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Optimizing for "Winging it"
Why I'm optimizing for failure and pain

Ironically, I’m bad at consistency.
Perfectionism and overthinking are two things I’ve struggled with over the past years.
The fear of failure.
The fear of pain.
With YouTube, the newsletter, and social media - I realized, this is going to be a bottleneck for me going forward.
Earlier this week, I had a call with Leon Hendrix (610k subs on YouTube), and he provided some useful nuggets I thought you guys might enjoy :)


Channel link: https://www.youtube.com/@leonjhendrix
Lean into what makes you uncomfortable:
The challenge for me is consistency…
Publishing consistently…
I overthink and overanalyze videos and posts...
Leon: “Then it probably means that uploading more often would be the right challenge for you - specifically because you know, other people, they have the opposite challenge where they just like putting stuff out there. And they don't think about it. They don't do an analysis, like “what actually worked here?” And sometimes these people succeed because they just happen to do the right things.”
Set ambitious goals:
The pursuit of an ambitious goal will lead to more results (even if you don’t achieve it).
Versus - aiming lower (with an unchallenging goal) and actually achieving it.
I set out a goal to get to 100k subs by the end of the year.
Leon believes this is more than achievable.
It took him 9 months to get to 1,000.
And 3 months thereafter to get to 100,000.
But fantasizing about achieving the goal isn’t going to get anywhere, which leads to the next point…
Ready, fire, aim:
Being the Type-A thinker we both are… our typically approach would be to:
Analyze everything
Have a clear strategy
Have a clear roadmap
However, this leads to paralysis by analysis.
What we should be doing is winging it.
Yup- winging it.
It doesn’t have to be perfect.
It’s faster and easier.
And it alleviates so much stress.
Then continue to iterate from there.
Content and business are a continuous experiment.
Hypothesize, do the thing, observe results, repeat.
Overanalyzing the thing isn’t doing the thing.
Preparing to do the thing isn't doing the thing.
Scheduling time to do the thing isn't doing the thing.
Making a to-do list for the thing isn't doing the thing.
Telling people you're going to do the thing isn't doing the thing.
Messaging friends who may or may not be doing the thing isn't doing the thing.
Writing a banger tweet about how you're going to do the thing isn't doing the thing.
Hating on yourself for not doing the thing isn't doing the thing.
Hating on other people who have done the thing isn't doing the thing.
Hating on the obstacles in the way of doing the thing isn't doing the thing.
Fantasising about all of the adoration you'll receive once you do the thing isn't doing the thing.
Reading about how to do the thing isn't doing the thing.
Reading about how other people did the thing isn't doing the thing.
Reading this essay isn't doing the thing.
The only thing that is doing the thing is doing the thing.
All of this made me realize…
I should optimize for imperfection.
I should optimize for failure.
I should optimize for pain.
(^ take from that however you will- I’m not telling people to go hurt themselves lol).
But growth never comes from being in a bubble…
Growth never comes from being in your comfort zone…
Growth never comes from reading what others do…
It comes from getting out of your comfort zone and doing it.
Two people can receive the same information, same knowledge, same process, same systems - but they’ll get entirely different result.
I’ve optimized out of not wanting to experience failure and pain - but maybe, the challenge is actually doubling down on it, and direct it where the stakes are high.
Where there is a high-level of accountability.
Where things are on the line.
Where failure is expected.
Where pain is expected.
Because, without it, did I even choose a worthy goal?
Thanks for reading my brain-dump, now go crush your goals :)