Times article on vacation anticipation claims that: “Anticipation is such a valuable source of pleasure.”

So rather than think through all the negative outcomes, envision the hugest possible win from the event. Open up creative energy to dream big about what might unfold and become possible.

Are you starting to feel excited?

4. Channel other people’s energy

And despite all that, it can be hard to mitigate the fear. The last strategy is to think about the other people who will be present at the event. Look to your co-collaborators or allies who are equally invested in everyone’s mutual success. Think about their excitement and have their words or actions fuel you.

Beyond your co-collaborators, consider the audience that will be present. Think about what’s drawing them to the event and how their lives or work might be transformed by the information they hear or the experience they have.

Bottom-Line

Often both fear and excitement will exist when preparing for a big event. Both feed off each other as natural companions. If you find yourself swirling with fear and anxiety, consider these four strategies to shift into excitement:

• Recognize that emotions are in our control

• Remember patterns of success from the past

• Reframe uncertainty into possibility

• Channel other people’s energy

How to Escape Burnout and Stuckness

Photo by Maria Lupan on Unsplash

How do you know if you’re experiencing an extreme, unsustainable level of burnout, stress, and stuckness or if it’s simply an unavoidable part of modern professional life? It can be hard to tell and I’m sharing some questions that might help you figure it out. I’m also sharing experiments & retreat spaces for finding a way through the burnout and stuckness.

One of my clients was a serial startup founder and came to me when he was on his third startup, this go-around as a first time CEO. We’d spent a year coaching together, covering topics such as creating sustainable high performance for his team, understanding his leadership style of high expectations, hiring up the right C-suite team, and supporting the team through a fundraising round. He kept going faster and faster, recognizing that he needed more space and perspective but not able to do anything different because the company was in the midst of raising their Series B. It took his body giving out with a stress-related health emergency—he’s now fine— to get him to pause and recognize that he was burned out and needed to do something different.

You don’t have to experience a serious health issue before recognizing that something needs to change. Instead, ask yourself these three questions to see if it’s the right time for you to do something different.

1. Can you name the patterns that are no longer healthy?

Often we fall into patterns that work well for us. Many leaders in tech have a hustle mentality and drive that gets us to achieve goals in our professional lives. We’ve learned how to work hard and keep going no matter what. We’ve learned how to demand the most of ourselves and our teams so that they deliver on our high expectations. This pattern serves us well in achieving professional success.

Patterns become unhealthy when they start to feel different. Rather than being exhilarated or energized by the work, we feel negative emotions. It can feel like:

• Deja-vu: “Oh I’ve seen this story play out before. I know what will happen. And it’s not good.”

• Exhaustion: “I’m physically and mentally completely drained. Not even the weekend helps.”

• Lack of control: “I’m not sure that anything I do can or will change things.”

• Apathy: “Do I really care about this any more?”

2. How long has this been happening?

Many people can push through intense working scenarios for days, weeks or even months. Sprinting or pushing through the intensity is possible for a short period of time, especially when relief is visible on the other side. This working scenario may be a cyclical or seasonal pattern that you’ve seen play out in previous years of your career.

However, if it’s been going on for months or years with no end in sight, it’s likely time to make a change.

3. Do you see possibilities of a way out?

Often when we first encounter a challenging boss, a demanding workplace, or a stuck relationship, there are many possibilities for a next step forward. You might try having a difficult conversation, or setting boundaries on your work hours, or spending more time building trust.

Utter burnout and feeling stuck happens when you’ve exhausted all possibilities. It’s likely time to make it change when it’s impossible to see another path forward, even after talking with supportive friends, mentors, or coaches.

If don’t see any other possibilities of a way out, you might have hit rock bottom.

OK, You’re stuck. Now what?

The Inspiration of Retreat Space

These three questions can help determine if it’s time for you to make a change. Or they may confuse you even more. Sometimes, it’s difficult to even recognize that you need to change until you get a tiny bit of a breather. If you’re stuck or think you might be stuck, it’s time to move to the inspiration of a retreat space.

Retreat space is time for us to intentionally shift behavior and try something different. It’s a pattern break that uses physical space and time to shift into transformation. A retreat space doesn’t have to be a 7-day break or long weekend away from home. It can be a couple of hours that you block out on your schedule on a weekly basis to do nothing other than think, focus, and move into a different modality. It’s a meeting-free time for you to devote to what matters the most right now. At Facebook, we used this method of creating ‘focus blocks’ to let makers spend heads-down time deep into a project rather than having your time carved up in 30 minute meeting chunks.

In Julia Cameron’s The Artist’s Way, she talks about blocking out a weekly artist date:

“An artist date is a block of time, perhaps two hours weekly, especially set aside and committed to nurturing your creative consciousness, your inner artist. In its most primary form the artist date is an excursion a play date that you preplan and defend against all interlopers. You do not take anyone on this artist date but you and your inner artist, a.k.a. your creative child.”

You don’t have to make it about creating something, however, consider blocking out a weekly two hour chunk of time to do nothing but recharge. This mini retreat space can help you find a way out of burnout or stuckness.

Perspective and Possibility

A retreat space is expansive simply because it’s different and breaks the typical pattern of stuckness by shifting something—time or physical location— which then shifts mental states.

Being in a new environment and slowing down our thoughts to a different pace allows us to zooming out to a 10,000 foot perspective. We often miss this because we are myopically focused on what’s urgent, what’s due today, what’s someone else’s burning agenda item that we must accommodate. Instead, embracing retreat space allows for zooming up to see what really matters, which then opens up possibility.

Learn in Different Modalities

Finally, when in retreat space, we can find different modalities to learn from. It can be going deeper with ourselves in contemplation, journaling, day-dreaming, all of which can unlock different insights. It can be going deeper with a book or podcast, singly focused on listening for the lesson rather than multitasking our way through the day. And if you’re on retreat with other people, it can be best to learn from similar struggles, and breakthroughs, that other like-minded leaders have experienced.

Bottom-Line

Learn to recognize the signs of burnout or stuckness before they become overwhelming or before your body tells you to slow down. When this happens, carve out retreat space for yourself. This can be in 2-hour chunks in a week, or a longer retreat period.

If you’re looking for a nourishing retreat, feel free to reach out and I can help you find one from the leadership & coaching communities I spend time in.

How to Recognize and Avoid Drama

Photo by engin akyurt on Unsplash

The best manager I ever had gave me this feedback in my performance review:

“The theme of occasional unnecessary drama is one that came through in your feedback that resonates... You have an amazing resilience that I’ve seen in action. Using this to provide stability to situations will help you apply the truth that things are almost never as amazing or terrible as they first appear.”

The caring response followed by specific examples prompted me to want to change and helped me become hyper-aware of any signs of drama. This is true for me at work especially during stressful times dealing with the unknown or pushing towards a deadline. It’s also true at home where my teen daughters call me on my sighing and dramatic first reactions to a TV show or something they did.

In the workplace, we do want to avoid unnecessary drama and conflict. I’ve recently been teaching corporate clients how to apply restorative justice practices in the workplace with my colleague Jim Herman. One tool that has proved invaluable both for reducing drama and increasing leadership responsibility is Karpman Drama Triangle, developed in the 60s by psychologist Stephen Karpman. I use this for my clients and for myself, both at work and home.

The Drama Triangle

In any situation that raises negative emotions, each person plays a different role that adds to the drama. The Victim, Persecutor, and Rescuer roles are all disempowered versions of a non-leader who is reactive and solely responds to the situations around them.

• Victim: Thinks that they are powerless and at the mercy of life circumstances or other people’s behavior. Is unwilling to take responsibility for what happens in their own life.
  Signature statement: “Poor me”

• Persecutor: Thinks that they must win at any cost. Controls others (or self) through blame, criticism, and oppression
  Signature statement: “It’s all your fault”

• Rescuer: Intervenes on behalf of others to save them from perceived harm, creating temporary, short-term relief. Fosters dependency (from others) and often leads to resentment when others don’t value your contribution.
  Signature statement: “I’ll fix it right now”

Let’s see how these drama roles play out in a workplace setting.

Workplace Story

Dao and Susan are peers working on a high-pressure project. Patrice is their boss. Dao misses his deadline by 2 days due to many factors beyond his control. The next day, he’s working hard to try to make up the time when Susan explodes at Dao in a team meeting. She blames him for the project being behind and that she now has to work on the weekend to make up for the lost time. She yells at him that he is unprofessional and a poor communicator.

Dao and Susan both report to Patrice. She tries to make them both happy by giving them an extra day of vacation. It doesn’t help. Dao feels that he was attacked and there was nothing he could do about it. Susan is angry and blames Dao’s lack of professionalism.

Dao plays the victim role. He had no control of missing the deadline. And now he’s yelled at. He doesn’t feel like there’s anything he can do.
Poor me.

Susan plays the persecutor role, attacking Dao, without taking any responsibility.
It’s all your fault.

Patrice doesn’t solve the underlying problem of communication or the missed deadline. Instead, she offers a quick-fix for short-term relief with a vacation day.
A vacation day should make them both feel better.

Role-Cycling

In a typical situation, we cycle between all the roles in the drama triangle. This can happen quickly and often within a 20 minute conversation.

For example, if in the meeting, Dao yells back at Susan that she never offered to help with his deadline or if he blames the other factors beyond his control, he moves from Victim to Persecutor.

Or if Dao reports to HR that he feels harassed by Susan, he also moves from Victim to Persecutor. And Susan moves from Persecutor to Victim.

Your Pattern of Drama

Which one of the three roles — Victim, Persecutor, Rescuer— is your typically pattern of drama?

For me, I often play the Persecutor. I can have terribly high expectations for others and even higher ones for myself. When we all inevitably fail to meet those expectations, a familiar instinct is for me to jump to self-criticism and blame. Many coaches often find themselves in the Rescuer pattern. It feels good to help out and be the problem solver or the hero to fix the issue. Or, we “rescue” ourselves from a problem by distracting with a short-term fix of scrolling instagram or eating chocolate cake without diving deeper into the long term solution.

Naming the Drama and Shifting to Taking Responsibility

The beauty of the drama triangle is that it provides a framework and tools to help us recognize the roles or traps we fall into. Once we are able to start naming the negative drama roles, we can start to shift and get out of this drama triangle.

Since all three roles demonstrate being reactive and passive to what’s happening around you, the leadership shift is to take responsibility.

