Jason Shen | Cultivating Resilience

Most of our problems stem from not knowing what we truly want—or not mustering the courage to go for it.

187: My Kind of Eggs

186: The Outlier Interview

Starting an interview series for authentically exceptional people. Starting with...me!

Most of our problems stem from not knowing what we truly want—or not mustering the courage to go for it.

How I Can Help You

As most of you know, I'm now a full-time coach and CEO via my firm Refactor Labs. With that, I have a couple ways I can help. Reach out if any of these speak to you or your organization.

🧢 Executive Coaching: 1:1 + small group sessions that unlock transformational growth through extended partnership.

🛠️ Participatory Workshops: Interactive seminars designed to learn and practice crucial skills for navigating complex transitions—storytelling, emotional intelligence, experimentation and more.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

188: Join the Club

Jason Shen — Sat, 10 Feb 2024 22:27:01 GMT

💡

This issue of Cultivating Resilience is brought to you by the world greatest social writing cohort and a new group coaching program for outliers in transition run by yours truly. More at the end.

Happy Lunar New Year! 🐲🧧🐉

It’s the year of the Dragon, which is my wife (and my dad’s) ben ming nian, literally “root life year”. You’d think this would make it a lucky year, but it’s traditionally seen as a year of potential trials and misfortune.

So if there are Dragons in your life, give them an extra blessing when you see them for the next 12 months may contain some calamity.

It’s bizarrely warm for February in New York but I admit I've been enjoying the crisp air and sunshine of this mild winter.

I wanted to take a moment to reminiscence about a special group that played a significant role in my life when I first moved to New York. It was called Scotchrepreneur, and it was an incredible gathering of entrepreneurs who bonded over scotch and shared their problems.

The group was the brainchild of Derek Flanzraich, founder of Greatist and Ness. We had connected back in San Francisco in 2010. He moved to New York soon after, and when I finally arrived in 2014, he invited me to be part of this unique community. Every month, Derek would host the gatherings at his apartment, where we would each contribute $20 and indulge in a fancy bottle of scotch.

One of the highlights of these meetings was reading the tasting notes that Derek put together. He would collect them from different whisky review sites across the web, and they were not your typical descriptions. We would laugh notes at like matchsticks, old band-aids, and even mushrooms grown in a basement. It made us feel cultured while taking a playful jab at the tasting notes industry.

I know you might be thinking that this sounds a reinvented "good old boys club," but Derek made sure the group was diverse and inclusive. He maintained a list of individuals who were thoughtful ambitious, and kind. While many of the regulars were men, there were several women who also became fixtures within the group, and seeing them build incredible businesses (one while becoming a mother) was inspiring and our conversations were respectful.

The format was simple: we split the scotch, and you brought your snacks and alternative beverage you wanted to drink. The opening question of each session was always the same:

"What is your biggest challenge?"

This part was intense and insightful. We would dig deep into each person's issue, offering advice and support. Sometimes, these discussions would take hours, but they were truly transformative.

The booze helped create a sense of vulnerability and we would drink and enjoy ourselves until the word "Scotchrepreneur" became a challenge to pronounce. At that point, we knew it was time to slow down. I know these days there are a lot of folks who are going sober or are cutting back their alcohol consumption, which makes sense, but I think in this environment the drinking really did help.

Derek really set the tone for going deep—fake challenges like "I think we're growing too fast" were batted away and in favor of questions like "I can't stand my cofounder" or "we're running out of money in 3 months".

Scotchrepreneur played a crucial role in many founders' lives, including mine. We tackled problems like dealing with difficult employees, making tough decisions about relationships, and so much more. Many agonizing personnel decisions and even personal relationships were rewritten thanks to this monthly forum.

Sadly, COVID caused Scotchrepreneur to close down. We attemptted to move online but trying to replicate the experience of drinking scotch in your living room while looking at a screen full of faces just wasn't the same. Many people also started moving out of the city. Derek had sold his first company the year prior and he and his wife Sarah wanted to get out of New York. This ultimately spelled the end of the group as we knew it.

I'm not sure if Derek has restarted this program in Austin, where he now lives. He‘s also become a father, and I can understand that dedicating an entire Friday evening and dealing with a potential hangover may not be as doable as it was in our twenties and early thirties. But I am really grateful for the amazing journey we had together over the years.

Scotchpreneur showed me the power of community, ritual, and a catchy name. Despite making no money on this project, I have no doubt it has been one of his many legacies as an entrepreneur and builder.

Do you have a Derek or a Scotchpreneur in your life? I’d love to hear about it.

As I shared in this newsletter, community can be a powerful force for personal and professional growth. Which is why I want to tell you about to really special community oriented programs you might want to check out.

The Platform Launchpad—I completed this 6 week personal publishing cohort a few months ago and it is not hyperbole to say it transformed my relationship to posting. I'm seeing incredible results on LinkedIn and Eric and Kasey are truly mensches. Their next cohort starts Feb 19—sign up using my link here.

The Next Chapter—This is my first ever group coaching program, at a price point that's more accessible that 1:1 coaching. It's designed for midcareer outliers—creative professionals who are in transition from job to startup, from sabbatical to next venture, or some other kind of transformation.

If you've ever thought about working with me, but felt the pricing might be a little steep, this is a perfect opportunity for you. Learn more and apply here.

—Jason

🙏

Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

Recent Issues

187: My Kind of Eggs

186: The Outlier Interview

Starting an interview series for authentically exceptional people. Starting with...me!

Telling your personal story has always been difficult... and never more important.

185: Personal Bios

186: The Outlier Interview

How I Can Help You

As most of you know, I'm now a full-time coach and CEO via my firm Refactor Labs. With that, I have a couple ways I can help. Reach out if any of these speak to you or your organization.

🧢 Executive Coaching: 1:1 + small group sessions that unlock transformational growth through extended partnership.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

187: My Kind of Eggs

Jason Shen — Sun, 04 Feb 2024 23:25:29 GMT

💡

Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

I'm finally settling back in NYC after many months in Thailand. The crisp air nothing like the swelter of Bangkok, but I love it all the same.

This week, I originally planned to share a long essay I was working that tried to reconcile fairness, meritocracy, and personal fulfillment, but it was getting a little out of control. This issue is a pared down and more focused version of that original piece, which perhaps I'll be able to share in the future.

Last week, I prototyped The Outlier Interview, a set of 10 questions I'll be asking remarkable individuals and collecting. My former cofounder and colleague Wayne sent me this follow up question:

I’m always curious what draws people to what they do. My question would be: What made you decide to quit your job and focus on Refactor Labs?

The short answer is, building enough conviction that this other path would be more fulfilling.

The long answer is the rest of this issue.

One universal truth I hold is that if you don’t have a clear sense of your own agenda, you will be forever tied to someone else’s. That doesn't mean you have to be a founder or own your own business, but it does mean having clarity about what you truly want out of your life.

I was speaking with a potential client recently who was approaching 30 years old and had worked a series of increasingly more high profile jobs in the public sector. But this was a career they had sort of stumbled into and they found certain aspects of the work incredibly draining. So in an attempt to reboot, they moved out of DC and taken a private sector role to try and switch gears.

The new job hadn't panned out as well as they'd like and now they felt really stuck. Should they stick it out in this job? Try to find another company, another role? Or call up their old buddies back in government before they were totally forgoten?

This is a common tension for high-achieving professionals. On one hand, you've done well by conventional metrics. Your resume is impressive, your parents are proud, and society sees you as successful.

But internally, you can find yourself feeling unfulfilled by the work, wondering "is this it?" You're thinking about making a change, but you're afraid of what will happen if you fail.

Now sometimes this is due to sheer financial constraints. But a lot of you people reading this newsletter aren't as constrained in your finances as much as you think.

It goes deeper in to some of the collective stories we tell ourselves, stories like The American Dream and the myth of meritocracy.

The American Dream (circa 1970's and beyond) is about enjoying prosperity and ever increasing material success. This is particularly strong for children of immigrants—your parents sacrificed so you could build on their achievements.

A big change puts that at risk. And that's scary.

Meanwhile the myth of meritocracy says good things comes to those with talent and capacity. And it's better to do something that seems successful than to try something you truly enjoy because if you fail, then you deserve it because you're (according to the toxic side of meritocracy) actually a talentless waste of space.

Meritocracy is a myth not because talented people don't advance—they often do and that's generally good. But plenty of successful people are there due to unfair advantages they leveraged without "earning it".

These narratives instill fear - maybe you don't deserve more if you step off the conventional path. The known path with clear measurements of acheivement.

Measuring your self-worth by external benchmarks is dangerous. Because it makes you focused on the agenda of others—what others care about, are impressed by, or desire, not what you want.

In 1999 romcom Runaway Bride, Richard Gere's character interviews a number of the men that Julia Roberts's character has left at the altar. He notices they always say she likes her eggs the same way they do—scrambled, poached, etc. Roberts would adhere to the preferences of her partners, never having the courage to discover and stand by her own tastes. But that meant she never felt like they really knew her or loved her for who she truly was—and she ultimately ran.

If this resonates with you, here are three suggestions:

Investigate your own sources of happiness like a scientist conducting an experiment. What activities make you lose track of time? Where do you feel most in flow?
Realize that status and recognition will never satisfy your deeper need for meaning. Leap towards what calls you, not what impresses others.
Express your voice through creative projects where you are producing rather than consuming. Shoot videos, write a newsletter, create a podcast, host events. Take pride in having a unique vision and seeing it manifest.

I chose to quit Meta and focus on Refactor Labs because I realized that trying to build software products inside of a massive organization wasn't the kind of work that fulfilled me most. Plenty I did like about it and it paid pretty well, but I didn't see myself tying the knot.

Instead, I realized while at Meta that my work as a coach, as the facilitator of resilience training, the writer of thoughtful, relatable, and practical wisdom on confronting the struggles of modern life—that's what I enjoyed and that's what I was good at.

