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To Balance Yourself Lean Back
What riding a bike with no hands taught me about progress
As I biked from the city center toward Manzanillo Forest, a thought bubbled to the top of my mind.
“I miss bicycling.”
“I haven't done this in a long time.”
Nowhere to go but straight. No tasks to accomplish or places to be.
If I ended up in Manzanillo, about 10 kilometers away, that'd be great.
However, if I stopped short and just biked through this straight road on the coast of Puerto Viejo, that was enough too.
Every few minutes, I would try to balance myself on the bike with no hands. It’s something I always admired watching others do as a kid but never gave myself enough space to be able to attempt and learn. When it comes to experiential (and maybe all learning) I’m starting to notice that: if you make the stakes small and enjoyable, the outcome not the end state vision but just the next level ahead of you, you make progress a lot faster.

For example, if I sat up of 1-3 seconds without falling, this felt like an enough of an accomplishment to get into the feedback loop to try again with a higher goal next time. I’ve noticed this particular principle a lot for me in kinesthetic fields, e.g., Olympic weightlifting, Muay Thai, yoga, et cetera. I have way more grace for myself here for some reason that has helped me gain higher proficiencies. I’ve always approached these disciplines with intense focus and effort, but never held them to the same narrative constructive value in my identity as my career. Compare this to my approach to business and startups, and it’s a completely different game.

I really struggled while trying to build learningtodj.com into a standalone business (See My 10K MBA). I could barely claim the “entrepreneur” identity, because I felt like a total imposter. The more books I read and outputs I saw not accumulating greater leverage, the more of a failure I felt like. Everything was taking too long!
I was constantly berating myself.
Opens the email list page —> sees only one lead —> “I'm a failure”
Checks view stats on latest video —> only 10 more views then last —> “My content sucks”
Haven’t made any sales in 3 months —> “I am a bad entrepreneur”

To maintain balance while riding with no hands, I learned over time, required me to sit upright and lean back a bit; keeping one hand on either leg while pedaling. When I felt too tense, I would wobble. If I panicked, I would wobble. But if I “leaned back” and relaxed, the bike would stay put. I think the same principles apply in surfing and boxing.
When boxers tense up, they throw rigid and stuffy punches. Instead, they try to imagine their arm as a wet towel with a knot at the end and make a snap reaction in order to create maximum impact with their strikes. My surf instructors would laugh telling me that I was “too tight”, and that “surfing was chill to relax”; if you rush the popup on the surf board, you either fall face forward into water or you miss the wave entirely

I noticed a subtle poetic meaning, or at least double layer as it relates to our lives in all this. Maybe the same way we learn to balance on the bike, is the same in our lives: lean back, relax and take a little of the pressure off if you can.
Maybe the move is simpler than we think: just lower the stakes. Try to detach from goal and what it says about you in five years. Instead ask “can I hold this dancer's pose a few seconds longer? Can I make this combo smoother by next session?”
Then when you get there, actually celebrate the damn thing! When I finally held my “no-hands” bike ride for ten seconds, I just yelled "I'm doing it! I'm doing it!" like a kid who'd never seen a bike before. There's neurological basis for this too, it’s the reward our bodies and minds crave.

The first month my business landed in the black after a year of bleeding money, I got up and danced around the room (I too encourage you to have a “profit dance”). I didn’t think “wow i made it”, I just thought “wow this is a literal first!”, savouring and letting in that good feeling right then and there (instead of being stiff and stoic).
That's the thing about relaxing into leaning back. It doesn't just help you keep balance. It might just free you up to enjoy the ride too.