---
name: regret-minimizer
description: "Reframe a hard choice through the lens of future regret — which option will you regret less at 80? — to cut through short-term noise. Use when asked which will I regret less, help me decide with the long view, I don't want to look back and wish, or use the regret test on this. Produces each option projected forward to old age (the regret of doing it vs not), a distinction between action-regret and inaction-regret (people regret inactions more), the fear that's really driving the hesitation, and the choice that best minimizes lifelong regret — for the decisions that echo."
---

# Regret Minimizer

For the choices that echo through a life — the leap, the risk, the road not taken — short-term pros-and-cons miss the point. This applies the regret test: project each option forward to age 80 and ask which you'll wish you'd chosen. It leans on a known truth — people regret the things they *didn't* do far more than the things they did — to cut through present fear and find the choice your older self will thank you for.

## What This Skill Produces

- **The forward projection** — each option seen from age 80: the regret of having done it vs. having not
- **Action vs. inaction regret** — the reframe that inaction-regrets ("I never tried") tend to haunt more than action-regrets ("I tried and it didn't work")
- **The fear underneath** — what's actually driving the hesitation (usually fear of failure/judgment, which fades; regret doesn't)
- **The regret-minimizing choice** — which option your future self is least likely to lament
- **A caveat** — where this lens *doesn't* apply (reckless, irreversible-harm choices where fear is wisdom)

## Required Inputs

Ask for these if not provided:
- **The decision** — the meaningful choice you're weighing
- **The options** — especially the bold one vs. the safe one
- **What's holding you back** — the fear or hesitation
- **The reversibility** — and whether a failure would be recoverable

## Framework: Look Back From The End

1. **Project to old age.** For each option, imagine looking back from 80 — which produces the wistful "I wish I had…"?
2. **Weight inaction-regret heavier.** Research and experience agree: people more often regret the chances they didn't take. Factor that in.
3. **Name the driving fear.** Surface what's really causing the hesitation — usually fear of failure or judgment, both of which fade far faster than regret.
4. **Test recoverability.** A bold choice is more regret-minimizing when failure is survivable — check that the downside isn't catastrophic.
5. **Land the choice — with a caveat.** Point to the option that minimizes lifelong regret, while noting this lens shouldn't justify reckless, irreversible-harm decisions where the fear is actually protecting you.

## Output Format

### Decision: [the meaningful choice]

**At 80, looking back**
- If you do it: [likely feeling — including if it fails].
- If you don't: [likely feeling — the road not taken].

**Action vs inaction:** [which regret tends to haunt more here].
**The fear driving your hesitation:** [what it is → does it fade or does the regret?].
**Regret-minimizing choice:** [the option] — because [reason].
**Caveat:** [where fear is wisdom, not to be overridden].

## Quality Checks
- [ ] Projects each option forward to old age
- [ ] Distinguishes action-regret from (usually heavier) inaction-regret
- [ ] Names the fear actually driving the hesitation
- [ ] Checks recoverability of the bold option
- [ ] Lands a regret-minimizing choice with an honest caveat

## Anti-Patterns
- **Short-term pros/cons** that miss the lifelong view.
- **Always pushing the bold option** even when the downside is catastrophic.
- **Ignoring that some fear is protective** wisdom.
- **No actual choice** at the end.

## Example Trigger Phrases
- "Which will I regret less — taking the job abroad or staying?"
- "Help me decide with the long view. I don't want to look back and wish."
- "Should I finally start the thing I keep putting off? Regret test it."
- "Use the 'what would I regret at 80' lens on this."
- "I'm scared to do it but scared not to — which regret is worse?"