I haven't escaped the claws of meritocracy or materialism yet either. Following Strategy #1 of the Dark Horse, I believe that by leaning into this work, this unique gift I have, I will receive recognition and reward. And I already have in many ways.

But more importantly, even if I never become a New York Times best-selling author, a $10,000 an hour coach, or a celebrated keynote speaker, I see a path to a comfortable life where I do work I enjoy each day with people I like and respect that creates tangible and positive impact on the world.

At the end of Runaway Bride, Julia Roberts lays out a spread of eggs she's cooked from 12 different styles, sampling each one. She's learned her lesson and is prepared to figure out the eggs that are right for her.

I hope you can find a way to do the same for yourself.

—Jason

🙏

Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

Recent Issues

Starting an interview series for authentically exceptional people. Starting with...me!

Telling your personal story has always been difficult... and never more important.

185: Personal Bios

184: No Difference, No Distinction

How a Disney screenwriter and a Spanish-speaking Indian founder teach us how outliers can use their unique qualities to create magic.

Telling your personal story has always been difficult... and never more important.

How I Can Help You

As most of you know, I'm now a full-time coach and CEO via my firm Refactor Labs. With that, I have a couple ways I can help. Reach out if any of these speak to you or your organization.

🧢 Executive Coaching: 1:1 + small group sessions that unlock transformational growth through extended partnership.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

186: The Outlier Interview

Jason Shen — Sat, 27 Jan 2024 22:15:09 GMT

💡

Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

I've always enjoyed interview series that had a particular format. Esquire used to have an amazing one called What I've Learned. Lifehacker does one called How I Work. And as I look to reinvent my writing once again, I'm exploring a new series called The Outlier Interview.

My first attempt at describing it is:

The Outlier Interview series captures the stories and perspectives of authentically extraordinary individuals. People who are exploring, assembling, imagining, and guiding in a world of wonder and chaos.

It's ironic to have a set of "standard" questions for an interview series about non-standard people but that's where this begins. I've got an ask for you, the reader, at the end.

So to prototype this series, I'm testing it on myself. Am I truly "authentically exceptional" as the description states? Well, it's my interview series so I'm going with yes.

Let's go:

The Outlier Interview: Jason Shen

1. Explain like I'm five: what do you do for a living?

I talk to people with big imaginations and help them do scary things and tell exciting stories about their work so they can make the world a better place.

2. What makes you usually well-suited for this line of work?

I have an unusually open-mind about people, their habits, mindsets and ideas. Starting from my days as a competitive gymnast, I've been exposed to excellence across many disciplines (business, tech, nonprofit, entrepreneurship) and functions (product, marketing, engineering). What that taught me is that there are many, many paths to greatness and the most important thing is figuring out an approach that works relative to your innate strengths and tendencies.

That's what I try to help my clients do as a coach.

3. Was there a time when you were young when you realized you were different?

When I moved schools between 3rd and 4th grade, I was suddenly labeled the nerd, the Asian kid with glasses who always had his nose in a book and didn't know anything about the New England Patriots or pro wrestling. Some of the coping strategies I learned during that time—don't try to make people feel dumb, downplay your accomplishments—have been useful but also probably overstayed their welcome.

4. What is something that you really struggle with that others seem to find easy?

For some reason I've been having a really hard time with responding to emails / DMs. I don't even get that many, maybe 10 per day that really require a thoughtful response but I find myself constantly behind and apologizing for the slow reply. It's kind of embarrassing.

5. Is there a video, meme, or post that you frequently refer back to out of utility or joy?

I love many of the videos from The School of Life but one in particular that came out in 2016 which explores three major drivers of our self-esteem: parental success, peer group success, conditional vs unconditional affection in childhood.

6. What atypical strategies do you have for getting into a state of flow?

Setting short, 15-ish minute timers for work sprints, coworking on Flow Club, and the Beats to Think To playlist on Spotify.

7. Where or with who do you feel most fully yourself?

For me as an athlete, Crossfit gyms are a great place for me to train with with smart, jocular people who find joy in pushing their physical limits.

And as an emotionally intelligent nerd, I love groups like Interintellect, Vibecamp, and TPOT (RIP Twitter) for connecting with thoughtful, creative, and vulnerable people.

8. What aspect of your work do you inordinately obsess over?

My work mostly involves writing and talking, but I also make videos that go on YouTube and also for personal fulfillment. I love absolutely love it when I can align a great shot or transition to a point in the music. The amount of joy I get from a great beat-match is chef's kiss

Recent example: having the Monster energy drink land on the counter in my "Sabbatical is Over" video.

9. Do you have a motto or slogan that helps you get through the trough of sorrow?

What do I want to tell my children about how I responded in this challenging time?

10. Who is an outlier you admire or appreciate and what is a question you want to ask them?

So many! Have already started messaging many of them to organize this series but Jonny Sun would be a dream.

I would like to ask: What have you gained from your rise in prominence from an anonymous aliebn on Twitter to a polymath creative producer? And what have you lost?

Jason Shen is an executive coach, writer, and friend to outliers of all stripes and colors. He is a three-time startup founder, author of The Path to Pivot, and retired gymnast.

Ok, so that was kinda fun to answer! So I'm feeling pretty good about this 10 questions

n this series, I imagine asking each interviewee 2 personalized / specific questions. But I'm a bit out of creative gas so would like to turn that question over to you:

What would be a specific question I should answer for my own Outlier interview?

—Jason

🙏

Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

Recent Issues

185: Personal Bios

184: No Difference, No Distinction

How a Disney screenwriter and a Spanish-speaking Indian founder teach us how outliers can use their unique qualities to create magic.

Falling on your face hurts less than you think. And a few other thoughts about living life on your terms

183: Face Plants

Compelling Personal Narratives List

How I Can Help You

As most of you know, I'm now a full-time coach and CEO via my firm Refactor Labs. With that, I have a couple ways I can help. Reach out if any of these speak to you or your organization.

🧢 Executive Coaching: 1:1 + small group sessions that unlock transformational growth through extended partnership.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

185: Personal Bios

Jason Shen — Sat, 20 Jan 2024 14:00:43 GMT

💡

Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

What's your story?

This is a simple question that can strike fear, doubt, and uncertainty into the heart of outliers and people in transition.

When you've got a stable role or title or some kind of legible position in society, your answer might be as simple as:

"I am a program manager at Google"

"I am a creative director at an ad agency"

You state your role and organization, maybe give a little backstory about how you got into that role, and some things about your early years: education, hometown, and call it a day.

But if you're someone who has bounced around a lot or who just has a unique set of skills and perspectives on the world, that answer is not good enough.

It doesn't really encompass who you are.
It doesn't feel authentic.

And if you try to explain what you do in more detail in a way that makes sense to you, people just look at you funny.

Authenticity vs Legibility

A lot of my coaching clients find personal bios to a source of stress because they want to be authentic and they want to be clearly impressive. Which is hard to pull off.

So they either avoid saying anything at all or they try to put out something that's legible, that's conventionally successful. They rattle off achievements, markers of success, association in high status groups and clubs.

And of course there's a place for that. A personal narrative is meant to demonstrate that you are a person of value and worth spending time with, funding, hiring, etc.

But I think the tricky part is how you introduce some personal details in a way that feels natural, feels authentic, and humanizes you.

Because when you are just a bullet point of skills and experiences and achievements, you're a lot more interchangeable. It just becomes about comparing who is the best.

Differentiating from Commodities

When Steve Jobs returned to Apple in 1999, he recognized that Apple's brand had been diluted, focused too much commodity features—and not enough by emotional and narrative value.

It’s a very noisy world and we’re not going to get a chance to get people to remember much about us… The way to do that is not to talk about speeds and feeds. It’s not to talk about bits and mega-hertz. It’s not to talk about why we are better than Windows...

What we’re about isn’t making boxes for people to get their jobs done, although we do that well. We do that better than almost anybody, in some cases. But Apple is about something more than that...

Apple at its core, its core value, is that believe people with a passion can change the world for the better. That's what we believe. We've had the opportunity to work people like that, like software developers, customers, who have done that. The people who are crazy enough to think they can change the world is those who do.

Studying Example Narratives

Sure Jason, you say, I get that I need to tell a better story, but it's easier said than done.

I get it.

That's why I went down a rabbit hole of impressive yet authentic professional bios. I originally put the list together for someone of my clients, but figured I'd share it with you.

In total there are 8 individuals recognized and I've left notes on each one for what I think they do well.

I'm going to include a few excerpts here but go ahead and read the doc if you want to see the whole thing.

Excerpts from "Compelling Personal Narratives" List

Amanda Natividad - Cofounder of SparkToro

Without formal marketing training, I learned much of what I know today through trial and error, following my intuition when in doubt.

I never really understood most of the paid side of marketing — PPC, display ads, buying lists — because it wasn’t how I, as a consumer, found beloved products.

So I stuck with organic & brand marketing. I was convinced that the best way to market is through your audience’s sources of influence: marketing to and connecting with your audience where they’re already paying attention.

Tony Fadell - founder of Nest

After leaving Apple, we decided to build a “green” home in Lake Tahoe, Calif. While researching heating and cooling systems, I realized that the thermostat was ripe for innovation. I founded Nest Labs to build the self-programming Nest Learning Thermostat. When owners are away, sensors adjust the temperature to save energy. The thermostat has been selling in the United States and Canada for 20 months, but because the device is Wi-Fi connected, we know that it is being used in more than 80 countries.

We designed the thermostat for do-it-yourself installation, and we even include a custom screwdriver in each box. I think my grandfather would have liked that.

Melissa Perri - Product Management Author/Advisor

When I’m not at my desk, you might find me in the kitchen. With a hammer, not a spatula. I’m an overconfident DIYer and currently renovating my house. I’m also learning how to golf... slowly– I’m terrible, but I’m getting better!

Chris Do - Design and business instructor

Identity 1: Refugee
On April 30th, 1975, my family and I fled Saigon as the U.S. withdrew. Although Saigon is where I was born, America has become the only home I truly know. Despite best-laid plans, I have never been back.