Victim to Creator: The Victim starts to identify their own needs and finds possibilities / brainstorms ways to get out of the problem.

Persecutor to Challenger: Instead of assigning blame, the Challenger identifies the facts of the issues at hand. They are unafraid to point out what has happened in a manner-of-fact way, allowing for everyone to have a shared understanding and move beyond the conflict.

Rescuer to Coach: Instead of fixing the problem, the Coach asks open-ended questions, holds space, and trusts that the other people will find solutions to their own problems.

Each of these three role shifts moves you out of the Drama Triangle and into The Empowerment Dynamic, coined by David Emerald. All three empowered roles asks: “How can I improve this situation? How do I take responsibility for making things better?”

Bottom-Line

Using the Karpman Drama Triangle helps us recognize the roles we play within conflict situations. We first start by naming the roles. Next, we shift to take responsibility for our actions, helping to resolve the conflict and develop our own leadership skills.

Leading Design Conference NYC: Live Sketchnotes

I’m live sketchnoting from the design conference I’m attending. I love drawing and miss it. And, drawing helps me to focus on what’s present right now, honoring my value of dancing in the moment.

How to C-Level

Cap Watkins

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Leading Through Ongoing Ambiguity

Leslie Yang

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Designing Creative Collaboration

Samantha Warren

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“I got you” A Meditation on Radical Inclusion

Dianne Que

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Designing Your Dream Job[s]: The Art of Ikigai

Alice Quan

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The Planck Value of Design Leadership

Ovetta Sampson

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Trust Between Teams

Hayley Hughes

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The Evolving Design Leader

Peter Merholz

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Own Your Leadership Seat at the Table

Photo by CHUTTERSNAP on Unsplash

Do you often wish that you could have a seat at the leadership table and listen to or be a part of the important conversations? That you’re missing out on something crucial because you’re lacking that seat. It reminds me of the Hamilton song where Aaron Burr craves being in the center of leadership with Thomas Jefferson and Alexander Hamilton. Burr mournfully sings:

No one really knows how the game is played
The art of the trade
How the sausage gets made
We just assume that it happens…

I wanna be in the room where it happens (I’ve got to be, I’ve got to be)

This is a feeling that many of us can relate to. It can feel that there’s yet another table that’s agonizingly out of reach, whether it’s a key leadership meeting, a C-suite powwow, or the board meeting. We’ve all been there. And sometimes, frustratingly, that’s not the most healthy or helpful thing to focus on.

What’s in your control is how you show up in the rooms that you’re already a part of. And how you show up is going to impact and affect the likelihood of an invitation to the bigger rooms.

Consider these 4 lessons as a reminder on how to own your seat at the table:

1. The dinner party metaphor: understand your patterns and habits

Think about a setting that you’re already familiar with, a dinner party. Take your mind back to those pre-pandemic times and remember some of the best dinner parties that you’ve attended. Consider the role that you typically play. Do any of these sound familiar?

• The host who has assembled this group of unique individuals

• The chef (or Grubhub account holder) who’s chosen the menu

• The storyteller who entertains with witty anecdotes

• The connector who draws everyone into the experience

• The jester who adds lightness to the conversation

• The appreciator who brings a sense of grace and gratitude to the gathering

At the dinner party, there are no silent observers —everybody plays a role. It’s not enough to simply want to be in the room “just to listen and gain context.” That’s not offering up additional value.

Instead, think about what patterns from a dinner party you could bring into the different tables (or meetings) at work. For each of these meetings, take a discerning look, imagine yourself at that leadership table, and intentionally decide what role you want to be playing. It might be a habitual role. It might be a new one. Your choice.

Consider your limiting habits and intentionally make a choice on the role to play at the leadership table.

2. Remember your unique strengths and values

It’s easy to fall into the trap of thinking that you’re the least powerful person in the room. It might be true in terms of title, however, that won’t help your confidence or state of ownership at the table. Instead, think about your unique strengths. You might bring in skillsets from your discipline or a way of processing information. For example, you might be:

• A quieter introvert who can observe the flow of discussion and then ask a key question to reshape the room’s thinking

• A researcher who can quickly bring in data or user observations that build upon the topics discussed

• A person who slowly processes and assimilates the info and can then summarize the chaotic discussion that’s been happening

• An engineer who can quickly estimate the cost and time of building that feature

Consider what unique strengths you bring into the table. How might that align with your overall values for what change or mission you’d like to play at the organization?

One of my clients is a product architect with an engineering background. He has the unique ability to see the long-term product vision, the technical background to understand the feasibility of each suggestion, and the curiosity to keep questioning the value of executing on purely tactical or iterative tasks. His unique strength is balancing the big picture against the short-term iterative roadmap. That’s what brings him the most energy and state of flow at work. That’s his unique strength to bring to each leadership table.

One of my wisest bosses would constantly remind the design teams that we were the only people in the company who could produce pixels and prototypes to bring that product vision to life. From that place of strength, one role of the designer is to create the artifacts that shape the dinner party conversation.

Spend a little bit of time brainstorming your unique strengths and values, then consider how they can support your role at the table.

3. Those stories in your head: are they fact or fiction?

And yet, we may still feel that we don’t belong. That everyone else has a higher title, or more knowledge, or more experience than we have. I’ve heard many people share these stories. I don’t want to speak up or my idea won’t work because…

• … I’m the lowest power position in the room

• … I’m not as close to what the customer support team does

• … I don’t know what’s been discussed at the board-level

• … I haven’t seen the latest feedback from customers

We all have these stories in our head that prevent us from owning our seat at the table. Know that these artifacts of imposter syndrome are normal, we all do this. Recognize that these are stories that we tell ourself and that they might be limiting our leadership. Pause for a minute, and ask yourself a question: is this story fact or fiction? If there’s even a small percentage of it that might be fiction, then perhaps you do speak up or ask a question.

4. Less naval-gazing, more action

It can be really easy to get lost in our thoughts and stories. We can complain to our work besties that no one will give us that seat at the table. But if we do that, it’s unlikely that anything will change.

Instead, pick one small action or experiment to try differently to own your seat at the table. Look at a meeting that you’re already a part of. Actively choose to play a different role in that meeting. Try it and see what it feels like.

Bottom-Line

We all feel that we want to be admitted into the room where it happens. Yet we can so often discount the current rooms where we belong. Use these rooms as spaces for experimentation. Take your seat at the table and own it by choosing a role to play which leverages your unique strengths.

Build Your Brand By Writing: Learnings from 100 Blog Posts

Photo by Toben Dilworth

This is my 100th blog post since I started writing about my career transition from a design leader to running my own business as a leadership coach, speaker, teacher, and writer. Writing weekly started with helping me process my own journey and my learnings in this transition. It’s become a pathway to a new identity, as a writer. It’s helped me hone my ideas and publish my first book. And most of all, it’s a way of developing my unique perspective and point of view on the world, AND getting feedback on it from readers.

From writing 100 blog posts, I’m sharing two of my biggest process learnings and four tips for what types of content has worked for me.

1. (Process) Writing is a muscle; You get better with practice

I’ve been writing regularly for 2.5 years, mostly publishing a blog post every week. For the first 6 months, here’s what worked really well for me to establish this rhythm:

• Topic. Each week I’d write about what I learned the most that week or a challenge I was grappling. Sometimes it was a problem that multiple clients were facing.

• Accountability. I posted on some leadership slack groups asking for an accountability partner who also wanted to write. When I found one, we would exchange our writing and provide feedback each week. It was valuable to have another pair of eyes on my writing and to know that I had a piece “due” to someone else.

Writing is a muscle. The more you write, the easier it gets. In the first 3-6 months, it would take me 2–3 days to write a post — perhaps a day to consider the topic, and maybe 4–6 hours to write it, broken up over several days.

Today, it might take me 5–10 minutes to find the topic. It’s a rhythm where I continually think about what I have to say this week and what would be relevant to others. I often still look at what’s topical this week, for me or my clients. The writing itself will take 1–1.5 hours. Then I step away from it, sometimes for half a day, sometimes overnight. When I come back, I give it a 10-minute read, make the edits, and post. It’s become part of my muscle memory from the years of practice.

Also, my major push last year on top of writing blog posts, was to write a book. The process was quite different, but working weekly with an editor gave me more confidence in my writing style and the muscle to produce many pages of content.

2. (Topic) Be in service; Solve needs and problems for others

I publish my articles both on medium and my personal website. Sharing your writing provides a valuable feedback loop for what others find relevant and interesting. When coming up with topics, think about what might be most valuable for others to learn or read about.

Some of my top articles have been how-tos to solve specific pain-points for people in my community — leaders in tech. For example:

• Salary Negotiation for Designers and Women (2.2K views)

• The Art of Giving Feedback (1.8K views)

It helps to know who your audience is. And you can get more readership if you submit your article to medium collections that have a similar audience to you.

3. (Topic) Have a Unique Perspective; Be contrarian

As humans, we’re naturally drawn to what’s new and different. You don’t want to read the same cliche story. I’ve learned over time that people are interested in articles that present a contrarian point of view. It helps when that POV matches your brand. For example:

• How to Work with Difficult People… When You’re the Difficult Person (5.2K views)

• The Cult of Busy (2.3K views)

4. (Topic) Write for What’s Timely

We all have a rhythms and contexts in life. If your writing can tap into a collective psyche of what’s happening right now, it will resonate more with someone who’s experiencing this context. I’ve especially learned this by writing for publications (Business Insider, Entrepreneur) who use both enticing topics and borderline-clickbait titles to get people to read. The takeaway is that what’s timely and present can be what’s most interesting.

So during performance review / annual review cycles:

• Stop Dreading Performance Reviews and Set Powerful Goals (2.9K views)

During the start of the pandemic:

• Covid-19: The Gift of Time and Space (2.3K views)

5. (Topic) Share YOUR Story

Most leadership books and many articles rehash a lot of the same teachings and concepts. You might fear that you shouldn’t write because everything has already been said about the topic. However, this is simply not true. Your perspective is unique because no else else has lived in your exact shoes. So share your story with vulnerability and honesty. People want more of that.

My top-read article had nothing to do with work or technology, but instead was an examining of my own privilege during #BlackLivesMatter.

• My Asian Privilege (9.2K views)

Sharing my personal values and North Star lets people peek into my life:

• Defining Your North Star (3.3K views)

6. (Process) Feedback is a Gift

It’s really hard to share our creative work and writing. It feels vulnerable to put something out into the world. What if it’s bad? What if nobody reads it? What if people hate it?

