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September 15th, 2022

Given any new endeavor, any new project or skill to learn, the path forward is often unsure - unknown. And yet, without fail, we try to imagine one. Vaguely and somehow specifically there’s a sense of how it should go. It’s exactly at that point - before even starting - that trouble begins to arise.


Rare is the person who is going to actively imagine a dozen different paths to the same outcome, but in reality, there’s an infinite number of ways to arrive at a given destination, be it a real physical one, or figurative. What differentiates people is how we navigate - toward the first step and from step to step. Instead of taking things one step at a time, the cognitive e convention seems to be to imagine the entire arc of progress, but how we navigate from one small step to the next determines exactly how and if we make it to our desired destination.


The matter of taking one small step towards achievement is a matter of the Optimal Challenge. It’s a bit like the Goldilocks story, but instead of bed sizes and porridge temperatures, it’s a measure of difficulty: Not too difficult or you’ll get frustrated, not too easy or it’ll be boring. And then there’s one more component to the optimal challenge and exactly which optimal challenge to pick: does the result of overcoming the challenge inspire further motivation?


Some challenges are an end unto themselves. Once surmounted we slump back in exhaustion and call it a night. Other challenges, however, produce a result that seems to have the opposite effect: we lean in with more energy, we keep working, and whoops, accidentally pull an all-nighter. As much as staying up all night is not recommended, these are some of the best times - when the flow state seems on another level of longevity, when the marathon session feels like flying.


These experiences hold keys for understanding the mechanics of our own personal navigation when it comes to novel projects and learning new skills. 


A practical example might help: I’m currently sprinting on a small project. A few days ago, an entry about Flip Chess was posted. And after some encouragement from a good friend, I’ve decided to whip up an app for the chess variant. But for this project, I’m using a tech stack that I’m not terribly familiar with. So what exactly should I do? The first day I sort of languished on all sorts of tutorials, feeling out exactly how to do what I wanted to do. By the end of the day I was tired and honestly doubting whether the project was even worth undertaking. But at that point I had a thought: just get a chessboard on the screen. That should be easy. And so 20 minutes later I’d pulled a library, plugged it into my bare-bones set up and voila, I at least had a chessboard to look at. But, I’m a bit picky about how things should look. It was at this point I remember having a little conversation with myself. I reasoned that I shouldn’t do anything aesthetic because that’s not how a good friend of mine would do it. I should get the guts of the application working, and then worry about aesthetics. But that’s when I realized all this that I’ve been writing about. That’s now how my navigation system for motivation and the unknown functions. Having a uniquely colored board in the style I imagine - I realized - would make me more motivated to tackle the trickier stuff that I was feeling daunted about. So an hour or so later, I had what felt like a very slick looking chessboard - and because of it, I was excited to do more, to make it live, to get the guts of the application working so I could see my chosen aesthetics actually function.


So to circle back: it seems that when people think about how the path through the unknown should look, we are trying to imagine the correct way, when it’s actually more practical to ask: what is the funnest way to go about this?

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