Decision making journal prompts

Joel Dean
Joel Dean, Founder of Joyful

Decision making journal prompts move a hard choice out of your head, where it goes in circles, and onto a page. You name the real decision, look at it the way a wise friend would, picture how each option could go a year out, and check which one you'd regret skipping.

How to use these. One decision, one that has a real deadline. Write the options down first. Spread the groups over two or three days and set the day you'll decide.

The real decision

Choices hide inside other choices. "Should I take the job?" can turn out to be "Am I ready to leave this city?"

The decision, in one sentence, is ___, and I need to decide by ___.

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What are all my options, including the ones I've been ignoring, like waiting or doing a smaller version?

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What question sits underneath this one?

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A friend's eyes

Your own problem is the hardest one to see clearly.

If my closest friend brought me this exact choice, what would I advise them?

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Write about the decision in the third person, using my own name: "Sam is deciding whether..."

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What would I want to have done, looking back at this from ten years out?

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A year from now

Write each option as if a year has passed and you know how it went.

It's a year from now. I chose option A, and it went badly. What went wrong?

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It's a year from now. I chose option A, and it went well. What made it work?

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Now the same two questions for option B.

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Which of those failure stories could I prevent, and how?

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Values and regret

Facts narrow the choice. Values and regret make it.

Which option fits better with the three things I care about most right now?

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Which would I regret more in five years: trying this and failing, or never trying?

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If I flip a coin and it lands on one option, do I feel relief or disappointment?

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Decide

A decision without a next step is still a question.

My decision is ___, because ___.

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The first step, and the day I'll take it: ___.

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Wiser about a friend's problem

People tend to reason more wisely about a friend's relationship problem than about the same problem as their own. Across three experiments with 693 people, they saw more clearly the limits of what they knew, other people's views and the room for compromise when it wasn't theirs.1

Then the researchers asked people to step back and look at their own situation from a distance. The gap disappeared, for younger and older adults alike.1

That's the job of the friend's-eyes group, the third-person prompt especially.

Writing it as if it already happened

Explanations for events framed as certain came out longer and more concrete than explanations for uncertain ones.2 The year-from-now group borrows that. It's the same idea as the "premortem" some teams run before a big project: assume it failed, then write why.

Which regret lasts

Actions people wish they hadn't taken sting more in the short term. Over the long run, the things people didn't do are what they regret more.3

That doesn't make the bold option right. It's one more weight on the scale, and it's why the regret prompt asks about five years, not five days.

Example entry: "Decision: take the Denver job or stay, by June 1. Underneath: am I okay being far from Mom? Friend advice: go, and set up the monthly flights now. Year out, Denver went badly: I was lonely and the team folded. Preventable? The loneliness, partly: join the climbing gym in week one. Regret test: never trying. Coin: landed on stay, felt disappointed."

  • Name it: The real decision, the options and the deadline.
  • Step back: Advise yourself as you would a friend.
  • Look ahead: A year out, each option went badly, then well. Why?
  • Decide: The choice, the reason and the first step with a date.

Weeks on the same choice

If you've done the prompts and you're still looping on the same choice weeks later, the loop may have become the problem. The journal prompts for overthinking are made for that.

If anxiety makes every decision feel dangerous, even what to order for lunch, that's worth more than a journal.

Questions people ask about journaling to make decisions

Is a pros and cons list enough?

It's a good start for the facts. It also treats every point as equal and leaves out how you'll feel living with the choice, which is what the year-from-now and regret prompts add.

What if I still can't decide?

Decide on the date you set anyway. If both options are reasonable, waiting is a third option with its own cost, so write that cost down too.

Why does the coin flip work?

It doesn't decide anything. It can show you which way you were already leaning: the relief or the small drop when it lands is a clue to the answer you were looking for.

In the journaling section: journal prompts for overthinking, journal prompts for self-discovery and journal prompts for new beginnings.

Sources

  1. Grossmann I, Kross E. Exploring Solomon's paradox: self-distancing eliminates the self-other asymmetry in wise reasoning about close relationships in younger and older adults. Psychological Science, 2014;25(8):1571-1580. https://doi.org/10.1177/0956797614535400
  2. Mitchell DJ, Russo JE, Pennington N. Back to the future: temporal perspective in the explanation of events. Journal of Behavioral Decision Making, 1989;2(1):25-38. https://doi.org/10.1002/bdm.3960020103
  3. Gilovich T, Medvec VH. The experience of regret: what, when, and why. Psychological Review, 1995;102(2):379-395. https://doi.org/10.1037/0033-295X.102.2.379