Journaling about regret: writing about the version that didn't happen

Regret is one of the few feelings that conversation genuinely can't help with. Tell someone about it and they'll say it worked out for the best, or that you couldn't have known. Both responses skip past the thing you're actually holding, which is a version of your life that didn't happen.

Writing is better suited to it, because it doesn't need to conclude.

Write the decision as it looked then

Regret is built almost entirely out of hindsight. You judge a choice using information you didn't have, and you convict yourself every time.

So write out what you knew, what you were afraid of, and what you were dealing with in that month. Not as an excuse. As an accurate record. Most people find that the decision was defensible given what was actually in front of them, and that what they're really angry about is that it was allowed to matter so much.

Ask what the regret is protecting

Regret is often easier than the alternative. Being angry at a past choice keeps the future feeling open: things went wrong because of a mistake, and mistakes can be avoided next time.

The harder thought underneath is usually that some things are closed now. Writing that plainly is grim for an evening and useful for a decade, because grief moves and regret doesn't.

Find the value inside it

Regret is one of the most precise instruments you have for finding out what you care about. You don't regret things you're indifferent to.

For each one, write what it says you value. Not going to the funeral means you value showing up. Staying nine years in the wrong job means you value security and now know its price. That's transferable to a decision you're facing this month, which is the only place a regret can still do any good.

The two kinds

It helps to sort them. Some regrets are about something you did. Those tend to be sharp and fade slowly but genuinely.

The others are about something you didn't do, and those don't fade, because the imagined version never gets tested against reality and so stays perfect. Writing the unlived version out in full detail, including the boring parts and the things that would also have gone wrong, is one of the few ways to make it ordinary enough to live beside.

Start your own private journal tonight.

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Prompts for the loop

• What did I actually know at the time?
• What was I afraid of in that month?
• What does this regret tell me I value?
• If the other choice had happened, what would have gone wrong in it?
• Is there anything still open here, or is this grief rather than a decision?

Reading it back later

Regret entries are among the most interesting to reread after a few years. Some of them dissolve entirely, which you'd never notice without a record. Others turn out to be the same regret in different clothes, appearing every eighteen months, which usually means it's still a live question rather than a closed one.

Why nobody else should read it

Honest regret often involves other people. Regretting a marriage, a move made for someone, a job taken to please a parent. Those sentences are true and unshowable, and if there's any chance of them being seen, they don't get written.

Innera keeps every story encrypted on your device, so the version where you name what you'd have done differently, including the parts involving people you love, can exist without ever becoming their problem.