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Remote Jobs and You · Aug 20, 2026

Can You Undo It?

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Remote Jobs and You · Remote Jobs and You

The week unfolds like this:

Mental Models

A long time ago, a captain named Cortés landed his ships on a beach. He was scared his soldiers would lose their nerve and sail back home. So he burned the ships. Now there was no going back. His men had only one choice: keep going.

That’s an extreme story. But it teaches something simple.

Some decisions can be undone. Some can’t.

If you can undo it, don’t overthink it. Just try it. If it goes wrong, you fix it and move on.

If you can’t undo it, slow down. Think hard. Ask for help. Because you don’t get a second try.

Most people get this backwards.

They spend 20 minutes picking a font for a slide. That’s a decision you can change in one click. Doesn’t matter.

But they’ll quit a job in a fit of anger, or send a nasty text at midnight, without thinking twice. Those you can’t take back.

Smart, experienced people ask one quiet question before deciding anything:

“Can I undo this if I’m wrong?”

Yes? Move fast. Try it. See what happens.

No? Slow down. Take your time.

That’s it. That’s the whole idea.

Jeff Bezos, the Amazon founder, said the same thing to his team. He called them “one-way doors” and “two-way doors.” One-way doors, you can’t walk back through. Two-way doors, you can. He told his people: stop treating every decision like a one-way door. Most of them aren’t.

Funny thing is, even Amazon Prime and Amazon’s cloud business, two of their biggest products ever, started small. Small enough to shut down quietly if they failed. Nobody bet the whole company on day one. They only became “permanent” once they started working.

So next time you’re stuck on a decision, ask yourself the same question.

Can I undo this?

If yes, stop worrying. Just go.

If no, take your time. That’s the one worth being careful about.

Read the original on remotejobsandyou.substack.com

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