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
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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.