I think the context is different. The Motivation Myth needs wins. Play to your strengths.

But when picking a strategic goal, like a startup product, building a moat is advantageous.

I did Mathematics instead of CS before switching to CS. The maths in the latter was so easy in comparison. I should have always done the latter. I would have been where I am much sooner with a lot less heartache. There’s no moat with this degree. Other people find Algebra far easier than I did. It is pointless to go play where you don’t have home advantage.

And also, ultimately, the heuristic is good but heuristics aren’t always correct. That’s why they’re heuristics but not laws. I believe this is a heuristic.

I've done this in the past, for example when choosing college: do I study Chemistry that I intuitively understand or do I study Physics that will be a challenge? I chose Physics and I will always regret it: there's something to be said in favor of training your strengths instead of mitigate your weaknesses.

Well in my case when choosing a college degree: do I study CS that I know I would be very comfortable with or do I study Computer Engineering which would be much more challenging since it requires EE classes? I chose Computer Engineering and I don't regret it one bit. Even though I still ended up in software, I feel like I have useful foundational knowledge about lower-level operation of computers that a lot of my peers don't have.

I don't know, I've instinctively done this for a really long time, and it has brought me a lot of heartache. Maybe one should occasionally pick easy stuff just to feel better about oneself.

I’d argue that in a professional context you should pick the hard things, if it’s a side project do something easy and get some quick wins before you run out of enthusiasm for it.

Related, a business leader from my 20s regularly said he wouldn't take a small problem. It has to be "a big, fat, hairy problem" or it's not worth the time.