However, the best part of sharing your work is that you get feedback. I can see what articles resonate with people and which ones don’t. My instinct is sometimes right, but equally often it’s wrong — some articles I think will be the most-read are a flop, and others are a surprise hit. You’ll never know what resonates for others unless you keep sharing. All feedback is a gift.

These are three gems of articles which have languished. I still don’t know why, though over time I’m sure I’ll keep learning more. Some of these are also quite recently published and may pick up readership over time.

• Learning to Ask for Help (24 views)

• Becoming Comfortable with the Unknown (35 views)

• The #1 Secret to Shifting Your Mindset (43 views)

I’m sharing the “failures” because I can get so attached to the outcomes. I want to write so I can reach thousands of readers. But most importantly, I want to write to express my opinion and share my thought leadership to help others. I CAN control my writing process… I can’t directly control who will read (or not read) what I write.

Bottom-Line

Writing will help you become a thought leader and develop a unique point of view. Working on both the process and topics will create this writing rhythm. What I’ve learned from the process of writing 100 blog posts is: Just keep sharing and keep experimenting. You’ll learn what works and what doesn’t.

Trust the process. You will become a better writer and hone your ideas through it. You’ll learn what topics resonate for your reader. I can’t wait to read more of your stories.

Becoming Comfortable with the Unknown

Photo by Edurne Tx on Unsplash

Like many of us, my family contracted covid over the past two weeks. My kids and their dad picked it up on the way home from a holiday flight to see their grandma. After two years of this, we’re all familiar with the isolation, the waiting for symptoms, and now the search for at-home test kits or test appointments. I’ve had a lot of time to ponder my impatient reactions to the waiting, and the fear of the unknown. 

I like to live my life in a state of certainty. I like to be confident of my decisions and have solid plans. The structure gives me comfort. It puts my mind at ease to have these knowns: 

• Dates for my speaking engagements, teaching commitments, events and retreats

• Dates for personal and professional travel

• Dates when my children are with me (I have shared custody with their dad)

• When I’ll have downtime for personal vacation and retreats

• What to expect with my weekly work meetings and weekend plans

• The months when I will be busy and slow (based on the seasonality of a consulting & coaching business)

Creating these plans gives me a sense of control over how I spend my time. Yet as we’ve all learned with covid, all these plans can be instantly disrupted and we can be dropped into an overwhelming state of unknown. 

These are four strategies that help me become more comfortable with the unknown. 

1. Reframe plans as fluid pencil sketches

Whether plans feel like a satisfying commitment or a disliked obligation, consider reframing your mindset around them. Make the plans, but know that they can always change. Global supply chain issues will cause a delay to the product release date with a major retailer. Unprecedented sick days will cause a team to be weeks or months behind and unable to hit a release date. Major events will get cancelled or postponed, making that major marketing campaign irrelevant.

If you count on plans as a certainty, you will be disappointed. 

Instead, make your plans. But consider them a fluid pencil sketch to be held lightly. External circumstances may cause them to change. Equally important, you can change your mind about the plans. 

2. Are you typically planned or spontaneous? Break your pattern and play with the opposite

What’s your typical pattern? For me, I’m a planner. This is my most natural mode both personally and professionally. What about you? Do you prefer to have solid plans or to leave your schedule up in the air and free for spontaneous events? Does this change in the personal vs professional contexts? 

Let’s try an experiment. Over the next 1–2 weeks, play with the opposite of your comfortable pattern:

• If you’re a planner, stop making plans ahead of time and take things day by day. When possible, decide what to do each day depending on how you feel.

• If you’re more spontaneous, start making plans over the coming weeks.

Notice what happens when you try your opposite pattern. See if it gets you more flexible and adaptable with the unknown. 

3. Always be curious. Notice what’s uncomfortable with the unknown

Whenever you feel uncomfortable with the unknown, stop and sit with the feelings. Many times, we will fail to stop and instead hurtle into our familiar patterns. I will typically start making those plan A, plan B, and all the other contingency threads of what could happen. For me, it’s far easier to act than to pause and think. 

Yet in order to become more comfortable with the unknown, it’s important to understand our relationship with it. This requires being curious and asking yourself the following questions: 

• What emotion am I feeling right now?
  For me, it’s often disappointment and frustration that there is no clear path forward. An uneasiness with not knowing. Which can also turn into hopelessness if it’s been happening for a while (like another covid surge).

• Where do you feel it in your body?
  For me, I feel tension in my neck and jaw and a fluttering in my stomach. The uneasiness is also sometimes a tingling around my entire body.

• What’s the gift in this situation?
  We can often feel stuck and powerless in the face of the unknown. Opening up to different perspectives lets us choose to tell different versions of the story. You don’t have to believe the gift… simply the exercise of brainstorming alternative explanations can help unstick our thinking.

• When I have felt this before? What did I do? What happened?
  Learning to look back at our history helps us see our patterns and actively make a choice on what to do next.

Through all of these questions, keep being curious and questioning. 

4. Take it one day at a time

Finally, even though the unknown may seem unbearable, time always passes. We continue our days with our work and home rituals. And as each day passes, either the unknown will seem less pressing, or we get more information and better understand the situation. 

Just keep going, one day at a time. And know that this discomfort will pass. And eventually, the unknown will become known. 

Bottom-Line

After spending 2 years worrying about covid and all the disruptions in plans, there was a tiny bit of relief to be finally have the virus in our home. I’m grateful that our symptoms were light, even as we dealt with the anxiety of finding antigen test kits and getting PCR test appointments. It reminds me that we’re often the most afraid of the unknown and perhaps spend more time in fear than in actually addressing the thing. 

These four tips are ways that I use to become more comfortable. I hope that they are helpful for you as well. 

Creating Your 2022 North Star

Photo by Marek Piwnicki on Unsplash

Adam Grant’s brilliant NYTimes article uses the term languishing to describe what many of us have been feeling during the second pandemic year of 2021. While there were many beautiful connections last year, there were also many times when I felt joyless and aimless and it felt comforting to think of a collective languishing.

As we move into 2022, even with the new strains, we can take advantage of the quirk of human calendars and get 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 a leadership framework revolving around your one word or one phrase intention to define your 2022 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 6-week group program that begins on January 18.

Last year, I wrote about Creating Your 2021 North Star and reflected on A Ritual for Closing the Year. My word for the year was whitespace —in design, the negative space between the content. I needed to slow down and pay attention to the restful space in-between the to-do list and packed calendars. I gave myself permission to read, sketch, surf, and write. I was proud to complete a book that kept to that theme, Make Space to Lead.

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. Instead, dream about would be amazing and fun to do 2022. How might you give yourself permission to desire big things. We’ll do all we can to reach it, and if it doesn’t happen, it’s OK. Try to remain unattached to the outcome, even though that feels so impossibly hard. A North Star is directional and not prescriptive.

Looking forward into 2022, I offer up a two-part strategy to set your North Star.

Part 1: One Word or One Phase 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 make people feel when they’re using it. Perhaps hopeful and excited to explore dating matches. Or relief to be able to save a video to watch later. Or accomplished when they were able to easily check out and buy their item. 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.

Creating an intention for 2022 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.

As you think about what your one word or phrase may be for 2022, consider these questions:

• What do you need more of in 2022?

• 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.

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 intention for 2022.

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 2022, 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 2022 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 2022, 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 2022, 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 2022.

My 2022 North Star

The epitome of satisfaction after a long hike. Photo by Toben Dilworth

My “one word” intention for 2021 is satisfied, to be sung out loud 🎵 I will always be satisfied . 🎵 to the Hamilton song. It layers upon the whitespace of 2021 and reminds me to keep my contentment top of mind. At the same time, satisfied has the association of a sense of accomplishment, a job well done. Brené Brown in her latest work of wonder, Atlas of the Heart asks us to ponder:

If we’re not satisfied with our life as a whole, does this mean we need to go get and do all the stuff that will make us satisfied so we can be content, or does this mean we stop taking for granted what we have so we can experience real contentment and enoughness?

Projects

• Attend personal retreats, including a 2-day Spirit Quest in the wilderness

• Research, outline, and start writing my second book that focuses on stories of Asian women in tech

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

• Speak in-person at conferences

• Surf more and read more

People

• Loving my tween and teen girls while supporting their emotional journey towards adulthood

• Having fun with my leadership partners-in-crime

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

Community

• I’ve joined a new mastermind of entrepreneurs/writers that I’m very excited to be a part of.

• Continue supporting the warm, transformational Positive Intelligence team

• Supporting my local San Francisco women in tech in some way

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 2022 leadership north star, my colleague Jim Herman and I are leading a 6-week group program that begins on January 18. And I eagerly embrace the hope for a sense of satisfaction throughout 2022.

2021 Year in Books

This was a slower reading year for me. 55 books broken down by fiction (31), nonfiction leadership & parenting (12) and memoirs (11). Some interesting patterns that I saw from this year: 

• I was over leadership books after overdosing on them in 2020. Instead, I followed my own pain-points and struggles for the 12 that I consumed. Since I spent a lot of the year writing a leadership book, I also didn’t feel like both consuming & creating in the same genre.

• Fiction is a lovely escape for me. Many of these were children’s series recommended by my 10 year old. Plus a fantasy interlude through the Bridgerton series.

• I’m obsessed with memoirs. For a long time, I thought my second book would be memoir. While I’ve since reconsidered that, I’ll continue to be obsessed with memoirs over the coming years while my own continues to marinate.

These 8 are the most memorable books of the year for me. I hope that you’ll also enjoy them. 

Fiction

The Midnight Library is a book that I wish I’d written and has all my favorite elements—mysticism, a troubled heroine faced with infinite choice, and a magical library that lets you dip in and out of different books representing different lives. 

Circe, my fave book choice from my feminist book club, shares the backstory of a woman best known for turning sailors into pigs and distracting Odysseus from his return home. It’s a story of an immortal’s transformation from her childhood as the least love child of a Titan through her own reckoning as a powerful and compassionate witch and mother. 

Memoir

Chanel Miller was the unnamed Stanford assault victim who wrote a powerful letter to her attacker and then shared her story with the world. The book was traumatic and shows the healing power of both art and storytelling. I was also pleasantly surprised to learn that like my kids, Chanel Miller is bi-racial. 

