The prize for saying no is small

and who cares, anyway?

I’ve spent a lot of my life being very pessimistic, for some personal reasons. I’ve written about this mindset before as the difference between “why not?” and “what if?” - I was a hardcore why-not-er, taking pride in myself when I was right and something worked.

This is one of the dumbest things I ever did in my career. For one thing, with very few exceptions (I’m looking at you, crypto), even if there are early problems, if there is enough value being pursued, they tend to get solved eventually. There’s really no point to being negative in this context - if you believe in the value being created, you should put that energy into solving problems, not criticizing. As others have said, the prize for being negative, and right, is very small.

And the penalty for being optimistic and right is also usually small, but it can feel uncomfortable in the moment. If you are an early believer (or at least a suspender-of-disbelief), you can feel foolish if the idea doesn’t pan out. Like, you were naive, or you let your excitement get away with you, and now, with the benefit of hindsight, you can see the enthusiasm was misplaced.

That’s ok! It’s (hopefully) part of life to learn and grow, and to change our perspectives as we do. I constantly look back at earlier versions of myself and think “wow, I am SO much smarter now!” and then think “yes, but there is a future version of me out there, looking at me in this instant and shaking his head”.

That early energy and enthusiasm, even if it turns out to misplaced, is much better than caution, which is another way of saying no. Enthusiasm and suspension of disbelief is a way of saying “what if”. Cynicism and caution is a way of saying “why not”. There are huge prizes for saying “What if” and being right. There are no prizes for any of the other choices. Play is rational!

(I’m going on vacation for a few weeks. I might write but I probably won’t. Change the world while I’m gone!)