Failing Well
January 14th, 2022

Let me open by saying that the motivation for writing is to refer back to this and use as a timeless reminder for myself. Failing well is what I aspire to do on my best days. Please don’t think for a second I got this completely nailed.

How to handle failure is one of the most important skills for any creative. IMO How adversity is handled is the best leading indicator of long term growth and success. We’re all bound to run into issues by trying to do ambitious work. It is part of the course. Not failing much is a sign of under-ambition. Wrestling with failure has a direct way of revealing limits, blind spots and what needs doing to improve. Success just isn’t as good a teacher.

How to handle failure in five parts

Do it fast

If your idea is doomed, then don’t waste time and move on. When going from 0 to 1, I like to write a list of risk hypotheses. They answer the question « what needs to be true for X to work in the long term? ». I rank them by danger level, and test the scariest parts first. This is just one of the many ways to avoid lying to yourself by exposing flawed thinking early on.

Do it small

Some failures are catastrophic. Big mistakes are often a bunch of small mistakes that compound with each other. This is usually the case for plane crashes for example. Unchecked, compounding mistakes create many problems at once, and it becomes very hard to contain. I treat individual variables in isolation and treat everything like an experiment. Subject every theory, belief and principle to a reality check. See if your ideas actually hold up and debunk flawed logic to avoid compounding mistakes.

Do it often

The most valuable class I got during my MBA was a negotiation class. Our assignment was simple. Get a no every day. Get used to rejection. Treat this like a physical work out and grow your failure muscles. Taking this logic further and say get used to messing up, to chaos, to being uncomfortable. Feel the heat daily. It can be approached like a competitive sport after a while.

Do it openly

Let everyone know when you messed up. Share your experience, as hard as it might be. IMO people who fess up are just way more credible. Ego is the enemy.

Do it to learn

Failure is a good thing. Failure is the successful discovery of what didn’t work (tm Shopify). At the end of the day mistakes are always part of the journey. But you’re better off making mistakes only once. Learning is the whole point of failing well. Without the learning part, then failure becomes problematic.

Bonus - Do it authentically

You only learn the really big lessons by wrestling with your own reality. The trials of building and failing are hard at times. Humans are drawn to stories of human struggle. Do share you war stories and your shortcomings. Own up to your experience, and who you are, warts and all. Humans are wired to resonate with tales of people rising through adversity and taking a chance when the odds are stacked against them. We’re wired for liking heroes, and sharing the story benefits the both one sharing and the ones listening.

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