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You’re treating a two-way door like a one-way door, and that’s why you’re stuck.
A friend of mine spent over a year deciding whether to leave his job. He’d outgrown it and he knew it. But every Sunday night he and his wife would have the same circular conversation about whether this was the right time, whether the market was good enough, whether he should wait another quarter.
When he finally left, he had a new role within two months. The thing he said to me after is the part I keep coming back to: “I spent more time deciding than I spent looking for the next thing.”
Fourteen months of agonizing over a decision that, if it went wrong, would have taken eight weeks to fix.
The idea that changed how I make decisions
Jeff Bezos laid this out in one of his Amazon shareholder letters and it stuck with me because it’s so simple it almost feels too obvious. But most people, including me, don’t live by it.
Every decision is either a one-way door or a two-way door.
One-way doors you can’t come back from. Having kids. A major surgery. Saying something to someone that can never be unsaid. Those deserve all the time and thought you want to give them.
Two-way doors you can walk back through. A new job, a new city, a new project, a hard conversation. If it doesn’t work, you adjust. You’re not trapped. The cost of being wrong is real, but it’s temporary.
His point: most decisions are two-way doors, and most people treat all of them like one-way doors. So they move through life at half the speed they could, agonizing over choices they could undo in a month.
Why we do this
I used to think the agonizing was about being responsible. Turns out it’s about something less flattering.
Kahneman and Tversky found that losing something hurts about twice as much as gaining something of equal value feels good. Losing $100 stings about as much as finding $200 feels great. It’s not rational. It’s just how we’re built.
So when you’re standing in front of a decision, your brain is doing math that’s rigged against action. The downside of getting it wrong feels enormous. The upside of getting it right feels smaller by comparison. And so you wait. You gather more information, have another conversation, tell yourself you’re being thoughtful when really you’re just scared of the loss, even when the loss is fixable.
My friend with the job wasn’t being careful. He was scared of making the wrong move. And the fear cost him a year of his life in a role he’d already left in his head.
Three years of avoiding six months
I had someone on the podcast who’d been sitting on a business idea for three years. Skills, savings, a plan. Everything was there except the willingness to start.
I asked her what happens if it fails. She thought about it and said she’d go back to consulting. She was good at it. She could pick up clients within a few weeks. The absolute worst case was six months of learning and some lost savings.
Three years of deliberation to avoid six months of risk. And the three years weren’t free. She’d spent them in a career she’d outgrown, doing work she didn’t care about, while the idea sat in a Google Doc getting more polished and less likely to happen with every passing month.
That’s the cost nobody talks about. You calculate the risk of the wrong decision, but you never calculate the cost of no decision. The months go by. The idea stays in the doc. And time, unlike the decision, is a one-way door.
The decisions that deserve the agonizing
True one-way doors are rare. Having children. Getting married or ending a marriage. A surgery you can’t reverse. Saying something that permanently changes how someone sees you.
When one of those shows up, take all the time you need. Talk to people you trust. Sleep on it. Those decisions earn the deliberation.
But the thing you’ve been sitting on for months? The career move, the project, the conversation, the city? Almost certainly not a one-way door. You could try it, and if it’s wrong, you could come back. You know this. You’ve known it for a while.
I sat on a hiring decision for way too long last year. I’d been talking to someone about joining the team, going back and forth for weeks about whether it was the right fit. If it didn’t work out, we’d shake hands and move on. That’s it. There was nothing permanent about it. But I kept “thinking about it” because thinking felt safer than deciding. By the time I finally made the call, I’d burned weeks of energy on a choice that could have been made and corrected in a fraction of the time.
One question
Think about the decision you’ve been carrying around. The one that came to mind when you started reading this.
If you walked through that door and it turned out to be wrong, could you walk back?
If you can, you’ve been spending months on something that deserves days. And every month you spend deciding is a month you don’t get back, spent on a door you could have walked through and walked back from a long time ago.
Thank you for reading,
Scott