I read Mother Daughter Me while on a 3 week trip to Thailand and spending time quarantined with both my mother and my two daughters. I sobbed through scenes of mother-daughter relationships, and loved seeing familiar strains of my San Francisco life as Katie Hafner shares her short experiment of living with her mother and teen daughter. 

Non-Fiction: Leadership and Parenting

These four books are references that I’ll continue to return to over and over again, both personally and as recommendations for others. 

Humor, Seriously is an entertaining read, with a built-in assessment to understand your humor style and how to be a funnier person in business and life. The Memo is a crucial understanding of the bias, gaslighting, and ways women of color have had to adapt in the workplace. 

More personally, I came to grips with how anxious I was over the past two years of the pandemic, and that I had likely been masking my anxiety for most of my life. Dr Jud’s Unwinding Anxiety helped me to better understand my triggers and ways to break out of these worry loops. Finally, as the mom of an 8th grade girl, I’ve been devouring parenting books. Lisa Damour’s Untangled shares her model for guiding teen girls into adulthood built upon her extensive research background. Both the book and her podcast have been my lifelines through these past months. 

Bottom-Line

I read to learn and experience the world. I’ve always been a reader my entire life and I feel unbelievably lucky to also embrace a new identity this year — that of a writer. As I’ve become more intimate with creativity, structure, narrative, and evocative language, I appreciate the books I read even more.

Hello! I’m your host, Tutti Taygerly. I’ve spent 20+ years in product design & technology, leading teams at startups, design agencies, and large tech companies. I left Facebook in the summer of 2019 to focus on leadership coaching full-time. I write weekly about topics related to design & coaching which you can follow or learn more about my new leadership book, Make Space to Lead.

A Ritual for Completing the Year

Photo by Toben Dilworth. The author walking a labyrinth at Land’s End San Francisco.

We’re approaching the end of 2021, the completion of another trip around the sun. I view these year markers as ways to celebrate different aspects of life whether it’s seasons, holidays, birthdays, or personally meaningful events. We can become so stuck both in the mindless monotony of our days and our behavioral patterns. The end of the year presents the opportunity to mark an occasion. It’s also the opportunity to use a ritual of celebration and gratitude to close out the year.

I use a leadership framework that defines your North Star for the next year (for reference, these are my north stars for 2021 and 2020) and an end of year reflection is a nice completion to celebrate how far you’ve come.

This past year, my intention word was white space. From my reflections at the beginning of the year, I shared:

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.

North Star Leadership Framework

Setting an intention makes it more likely that you’ll move in that direction for the year. I’m happy to share that while it’s quite imperfect and there are some days that are still packed, both my work life and personal life feel much more spacious. Paradoxically, in giving myself permission to slow down, I’ve been filled with more energy to get more done.

I’ve taught and applied this leadership North Star framework to multiple groups and 1–1 clients for many years, so it’s been well tested as a useful model to think about aspects of our leadership and professional life. Running through the points of the star is the basis of the year-closing ritual.

1. Projects

Think back on all the things you’ve done this year. Think of the projects and processes you’ve put in place professionally and also at home. Which ones are you most proud of? Which ones did you do for yourself, and not simply to please someone else? Which ones gave you the most energy and satisfaction?

Think about both the wins and the misses: the incomplete, lost, discarded pipe dreams that never happened. We always have both. When you look at both, is there anything you want to do differently in the future? Anything you’d like to remember or change up?

For me, the top three projects I’m proudest of are:

• Writing, launching, and marketing my first book, Make Space to Lead, which closely follows my stories of creating more white space in life. We teach what we most need to learn.

• Creating regular space for surfing in my weeks. Through much of 2020, the first full year of my business, I hustled and packed my calendar with conversations. At the start of this year, I set what seemed like an impossible goal, to surf twice a week. Buoyed by a surf group of designers, my partner Toben, and my trusty 6am alarm, I kept practicing this new habit. I’m proud to say that I now surf 2–3 times a week. It’s been transformative to notice my mood. I am significantly more cranky when I go a week without being in the water.

• My favorite project of the year was creating an in-person women’s retreat, The Heroine’s Journey. It was what I most needed for myself, to be able to gather face to face with a group of strong, bad-ass women in the beauty of coastal Mendocino. This project wasn’t even on the radar at the start of the year, but it became something that felt inevitable the more I craved community.

What I’d do Differently:

• I ran three public group coaching programs last year. It felt really hard to enroll people, that I was painstakingly pulling in one participant at a time. I would change up the enrollment process to add more ease, more play, and more patience with a longer lead time.

• One corporate coaching program really did not give as much value as I had hoped. While I’d spent time interviewing the project sponsor and stakeholders, I would add more rounds to interview the not-so-willing participants to get a better sense of what they believe is the biggest benefit.

• Coming up with a book concept, writing it, and launching it within 10 months in retrospect feelts bat-shit crazy. I will give myself more space for my next book. Right now, my current timeline for book #2 is four years. This helps me drop the single-minded focus and drive that got book #1 done.

2. People

Relationships are the cornerstone of our happiness and satisfaction. When we have a fight or negative interaction with someone, we can continue to obsess over the emotions and replay all the different ways we should have responded. In contrast, we often fail to acknowledge all the people who have touched us in some way.

Think of all the people who you’ve encountered this year, both personal and professional. Which relationships grew the most? Where did you build unexpected trust? Who gave you the most support? Which relationships were you most grateful for? When you think of the people, dive deeper into what was most impactful about that relationship this year.

The top three relationship themes that most impacted me this year are:

• Co-Leaders. I taught separate programs with two wonderful co-leaders, Jim and Irene. We’ve co-created and improvised our way through multiple iterations of content. Most importantly, it’s been creative, inspired, and fun (well most of the time at any rate).

• Family. I spent 3 weeks in Thailand, 14-days under quarantine with my two daughters and my sister and her family. It was both boring, mundane, and wonderfully beautiful to spend the 14 days together. The end result was that we were allowed to see my mom in Bangkok. That family time, was a huge cornerstone of the year. An entirely restful break with the space to be bored.

• Romantic Partner. My partner and I are both divorced with two kids each. We’ve navigated this second year of the pandemic with more intentional dialog about where we want this relationship to go and how we want to combine our complicated lives. I’m proud of the difficult conversations, the tears, the heartache, and the joys that we’ve shared together as we deepened our understanding of each other.

What I’d do Differently:

• To be more intentional of which 1–1 clients I choose to work with. To let go of some clients who I can’t serve as powerfully.

• To better parent my 13 year old daughter. Through their younger years, I’d been proud of my parental instincts around boundaries, rules, and where to push them. Now, my direct style, propensity for planning, and continual desire to problem-solve means that I need to relearn how to parent a teen. She needs to create her own life choices and make her own mistakes in a safe environment. I can do a lot better in biting my tongue and dealing with my emotional fallout to her teenness.

3. Community

Community refers to the system 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.

What communities have supported you or that you’ve valued in 2021?

My biggest emotional peaks around community have been two highlight memories and three communities of support:

• It was the first night of the Heroine’s Journey Retreat, set in a glamping location for COVID safety. A group of strangers had vulnerbally shared some of their history with each other. They were tired, they’d just arrived that day, but we all felt the magic. Each woman had gone back to her space in a neighborhood of tent cabins. It was a cold starry night and as I strolled, I saw the warm glow from each tent. I felt an inexplicable sizzle of bubbling job, excitement, and pride that I had brought together the people and lit up all these tents. It felt like the perfect community.

• I was stressed out from all the pre-launch activities for Make Space to Lead, and decided to spend the last weekend before launch in a hot spring retreat with no cellular service. As we drove back to civilization and my cell service returned, I started seeing and reading all the feedback that early reviewers had left for the book on Amazon. It was the first time that the book felt real. That it had readers who enjoyed the book, and learned from it. I felt like I had done something good for the world, bringing this a valuable message out to the greater community.

• Most of the time, I work alone. I spent my days writing, creating programs, and coaching people 1–1 over zoom. There have been three communities that have fed my soul through this year: the Positive Intelligence team that I’ve consulted and coached with, a group of witchy women working through relationship and life learnings, and finally, a small group of four coaches that have met almost every Friday this year. I’m so grateful for all three communities.

What I’d do Differently:

• I tried to build an online community on Facebook at the start of the year. Somehow it didn’t work out. It felt too forced, too rigid and I abandoned it. I may start another online community in the future.

4. Me

In the North Star framework, leadership starts with Me in the middle. To be a better person, leader, or human being, the most impact we can make is by changing ourselves.

Consider how you’ve most changed this year? What behaviors have you let go of and which new ones have you adopted? What patterns have you successfully broken? What are you proudest of learning? What new identities have you adopted?

The top three changes for me are:

• I’ve run many different programs and shared teachings via weekly live videos. The way that I show up has completely changed. I used to have to plan out the agenda and lesson plans down to the minute and stick to it like chewing gum to a wall. This year, I’m more of a jazz musician, learning to improvise and play different notes. I adapt when I teach with different people. And I’m more at ease when I teach solo.

• I’ve embraced my identity as a writer. I wrote my first book! I’ve had a two years of a weekly writing practice with my blog. And I’m now paid to write as a published contributor to Business Insider and Entrepreneur. It feels fantastic to return to an identity that I shed in college.

• I’m more familiar with my self-critics and saboteurs. I now recognize them and their voices. I am a little bit less hard on myself. When I’m in the grips of these saboteurs, I can often see what’s happening. Being able to change behaviors, emotions, and thoughts more rapidly is a future goal. I’m taking one small step at a time.

Bottom-Line

Create your own year end ritual by taking the time to introspect and reflect. Elevate the ritual by sharing your process or these thoughts with someone else. You could also write it down on paper and do a ceremonial ripping and burning of the paper. Both the acts of sharing or the physicality of ripping and the changing state of the burn are small rituals that mark something important.

Reflection IS ritual. Celebrate your 2021 using this leadership framework that looks at the year through the lens of Projects, People, Community and Me.

How to Lead Teams When You’re Hard to Please

Photo by Syed Ahmad on Unsplash

Do you identify as an intense, passionate leader with sky-high expectations? Are you afraid that being “too compassionate” or “too empathetic” will mean that your teams won’t hit their deadlines and milestones? On the other hand, are you worried that you might come across as a dictator and inadvertently be shutting down creative ideas and innovation?

Many of us struggle to find the right balance for a leadership style that is both supportive AND pushes for the highest quality standards. Try these three strategies for a different approach that inspires your team to get results.