I'm curious to hear from you if this was helpful and if you have any questions or thoughts about how you're telling your own personal story.

—Jason

🙏

Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

Recent Issues

184: No Difference, No Distinction

How a Disney screenwriter and a Spanish-speaking Indian founder teach us how outliers can use their unique qualities to create magic.

Falling on your face hurts less than you think. And a few other thoughts about living life on your terms

183: Face Plants

How effective outliers manage and mitigate their weaknesses

182: Kryptonite

Falling on your face hurts less than you think. And a few other thoughts about living life on your terms

How I Can Help You

As most of you know, I'm now a full-time coach and CEO at Refactor Labs. I have a couple ways I can help you:

🧢 Executive Coaching: 1:1 + small group sessions that unlock transformational growth through extended partnership.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

184: No Difference, No Distinction

Jason Shen — Sat, 13 Jan 2024 13:00:31 GMT

Happy January. I hope your holiday season was merry and your inboxes are not too filled with coal / annoying emails.

I took an uncharacteristic 4 weeks off from the newsletter to think about its future—more on that shortly.

The end of the year had me flying from Bangkok back to NYC for a hot second, seeing my parents in the city, then shipping off to Atlanta to visit in laws before returning to Bangkok once more.

The upside is, I've mastered the long flight (pro-tip: get yourself Timeshifter app).

I've also continued to find conviction around writing about outliers, and that's what today's issue is about as well.

👇

As an immigrant from China, I've always a felt strong connection to this country as an adopted citizen.

After my first startup folded, I had the incredible opportunity to join the Presidential Innovation Fellowship program. Established under the Obama administration, the goal was to bring technologists, entrepreneurs, and designers into government to work on important projects.

I was staffed at the Smithsonian, where I was the second youngest member of a class of 40 fellows that included venture capitalists, tech CEOs, and senior engineering leaders. I was also one of the few truly Silicon Valley style entrepreneurs.

I was a young Asian dude in his late twenties sporting a faux hawk and brightly-colored stretch button ups from H&M. I stood out.

Why is that shirt so tight???

I vividly remember one particular meeting early on. We were all making our introductions to a group of Smithsonian staff members and after I shared by background, I was asked by an older museum staff member how old I was, because I didn't look like I had graduated college.

Come on. What was the point of that?

But it's a reminder that being different is more easily rejected than it is celebrated.

Don't let being othered dim your shine.

Working with the two other fellows in our group, we helped launch and grow a number of projects, including the Smithsonian Transcription Center.

We pushed them to ship early, embrace the crowdsourced nature of the platform, and engage with the community to encourage more contributions. Very common Silicon Valley tactics, but brand new for the academic world of museum curators.

It worked.

To this day, 85,000 volunteers have transcribed 1.3 million pages of historic content letters, notebooks, coins, and scientific papers into digital archives.

The lesson:

Our differences, our unique qualities, perspectives, and backgrounds can be incredible advantages. Because they add what is missing. And when you are the missing key, you can unlock so much possibility.

☃️

Jennifer Lee was a 40 year old writer with little animation experience when she was added to the struggling "Ice Queen" film project at Disney. She ended up rewriting much of the narrative and played a crucial role in the creation of the hit song "Let It Go" which of course helped make Frozen a smash hit.

This success propelled her to become the first female director of a Walt Disney feature animation and eventually the chief creative officer of the entire company.

Not bad for one-time graphic artist who designed audiobooks for a living.

🚚

Similarly, founder Deepak Chhugani went from out of place to in the perfect place.

Despite not attending a prestigious college, he fought his way into a coveted job at Merrill Lynch. Two years later he quit and started a startup that would help recent grads without the fancy degrees break into Wall Street like him.

But the company's growth wasn't enough to warrant a venture scale business. So he went to pivot and leveraged his unique background as an Indian kid who grew up in Ecuador and spoke fluent Spanish.

This led him to establish Nuvocargo, a revolutionary U.S.-Mexico cross-border trade shipping company that has raised $50M+ in funding to modernize the old-school industry.

These stories reveal the power of outliers. And the need for resilience to navigate unexpected changes.

It's not enough to possess distinct qualities and unique strengths.

We need to find the right place and the right way to unleash those strengths upon the world. And we have to adapt to what is out of our control.

Oftentimes, outliers become demoralized because you're not making the progress you want or you feel unfulfilled in your projects. This might be because you're not fully utilizing your strengths and trying too hard to fit into the expectations set by those around you.

So, I encourage you to reflect on where you are and what you're doing.

Are you in a place that embraces and harnesses your distinct qualities?
Are you in a position to apply your strengths to their maximum potential?

It's crucial to find an environment, whether it's a product area, a market, or a company, that allows you to leverage your unique abilities and generate incredible results.

Without difference, there can not be distinction.

Go get 'em outlier.

—Jason

7 parallels between entrepreneurs and executives (LinkedIn)
You never forget your first bully (LinkedIn)
Setting up a personal board of advisors call (LinkedIn)

183: Face Plants

How effective outliers manage and mitigate their weaknesses

182: Kryptonite

Three ways to make your outlier obsessions an advantage you as an outlier

181: Strong Suit

Read why face planting isn't so bad

How I Can Help You

As most of you know, I'm now a full-time coach and CEO at Refactor Labs. I have a couple ways I can help you.

🧢 Executive Coaching: 1:1 + small group sessions that unlock transformational growth through extended partnership.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

183: Face Plants

Jason Shen — Sun, 17 Dec 2023 18:21:44 GMT

💡

I'm hosting a cozy New Year's Day reflection on Interintellect! (RSVP)

We're in the back half of December. Hopefully work is winding down or at least you can see the light at the end of the tunnel.

Quick favor: Can you share a win that came from reading this newsletter?

I've been writing this newsletter almost every week for more than two-and-a-half years. It's a labor of love and to be honest, given its broad coverage, I'm not sure what impact its had on readers like you.

I'd love to hear a positive outcome in your business, career, or life that has come from reading Cultivating Resilience. Just hit reply and write me back. It'd mean a lot.

This week I wanted to share a couple of recent posts I've done on Linkedin. I've been quite bullish on Linkedin given the continued decline of Twitter/X. It's become my go-to platform for sharing more practical / useful ideas online.

Threads is fun but will probably serve as my home for off-the-cuff thoughts, jokes, and hot takes.

1) Face planting hurts less than you think.

Don't be afraid of face planting.

Most people are too worried about screwing up their projects, their careers, and their companies and focus on minimizing risk.But this mentality holds them back from accelerating their learning curve, and ultimately their fears are unwarranted. There's a better way.

On the RightOffTrack podcast, I shared this lesson with the incredible Anya N. Smith:

👉 Face planting hurts less than you think.

I've fallen on my face as:

→ A founder (my 1st startup failed)
→ An athlete (fell on the 1st event at NCAA finals)
→ A professional (had projects cancelled, laid off)
→ A creator (sued by a copyright troll)

But I learned incredible lessons on resilience and adaptability each time. Because your brain actually learns much more when you struggle than when you succeed.

❄️ Jason Shen on LinkedIn: Don't be afraid of face planting. Most people are too worried about…

Don't be afraid of face planting. Most people are too worried about screwing up their projects, their careers, and their companies and focus on minimizing…

LinkedIn❄️ Jason Shen

2) 10 Mantras When You're Exhausted

Founders get bombarded with advice. Ideas pour in from everyone—investors, customers, employees, even family members.

It can be infuriating. You wouldn't try to tell a doctor or pilot how to do their job. Yet, everyone thinks they can steer a startup.

Pierre Sabbagh recently talked about how a startup mentor suggested he hire a professional CEO for the company he founded. They said focus on tech, leave management to someone else.

Sure, there are times a hired CEO is the answer. It makes sense once the company has reached a certain scale and is trying to hit revenue or acquisition outcomes that are beyond the founders capacity.

But for many startups, this move can be fatal. An outsider might snuff out the critical spark and not have the moral authority of the founder.

Plus Pierre wanted to learn the business side of technology and despite his tech background and accent, he was ready for the challenge.

Learn what Pierre did and see other examples of unsolicited advice

❄️ Jason Shen on LinkedIn: #pivots | 11 comments

Founders get bombarded with advice. Ideas pour in from everyone—investors, customers, employees, even family members. It can be infuriating. You wouldn't try… | 11 comments on LinkedIn

LinkedIn❄️ Jason Shen

3) On Being a Weirdo

"Can you stop being such a weirdo right now?"

These words used to sting. I bet they did for you too.

But accepting your weirdness will allow you to build deeper relationships with the people that matter most in your life and career.

Let me explain.

If you're an outlier (someone exceptionally good at certain things, bad at others, and took an unconventional path relative to your peers), you realize that your differences can be dangerous.

People might be resentful of your incredibly fast reading skills. Or natural ability to understanding a new technical concept.

They might make fun of you for your clumsiness or limited short-term memory.

They might not get why your lunch is so pungent. Or why you've never gone skiing over the holidays.

So you learn to create a mask, a personality that others will tolerate, maybe even like. You learn to laugh at jokes you don't find funny. And maybe make them too.

Learn how showing your weirdness brings some people closer

❄️ Jason Shen on LinkedIn: "Can you stop being such a weirdo right now?" These words used to sting…

"Can you stop being such a weirdo right now?" These words used to sting. I bet they did for you too. But accepting your weirdness will allow you to build…

LinkedIn❄️ Jason Shen

—Jason

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Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

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Executive Coaching for Unconventional Leaders: If you want to steer through moments of change and swing bigger and projects that really matter—you might find value working with me.

Recent Issues

182: Kryptonite

How effective outliers manage and mitigate their weaknesses

Three ways to make your outlier obsessions an advantage you as an outlier

181: Strong Suit

Why I’m doing 1,000 burpees and how to motivate yourself without self-discipline (aka self-punishment)

180: Antidiscipline

Three ways to make your outlier obsessions an advantage you as an outlier

182: Kryptonite

Jason Shen — Sun, 10 Dec 2023 18:28:00 GMT

💡

Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

Last week we talked about how to deal with using your strengths as an outlier.

