Start Here


I've covered a lot of ground over hundreds of newsletters, blog posts, and bylines in other publications. If you're looking to go down a rabbit hole of my best stuff, you can start here.


Being an Outlier

214: A Weirdly Brilliant FAQ
5 Questions & answers about my new book and the future of this newsletter
179: Being an Outlier
Getting a Kindergarten PIP and what to do when you feel remarkably different from your peers.
181: Strong Suit
Three ways to make your outlier obsessions an advantage you as an outlier
182: Kryptonite
How effective outliers manage and mitigate their weaknesses
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.

Hard Pivots

After two pivots as a founder (one failed, one that led to an acquisition) and studying dozens of pivots, I wrote a book about the art of the startup pivot.

195: I Wrote a Book
How I wrote The Path to Pivot, who it’s for (venture-backed founders), why I self-published, and what’s next
197: Two Pivots
How my first failed startup laid the groundwork for the successful second act
In Defense of Hard Pivots: why we sold our hiring platform to launch an esports company
In 2017, I started a tech screening and hiring business called Headlight with my friend and former Etsy teammate Wayne Gerard. A few days…
125: The Double Loop Pivot
Why The Double Loop Pivot Is the Best Way To Explore Changing Your Business + Strategies for Managing ADHD
Conviction: A Startup Founder’s Most Valuable Asset
Part 1 of the Reinvention Series
How Notion Transformed Into the Internet’s Second Brain [Pivot Case Study]
The story of Notion’s pivot from a no-code app builder to a revolutionary all-in-one workspace that’s now valued at $10 billion with over 30 million users.
How Hugging Face Transformed a $4.5B AI Powerhouse [Pivot Case Study]
The story of Hugging Face’s pivot from an AI chatbot for teens to the leading open-source AI platform and how they revolutionized the machine learning ecosystem.

Career Advice

I am not a career coach for a reason—getting jobs and promotions is mostly about adapting to The System. I'd rather help you find a Frontier to thrive in. Nonetheless here's what I've got.

The 10x Job Application
The 10x job application is when you get creative and build something potential employers can’t ignore. Here’s how to do it.
Play to Your Strengths
Why you’ll never win by staying on defense
Getting Turned Down By Google Helped Me Get Hired At Etsy
A product manager explains how trying to oversell his technical chops to Google helped him switch gears while interviewing at Etsy.
The No. 1 habit all highly resilient people have, according to a career expert
The No. 1 habit I see in my most resilient clients is the ability to shift their stress response from “fight-or-flight” to “tend-and-befriend.”
How to Become More Adaptable
Republishing my piece from TechCrunch

The Networking Secret That Only Requires Writing Four Emails A Year (fastcompany.com)


The Resilience Rules Series (Every)

I was commissioned to write a series of articles about resilience on Every.

How to Cultivate Resilience: A Four Part Framework
Part I of Rethinking Resilience
Oh Shit, You’re Going Through a Reorg
How to approach it with a resilient mindset
Why “Suck It Up” Isn’t a Solution
The problem with toughness as a resilience strategy
What Getting Sued, Scammed, and Arrested Taught Me About Resilience
How quickly things can go from good to bad—and how to endure the long road back
You Got Laid Off. Now What?
How to act with resilience when you’ve been let go

Ultimate Guides (Medium)

I wrote a series of extensively researched / experience backed articles for the Better Publications on Medium.

How To Dramatically Improve Your Public Speaking Skills — With Jason Shen🎧
Stories are powerful. Learn to tell yours with clarity and confidence.
The Complete Guide to Deliberate Practice
We are capable of incredible feats, but they won’t come without focused effort, consistent feedback, and expert guidance.
How Great Writing Begins
Analyzing the patterns of first paragraphs from 94 of the most compelling feature articles from The Atlantic, Fast Company, and NYT Opinion…
How Great Writers End Their Articles
What you can learn from the final paragraphs of 100 top feature articles from Malcolm Gladwell, the Atlantic, Fast Company, and the New…
How to Use Surveys to Build Audiences and Reach Your Customers
Jump start an audience and position yourself as an expert
The Extraordinary Power of Self-Reflection
I recently stumbled across an old document on my laptop. It was a PDF with journal entries from several years ago. While many of the entries were typical day-to-day activities, I also found about 100 short lessons that I had captured during this journaling period and I shared a few

Op-Eds

Occasionally I write more pointed opinion pieces that comment on an issue that matters a lot to me.