1. Slow down to build trust one person at a time

Yes, you might be an intense, passionate, and emotional person. It’s hard to turn that intensity down when you’re excited about an idea and want to push forward to define what’s next. However, your ideas and expectations will be more widely accepted if there is high trust between you and your teams.

In addition to the presentations, meetings, and high stakes conversations, also slow down and spend the time to build trust. The easiest way to connect during 1–1 conversations with your people. One handy rule of thumb is to open the conversation with topics that are outside of work. Spend the first five or ten minutes of the meeting build trust before diving into the to-do list of problems or deliverables to be discussed.

One of my clients, let’s call her Jingyi, is a first generation immigrant and new to American culture. She often bemoaned: “I’m terrible at small talk,” yet know that as a vice president at her enterprise software company it was crucial that she build relationships with her peers and the executive team. We developed a system to talk about non-work projects across the following themes, with some example questions:

Social & Cultural Events

• How did you spend your time this past weekend?

• What do you do for fun?

• Did you watch the Superbowl / Oscars / news about the Elizabeth Holmes trial?

• What stood out for you from our last offsite / dinner / lunch & learn?

Family & Pets
Pick up on cues from peeks into their personal life during these zoom times. Are there photos or indications of who they live with? You can ask how their kids are doing in school or how puppy training is going. Or, if they are typically off-video or with a blurred background, know that they may be less comfortable talking about these personal topics.

Mutual Passions
Figure out what you might share as a mutual passion. Perhaps you’re both foodies or love to travel. Perhaps there’s a shared love of music, shows, or artists.

Work Related Opinions
These aren’t directly about the work, but more to get a sense of shared common ground and to better understand the other person’s perspective of the world.

• How do you feel about our new CEO?

• What did you think of that last presentation?

• Did you see that the company is offering a new health benefit?

Personal / Vulnerable Check-Ins
This category can feel a bit more intrusive but is helpful when you already have built up some trust. These topics are better for ongoing 1–1s especially when the person has indicated that they are more open to discussing these topics.

• How are you coping with the rapid pace of this project / new COVID restrictions / the new in-person schedule?

• Is there anything I can do to support you?

Finally, when building trust, the #1 way to get someone to open up is to first share something personal and specific. You can set the tone for the conversation by going first and sharing how you feel about any of the above topics. The other person’s response will give you a hint of whether they’re also eager to share and connect or if they’d prefer to move on to the next agenda item in your 1–1.

2. Listen first in team meetings

Many leaders who have sky-high expectations can tend to command and take control of a team meeting. We assume that setting the agenda and clearly laying out the expectations will make it easier for others to follow our lead.

If you’re hard to please, it can be difficult for others to continually listen to what they perceive are unrealistic expectations or a leadership style that doesn’t leave room for other opinions.

Instead, try a different tactic and take a back seat in the team meetings. You could try:

• Asking open-ended questions and truly listening to what others have to say. If this is a new communication style for you, you might have to pick a trusted team member and ask them to go first in answering the question. Alternately, call upon someone who is comfortable giving an answer on-the-spot.

• Have someone else run the team meeting and set the agenda. Consider rotating this role between team members.

You can always summarize the meeting and clearly set out next steps and expectations moving forward.

3. Match your people’s communication and emotional style

You work with a number of different team members. Think about the people who you have instant chemistry with. These people are likely to have similar communication and emotional styles to yours. For example, f you are a person who is direct, pragmatic and caring, you likely have an affinity for others who share those values.

To be an effective leader, focus on building range. You can be more intense and direct with people who are like you. For other quieter team members, this intensity will shut them down. Try to match the other person’s communication and emotional style and act in a way that gives them space to process information in a way that’s comfortable for them. For example, a quieter leader may feel the pressure of having to come up with a brilliant answer on the spot. Instead, give them the space to consider the question and share their thoughts with you later on.

Bottom-Line

As an intense, passionate leader you can both have high expectations AND practice the servant-leader mindset of being compassionate and empathetic. Experiment with showing up differently as a leader by 1. Slowing down to build trust one person at a time, 2. Listening first in team meetings, and 3. Matching your people’s communication and emotional style.

The #1 Secret to Shifting Your Mindset

Like it or not, it’s about breaking through your resistance and establishing that f*cking gratitude practice

Photo by Manja Vitolic on Unsplash

Cats, and us humans too, are resistant to change. We cling to existing patterns and behaviors, hoping that things can stay the same. Even when we know that things are good for us — exercise, eating well, taking rest breaks— it’s really hard for us to do them.

We often base our daily performance and happiness on our state of mind. The good news is that unlike our ability to control others, we can start by impacting our own mindset. A gratitude practice is the simplest, most straightforward way to shift our minds. There’s a ton of research that backs this up¹. Yet like many of us, I’ve personally started, paused, and fallen off the wagon with gratitude so many times that I mentally refer to it as that f*ucking gratitude practice. I’ve seen this resistance and embracing of the practice happen for many of my clients too.

These are four techniques to help build the muscle of a gratitude practice. And maybe, eventually, we can even be grateful about it.

1. Be hyper-specific

It’s easy to half-ass an answer by retreating to the safety of generalities and platitudes. Specifics give us a way to drill down to the kernel of what’s most important. It can help elicit emotions and really help us feel the thing that we’re grateful for. Notice the difference between saying:

I’m grateful for my cat.

vs.

I’m grateful when my cat Mochii sits on my lap during client calls. I can feel the mighty rumble of her purr. Stroking her soft fur helps center me and focus my listening.

Part of a gratitude practice is feeling and experiencing the object of your gratitude. The more specific you can get, the more impactful it will be.

2. Keep it interesting

Repeating a daily gratitude practice can get boring. There’s a litany of things we might be grateful for: our health, loved ones, friends, a team at work, a meal, or something we did today. It can start to feel tedious when we keep repeating the same things we’re grateful for. One way out of this is to be specific. A second way is to think of categories and thought-starters for types of gratitude. Categories and thought-starters will help us get started when we can’t think of anything and want to retreat to the platitudes, but also keeps it interesting to provoke a brain thinking in different ways. These are some categories that I have personally experienced and also hear as tips from many others:

• Of all the people you encountered today, who helped you or who did you help the most?

• What object or person was most inspiring or thought-provoking?

• What made you laugh? Or elicit a strong emotion, either positive or negative.

• Which one of your senses experienced something different today? It could be something beautiful you heard or saw, an unexpected taste or smell, or perhaps a pleasing texture you touched.

3. Establish a routine

It’s hard to start something new, especially something that might feel like a dubious practice. Try to create a daily or weekly gratitude practice by tying it into your routine. Some things to consider:

• End your work day or work week with gratitudes

• If you have a regular journaling or mediation practice, add gratitude to it.

• Think about what you’re grateful for either first thing in the morning, or the last thing at night before you fall asleep.

• Incorporate it into regular activities such as brushing your teeth or mealtimes

You don’t have to commit to doing this forever. Simply try it for a couple of weeks and see if anything feels different. 

4. Create a ritual with others  

Taking the routine one step further is to incorporate another person or group of people as an accountability partner into your gratitude practice. When my daughter was younger, one of our bedtime rituals was to take turns sharing all the things we were grateful for that day. Some families play rose/thorn/bud at the dinner table, sharing something you’re grateful for (rose), a challenge from the day (thorn), and something you’re looking forward to (bud). 

In a corporate setting, teams can start a weekly meeting or a regular 1–1 with sharing something they’re grateful for. If you have remote team members or loved ones that are far away, consider texting as a way to share grateful parts of your day. 

Bottom-Line

It is hard to establish and maintain a gratitude practice, hence my calling it that f*cking gratitude practice. 

Remember, don’t beat yourself up if you fall off the wagon. It happens to all of us. The next time you remember, perhaps when you’re in a bad mood or dealing with an emotional setback, try starting again. You may not feel its immediate impacts, but like doing reps in weightlifting, a gratitude practice slowly shifts your brain over time, building resilience to help shift your mindset.

Try the four techniques of 1. Be hyper specific, 2. Keep it interesting, 3. Establish a routine, and 4. Create a ritual with others to play with your gratitude practice. 

For me, I find that sometimes the best way to go is through the path of resistance. So it’s when I’m most resentful of that f*ucking gratitude practice is when I’m likely to need it the most. 

¹A brief gathering of research into gratitude

• Brené Brown on Joy & Gratitude

• Your Brain on Gratitude and Neural Correlates on Gratitude

• How Gratitude Changes You and Your Brain

Leadership Seasons & Rituals

Photo by Chris Lawton on Unsplash

There are six weeks left in 2021, and I am acutely aware of the season change into winter and the warm-but-frantic end of year period with Thanksgiving, December, and the New Year. Many of us are acutely aware of seasonality in our personal lives, with the upcoming holidays as simply one example. Seasonality contrasts summer and the school year if we’re recent college grads or have children. Seasonality is the recognition of the shorter days and longer nights or celebration of yearly rituals.

In addition to our personal lives, seasonality also exists within a professional context. Taking advantage of the right seasons for you is one way to amplify your leadership growth. Here’s how.

1. Be aware of the seasonality within your career

I’m broadly using the term “seasonality” to refer to periods of time, ranging from months to quarters to years, and the intentional transition between them. Think about the different seasons you encounter in your professional life.

Looking at the time scale of weeks / months / quarters, each “season” will have different characteristics, for example:

• The quarter close acceleration to hit sales numbers or other key metrics

• Important projects with a kick-off, heads-down busy execution, and launch

• A busier end of year retail time between Thanksgiving and Christmas (from my U.S.-centric context)

• A slower summer time when many people take time off or have the summer Fridays as half-days or entirely off

• Your first 30/60/90 days at a new job or getting to know a new boss

Often, high performers will rush to the next demanding season without taking time to pause / rest and evaluate if anything has changed. No rest or pausing can lead to burnout or many years of routine in an unfulfilling job. Acknowledging seasons can help provide a pause for reflection.

Looking at the scale of half-years or years, there are different examples:

• Half-yearly or annual performance reviews to look at the feedback and the hoped-for rewards

• The exciting period where you’re looking to acquire a new set of skills or learnings

• The restless time when you’re ready to move positions, either inside the company or externally

• The period of time before a company re-org and dealing with the fall-out of it afterward

• A time to consider a sabbatical or explore a completely different career

These career seasons are cyclical and will like repeat through different times of your life. Often it’s hard to see that you’re in a season unless you look back at patterns of your career.

