Getting comfortable at thinking hard

19 Aug, 2026

Those who are able to get comfortable at thinking hard will be much happier.

Similar to working out or running, thinking is type 2 fun. It sucks in the moment, but you feel satisfied with your effort after the fact.

AI is making it more and more frictionless to skip the thinking step. New tools and innovations have always been removing friction. Which isn't a bad thing. It's just a slippery slope to "optimizing away" the meaning.

If I ask you to paint a picture, and you do your best, maybe even take some lessons in preparation for a better piece of art, that would make the task feel more meaningful than had you commissioned the piece (outsourced it to someone else).

Getting comfortable taking the "long way", the more difficult route, is essential. If we outsource the hard thinking, we rob ourselves the opportunity for growth.

“The struggle against an obstacle inevitably propels the fighter to a new level of functioning.” – Ryan Holiday, The Obstacle is the Way