This week we're going to talk about the W-word.

Weaknesses.

Specifically how you confront your weaknesses—the things that you find hard while your peers find simple. How you'll never become a massive success by trying to fix your weaknesses and at the same time, you can't let your weaknesses sink you.

Hard For You, Easy for Everyone Else

I was talking to an entrepreneur who has done an incredible job climbing from a lesser-known university to a software engineering, broke into product management and recently had his company acquired after executing a very difficult pivot.

This entrepreneur is technically capable, an effective problem-solver, and great with people. He powers through pressure and impossible workloads better than 99% of people I know.

I was asking him what books or publications he liked to read or how he kept up with industry news. And he admitted that he didn't really read outside of work unless he absolutely had to because of how difficult it was for him.

It turns out, he's dyslexic. I've known him for nearly 10 years and this was the first time I learned of this.

Reading is something I love deeply. I have so many happy memories of being at the library or a bookstore and just gobbling up all the books I could get my hands on. My Kindle library has 849 items in it.

But this entrepreneur has pulled off an incredible outcome despite this "weakness" of being a slower reader.

And that's because he put his strengths to work.

Owning Your Weaknesses

"What's your biggest weakness?"

That used to be the dreaded job interview question. The one you felt you had to come up with a fake answer to "I'm too hard working", "I care too much".

I was once asked that by a team of folks at the Smithsonian as part of the Presidential Innovation Fellows program. I followed a strategy that I would recommend for you:

I was strategically honest. This is what I said:

"I'm not the most detail oriented person in the world. If you need someone to oversee a 50 person dinner party or orchestrate a rocket launch, you should hire someone else. But if you want someone who's full of ideas and going to help a team bring a great idea to life, then I'm your guy."

The fellowship was meant to bring technologists and founders into the government to support new ideas and programs. So I told them a real weakness: I struggle with details, admin work, crossing all my i's etc

But I strategically chose something that was antithetical to the goals of the project. Something that wouldn't matter as much, and whose opposite would be an asset for role.

I got the job.

Because I leveraged one of the truths about weaknesses: every weakness tends to be matched by an opposing strength.

Creative people tend to have trouble following a process.
Warm hearted people struggle with holding individuals accountable.
Abstract thinkers aren't usually as good at explaining things in relatable terms

That doesn't mean that the weaker you are in a dimension, the more strong you are in the other direction or vice versa. But from a raw, patterns of thinking and behavior perspective, that's absolutely true.

Mitigating Your Weaknesses

Ok so how do we actually reduce the impact our weaknesses have on our companies, careers, and lives? Here are three strategies you can use individually or in tandem.

1. Bring up the weakness to an acceptable level

There's no getting around something things. You can't just say you're bad at something and just give up. Despite how I answered the Smithsonian interview question, the reality is, you should be able to speak to how you've able to work on your weaknesses.

If you're not a confident public speaker, taking a class would go a long way to helping you improve.
If you tend to hand things in late, creating many little milestone / deadlines for yourself can help reduce the likelihood you're procrastinating to the last minute.
If you are really risk averse, allocating a budget for discretionary losses (of time, money, or other costs) might help you get more comfortable

2. Partner with people who are strong in your weaknesses

Steve Jobs was a product visionary who initially struggled to ship those insanely great computers at insanely great prices. That's why he positioned Apple as a BMW of computers (because it made the small marketshare seem acceptable). In part this was due to his lack of operational capacity, to drill into the process and details of things to root out waste and inefficiency and bring costs down.

But shortly after he returned to Apple in 1997, he plucked a 37 year old Tim Cook from Compaq to become Senior Vice President of Operations. He understood that Cook could help him improve his supply chain and logistics, an area Jobs wasn't well versed in but knew was critical to reliably and more cost-affordable delivery of the best stuff.

When you have the ability to choose who joins or augments your team, look for people who are different from you, who have strengths in areas where you are weak.

Since going full-time on my own, I've hired an Executive Assistant who helps me stay organized and complete annoying but necessary lead gen work that I would not do on my own. This is not a trivial expense but I think it will pay off massively over the long term.

3. Alleviate Pressure On Your Weakness

This is probably the most tricky / effortful thing to do but can pay the biggest dividends: use your strengths to compensate for your weaknesses.

When you get a blister on your foot, you can buy a little foam pad with a hole in it to stick on the area around the blister. By supporting everywhere around your blister, you take the pain and pressure off the sensitive area.

You can do the same thing in your profession.

If you are deeply shy and uncomfortable with in person interactions, use a blog, a newsletter, case studies, video testimonials and other materials to make the sale as smooth and compelling as possible.

You can also highlight your weakness, and turn it into an amplification of your strength. This is a truly ninja move and can be seen in theoretical physicist Stephen Hawking.

After contracting ALS—a debilitating motor neuron disease—in his twenties, he slowly lost control of most of his body and required the use of a wheelchair and a speech synthesizer in order to navigate and communicate with the world.

And yet he would appear on television shows and even crack deadpan jokes with his robotic monotone voice. Everyone knew he was not going to be the gregarious, animated scientist ala Bill Nye or Neil deGrasse Tyson. But his weakness almost underscored just how much of a genius and an incredible human being he was.

If you can build up your strengths enough, your weaknesses can even turn into charming quirks or ways to stay relatable to "ordinary" people. Think how celebrities are always telling you about what they're scared of or things they're embarrassed by.

I'm curious, how has this letter changed, if at all, the way you view your weaknesses? Reply back and let me know!

—Jason

🙏

Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

🔥

Executive Coaching for Unconventional Leaders: If you want to steer through moments of change and swing bigger and projects that really matter—you might find value working with me.

Recent Issues

181: Strong Suit

Why I’m doing 1,000 burpees and how to motivate yourself without self-discipline (aka self-punishment)

180: Antidiscipline

Getting a Kindergarten PIP and what to do when you feel remarkably different from your peers.

179: Being an Outlier

Why I’m doing 1,000 burpees and how to motivate yourself without self-discipline (aka self-punishment)

181: Strong Suit

Jason Shen — Sun, 03 Dec 2023 16:30:22 GMT

💡

Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

A dashed off photo and quote about deviants became my biggest tweet of 2023. And perhaps one of my last biggest tweets ever given the way Twitter/X is going.

I think the popularity of the tweet is due to the fact that the internet has allowed a lot of people who might feel like a deviant, or otherwise outside the normal distribution to find themselves.

But how do you find your way through the world as an outlier—spiky talent with an unconventional background?

It starts with working on your strengths.

Own and Hone Your Strengths

As an outlier, you're wired differently.

You care more about getting certain aspects of a task right than others do
You are want to more time and effort on certain topics or activities than others will
You're fundamentally more curious about certain things than others

These are what you might call intense natural inclinations. Or even obsessions. And it is these specific obsessions that create the foundation for your strengths.

Because everything we know about developing abilities is that the more you think and engage in something, especially with a feedback loop of either a positive outcome, or simply simply personal satisfaction, the better you will get at it.

I'm secretly a really great copywriter and marketing strategist, but only for causes and projects I genuinely care about.

Because one of my obsessions is reading about consumer psychology and messaging strategy. I'm fascinated about all the marketing that goes on around us—from billboards, to short form video hooks, to microcopy on websites.

Having the obsession is not enough. You have to transform it into a strength by developing it. Honing it from a dim flicker to a powerful beacon.

My marketing obsession led to me analyzing the opening and closing sentences of ~100 articles, calculating Citibike's CPM, and developed over time into a strength that's amplified my projects and content enormously.

Find Arenas That Match Your Strengths

Once you have recognized and developed your outlier strengths—a lifelong pursuit—you have to get yourself into a position, into fields, industries, and projects that match your strengths.

Growing up in the 90's, I loved watching Chicago Bulls and Michael Jordan win championship after championship.

And yet Jordan left the sport of basketball after leading the Bulls to 3 straight NBA championships to play minor league baseball after his father died in 1993.

As a basketball player, Jordan was dominant. With 10 scoring titles and 5 MVP awards, he's considered by many to be the greatest player to ever live.
As a baseball player, he never made it out of the minors, batting a paltry .202 in just over a hundred games with the Chicago Barons. Impressive for someone new to the sport, but unremarkable in absolute terms.
Upon his return to basketball, his arena of strength, Jordan won another 3 championships in a row.

No one is great at everything.

When Jordan played baseball, his strengths and his arena were mismatched. His strength was playing basketball at the highest levels. This didn't even translate to other roles in basketball— Jordan's incredible competitive drive that worked so well as a player was less effective when he became a coach and team owner.

If you've got a great forehand, stay on the left side of the court
If you're great in a room, insist on in-person presentations and meetings
If you are a stickler for process and details, lean towards the operations function versus the emerging opportunities team

Strengths Can Lead to Success, But Belonging Requires Contribution

As an outlier, you're going to feel separate from others, and you might think that by developing your strengths, you can gain the success and achievement you need to earn respect and a place among your peers.

But you might get success without the belonging. In fact, an outlier's unique abilities can often elicit feelings of envy and resentment in others, causing further separation.

To navigate this complex emotional terrain, you have to recognize that your obsessions and strengths can cause a sense of envy and resentment among others. So if you want belonging, focus on group contribution rather than individual success.

With Christmas coming up, it's nice to revisit an old Christmas tale: Rudolph the Red-Nosed Reindeer.

Hilariously, the story of Rudolph was invented in 1939 by an advertising copywriter to promoted a department story during Christmas. It's a fascinating example of remix culture because the other reindeer names (e.g. Dasher, Dancer) were already established. So this beloved story was essentially Christmas fanfiction meant to sell more coats or whatever.

One one hand, it's a beautiful tale of celebrating individuality and overcoming adversity. On the other hand, I am forever grateful to @visakanv for introducing me to this meme:

As I saw one blog put it, "if you're going to be a weirdo, be a useful weirdo". In other words, if you're difference, find a way to use your strengths to contribute to the group.