The response to Simone Biles’ exit shows we still have a long way to go on mental health
Everyone’s eager to talk about wellness when it means bubble baths and meditation apps. But supporting mental health—especially when it’s inconvenient—is something we need to do better, whether on the Olympic stage or in the workplace.
Professional Athletes Don’t Train 70 Hours a Week and Neither Should You
Long hours are BSLots of people in tech are obsessed with putting in long hours. Elon Musk once said that “nobody ever changed the world on 40 hours a week” and suggested that the correct number was between 80-100 hours. Freelance marketplace Fiverr, with venture funding to the tune of
Why Always Be My Maybe’s Asian American underachiever is groundbreaking
We need more stories about Asian Americans. Especially the underachieving ones.
An Open Letter to Managers of Women
Dear manager,

Company Lessons Learned

Sometimes I do deep dives on companies.

The Art of the AI Pivot
How one startup turned failure into 3 million users in three months
The Product Genius Behind Jackbox Games
This article first appeared on TechCrunch [https://techcrunch.com/2020/05/04/all-product-creators-can-learn-something-from-jackbox-games-user-experiences/] During this periodof shelter-in-place, people have had to seek out new forms of entertainment and social interaction. Many have turned to a niche party series made by a company best known for an irreverent trivia game in
The New Napster
There has been an explosive new development in how scientific research is read and distributed. It’s name is Sci-Hub [https://web.archive.org/web/20181007100235/https://sci-hub.cc/]. Founded in 2011 by Alexandra Elbakyan (who was, at the time, a 22 year-old graduate student based in Kazakhstan), the site
Product Insights from Pokémon GO
As you probably have heard, Nintendo has partnered with game developer Niantic to launch a wildly popular game for iOS and Android called Pokémon GO. The game has already reached over 21M daily active users [https://www.surveymonkey.com/business/intelligence/pokemon-go-biggest-mobile-game-ever/] , dominated the in-game purchasing market [https://intelligence.slice.
Ridejoy: Lessons Learned
On April 24th, 2011, I sat down with my friends Kalvin and Randy for an intense 10 minute interview with Paul Graham, Sam Altman, Jessica Livingston and several other partners at Y Combinator (YC). We were hoping to convince the world’s most powerful startup accelerator to accept our Reloveit,

Big Tech Insider

There's a lot that people wonder about regarding the inner workings of Big Tech. Here is a look inside.

158: Meta Lessons—Managing Achievers
This week I unpack 5 concepts Meta taught me about managing high achievers: expectations, calibrations, showing care, HPMs, and alignment.
154: How Meta Makes Use of Metrics
My birthday lessons will be a 3 part series on lessons learned at Meta: this is part 1.
What People Don’t Tell You About Product Management
How to Be a Successful Product Manager

Book Notes

When I find a book I really like, I try to do a book notes post on it.

