Being grouchy now but cheerful always - or why does being macro-optimistic and micro-pessimistic on most things work?

Yup!

So for a while now I’ve been using the phrase “macro-optimist and micro-pessimist” to explain my approach to some projects at work particularly when you’re building a product. I was wondering today where I’d heard it. The Internets suggest it comes from Patrick Collison. His video about it here, but I don’t remember ever watching this talk and also seem to have used this in a public talk before this video came out, so I’m still figuring out whom I heard it from but I think perfectly captures a lot of what people need to do to build awesome products.

Here’s my interpretation of it - which is a little different from the video. When you’re taking on something ambitious - which is most projects I’ve worked on - your default long-term position has to be of extreme optimism. You have to believe you’re going to build something incredible. This default optimism is particularly important if you’re a leader on the team. You need to give people energy, inspire confidence, encourage ideas and risk-taking. Without this, most ambitious projects don’t work particularly when things aren’t going as expected.

However, this only works if you’re also doing the other part of the leader’s job - examining each idea carefully - understanding that most ideas you’ll hear are likely not going to work and being incredibly diligent about what you prioritize. You have to look at what you’ve built so far and almost immediately feel what’s broken and hate it. Not criticizing the small things and questioning things day-to-day is another sure-fire way for a project to die.

Balancing these 2 things is critical - which is why I really like Collison’s point about making it a cultural norm. So remember, it’s ok to be gripe about the small and short-term things if you’re positive and uplifting on the bigger and longer-term things. :-)