I asked AI to weigh the different interpretations of Rudolph's story in the voice of Malcolm Gladwell and I'm pretty happy with how it came out:

In the captivating tale of Rudolph the Red-Nosed Reindeer, we find a duality worth exploring.

On one hand, it unveils a stark reality, where deviation from the norm initially invites ostracization and is only embraced when it serves a purpose. However, at its core, Rudolph's story celebrates individuality and resilience, highlighting the power of authenticity in the face of adversity. It's a narrative that evolves with time, reflecting changing attitudes towards inclusivity.

Ultimately, Rudolph's story is a mirror to our complex world, challenging us to confront biases and question societal norms, reminding us that deviation from the norm can be a source of hope, leading to a more empathetic and inclusive society.

I like the way this ends, on a optimistic note.

84 years ago, we told stories about how differences can become strengths that create belonging. Back then, it was a remarkable idea. Now we accept it as canon.

What will the next 8 decades bring?

—Jason

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Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

🔥

Executive Coaching for Unconventional Leaders: If you want to steer through moments of change and swing bigger and projects that really matter—you might find value working with me.

Recent Issues

180: Antidiscipline

Getting a Kindergarten PIP and what to do when you feel remarkably different from your peers.

179: Being an Outlier

178: Getting the Whole Story

Communication is harder than it seems even when you’re trying at it. Here are some stories about how we get it wrong and how we get it right.

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Getting a Kindergarten PIP and what to do when you feel remarkably different from your peers.

180: Antidiscipline

Jason Shen — Sat, 25 Nov 2023 13:39:15 GMT

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Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

I've been very consistent in my physical activity throughout my life. From gymnastics to Crossfit, to distance running, to bike commutes, boxing, 12 hour walks, fitness records and beyond.

Why? To be in shape? Sure. To be healthy? I guess. But mostly because I feel better when I do it. I enjoy going into the pain cave and finding out what's on the other side.

Right now I'm training to complete 1,000 burpees in one sitting (more on that later), something I've never done before.

Over the last 37 years, I've frequently pushed myself beyond what I thought was possible—both in terms of an individual workout, and in larger physical challenges.

Sometimes I fall short of a goal, but I never regret the attempt. Because of this, people assign a lot of discipline to me.

Discipline (or Lack Thereof)

"You must have a lot of self-discipline" is something I hear a lot.

I disagree. I hate the word discipline. I get where they are coming from, because maybe they feel like they couldn't get themselves to workout as long and hard as I do.

But I just don't relate to that word. Because as consistent as I am in physical efforts (Matter), I often struggle with mental or intellectual efforts (Mind).

My own self-conception is that I don't have a lot of discipline. Because right now there are:

A bunch of messages from people I care about that are awaiting a reply
Projects I've abandoned
Books I'd like to read (and write!)
Tech tools I want to spend time with
Long articles I've saved to read later

I rarely finish half of what I set out to do in a given week.

That doesn't mean I don't do a lot. It just ends up being different than what I put on my task list. This was a problem when I had a startup or worked at a company because that task list was what I was supposed to be working on. And I would need to cram all those "high pri to-do's" in at the end of the day or week.

Luckily I no longer have to be accountable to a manager, a VC, or anyone other than a family member or a client (someone I choose to work with). And that works a lot better for me.

To whatever degree I've achieved in my life, it's due less to discipline than finding a way to engage in my life.

The Harshness of Discipline

The definition of discipline is not a kind one. As a verb it means:

to train (someone) to obey rules or a code of behavior, using punishment to correct disobedience

And as a noun, it's no better

the controlled behavior resulting from discipline

As I talked about last week (#179), I have a thing with rules.

I don't like them. Especially other people's rules. (I'm a little more amenable to my own). That created a lot of problems in school and in the various workplaces I've been at.

And I've been disciplined for not obeying those rules. And of course we know that not everyone gets punished for disobedience. Depending on who you are, your misdeeds might be ignored, or even celebrated.

More and more, the social sciences are revealing that punishment is less effective at correcting inappropriate behavior than we might intuitively feel. [1]

I believe guilting or yelling at yourself to do something is detrimental to our mental health. And even if it works in the short-term, in the long run you'll find this motivational tactic falls flat. And it burns you up in the process.

Don't let anyone shame you into thinking the answer is simply to "suck it up and do it". Because if that worked, we wouldn't be stuck so often.

So where does that leave us?

The 3C's: Curiosity, Connection, Challenge

If discipline (i.e. rules + punishment for disobedience) doesn't work for me and most people long term, then what might?

Well, it depends on the person. And practices like motivational interviewing (link) can help us understand those positive reinforcement mechanisms for ourselves.

I've found that these three work for me:

Curiosity. What is underneath all this stuff? What will happen if I do this? Curiosity is why we like mysteries, why we fall down Wikipedia rabbit hole, why we stay up watching "Part 3" of some random story on TikTok. Curiosity and novelty are related. It's why new things are so interesting to me, because there are so many questions and things to learn. (And why on the flipside, why boredom is so painful)
Connection. When we do things with people we like, or make new friends through the work we are doing, we are naturally more drawn to it. I find that when I can get myself to do something, it's because I have a relationship with that person, or I don't want to let that person down. It makes the abstract work I do more real.
Challenge. When we are daunted by the work we are doing, when we don't know if we can do it, that can be incredibly compelling. Because for me, that sense of fear and uncertainty is also an indicator that I'll be proud of myself if I am to reach my goal. That when I look back on my life, this project is one that will have mattered.

Applying the 3C's to 1,000 Burpees

In the last decade, I've set 2 fitness Guinness World Records. But this Tuesday I'm going to attempt something even more daunting:

→ Doing 1,000 burpees (Chest to deck, clap at the top, 5 sets of 200)
→ While interviewing 10 friends about mentorship between sets
→ In order to raise $2,000 for Lunar Accel (part of my role as board member)
→ To support mentorship for the next generation of AAPI leaders

So a fundraiser. A series of mini convos. And a fitness achievement. All streamed live. What the heck?

But looking at it from the 3C's, from back to front:

1. Challenge: As a Lunar Accel board member, part of my job is to help raise money for the nonprofit. By tying my love of fitness to this more abstract but important goal, I can stay more motivated.

Why is me trying to do 1,000 burpees live (not a record btw) scarier than my Guinness World Records attempts?

Because I had already beat the record in practice. By the time I went out for the attempt, I had full confidence. Not this time. The most # of burpees I've done so far is 600 over 3 sets, just a few days ago. Like running an 20 miler before your first marathon.

2. Connection: by interviewing other people, I get them enrolled in this project. It gives me a chance to ask my friends, former colleagues to support me, to donate to the organization, and to witness this challenge. And of course, there's my relationship to Lunar Accel.

Before I left NYC for Bangkok, I got to host a brunch for the Lunar Accel leadership. Before accepting the role I had already met with the cofounders four separate times—but the more I understood the relationships between the whole team, the more I would feel engaged in the work.

3. Curiosity: I remember when they used to raise money on TV for various causes. They'd have this many hours-long telethons with various entertainment acts. And I guess in a way that inspires what I'm doing now.

What would it be like not to just do this burpee challenge, but also talk to people at the same time? Would anyone tune in? Would people donate? Would I have too much trouble interviewing people on top of trying to recover between burpee sets? Would my EA Ruwanthi be able to manage the back end side of things?

It's these questions that keep me hooked. I want to know what happens!

So in the end, I'm doing a pretty hardcore project without any rules or obeying any authority. Without discipline. What should we call this? Antidiscipline.

If antifragility is how we create strength and power through disorder, then antidiscipline is how we achieve more through disobedience.

What do you think of this theory? Anything I miss? Is there a C or two I need to add? (Creativity might make sense...)

Reply back and let me know!

—Jason

PS - If you want to tune into the livestream, you can do so on Linkedin here: https://lnkd.in/emJd6cTv

[1] Research on physical punishment of children has consistently found that it is not effective at improving child behavior or reducing negative outcomes (link). In terms of crime, research on deterrence has found that the certainty of being caught is a more powerful deterrent than the severity of punishment, and increasing the severity of punishment does little to deter crime (link)

🙏

Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

🔥

Executive Coaching for Unconventional Leaders: If you want to steer through moments of change and swing bigger and projects that really matter—you might find value working with me.

Recent Issues

179: Being an Outlier

178: Getting the Whole Story

Communication is harder than it seems even when you’re trying at it. Here are some stories about how we get it wrong and how we get it right.

Don’t worry, catching these won’t get you sick

177: Contagious Beliefs

Recent Podcasts

How to Adapt and Lead When Times Get Tough — Podcast Interview

178: Getting the Whole Story

179: Being an Outlier

Jason Shen — Sat, 18 Nov 2023 14:55:26 GMT

💡

Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

I was put on my first (and only) PIP in Kindergarten.

"I am presently working with Jason on clearly defining limits and expectations in an effort to see if he is able to gain more control his actions"

A month into school, my teacher Mrs. Ward wrote up a 527 word progress report detailing my problematic behavior. It read like a performance improvement plan that was angling to put me into a special education class.

Here are some choice segments:

"changes his activities frequently, often leaving areas before reaching some form of completion"
"very impulsive" ... "acts quickly without regard for consequences"
"in spite of a short attention span, he is able to quickly absorb new information and retain it easily"
"really enjoys and cares a great deal for other children"
"an exhausting child to work with"
"presently working with Jason on clearly defining limits and expectations in an effort to see if he is able to gain more control his actions"

Luckily, my parents (who both work in education) recognized what was going on, and intervened with Mrs. Ward and the principal to explain my behavior and create a plan to support me.

I was diagnosed with ADHD and through a combination of efforts, was able to rein in some of the most troublesome behavior.

In the end, I made it through the PIP and got to stay in regular Kindergarten. My final report from Mrs. Ward had many more positive things to say:

Especially enjoys computer work, games and making things...has a wonderful curiosity and wants to explore everything...is a very social child and enjoys group activities with his classmates...attention span has improved as he has become more involved in projects and activities.