2. Fighting against a season’s nature can be energy draining

Seasons, and your experience of them, intrinsically have their nature. When it’s monsoon season in the tropics, I want to cozy up indoors and have long conversations with friends. When it gets darker at night, I want to nest and cook warming stews and roast vegetables. When summer comes, I get an itch to travel far.

Yet, many of us in a professional context will fight against a season’s nature.

• If it’s your first 30/60/90 days at a new job, you’re expected to be the new person and not know how things work. Yet so often, we want to come in and quickly prove ourselves as the expert. Trying to establish yourself as an expert can backfire, setting us up with an unlikeable know-it-all reputation and potentially sour relationships that haven’t had enough time for trust to flourish

• After returning to work postpartum, many working parents want to be their same professional self without acknowledging the burden of raging hormones or the need to pump breast milk (for biological mothers), or the haze and fatigue from sleepless nights with a baby.

• Performance review season is often an unwanted burden. We try to complete all our regular work at the same business-as-usual pace while simultaneously shifting to a reflective state of mind to consider our own self-reviews and reflect on how our team has done. Managers shift into combat mode to rally promotions and bonuses for their teams while continuing to execute the daily tasks. This context shifting is draining.

Finally, the nature of seasons is change. You might have been in the same job for years, and it’s now feeling boring or you have no opportunity for advancement. You might have been running through years of grind and hard work with meagre long weekends or 5-day vacations to see you through. There’s nothing wrong with you if you feel like something is missing or you want to change. This change is the normal rhythm of seasons.

3. Celebrate the seasons with rituals

After that doom-and-gloom view of seasons, you might wonder what we can do about the seasons of our professional life. My advice is not to fight against seasonality but to name it and embrace it wholeheartedly with rituals that celebrate the passage of time and changing of seasons.

Rituals make magic out of the everyday and sanctify it into something worth remembering and acknowledging. Think about how you might celebrate some of the professional seasons named above that resonate with you. Some things to consider are:

• At the end of each week, celebrate what matters to you and your team. It could be the wins or shout-outs to team members. It could be the top customer insights or the biggest mistakes.

• Prepare for performance review season by clearing your regular calendar and kicking it off with a ritual that acknowledges how much you care about feedback and continuous learning for the team. Close the review season with a group ceremony. Continue this ceremony into the 1–1 feedback sessions.

• Tie off-sites to the personal seasons. Consider volunteering at a food bank as a team around the holidays.

• Take the time to do quarterly or half-yearly futurecasting sessions to imagine where the team or company is going. Kick these off with a celebration of the everyday execution and a ritual to signify that the coming workshop days are different — we’re going to think about impossible dreams.

These are examples of possible rituals around work seasons. Some of these will sound ludicrous, while others may resonate. Which ones do you want to try?

4. Experiment with Seasons & Rituals

I’m entering the third year running my own business. I’ve learned that there is a rhythm of when people seek out coaching, when corporations plan for workshops, how conferences & speaking engagements work, and when to launch books. Most of all, I’ve learned that I need to build in my seasons of rest.

Some of the rituals that I keep are:

• A weekly mastermind with a group of three other coaches where we actively share our success that week

• A monthly meeting of design leaders turned coaches & consultants where we celebrate our sense of connection

• I create an intention word and North Star as a theme for my year. My word for 2021 was whitespace, and it’s tied to pacing myself as an entrepreneur and launching my first book, Make Space to Lead.

The new ones that I will try for next year are:

• Block out the weeks and months of the year when I travel with my family and seek my solo retreats for personal growth.

• Map out my group programs and retreats. Genuinely understanding the time it takes to share about them, both before and after the session dates.

• And more to come!

Finally, as the New Year approaches, if you want to experiment with seasons and rituals, I’m offering support to discover your Leadership North Star in a 6-week program to explore and set your 2022 roadmap.

Bottom-Line

Which seasons in your professional life are important for you to name? Which ones have you been ignoring for too long? How might you actively celebrate and add rituals to mark the transition between seasons?

Advance your leadership by 1. Naming the seasons that matter in your career, 2. Work with the energy of a season, 3. Celebrate the seasons with rituals, and 4. Keep experimenting.

Book Insider: Winning the Amazon Best Seller Game & How to Create Your own Leadership Rules

My first book, Make Space to Lead, came out last week and within several days was at the top of six best-selling Amazon categories. But let me tell you a dirty little secret. While this book is considered successful by many standards in the publishing industry, especially for a first-time author and an independent publisher, it’s about learning the rules of the game and choosing which ones to follow. You see, it’s really not that hard to become an Amazon best-seller. And I’m a good student at learning and following the rules.

Read on to learn the secret to becoming an Amazon best seller. Perhaps more importantly, I’ll share how leaders can learn from understanding the rules of the game they’re playing in, whether at their corporate jobs or fund-raising or entrepreneurship, and how to find internal success within these external metrics.

How to Become an Amazon Best Seller

Feel free to skim through this “how-to”-ish section and jump ahead to the leadership learnings below.

1. Pick Your Ten Categories

First of all, know that my reporting is based on personal experience and a week’s worth of data. One of my values is experimentation, and I continue to be fascinated by how different industries work. I like to observe, watch, and then share.

Amazon organizes its book browsing by ebooks and books, then further splits them into additional categories. The easiest way to become a bestseller is to pick an obscure category to have your book highlighted within. Pick categories that are attainable but also believable.

So, I chose three competitive categories, four medium (or evergreen), and three easy categories. And as advised, I focused on ebooks versus books because it’s far easier for people to make quick digital sale, and as an author, I won’t incur the printing & delivery costs of a physical book.

Pick your categories by browsing through the kindle ebook store and scrolling down to the Department section on the bottom left. Expand each of the categories to view subcategories and see the books listed. If they are popular books that you’ve heard of, then this is likely a competitive category. You can review the Amazon Best Sales Rank (ABSR) of the #1 best sellers in these categories to see which ones might be beatable. These were my categories.

Competitive

• Business & Money > Management & Leadership > Leadership

• Self-Help > Personal Transformation

• Business & Money > Business Life > Motivation & Self-Improvement

Medium (Evergreen)

• Computers & Technology > Computer Science > Human-Computer Interaction

• Self-Help > Creativity

• Computers & Technology > Tech Culture & Computer Literacy > Social Aspects

• Computers & Technology > Business > History

Easy

• Computers & Technology > Interactive & Multimedia

• Education & Teaching > Higher & Continuing Education > Graduate School > Business

• Computers & Technology > Digital Media

However, Amazon does not make this process easy. Once your book has been uploaded and published to Kindle Direct Publishing (KDP), you must submit a help request to customer support to request that they manually add you to these selected categories. It’s a seamless process, and they updated my categories within 12 hours.

Requesting an update to your Amazon Categories via KDP

2. Gather Reviews for Social Proof

The next two parts of the process are likely more familiar. Potential book readers want to read reviews and know what others thought of the book. Amazon lets you set five free days for your ebook, which I did before the launch, and personally asked about forty-five friends and colleagues to read the book and leave reviews. Several weeks earlier, I had sent them PDF copies of the book to read beforehand. On launch day, I had about twenty reviews.

3. Ask People to Buy. Make it Easy.

The expert advisors told me to set my ebook price at 99c for the first week of launch. This makes it an easy yes when you ask your friends & family members to buy the book. Anyone can spare 99c to support you. It also helps make the message less uncomfortable; rather than asking someone directly for money, you can let them know about the special promotional price.

My Results

My book launched on Tuesday. By the end of the day, it had made #1 in some of the easy categories. By Friday, it had made #1 in six categories — three easy and three evergreen. And the true dirty little secret?

In four days, I had sold roughly 100 ebooks. That put me as a #1 best seller in six categories.

That low number—only 100?— was a little crazy to me given the numbers I’m used to dealing with in tech or even for the readership of my medium posts; however, I needed to understand the different rules of the book publishing ecosystem.

That is how to win at the Amazon Best Seller Game. You too can play and choose what rules to follow.

What about leadership?

You can apply all the lessons from understanding the Amazon best-seller game to both leadership and entrepreneurship.

1. Understanding a new industry (or company) requires knowing the rules of the game

As a leader, you will constantly face new challenges and spaces. It might be expanding into a new industry, or starting work at a different company with its own unwritten norms and rules. First, recognize that all of this is new to you. meaning that you’ll need to put in the time to understand this system. Treat it as a game where you’re still figuring out the rules.

2. Build relationships and do your research

To learn the game, seek out people who can help educate you. Building relationships is best through asking for 1–1 conversations and approaching them with a genuine sense of curiosity. For the most part, people want to share their expertise. You can seek people out via recommendations in your network, or you pay expert consultants. Another approach is to do your own research through reading or consuming media.

3. Understand your internal motivations for playing the game

Everyone will have their own motivations for starting something new, whether it’s a new company or a first book. For me, I wrote my book to both process / share my internal growth as well as share frameworks and experiments that have worked well for clients that I support. There’s only a limited number of 1–1 clients I can work with directly, and I wanted to share some of these leadership lessons more widely. I’ve spent years writing blog posts, and the long-form book creation process felt like a culmination of all the learnings, packaged in one place.

It was important to me to realize that intrinsic success was comprised of:

• Writing the book and honing my skills as a writer

• Sharing the Make Space to Lead messages more broadly and to different audiences

• Providing tried-and-true coaching frameworks, tools, and experiments in one consolidated package

4. Understand what external motivations matter

For me, achieving Amazon best seller status as well as gathering reviews meant that I had social proof that the book was worth reading. These external measures would help spread the content more widely.

It was clear that the book wasn’t about the money from book sales but a way of scaling my business so that my message could reach more people and perhaps a different audience than my existing network of people in technology.

It’s okay to care about external motivations. Caring about what other people think of you is simply a part of being human. Understanding what external motivations mattered to me made it easier to follow the rules and play the game.

Bottom-Line

Ultimately leadership is about following your own rules. It’s crucial to first understand the rules of the system because we all exist within that container. With that understanding, you’ll have the knowledge of what rules to keep and which ones to break. Making that decision will depend on your internal and external motivations.

I’m proud of having my first book achieve Amazon best seller status, and I’m even prouder of having a greater understanding of the publishing world and what goes into the success of a book.