Range: Why Generalists Triumph in a Specialized World
Why it’s ok to be a jack of all trades
Dark Horse: Achieving Success through the Pursuit of Fulfillment
How to achieve breakout success and deep fulfillment when you don’t fit the traditional mold
ADHD 2.0: New Science and Essential Strategies for Thriving with Distraction
“However ubiquitous the term, one thing remains very much and frustratingly the same: Most people, even now, don’t understand the power, magnitude, and complexity of this condition. Nor do they know the tremendous advances in understanding and treatment that have been made in recent years.” estimated that 5% of
Upstream: The Quest to Solve Problems Before They Happen
Reading Notes on Preventative Interventions In a Nutshell: Upstream is a book about prevention: how to not just mitigate the damage of problems after they happen (downstream) but address the underlying drivers of the problem such that the problem no longer occurs or is much less severe. * This type of
The Year Without Pants
One of the few people who can match Paul Graham [http://paulgraham.com/] as writer is Scott Berkun [http://scottberkun.com/]. They have both succeeded as technologists, Graham in Viaweb + YC, and Berkun in Microsoft and Automattic. They both write thoughtful essays on a wide range of topics, like the
Zero to One: Notes on Startups or How to Build the Future
In spring of 2012, Peter Thiel, cofounder of Paypal and Palantir and early investor in Facebook, taught a course at Stanford in the Computer Science department calledCS183: Startup [http://blakemasters.com/peter-thiels-cs183-startup]. One of the students in the class, a law student named Blake Masters, took meticulous notes that were

Interviews

Talking to others can be insightful—here are some interviews I've done with others (and one with myself!)

Deepak Chhugani on the hard pivot | Meridian
How the founder pivoted between industries and kept up his mission.
169: 📦 From Warehouse Associate → OpenAI
Our most popular letters from 2022 were about Philip Su, the burned out engineering leader who did a stint as an Amazon warehouse associate. Here’s a look back at that story and how things have evolved for Philip.
Solve for the Harder Problem [Interview with Bilal Mahmood]
How ClearBrain’s CEO Used These 7 Lessons to Create a New Product Category
Beyond the 10,000 Hour Rule
We’re all familiar with the 10,000 hour rule, which was made famous by Malcolm Gladwell in his 2010 bestseller Outliers: The Story of Success [https://web.archive.org/web/20171128084400/http://amzn.to/1ZMKchl]. In it, Gladwell makes the argument that 10,000 hours of practice is a
Career Spotlight: Jason Shen, Product Manager at Facebook, Serial Entrepreneur, NCAA Gymnast, Angel Philanthropist
Lessons from founding multiple companies, qualifying for the US Junior National Gymnastics team, and setting two Guinness world records.
Product Design for the Web: Principles of Designing and Releasing Products for the Web
No Silver Bullets: An Interview with Author Randy Hunt While on my Peru trip earlier this year, I read a great book called Product Design for the Web: Principles of Designing and Releasing Products for the Web [https://www.amazon.com/Product-Design-Web-Principles-Designing/dp/0321929039]. As one of two interaction designers

Fitness / Gymnastics

My life and worldview is shaped by my 16 years as a competitive gymnast.

How I Blew Out My Knee and Came Back to Win a National Championship
On January 19th, 2007, while competing for Stanford Men’s Gymnastics at the UC Berkeley, I suffered a total knee dislocation while performing a double-twisting Yurchenko. My ACL, PCL, MCL, LCL and meniscus were instantly torn. It hurt a lot. I underwent multiple surgeries, required the use of crutc…
What I Learned from My First (Blunder-Filled) Marathon
This piece was originally published in 2014 on the health and wellness site Greatist but has been lost after the site was acquired in 2019. Republishing it here because it’s a great lesson in humility and resilience. Entrepreneur and former collegiate gymnastics champion Jason Shen had a less-than-awesome experience
Six Blistering Bodyweight Workouts You Can Do in Under 30 Mins
One of the biggest reasons why people say they don’t exercise is because they don’t have time. Of course, we all have the same amount of time, and there are plenty of really busy people who work out [https://web.archive.org/web/20161001013436/http://www.businessinsider.com/
MC#011: The Gymnastics Edition
🐥 Why gymnasts are young + 🎬 Athlete A + 👩🏾‍🏫 Simone’s Masterclass
MC#020: The Sweat Edition
6 takes on Peloton, Mirror, Aaptiv, and the fitness tech space

On 10 years in CrossFit