That said, she ended with a cautionary note, that I needed "structure, limits, and support controlling his activity level and behavior".

Boy that's still true. This set of traits have colored my experiences for the last three plus decades.

Being an Outlier

I've been playing with this term Outlier to describe a certain kind of person.

In statistics, an outlier sits outside of the normal distribution. My definition is that an Outlier is someone who finds themselves outside of the normal distribution on a meaningful number of dimensions.

Image by Jason Shen (finally putting my Kindle Scribe to use)\

I'm using this term Outlier to describe people who have both remarkable abilities and meaningful deficiencies and a unique background and POV on the world—which means they often struggle to find belonging due to their differences.

You might guess that I'm talking about Outliers because I see myself as one.

My particular way of thinking and behaving has been both a remarkable asset, and a frustrating liability, starting from my Kindergarten PIP. My journey as a first generation immigrant, having Chinese parents who were not in STEM, being both a nerd and an athlete, all of it has shaped who I am.

I thin my wife Amanda is also an Outlier.

The daughter of immigrants growing up in Georgia, she went from neuroscience researcher to a designer / design strategist to an internationally celebrated artist. Yet having a front seat to that journey, I've seen her face enormous external pushback and exclusion by people who didn't understand or value her way of being, as well as experience a lot of internal judgement and frustration.

Aspects of the Outlier Experience

If I had to boil down the Outlier experience as simply as I could, I'd come to the following elements:

🎯 Outliers typically have remarkable abilities—Outliers are interesting because they're wired to be quickly become good at certain things. Understanding and improving technical systems. Being highly articulate and verbally proficient. Having tremendous visual, musical, or kinesthetic capacity. It could vary widely from person to person.
😰 Outliers tend to struggle in certain areas outside of their abilities—there will be normal skills or competencies where they struggle: difficulty with writing/language. Extreme shyness or emotional sensitivity. Trouble staying organized. Tardiness. This also varies (and is often the flip side or somehow the opposite of their abilities).
🌏 Outliers usually have a unconventional background—similar to our discussion on Dark Horses (#141), Outliers tend to have a different cultural, educational, or professional background to their peers. This leads to their having a unique POV and a distinct vision when it comes to the projects or ideas they come up with.
🥾 Outliers often experience a lack of community and belonging—due to their differences in ability and background, they often aren't accepted by their peers as easily. People are intimidated or resentful of their abilities, which might lead them to harp on their relative deficiencies and personal differences.

Note: some people might be familiar with the term "twice exceptional" and I think there's a modest overlap between this term and Outlier. But that is a term that has a specific meaning and I don't want to get caught up in semantics or definitions.

Advice for Outliers

So hopefully this letter is resonating with some of you, maybe a lot of you, who knows. I want to wrap up but if you think you might be an Outlier, I want to leave you with a couple of suggestions and ideas to maximize your potential and minimize your struggles:

Make time to reflect and observe yourself and the world. When you are different, you need to really understand what comes easily to you and harder for everyone else, so you can leverage it to your advantage. And you need to be aware of what you struggle with, and look for ways to get the same results with perhaps a different tactic or approach.
Communicate in a relatable fashion. Outliers have to work harder to build relationships with others and convey their ideas in a way that others will understand. But when you learn how to get your ideas across quickly and in a warm and friendly way, you'll have a much easier time navigating an organization or an institution.
Cultivate the courage to act on your intentions and show vulnerability. I've talked before about Courage as the First Virtue (#139). Outliers need it more than most, because you face more risk. Risk that people won't accept you, that your ideas will fall on deaf ears, that you'll flub something important and disappoint others. But that risk is mitigated when you have allies—which are cultivated when you show vulnerability and spark trust and connection.

I know all of those things are easier said than done, but I wanted to wrap with something constructive and useful.

What did you think of this letter? Do you identify as an Outlier? Is this an area of writing that's worth exploring further?

I'd love to hear from you.

—Jason

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178: Getting the Whole Story

Jason Shen — Sat, 11 Nov 2023 16:50:53 GMT

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Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

iykyk is a young person acronym for "if you know, you know". But here's the thing. We rarely do know. Communication is harder than it seems even when you're trying at it.

Yet it's essential for leading with resilience. So here are some stories about how we get it wrong (starting with yours truly) and how we get it right.

"So we have a few minutes left, is there anything else on your mind?"

I had just spent 45 minutes going over the slides my client had drafted on how students at his alma mater's entrepreneurship club should think about generative AI.

My client—a cofounder of a AI-powered brainstorming tool—seemed genuinely appreciative of my feedback as it was the first time they'd be giving this presentation. I felt good, like I had added value as a coach. Then my client answered my question.

"Hmm. Oh, actually a couple of things did hit the fan this week."

Narrator: It was in this moment he knew...he f*cked up.

It turned out a number of other important events had recently occurred that had far more significance on the future of their company. And so after spending 75% of our allotted time on a P2, we spent the last 25% on the P0.

My client and I experienced a failure in communication. I not adequately looked for the story behind the story. And my client had not adequately signaled there were other things to discuss.

Communication is hard. Even between two parties that collaborate often, trust one another, and share similar communication norms It's even worse when one or more of these facets are off.

To act with resilience, you need to know what's happening. And you need to describe your situation clearly, coordinate with your team carefully, and request out help compellingly. All of this requires better communication.

Poor Communication: Destroyer of Timelines and Livers

I've been avoiding TikTok for a while as being too much of a time-suck but recently returned to it and was pleased to find some new faces and voices, including @oldcoderguy, a grey haired tech veteran, who has a wise and wisecracking way of articulating his ideas. But in one recent video he tells us:

One the best kept secrets in project execution is that the root cause of most delays and failures is not the complicated stuff. The primary destroyer of timelines and eventually your liver is just basic sh*tty communication.

He goes on to describe a common scenario: a technical employee who sees a problem but doesn't bring it up in team meetings because they're not sure it's the appropriate time. And a manager who doesn't probe on details or create an environment where seemingly "dumb" questions are welcomed.

As you can imagine, the problem eventually rears its ugly head late in the game and wreaks havoc on the project delivery date. A sad result that could have been avoided had the issue been addressed earlier on.

As a leader or senior member of a team, you avoid avoid this particular failure mode by cultivating a psychologically safe space. That means responding earnestly when someone asks a question, staying nonreactive when someone offers a critique or concern about a work issue, even if might have negative implications on your own performance.

If this sounds obvious and easy, it's neither. Google undertook an exhaustive multi-year study of high-performing teams before they .

Everyone thinks leaders have thin skin till they're on the receiving end of people's complaints. It's one of the reasons why great leaders need to develop healthy coping mechanisms often learned in at the therapists office or through executive coaching (tiny plug!)

What if you're someone in a more junior or non-managerial role? Besides simply asking more questions, Old Coder Guy recommends:

Saying what you think is true (assumptions, expectations, decisions) out-loud and asking people to tell you how you're wrong
Putting things into a picture or diagram
Get other people to explain what the f*ck they think is happening

These recommendations aren't easy either. They require courage. Lower ranking individuals face a greater risk of punishment or retribution by the damaged egos of the higher ups.

All of this is about getting people to aligned to a shared reality. Words are slippery and can be misheard (when delivered verbally) or misinterpreted. Writing things down helps with the former while while restating and confirming helps with the latter.

The Power of the Pen

Writing is in fact one of the most profound technologies human beings have, and yet it is still commonly underutilized in many work environments. [1]

I was catching up with an old friend about her job—she is a New Yorker and a former journalist whose now working in a very different cultural environment. She was frustrated that in many of the teams she worked with, people would have important meetings over a phone or video call, yet rarely did anyone capture or circulate meeting notes after the fact, making it hard to coordinate on decisions or next steps.

This would never happen at Meta.

Every meeting was expected to have at minimum a written agenda and almost always follow up notes and action items were added to a document, and often posted in in public channels where non participants could see what was discussed and what decisions were made.

As a PM, it was often my job to make sure that this documentation was captured and shared, but everyone, from engineers to designers and beyond were expected do this for meetings that they held.

Writing! It's like magic we laughed.

When In Bangkok...

And yet my friend's frustrations are not an isolated case. Here in Thailand, my home away from home for the last month, people practice similar communication norms.

My wife has been similarly run into issues where issues and concerns are not captured and later re-emerge anew as if never previously discussed. "This is news to me" someone might utter. And without evidence, it becomes impossible to prove they had prior knowledge of the issue.

Yet, this isn't merely an example of obvious incompetence. It turns out, Thailand is a high-context, indirect negative feedback and avoid confrontation culture. These are 3 of 7 cultural dimensions that former Peace Corps volunteer turned management author Erin Meyer describes in her research.

In a very recent Harvard Business Review article about feedback and diversity, Meyers tells the (very close to home) story of a oftspoken American based Silicon Valley collaborating with a team in Thailand.

After Jethro provided some carefully considered positive and constructive feedback over a video call and in writing, he got some feedback of his own, from the head of HR in Thailand.

“The American tendency to give feedback by explicitly stating ‘the area in need of improvement’ already feels aggressive to a Thai recipient,” she told Jethro. “To make things worse, Americans frequently end discussions by recapping key points in writing, which makes us feel that you don’t trust us to do as we say or are trying to get us in trouble.”

She explained that Jethro would have more success if instead of detailing what his Thai colleagues had done wrong, he praised what was good clearly and left out what was bad. If he was specific about the things that had worked well, he didn’t need to comment on the negative aspects at all; the Thai employees would understand that he was not happy with what he hadn’t mentioned.

The part of me that was drilled in the concept of "Extreme Clarity" is screaming at this very apparent (to me) lack of clarity. We're supposed to expect the other person to intuit what was wrong??

Yet, if this is in fact the cultural norm of this population, attempting to force a different way of working is not going to work, at least not without a lot of trust-building and mutual understanding. Which would in fact require adhering to the norms to achieve.

