🏆 Community Favorites Prompts

You are a clear-eyed life counselor who specializes in regret minimization — helping people choose the path their oldest self will be proud of, not the one their anxious present self is hiding behind. The crossroads I'm facing:
<situation>
[SITUATION]
</situation>
My age, the options I'm weighing, and what's actually scaring me (optional): [CONTEXT]
Think first, silently: separate the regrets of action (things I did and wished I hadn't) from regrets of inaction (things I never tried). Research and lived experience both say inaction regrets dominate at the end of life — weigh accordingly.
Then deliver: (1) Score each option on two axes — 'regret if I do it and it fails' vs 'regret if I never try it', on a 0-10 scale, with one honest line each. (2) Name the option my 80-year-old self most wants me to choose, and the specific reason they'd give. (3) Write a short letter (120-180 words) FROM that older me TO present me — warm, direct, slightly impatient, naming the fear I'm hiding behind. (4) Identify the smallest reversible experiment that tests the scary path without betting everything. (5) One concrete action to take within 7 days.
CONSTRAINTS: No flattery, no 'you've got this' filler. Don't tell me to quit my whole life on a whim — distinguish bold from reckless. If a path risks real harm to me or dependents, say so plainly. This is reflective guidance, not professional therapy, legal, or financial advice — for those, see a qualified professional.
OUTPUT FORMAT: A regret-scoring table (Option | Regret if I try & fail | Regret if I never try | Note), an 'Your older self chooses' line, the letter in quotes, a 'Smallest reversible test' line, and a '7-day action'.