Leading Through Fear

Photo by Melanie Wasser on Unsplash

Last Saturday, I had a surfing accident on Ocean Beach in San Francisco. I have a bruised face and a black eye, however, I’m grateful that there is no permanent damage to my face or my eye. Right after the accident, I was sobbing and shaking on the beach, gripped by pain and fear. Twenty four hours later, I started experiencing flashes and black spots in my left eye, leading to extreme anxiety and fear of losing my vision. Happily I’m fine, having been checked out by talented opthamologists.

Bruises will fade, the resilience and lessons persist. Fear is a natural part of leadership and I’m sharing three lessons on how to feel the fear to become a better leader.

1. Fear is normal. Fear is part of leading.

Many of us want to think that our leaders are fearless and always have the right answers in the face of uncertainty. This expectation makes it tough to be the leader. Leaders feel that we have to be perfect, to have our acts together, and always know what to do next. If we feel any fear, the first instinct is often to bury it, to ignore this inconvenient emotion and instead move into action and problem-solving.

That’s not the healthiest way of addressing fear. Unrecognized fear, like the unacknowledged elephant in the room, will pop up later, perhaps as anxiety and sleepless nights.

Instead, take another approach. Recognize that fear is a normal part of life and leadership. We all felt it collectively during the unknowns from the early months of 2020 when we had very little understanding of COVID-19. Fear hits us all whether we’re the the CEO or the intern, the dad or the first responder.

Consider feeling your fear.

• If your first response is to cry, hold your pets tight, or call your mom, it’s okay. Go with it.

• Notice where the fear manifests in your body. For many people, it’s a constriction in the jaw, shoulders,or stomache. For others, it’s a tightness in their throat, or the feeling of carrying a heavy weight on their back.

• You may want to verbalize the fear to a trusted friend, or write it in a journal. It’s okay that the fear sounds ridiculous. Fear is not rational.

• Sometimes fear also morphs into other emotions. It’s normal to laugh or make a joke about it. Humor helps disperse the tension.

“Fear is excitement without the breath.”

— Fritz Perls, founder of Gestalt therapy*

The physical feelings of fear are similar to excitement. It is helpful to focus on the present and pay attention to your breath. The simply act of breathing in and out, focusing on the feelings of fear in your body, is grounding.

For more on controlling emotions, watch this 18 minute TED talk with Dr. Lisa Feldman Barrett for techniques on how you can influence whether you’re feeling excitement or fear with a change in perspective… and lots of practice.

2. Consider the Best and Worst Cases

When we’re in fear, our brains can get stuck in an unhealthy cognitive loop. One technique that helps me is to actively do research to consider both the best and the worst cases, and then to anchor on the ones that are most probable.

One of my clients had done a bad job with a leadership team presentation. We went through the possible worst cases:

• My boss is disappointed. He’ll never trust me with presenting again.

• I made a fool of myself. I let down my team. They won’t work hard for me any more.

• The strategy will get rejected and we’ll have lost 3 months of work.

• I’m going to be fired.

And the possible best cases:

• My boss and I will become closer as he gives me feedback, and we build trust

• I’ve learned that this presentation method doesn’t work. Next time I’ll send a pre-read, or have separate conversations with key stakeholders to get their buy-in ahead of time.

• The next presentation will go better.

Listing out the different possibilities calms the mental loop of fearful self-recrimination. Simply stating out some of the worst fears — e.g. I’m going to be fired — lets us realize that these are improbable outcomes. Instead, generating many possibilities helps to focus the mind. From these possibilities, a next step can be generated, for example, to hold a neutral retrospective with the boss or the team to learn from this experience.

A related tool is Tim Ferriss’ Fear Setting exercise that similarly uses your brain to go through a series of “what if”s.

3. Fear Doesn’t Last Forever

On Sunday night, I experienced light flashes, large floaters, and black spots in my injured eye. I was able to talk to an on-call opthamologist who walked me through the worst case (surgery for a detached retina) and the best case (vitreous jelly knocked around which will resolve itself) scenarios. I was scheduled to go into their practice at 9am on Monday morning.

That morning, I woke up scared. I was afraid of going blind. In the car ride to their practice, I was hyperventilating and having trouble breathing. At the office, I filled out paperwork… and then waited. My eyes were dilated, so I could no longer look at screens as a distraction. I waited to be processed by a first nurse… waited some more… and then saw a second nurse. More waiting… almost five hours in total. In the last 30 minutes before I saw the doctor, about six hours after I’d woken up in fear, I noticed that my fear was gone. It had turned into boredom, impatience, irritation, and finally goofiness as I took selfies with the medical equipment.

The fear shifted over those six hours. When you feel the emotions rather than suppressing them, they will naturally change over time.

Do you remember that sense of fear you felt at the start of the pandemic? There was a period where some of us were quarantining groceries and deliveries at the front door for 12 hours, and severely sheltering-in-place. Over the past year and a half, we’ve gotten more information and gotten used a different way of life. The fear has shifted as we settle into habits and keep experiencing work and home.

Fear doesn’t last forever. When you lean into the fear and accept that it’s there, the emotion will eventually change. Change is a part of leadership and of being human.

Bottom-Line

Fear is a normal part of leadership. We all feel it when we face adversity and uncertainty. Feel the fear rather than suppressing it. Three reminders through this process are 1. Know that fear is normal, 2. Consider the best and worst cases, and 3. Appreciate that fear doesn’t last forever.

*Thank you to Jim Herman for reminding me of this quote

Leadership Tool: The Power of Being Specific

Photo by Steven Wright on Unsplash

Many of us fall into a common pattern of speaking in platitudes, abstractions, or generalities. This often happens when we are distracted and not completely focused. Think about the last time someone asked, “How are you?” Many of us automatically reply, “Fine, thank you. And you?” and then we continue on with our day. We back on these habitual communication patterns.

If you’re trying to influence others in an organization or build trust with key relationships, a powerful leadership technique is to stop talking in abstractions. Instead, dive deeper into the specifics of a conversation. Moving into specifics makes the experience of the conversation more engaging, leading to a stronger connection with the other people. Here’s three ways you can experiment with being more specific.

1. Share a problem

People love to problem solve and give advice. Ground the conversation you’re having with the specifics of a problem to engage your listener. Imagine that you’re leading a team and looking to connect with other leaders in your company. Here’s a contrast between abstract versus specific problem sharing.

Abstract problem: I’m having an issue with one of my team members. He often fails to meet my high expectations, and I’m worried that this will be an ongoing problem.

Specific problem: I’m having a problem with Joe who runs recruiting on my People Ops team. He does a great job with meeting his targets. His team always hits their outreach and close numbers. However, I’ve noticed that Joe doesn’t tend to be open about problems he runs into. He doesn’t want to come to me with problems, and I believe he wants to reassure me that he can handle them himself. I expect my direct reports to be open about their mistakes and challenges so I can support him, and also so that they can learn from each other.

Going specific provides more fodder for the conversation. Sharing a problem invites the people you’re talking to engage and collaborate on problem solving with you. Going specific can also help you get personally unstuck and see some ways out of the problem.

2. Tell a story with emotion

It’s impossible to tell a story without going into details. Part of storytelling is having a protagonist who goes through an experience—positive or negative—and comes out the other side having learned something insightful.

If you’re sharing a presentation about strategies for how to improve email list conversion for a retail brand that sells face masks, consider telling a story rather than relying on bullet points within a slidedeck. For example:

Kareem subscribes to our email list. He’s a busy with a full-time job and also has twins in elementary school. He receives a large number of emails, both personal and professional. He’s worried about their health now that his twins are back to in-person school and it’s the start of flu season. Each evening, he sorts through his email as quickly possible to clear out his inbox. Yesterday evening, he notices a subject line: “We’ve restocked kids’ mask sizes for cold & flu season” and opens it.

The specifics in this story can help a leader pitch ideas for marketing strategies to her leadership team. It grounds the business problem in a story experienced by a customer.

For bonus points, tell the story with emotion, walking through the protagonist’s pain points and slowly unveiling what happens next.

3. Be personally vulnerable

Finally, one of the most accessible ways to be specific is with sharing our own stories. Being personally vulnerable and diving into details models behavior for the other person and can establish a foundation of trust.

For example, for one of the companies I consult with, we kick off our weekly team meeting with gratitudes. Some can be high level:

• I’m grateful for the sunshine today. It’s a welcome break from the frigid unseasonable lows of the past few weeks.

However, the entire zoom room buzzes with connection when someone shares something personally vulnerable and specific:

• I’ve been having trouble getting my teen son to open up with me. He’s been having trouble turning in homework at school. Yesterday, he got into such a deep hole that he was completely overwhelmed. I’m grateful that he finally came to me for help. We looked at the work together and will talk to his teacher later today.

Sharing details of our personal lives, perhaps in a team meeting or in a 1–1 situation helps model that we care about the entire human. Going first with a personal story requires courage and vulnerability, but often these specifics are what builds the long term relationships that leaders need to develop.

Bottom-Line

One of the most powerful leadership tools to foster connection and greater influence is to be more specific. Three ways on how to be more specific is by 1. Sharing a problem, 2. Telling a story with emotion, and 3. Being personally vulnerable. Moving away from the abstract can feel uncomfortable, but when used in conversation will result in stronger connections.

Learning to Ask for Help

How often in your days or weeks do you support and help other people? Many of us believe that it’s our job, whether in our role as a servant-leader in corporate management or as a coach / consultant who is paid to help others.

How often do you ask someone else for help?

This is the far more difficult step. We want to appear as self-sufficient, seemly-confident leaders who have all our shit together. Asking for help can feel weak or that we’re an imposition on others. But what if practicing asking for help is the power move of leadership? This might be especially good to practice if asking for help is an atypical pattern for you.

I’m sharing three tips to remember. Thinking about them may make it easier for you to practice asking for help.

1. It feels good to be helpful

The first tip is to start with empathy. Asking for help can feel icky. To shift your mindset, think about a time when someone asked you for help AND it felt good.

Have you ever been asked by a former coworker to make an introduction to someone else you knew on LinkedIn? If it was serendipitous enough that you *actually* knew them both well and thought that they would get along, you likely made the introduction. My guess is that it felt good to connect two people.

Similarly, if it’s easy enough to help someone else, it feels good to say yes and to support their work / goals / passions with a small gesture.

Remember that feeling, that it feels good to be helpful.

So if you’re on the other side, perhaps you’re offering up a gift by giving the other person an opportunity to feel good.