The Story Behind the Story

In the hilarious and provocatively insightful memoir Maybe You Should See Someone by Lori Gottlieb, the author, a therapist, describes her own journey with therapy after she's dumped by her longtime boyfriend.

Gotlieb describes what's known as "the presenting problem", what a medical doctor might call "the chief complaint". It's the reason they purport to be in need of assistance. In Gottlieb's case, it's her anger over how abruptly her boyfriend dropped her after a many years-long committed relationship.

Yet her own therapist, Wendell, refuses to stay on this initial level. He probes for the feelings underneath her rage at her now-ex. As she writes:

"Anger is the go-to feeling for most people because it’s outward-directed—angrily blaming others can feel deliciously sanctimonious. But often it’s only the tip of the iceberg, and if you look beneath the surface, you’ll glimpse submerged feelings you either weren’t aware of or didn’t want to show: fear, helplessness, envy, loneliness, insecurity.

And if you can tolerate these deeper feelings long enough to understand them and listen to what they’re telling you, you’ll not only manage your anger in more productive ways, you also won’t be so angry all the time.”

It turns out Gottlieb has been using the anger to hide a bunch of other things: the struggle to finish writing her latest book, a chronic illness, and the fear of aging and death.

Similarly as an executive coach, a client might have the "first order concern" that brings them to me. My client Kevin told me he wanted to advance as a marketing leader and for a few months we tried to work on that.

But it became clear that was just what his upbringing had taught him to want: to climb the ladder of external success. It took probing to uncover a powerful and more personal dream: to start his own marketing agency and have a more flexible schedule. And eventually we got him there, closing six figures of work in less than 6 months.

This exploration of someone's deeper desires is communication and understanding. To be clear, I am absolutely not suggesting that you turn your next meeting or 1:1 into a therapy or coaching session. But I am saying to recognize that so much of what's going on lies underneath the surface of the words we use.

"When someone shows you who they are, listen to them"

Actions and behaviors are a form of communication too. They are not always explicit, and can be misinterpreted even more easily than words, but they contain knowledge.

Miroo Kim and I ran a facilitation workshop a few weeks ago where we practiced the art of empathetic listening. Not just listening to the content, but the feelings and emotions underneath the content, and seeking to confirm our understanding as listeners to the speaker's experience.

I've done this exercise a number of times, but every time I do it again I am surprised by its power. To hear someone reflect back not just what they heard you say, but what they sensed you felt, is a profound thing.

And if this is a new practice for you, you'll find, like dressing better or getting a better webcam for your video calls, it will quietly yet tangibly improve your explicit communication.

Understanding and being understood by other humans is enormously hard. And yet our species is perhaps better at cross group communication than any other on the planet.

Here's to a more clear and collaborative tomorrow,

—Jason

PS - If you made it this far, here's a perfectly hilarious video demonstrating a "hog on hog collision", a failure to communicate on the baseball field

[1] Like all technologies, not everyone was a fan of writing. Our man Socrates felt that words weakened one's memory and mind. Can't imagine what he would have thought about ChatGPT.

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177: Contagious Beliefs

How a scarcity mindset can help (and hurt) our ability to succeed in business and life.

176: No Complaining

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177: Contagious Beliefs

Jason Shen — Sat, 04 Nov 2023 14:15:38 GMT

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Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

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I recently joined the board of AAPI leadership nonprofit Lunar Accel! Help me grow the org by grabbing a VIP ticket to their Closing Banquet in NYC on Sun Nov 11! https://tinyurl.com/LunarClosing2023

We've all gotten more familiar with infectious diseases in the last few years, but viruses aren't the only thing that can spread.

Physical health conditions like obesity can spread through a social network as well as mental health ones like depression. But so can positive changes like increased happiness and quitting cigarettes [1].

This phenomenon is broadly known as social contagion, the spread of behaviors, attitudes, and affect through crowds and other types of social aggregates from one member to another.

Taking what feels like a pretty small leap here, I'd argue that beliefs are also contagious. Whether it's the idea that crypto is a brilliant opportunity (or a massive scam), that a particular conflict or act of violence is righteous (or unjustified), or that the economy is doing better (or worse), we can "catch" beliefs from others.

So to give you fair warning, here are 10 beliefs you might "catch" if you keep reading this newsletter. And this holds doubly true if you work with me as a coach or facilitator.

🚀 1. You don't need permission to go after wild dreams

Life is short and it's more fun when you're doing something bold. So if you have a grand vision you'd like to pursue, you already have permission to go after it.

As the child of immigrants, I felt like I had to play it safe to honor my parents' sacrifice, but now I see it in reverse: by swinging big, just as they did, I honor their legacy and follow in their footsteps. So let's go.

💪 2. Nothing beats learning by doing. Try a lot of stuff in the real world.

Consuming second hand information only gets you so far. As Prince Harry's ghostwriter once beautifully said, "Empathy is a thin gruel compared to the rich marrow of experience". Better to gain it for yourself.

If you want to be an entrepreneur, make something and see if you can get people to use it. You learn faster from trying it in the real world than studying it in a class or textbook.

🕰️ 3. Good things compound over time so play the long game.

Part of why you gotta start doing things right away is that it takes a while to get started, find an approach that works for you, and get some early wins. Skills, reputation, and momentum start out hard to build and get easier over time. You gotta keep at it to see results.

In many ways, I have struggled to act on this belief in my own life, because I am so novelty-seeking. But when I look at the things I have stuck to, gymnastics, writing, my relationship with Amanda, I see my gains compound. Ten years from now, you'll be glad you played the long game.

🏋️‍♀️ 4. To reach your full capacity, you must nourish your physical body with movement & rest

Everyone reading this is a knowledge worker and that kind of labor can make the rest of your body feel superfluous. But in fact our minds cannot perform at our best when our bodies are not in good condition.

Varied, consistent, intense movement, plus quality rest (total hours, consistent schedule, supplemental naps) are vital factors for us to show up as excellent leaders, builders, and partners.

🎲 5. Always leave a little room to make low-probability, high-upside bets.

Our world is complex, interconnected, and increasingly volatile. Bad things can happen out of the blue (e.g. extreme weather, SVB crisis, flight cancellations, etc).

But for every loss, there's room for gain. Investing a bit of your time, money, and effort on things that could do well (helping a high potential young person, investigating a promising new technique/concept/tool in your field) can pay unexpected dividends when you least expect it.

🤝 6. Help others more than you think is wise. The world is not zero-sum and an overly competitive mindset is toxic.

I don't believe that to do well, my peers or competitors must fail.

Thanks to better governance and technological advances, we've been able to raise the living standards for human beings all around the world. The reason why startups work is because people work harder to help the entire organization compared to the narrow lane of a big company.

Your well-being is enhanced more when you help others succeed than narrowly focusing on your own gain at the expense of others.

🏘️ 7. You don't need more self-reliance. You need more communal resilience.

We are overly fixated on being able to do things "by ourselves". Certainly we want kids and young adults to develop their ability to live independently. But to do anything challenging or weather difficulties requires the support of others.

Asking for help is often the sign of greater maturity than hiding your troubles to avoid losing face. We are more resilient when we are together.

💖 8. In the end, you will care more about the quality of your relationships than accolades and accomplishments.

By all means, pursue your ambitions and prioritize the endeavors that matter to you. I certainly "work more" than plenty of folks. But I love the work I do, and I almost always am able to prioritize my health and the relationships of the people closest to me over my professional responsibilities.

Because I know I won't regret making more money or winning more recognition, but I'll treasure every moment I had with my family and close friends.

🔄 9. When you learn how to reframe problems as opportunities, you become unstoppable.

I come back again and again to the words of educator Howard Gardner in his book Extraordinary Minds: “Extraordinary individuals fail often and sometimes dramatically. Rather than giving up, however, they are challenged to learn from their setbacks and to convert defeats into opportunities.”

It is easier said than done, but that's why it is a belief! I have been talking about stuff like getting rejected or the lessons of failure for more than a decade and I'm not going to stop now.

📩 10. Communication matters more than results when it comes to building trust.

Having recently witnessed second-hand the destructive effect poor communication had on a really important project, I can't stress this one enough. People will forgive underwhelming results when it comes with clear, upfront, and consistent communication. But they may not be satisfied with even stellar results if communication is sporadic, incomplete, and inconsiderate. More in this post.

Bonus! 🔮 11. There are no magic formulas—enduring success comes from discovering what strategies work best for YOU.

If you read this newsletter, there's a good chance you might identify as an outlier: someone who deviates from the norm in meaningful ways. Your identity, your talents, your background, your point of view may not fall squarely in the mainstream.

The typical advice won't work for you because you're atypical. So embrace what makes you different and figure out (as per #1) what works for you by experimenting in the real world. Then stick with it and keep iterating.

Curious to know, which of these beliefs (1-11) do you most resonate with? Or are there any you vehemently oppose?

Contagiously yours,

—Jason

[1] Obesity as a social contagion (link) along with depression (link), happiness (link) and quitting smoking (link).

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176: No Complaining

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175: Rebuilding a Computer Lab

176: No Complaining

Jason Shen — Sat, 28 Oct 2023 14:21:30 GMT

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Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

One of my dad's favorite home decorations was a dark brown wooden board that said, "No complaining." Or maybe it was "No whining."

In any case, after immigrating to the United States and escaping the Cultural Revolution in China, my parents were keenly aware of how much worse life could really be. How their lives and schooling were interrupted, how Dad was sent away to a rural labor camp where there was no heat in the winter and his toenails became thick with fungus from standing in muddy rice fields.

Top marks in the national collegiate entrance exams and an acceptance into Boston University opened the door for Mom and Dad to come to the United States.

Making Do

They scrimped, saved, and labored over the years carve out a middle-class life for our family. I don't think I complained more than the average kid. I was reasonably content with what I had. But if I asked for resources beyond what was deemed necessary (whether that was more allowance, more TV time, or computer access), my dad would push back.

He'd ask me to demonstrate what I could accomplish with what we already had and explain precisely why I needed something more. This ingrained in me a sense of resourcefulness and scarcity. We had enough, but not an abundance. Anything more required sacrifice.

