222: Treading Water

222: Treading Water

Resilience

3 questions to ask yourself when you feel like you're going nowhere


I was in San Francisco recently—meeting with my West Coast clients in-person, and connecting with new friends: founders, coaches, and builders.

When you're surrounded by high-achieving people, its easy to fall into a bit of an echo chamber. Everywhere you look there's someone who just landed a big round for their AI company, 3x'd their monthly growth rate, or hit a major revenue milestone.

It's easy to look at your own meager progress and feel discouraged. After all you're not doing that well—so what do they know or have that you don't?

Maybe you're not cut out for this. Maybe you have no business being here.

But that's just your inner critic talking. Here's a reality check:

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Next Monday I'm kicking off my first of four Outlier salons—more here

First off, unless you are very close to someone, you don't see their struggles. You don't know how close they came to giving up, shutting down, or getting crushed. There are a few people in the world who cruise through life because everything was handed to them—and none of them do anything truly meaningful because they never truly fought for what they wanted.

Secondly, the winners are constantly changing. New players enter the arena, and people who were hot a few years ago are struggling today. Just look at the string of AI companies that were funded in 2021 and 2022 who are now no longer the media darlings. Having a great quarter or a singularly good outcome is one thing, but few can sustain it year after year without some major downswings.

Thirdly, maybe you don't have what it takes to be them—yet. Maybe you really don't understand the market, the technology, how to hire and how to lead. And there's nothing wrong with that. What is there to do but figure it out? Why would we spend 16 or so years in formal education and then think our learning ends there? The real lessons have just begun.

If you're in your 20's or 30's, you should expect to face a huge learning curve around what you're doing. Expertise matters and expertise is learned through experience, and experience usually comes from making uninformed decisions.

And fourthly luck and timing is real. Sometimes you just aren't lucky. Mark Zuckerberg knows he could not start another company and make it as successful as Meta.

Here's what you should be asking yourself when you feel like you're just treading water and going nowhere:

  1. Am I making swift but considered decisions based on what I know about myself and my circumstances?
  2. Am I putting in max or near-max effort (90%+) on the activities I know matter most?
  3. Am I reviewing past decisions and actions of myself and other players in my space to improve my judgement and understanding?

If you can honestly answer "yes" to all three questions, then you are going as hard as you can and putting yourself in the best position to learn and grow.

There's basically nothing more to do at the moment, unless you want to completely pivot your product / company / life (in which case read my book The Path to Pivot).

If not, then you know what to do. Make better / faster decisions. Over do it. Reflect more.

As a coach, my job is to assist in those three areas. I help clients think through and make hard decisions, encourage and hold accountable towards strong effort, and review past activity for learnings and improvements. But anyone can and should be doing this on their own anyway.

Remember: practice makes perfect doesn't just apply to piano or three-point shots. It applies to building ambitious ventures too.


Do you feel like an atypical achiever? Do you see and move through the world in a different way? Do your talents lead people to comment that you're not living up to your potential?

Fuck your potential.

Join me on Monday October 14th at 9:30pm Eastern for a salon about defining your ambition and going for what really matters to you.


Jason Shen

The Outlier Coach—helping founders build conviction in what's next · 3x venture-backed startup founder (acq by FB) · Author of 'The Path to Pivot' & 'Weirdly Brilliant' · ADHD · Former NCAA gymnast