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095: My Journey into Resilience

🤔 Are you listening? 🧠 Sharing my resilience story 🖼 A Besieged Museum 👉 Chasing Merit Badges

Jason Shen
Jason Shen
5 min read
095: My Journey into Resilience
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Cultivating Resilience is a newsletter that helps innovators navigate change and bring new product and ideas into world. It's published by Jason Shen, a resilience coach, product manager, 1st gen immigrant, ex-gymnast, and 3x startup founder.

🤔 Are you listening?

On a scale from 1-10, how well are you listening to your inner voice? What is it telling you?

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Reply back to this email with your response and I'll send you mine!

🧠 Sharing my resilience story

Published as part of Foster's Season One and now on Jason's About Page.

My first business took less than two years to fall apart.

I remember huddling over the phone with my cofounders as one of our investors chewed us out for wanting to give up. “Do you know how many founders would kill to be in the position you’re in?”

We had launched out of a top Silicon Valley accelerator with a long-distance ridesharing service—at a time when Lyft didn’t exist and Uber was an app for getting limos in San Francisco. But when our only effective growth channel, a community news platform, threatened legal action to keep us from siphoning users off their platform, we needed to make some big changes.

My cofounders and I tried to explore adjacent opportunities in the travel space. When that exploration went nowhere, we were forced to lay off the team to preserve cash and retrench. We spent 6 months jumping from idea to idea, unable to agree on a direction to  start building. We didn’t run out of money—we ran out of resilience.

Discouraged and ashamed by my failure, I took off, leaving behind our shared San Francisco apartment, and the Bay Area startup scene entirely. Over the next five years, I changed career tracks, got laid off, dated, broke up, entered two marathons and finished one, fought a lawsuit, gave a TED talk, lost 12 grand in a credit card scam, set two Guinness World records, and eventually started a new startup.

We got 18 months into building a business to improve tech hiring and realized the demand for our product wasn’t as strong as we had expected and we didn’t really love working in the space. This time, we were able to adapt.

My cofounder and I took a week to brainstorm as many ideas as we could and pitched our favorite ones to a few close friends and advisors. Their feedback helped us converge on two related concepts in the gaming industry that we got started on right away.

We rewrote our pitch deck, landed new investors, built a new team, and launched a slew of new products into the market. Our efforts got the attention of Facebook (now Meta) and they later acquired us. For two years, I've led product teams building knowledge & documentation tools while teaching the core skills of resilience to employees.

This journey wouldn't have been possible without the struggles I faced and the practices I took up. I meditated. Journaled. Read stacks of Brene Brown and Kelly McGonigal books. Spilled my guts in breakout rooms. Worked with two executive coaches. Married a fiery artist and learned to make space for both our sprawling ambitions under one roof.

I was forced to unlearn and relearn many things about resilience. That trying to tough it out solo might have worked (at least partially) for my immigrant parents but not for me. That expressing my emotions was not a sign of weakness. That giving up old dreams in favor of new ones didn’t mean I was a failure. That life is full of surprises but that we can always find a way through.

Read more: https://www.jasonshen.com/about/


🖼 A Besieged Museum

I made these two pieces using conjure.art, a GPT-3 powered AI engine for creating visual images. It truly feels like a piece of magic.

Using my newly delivered Story Engine, I assembled an intriguing prompt, which I then ran theough Conjure.

A misunderstood archivist wants to restore the former glory of a besieged museum but they will have to get close to a beloved imposter whom he despises.

Note: The Story Engine is made by Peter Chiykowski, who also wrote the AND WHEN YOU SURVIVE THIS piece featured in 091


👉 Chasing Merit Badges

I wrote a short poem about chasing fewer merit badges and encouraging your inner voice to speak up again.


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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?

Recent Issues

094: Sacred Words
🤔 Celebrating 100 editions🧠 Poetry as Spiritual Practice🖼 Team Morale (S&B #042)👉 Easing into Writing Poetry (exercises)
093: The Role of Fear
🤔 Your life on the silver screen🧠 What losing taught a UFC champion about fear and confidence🖼 Airport (S&B #041)👉 Encanto (Disney movie)
092: Forever War, Forever Peace
🤔 How are you feeling?🧠 Waging Forever Peace🖼 A Vietnam Execution👉 Gibbons (game)


More Resources and Fun Stuff

  • Book Notes: Summaries / quotes from great books I've read
  • Scotch & Bean: a webcomic about work, friendship, and wellness
  • Birthday Lessons: Ideas, questions, and principles I've picked up over the years
  • Career Spotlight: A deep dive into my journey as an athlete, PM, founder, and creator.
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Jason Shen Twitter

Writer, executive coach, and resilience expert helping founders & product leaders move through adversity and ship things that matter.