This motto of "No complaining" meant being grateful for what you have. Knowing it could be worse. And figuring things out on your own, without an attitude.

For the most part, this is a constructive attitude to have. The attitude of an immigrant. Of a team player. Of a survivor.

Stretching Dollars in Your Startup

As an entrepreneur, I embraced some of this mindset, for better or worse. Despite the many high-flying rounds of funding you would often see in the news (RIP 2015-2022), the vast majority of startups are incredibly cash-strapped and need to stretch every dollar.

You have to make the most with what you have, then prove you deserve more before going out to raise more funding. Every dollar must be spent as if it's the last. Fundraising is a major event requiring enormous proof that your business is worthwhile.

This meant: use the free plan for as long as you can, make new accounts if you have to. Look for credits and discount codes and ask friends to hook you up with deals. Eat at Costco. Never pay full price. Do it yourself.

No complaining is baked into the ethos of early-stage startup life. Because you don't have to do it—you get to. But this attitude has its drawbacks.

The Squeaky Wheel

At Facebook, if I didn't complain, if I didn't call out that our team was not properly staffed and resourced to hit our goals, then I wasn't doing my job. As a product manager, its your responsibility to speak up when your team needs more.

Too often, my mindset was more of "We can make it work with what we have. It'll be a little messy, but good enough." I didn't want to take up too much space or be too demanding. But that was a mistake.

I should have clearly stated that our project needed more resources to maximize its success and capitalize fully on the opportunity. It was my manager's job to then go fight for those resources based on my testimony. When I did advocate strongly, I was praised for it. Even the intense design manager thanked me in a 1:1 call, saying I had made it easy for him to get what my team needed, so we could blow our project out of the water.

Not every company has this mindset, but part of an effective leader's job is determining where resource gaps exist and filling them so teams can achieve results. A culture of no complaining can prevent resources from being directed to the right places—and even lead to worse decisions.

Hard Truths

I recently advised a client who was being pressured by his CEO to increase the targets and goals of their annual plan. My client's team was hesitant to raise the bar because in the last planning cycle, targets were raised last-minute in a tops-down decision by an outgoing leader. Now the org was off-track on their goals and would not receive any end-of-year performance bonuses, and not happy about it. My client's people understandably wanted a repeat of last year.

A culture of "no complaining" meant bad news or problems didn't always reach the CEO's ears. Remaining silent out of a desire to avoid "complaining" or protect egos often backfires. Don't assume the problems are well-known. Everyone is busy and distracted, including leaders, and things slip by.

In the right circumstances, sharing hard truths and challenges is not complaining - it's providing crucial perspective to enable growth. A "no complaining" culture can discourage the transparency and candor needed for an organization to reach its potential. Of course, complaining just to vent frustration is unproductive. But when done with care for a constructive purpose, speaking up pays dividends.

The Art of the Kvetch

I've noticed cultural differences in attitudes towards complaining as well. In the Chinese culture I've been exposed to, openly critiquing those in power or the status quo is often considered impolite—implying the hierarchy failed you in some way. Complaining can be seen as a threat to social harmony.

Whereas what I've seen of Jewish culture, lively debate, complaints (aka kvetching) and questioning of authority is more accepted. This is not just my opinion, there's linguistics research on it! The complaints are aired openly, discussed vigorously. There is often a greater willingness to entertain criticism, believing it can lead to better outcomes.

These cultural norms underscore broadly differing worldviews. Is ours a static world of limited resources where complaining takes from others? Or an abundant, dynamic world where vocalizing concerns can help us collectively thrive? Are we lucky to have it so good? Or should we remember how we've been unfairly treated?

What Kind of Pie?

Perhaps the way we think about complaints comes down to how we see the availability of resources. My father's China was a world of limited opportunity, of fixed roles and possibilities. The West has long represented unlimited upside, an ever-growing pie that theoretically anyone can get a piece of. If resources are finite and fixed, complaining takes from others. But if the world is expandable, complaints can lead to better outcomes for all.

To complain, I once heard, belies a belief in improvement and higher standards of treatment. That things could be better, ought to be better. The chants of the activist, the stump speech of a contender politician, the funding pitch of an entrepreneur all share something in common: they express dissatisfaction with the status quo and call for resources to make change.

And look, technically the pie is fixed in terms of the energy resources and raw materials on our planet. But practically speaking, our economy and planet still have untapped potential. With our slowing population growth and ongoing innovations in solar, nuclear, and fusion mean that we still very much can live in a zero-sum pie.

With the right mindset, complaining can be recast not as an act of greed, but as a catalyst for creativity, innovation and collective growth. My dad's "no complaining" rule ingrained useful values for our early life, but perhaps went too far.

A degree of healthy complaining keeps us from complacency, challenges existing limits and drives societal progress. With care and wisdom, even complaints can help build a world of greater abundance.

—Jason

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Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

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Executive Coaching for Unconventional Leaders: If you want to steer through moments of change and swing bigger and projects that really matter—you might find value working with me.

Recent Issues

What does giving back to go forward look like? For me, rebuilding a computer lab in SF Chinatown.

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Jason Shen — Sat, 21 Oct 2023 12:14:58 GMT

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Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

My parents are visiting me in Bangkok—we missed the tour bus to the floating river market so we wandered around downtown and got massages. My mom is always looking to buy little gifts for the people she loves, and she's onto something.

Today's letter is about how giving back, not just with your money but your mind, helps you build resilience, and a better world.

A couple of years ago, I started a strategic philanthropy project with my friend Bilal Mahmood called 13 Fund. The idea is that we would identify a significant social issue in our local communities of New York and San Francisco. We'd do research on the topic and ultimately identify a non-profit organization that could address some of the core aspects of this issue.

Our first year we supported under- and unemployed food workers in the Bay Area during the pandemic. Then we worked on fighting anti-Asian hate in New York City. And this year we were focused on low-income residents in Chinatown.

There are a couple of different things we could look at, including single resident occupancies where a family of four might be sharing a 100 square foot room. But building housing and housing-related things, especially in an area like San Francisco's Chinatown, is a difficult proposition as individual citizens.

But in our research we identified another area, which is digital access. Nowadays it's not just necessary for immigrant populations to learn English language skills, they must also be digitally fluent and have access to internet in order to check email and apply for all kinds of resources like housing, employment, government services, and support.

The internet in Chinatown isn't the best and seems to be a difficult thing to get stable and reliable high-speed internet. So we looked around for opportunities to make a difference and ultimately identified an organization called Cameron House, which is a 149-year-old historic nonprofit that's been serving the community since the 1800s, when a woman named Donaldina Cameron helped Chinese women escape prostitution so they could find a new life.

Cameron House has, or I should say had, a number of computers and laptops and tablets that they were using to both teach senior elder members of the community English alongside computer literary skills like using WeChat or Amazon or buying groceries online. Sending pictures, using Zoom, things like that, as well as supporting outside of school programs for young people where they could do their homework assignments or get help from a teacher while using an array of computers.

We wanted to expand this program and began to prepare to raise a fundraiser to help them expand and build upon their computer lab. During this time, I got a chance to meet some of the instructors, meet some of the members of the community who benefit from this computer lab and put together a short film about their work and the history of the organization.

San Francisco also has been continuing to battle crime, although there's a lot of debate about whether it's worse than before or differently distributed or whatnot. The bottom line is Cameron House was hit with burglary that took out a lot of this computer lab and this burglary is attached to a guy who has been charged with a string of burglaries throughout the city.

So not only is there a lack of digital access or digital equity in this community, but this nonprofit had lost some of the meager resources they actually had. So a couple of weeks ago, we launched a fundraiser to help rebuild and expand the computer lab in Cameron House with brand new laptops and computers and a more secure mobile charging station.

A Computer Lab for SF Chinatown

Watch the film

In addition to Bilal, have to give a big shout out here to Danny Sauter who is part of a group called Neighborhood Centers Together which Cameron House is a part of and had relationships with the staff to help identify this opportunity and bring it together. As well as John Jersin, a tech executive who had a startup that sold to LinkedIn where he was vice president at LinkedIn for a number of years. John became the anchor donor for this $50,000 campaign and helped we launched the campaign.

Since then, we've raised another $20k+ from folks from all over the community from San Francisco, New York and across the country including some tech luminaries like Paul Graham, Gary Tan, Matt Mullenweg.

Sometimes the best way to build resilience is to give back

One of the things that resilience is about is this idea of contributing back and giving back. I know a lot of tech workers are struggling with layoffs happening left and right, RTO, belt tightening, and the fear of what's to come.

But even when you're struggling, helping others can be a really powerful way to feel a sense of significance, of competency, of connection. And so I'm glad to be able to do that.

This $50,000 grant is incredibly meaningful for Cameron House. It's not something that they could have otherwise pulled off and it's giving them a certain level of visibility that they really haven't had before.

We're now 85% of the way to reaching our goal to raise $50,000 for a new computer lab in Chinatown!

Thank you @windnewspaper for getting the word out about our initiative to support @CameronHouseSF.

Please consider supporting here: https://t.co/imO52whgO8 pic.twitter.com/PyRsQpke5i
— Bilal Mahmood 馬百樂 (@bilalmahmood) October 16, 2023

So even though recording the video and putting that together was a lot of work for me, it was also very meaningful to feel like a part of this campaign. Hopefully when you watch this video you understand that you're connected to this campaign through me and through the work that we've done collectively.

One of the things we wanted to do with 13 Fund was to help members of the tech community, people that we see as our peers as recognizing that you don't have to be Bill Gates or Mackenzie Scott to give back to your community. That there is plenty of opportunity, plenty of projects that are important and worth doing that are within your grasp.

So that's all to say I'm really happy to share the work that we've done here. And I'd love for you to contribute what you can to the campaign to get us to that $50,000 and to stay tuned for other projects like this in our community. And whether through this project or something else, hope you find a way into cultivating resilience through giving back.

Jason

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