I had a similar realisation a few years ago. I used to try to come up with side project ideas by sitting down with a piece of paper and writing down every idea I could think of. Then, I’d decide which of these ideas seemed in the realm of possibility for me with my current skill set. Out of that whittled-down list, I’d then choose the idea that I thought would have the most chance of success.
The problem? I could never remain motivated. It turned out that I had invented a formula for choosing ideas that neither extended my skills nor spoke to my inner curiosity. Things only changed when I asked myself the question “has this ever worked for me in the past? Even once?”
I decided my new philosophy was to work on whatever I was most curious about — even if it seemed way too hard for me, or if everyone else thought it was stupid. I haven’t exactly made millions of dollars from this approach, but I’ve learned more in the past four years (and had more fun doing it) than I did in the previous 10.
It makes me wonder what other things I might be doing out of habit that have never actually worked.