Write the failure first

Most plans are written by optimists. That’s fine; you need optimism to start anything. The trouble is that the optimist writing the plan is also the person checking it, and optimists are bad at finding the hole in their own boat.

I use two tools to get around this. Both work by making failure concrete before it happens.

The pre-mortem

A post-mortem asks why something failed. A pre-mortem asks the same question while you can still change the answer.

The method, borrowed from the psychologist Gary Klein, is simple:

Assume it already failed. Not “might fail.” Picture the date six months out and accept that the project is a mess.
Write down why. Everyone involved lists the reasons, independently, before discussing. Independence matters: once the most senior person speaks, the list shrinks to their list.
Rank by likelihood and damage. A likely, survivable failure and an unlikely, fatal one need different responses.
Set a tripwire for the top few. A tripwire is an early, observable signal and the action you will take when you see it. “If X happens by date Y, we do Z.”

The reason this works is psychological. When you ask a team “what could go wrong?”, people hedge, because criticizing the plan feels like disloyalty. When you tell them it already went wrong and ask them to explain it, finding the cause becomes the assignment. People stop protecting the plan and start protecting the outcome.

Anti-goals

Goals tell you what to chase. Anti-goals tell you what you refuse to become while chasing it.

Most damage in a career or a life doesn’t come from missing a target. It comes from hitting it in a way that costs something you didn’t price in: the promotion that ate your health, the deal that cost a relationship, the growth that made the team miserable.

An anti-goal makes that price explicit and non-negotiable. “Grow the business” is a goal. “Never grow it in a way that requires me to miss dinner with my family more than one night a week” is an anti-goal. The second one makes the first one smarter.

A worked example: this website

Before building this site, I ran a pre-mortem on it. Assume it’s April 2027 and the site has failed. Why?

It became a dumping ground for AI-generated text. This was the most likely failure, and the most damaging. I run a lot of automated research, and the tempting move is to publish its output directly. Readers can tell. A site full of competent, faceless text proves only that I can run software, which is the opposite of what I want it to prove. Tripwire: nothing goes live unless I have rewritten it in my own voice and added a judgment only I could make.

It went quiet. Personal sites usually die of silence. The last update date becomes a timestamp of when the owner lost interest. Tripwire: a minimum rhythm of one new piece every two weeks, drawn from reading and study I already do. If I miss two in a row, I cut scope instead of pretending.

The front page got cluttered. Every new note feels important the day you write it. Tripwire: the essays on the home page are reviewed once a quarter and are otherwise left alone.

Something private leaked. Unlikely, but expensive. Anti-goals: this site will never carry my children’s details, health data, anything from my employer’s internal work, investment positions, or contact details beyond a public profile link.

Writing this down took an hour. It changed the design of the site more than any other hour of planning.

Judge the decision, not the outcome

One more habit makes both tools work. The poker player and author Annie Duke calls the mistake “resulting”: judging a decision by how it turned out.

Good decisions sometimes lose, and bad ones sometimes win. If you only learn from outcomes, you learn the wrong lessons from luck.

A pre-mortem leaves a record of what you knew and feared at the time. When the result arrives, good or bad, you can compare it with that record and ask a fairer question: given what I knew then, was this a good bet? That question is how judgment improves over years instead of swinging with every result.