Pessimism is easy, boring, and safe.

Teju Adeyinka
3 min readMar 3, 2024


an unrelated picture of sneakers and daisies

Pessimism is easy. Talking about why something will not work, and how everyone else is wrong and we’re right feels gratifying. It feels like doing productive work — like we’re generating and sharing insights. But unless those insights point us in the direction of what to do and how to win, eventually they will become a crutch. We will spend an absurd amount of time obsessing over them because they give us the satisfaction that we are getting a better understanding of our environment and the systems within which we operate. They will delude us into believing that we are sharper than everyone else.

Pessimism is boring. It makes us drone on and on to everyone who will listen to our spiel about how everything sucks and will continue to suck. It does not inspire, and it does not spur to action. My Twitter timeline is overflowing with gotchas and “I told you so”s on just about every topic. Everyone knows why company Y imploded or will implode — in fact, they foresaw it five years ago. But of course, most of them also never successfully predict the winners.

Pessimism is safe. It can help us mask the fact that we don’t actually know how to win. It gives us reasons to stall and keeps us passive. At least we’ll not be doing something wrong; but also, we will be doing nothing at all.

This isn’t to say that pointing out evident faults and flaws isn’t valuable — it is. Leveraging insights to avoid repeating mistakes is a critical part of learning to succeed. Personal experience is a painful teacher and learning how is avoid booby traps is a cheat code for moving through life. But eventually, all good leaders and thinkers must put their stakes behind something. After deciding what to avoid, we must decide what we will be optimistic about — what we will do.

Idea A might not work as is, but what version will work? What will create the impact that we’re looking for based on the admittedly limited data available? That’s where the power is — not just in declaring what is doomed for failure, but also in making bets on what will win. That is the money shot. The attempt. Not the lack of it.

Personally, I have been passionate about a problem space for years now. And, I’ve come to terms with the fact that what’s stopping me from trying it out is that while I have a laundry list of answers for “what will not work?”, I don’t have a similar clarity on what will work; the version that people will pay for and will change the world (even if slightly) in the direction that I care about.

So, this year, I’m challenging myself to answer “what will work?” and “why will this work?” questions more often. You should try it too.