2. People are busy; make it easy

But, but, but… you say. Sometimes it feels terrible when someone asks you for help, and you’re too busy, and you forget about it and feel bad. You end up completely ghosting them. And feel guilty about it.

It’s okay, we’ve all been there.

The reality is that people are busy. If you’re asking someone for help, make it easy for them. Many clients I work with struggle with networking. They may want to stay in touch with former coworkers or want to reach out to folks to have casual chats about potentially moving jobs. If you want to ask a friend, call her Amira, for help with an intro to Patrice, make it easy for Amira:

• Amira will likely want to get Patrice’s permission to make the intro

• Give Amira a short paragraph about yourself. Write it to be interesting / compelling for Patrice

• Do your research and share one or two sentences about what draws you to Patrice. Bonus points: share how might you be helpful to Patrice.

• Have an ask for Patrice, the more specific the better. For example: I’d love to learn how you moved from being an engineer into the sales organization or Given that I’ve only worked at startups, I’m curious about what different skills are needed to be a marketing lead in a large company.

People are busy. Put yourself in their shoes and make it as easy as possible for them to say yes to your ask.

3. Let go of expectations (around the outcome)

Finally, consider that the simple act of asking for help might be enough. Let go of your need for the person to respond with a “Yes” or “No, I’m too busy.” Drop the expectations around the outcome and celebrate that you were able to practice a new leadership muscle.

Often we can be paralyzed with anxiety after we make the ask:

• Will they think that I was too needy or self-promotional?

• They didn’t respond yet. I think they hate me.

• What I asked for was really dumb. And how I asked was also dumb.

• I shouldn’t have asked her.

These are all common, human self-judgements that we put on ourselves as we wait to hear the outcome of the ask.

Instead, consider that people are busy, and it’s most common that you won’t get a response. It’s okay to not get a reponse. Let go of the expectations—though you should also follow up with a polite email or text a week later, people are busy—and know that you have very little control over whether or not someone responds.

All you can do is continue to practice asking for help.

Bottom Line

For many competent leaders, it can be really hard to ask for help. If you’d like to practice more of that leadership muscle, consider that 1. it feels good to be helpful, 2. people are busy; make it easy, and 3. let go of expectations (around the outcome). I know that asking for help is a skill that’s hard for me. Yet every time I practice it, it leads to stronger relationships and my own leadership growth.

The Power of Being a N00b

Photo by Tobias on Unsplash

This is scary. I don’t know what to do next. I’m such an idiot. I’m making so many mistakes. Do I belong here?

Being a n00b or a newbie, no matter what the unfamiliar situation— job, school, community, career, or learning a new skill—is deeply uncomfortable. It fills us with mental anxiety as well as the large barrier of getting up-to-speed in an unknown domain. These feelings of imposter syndrome are entirely normal.

I’ve felt this when I started writing my first book, Make Space to Lead, and embraced a new identity as an author. Gradually as I eased into a writing rhythm, supported by a book coach, the n00b feeling eased, only to reemerge at 10x scale when I’m now transitioning into marketing and promoting for a November 2nd book launch.

A wise coach friend of mine reminded me to enjoy the process. She wished for me ”to treasure and enjoy the experience. You only ever publish your first book once!”

So, if you’re feeling like a n00b, no matter what your current situation, channel some Brené Brown and acknowledge that you’re experiencing a Fucking First Time (FFT). FFTs are often ridiculously difficult and feel like they’re kicking your butt. Instead, pick one of these three strategies to embrace the power of being a n00b.

1. Celebrate Beginner’s Mind

Beginner’s mind is the practice of seeing life without the preconceived notions and expectations of the more skeptical expert’s mind. As a newbie, we know very little. But our advantage is having all the questions and knowing none of the answers. Plus, because we’re new, we’re not expected to know the answers. This can be easy to forget when we’re in a new environment. Our anxieties and personal expectations want us to be as knowledgeable as the more experienced people. Simply remember that there are no stupid questions. And even if there were, maybe it’s okay to look foolish as a beginner.

The advantage of this approach and fearless curiosity is that it can uncover new insights for others. You bring in a fresh perspective to a company or a situation in a unique manner that more tenured professionals are no longer able to see.

Be curious. Be humble. Seek to learn. Drop the expectations.

2. Appreciate Fresh Energy and Enthusiasm

I’ve started meeting weekly with an accountability partner as we both have books launching in November. The difference is that he’s a bestselling author and has written five books (fiction and non-fiction). I feel that I’ve lucked out to find a partner with such experience, and to my surprise, he acknowledged that it felt like a breath of fresh air to see my energy and enthusiasm.

As a n00b, we may have low skill in the domain, but can make up for it with will. It’s a new subject area, and there is a gleam to shiny new objects. Many of us have heaping amounts of enthusiasm when doing a thing for the first time. This activation energy can be contagious to those around us.

You may have experienced this energy when working with a new grad or an summer intern at a job. Many of them are hugely motivated, eager to learn and try anything new, and bring in a youthful energy.

When things feel frustrating, remember that you’re learning. Try to feel that burst of energy and enthusiasm and let that carry you through this period of unfamiliarity.

3. Opportunity to Reframe Your Mindset

Finally, use this n00b state as the opportunity to reframe your mindset. It will feel difficult and overwhelming to grow in a new area, however, reminding yourself of these tips will help with the reframe:

• Relish the experience

• Embrace the mess and know that you will make mistakes

• Build a community of guides and fellow n00bs to share the journey

• Don’t forget to laugh (at yourself)

Bottom Line

Change can be deeply uncomfortable and have aspects of both fear and exhilaration. Remember that when you’re a n00b, you can embrace your power by 1. Celebrating beginner’s mind, 2. Appreciating the energy, and 3. Finding opportunities to reframe.

Book Insider: Marketing with Integrity

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Many leaders do their work from a sense of service and purpose. Many are quiet leaders who simply want to do the best job and not toot their own horn. Yet we can run into a blocker when we do work we’re passionate about and want to share it on a bigger scale. We ask ourselves: 

What’s my personal brand? How do I share it or my passion projects with others without seeming self-promotional?

As a first time author newly connected to the writing community, I’m hearing this same issue with authors who love book writing but dislike the act of promotion or marketing for their book. However, if we can be connected to our message and to spreading it from a sense of service, we can shift our mindset. We can define our personal brand, and also market with integrity using these four core learnings. 

1. You have something to say

If you’re a new author or early in your career, you might not call yourself a leader, or think that you have any type of expertise that anyone else would care about. We often feel unqualified, that there’s so many other people out there who have written or spoken on the subject and tell ourselves: “Who am I to have an opinion? What do I have that’s worth sharing?” 

In reality, that’s not true. Case in point. I read a lot of leadership books. Many of them repeat the same core messages: 

• Think bigger. Don’t be afraid of dreaming and reaching for your full possibility

• Celebrate your unique strengths

• Be aware of your limiting beliefs that hold you back

• Connections & relationships matter

• Here’s some tools & frameworks to help

What’s unique about each one is that the author is experiencing leadership through their own lens, whether it’s as an ex-FBI hostage negotiator, a relationship therapist, or a black woman in corporate America. (those also happen to be three of my most-recommended leadership books).

You always have something to say because your experience comes from a unique place. You might be the son of a Southern chicken farmer who’s the first in your family to attend college, or an intern at an fast growing tech startup in LA. Your perspective will be fascinating to some number of people, and the story is yours. 

2. People love stories

I believe that as humans, we are continually seeking connection. We do this through revisiting memories and stories with our long-lasting relationships. And we do this with new relationships. We listen to their stories and we share ours. We do this to learn what we have in common and perhaps also to be entertained or discover a new insight. 

This TedX talk by Abbey Gibb inspires people to “Share Your Shit.” She shares that we are a connect-starved society. And that’s even more true than ever after 18 months of COVID isolation. Everyone is craving interactions and stories. So be emotional. Be vulnerable. Be real. And that will draw others to your story. 

What if marketing was simply sharing your story? We all know how to tell stories to our family or to our friends over dinner. The story can be funny, whimsical, sad, or self-deprecation. And it should also be entertaining. Stories are the way we connect with others. 

3. Know who benefits from your message

Part of this connecting with others is knowing who would find the story to be interesting. If you think about connecting to someone else from a sense of service, think about who would most benefit from hearing your message. 

On the surface level, my book Make Space to Lead shares my journey of leaving Facebook and starting my own business as a leadership coach / consultant / speaker / writer. But on the emotional level, I wrote the leadership book to help people make change in their life. 

The clients I’ve been working with have benefited from the teachings, tools, and coaching shared in the book. The book is written for them and for others who share my struggles: 

• High-achieving professionals who have always believed that we must continually drive ourselves to work harder to gain the success we desire. But the reality is that this is a pattern of busyness and overwork that we’ve trapped ourselves within.

• Goal setters and planners who have reached for the next gold star their entire lives. And when they achieve it, they quickly reset the goalposts to aim for the next milestone. Yet now, this approach feels hollow.

• People who feel burned out, overwhelmed, anxious, and unsatisfied with our work lives. Now, we might be willing to explore a different way and learn how to design our best professional and personal lives.

Marketing with integrity happens from a sense of service. It comes from knowing that you have something unique to share—it could be big or small— and that it’s valuable for a certain audience. It doesn’t matter how big the audience is, and it always helps to start with the smallest possible niche. 

4. Be authentic and direct. Make the ask. 

Finally, approach this marketing from a sense of knowing and confidence in your story. No-one else is an expert on the story like you are. You don’t need to beg other people to listen to you or to buy your products. That’s the energy of neediness and desperation. It’s a huge turnoff. 

Don’t be needy.

Instead, remind yourself of what you’re good at and of what you’ve done. Share your story. If you’re talking to people who would benefit from the message, then it should resonate. 

Finally, don’t forget to make the ask. This is being direct, and not needy. The ask could vary. For example: 

• Would you try reading my book?

• Would you buy my book?

• Would you share my book with your friends who might enjoy this message?

• Can you give me feedback on the idea?

• Do you know anyone else I might talk to?

Many of us chicken out of this last step of making the ask. It’s important to be direct and make the ask from a sense of service. 

Bottom Line

As I finish with the writing part of the book, I’m shifting to marketing and promotion. Many authors struggle with this part of the work. Similarly, many leaders struggle with defining and sharing their personal brand and passion projects. Yet we can market with integrity by remembering these four core messages: 1. You have something to say, 2. People love stories, 3. Know your audience, and 4. Be authentic and direct.