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
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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.