Embrace your Micro Pessimist


In this interview with Patrick Collison, the CEO of Stripe (the company behind the infrastructure that powers internet online payments) mentions an excerpt from their quick guide to Stripe’s culture about “being a micro pessimist and a macro optimist.” What brilliant though initially counter-intuitive advice.

 You typically hear about people being micro optimistic and macro pessimistic. Perhaps you are concerned about your long-term future while still being excited by what you are currently doing to affect future change. You may be overwhelmed with macro prospects but confident in addressing present challenges that are right in front of you.

 New ideas themselves appear within a halo of excitement and optimism. The Stripe culture guide highlights “When considering ideas, we think ‘how might it work?’ is more interesting than ‘why will it fail?’. Both questions are equally worth considering, and that’s why a well-executed Concept Poster addresses both potentialities. Stay pessimistic about ideas and let them prove themselves worthy via prioritization and experimentation. However, let's save that discussion for another post.


What I especially love about the reversal to micro pessimism and macro optimism, is how this pertains to company culture and product vision. The values and principles you create to maintain focus and make decisions are positive, optimistic beacons that don’t change that often.

You need to be relentlessly micro pessimistic and reactive to near-term problems and efforts. Have you been avoiding that awkward conversation with a disruptive member of the team? Are you delaying that incremental, yet impactful improvement over that sparkly new feature?

Micro threats that go unaddressed accumulate over time. They become sources of customer frustration and employee conflict. Your customer and company experience begin to erode. "But like cliff erosion sometimes you don’t notice it until the cliff starts falling into the sea."

Once you have design principles and vision in place, take the time on a regular basis to embrace your micro pessimist.


Photo by Ryoji Iwata on Unsplash

Darren Evans