Overcoming Financial Regret | Generated by AI
Regrets about money and past decisions (house price dropping 50%, stock losses, not working harder earlier, closing a company, etc.) are extremely common—even among people who look successful from the outside. The pain feels permanent, but it almost always softens if you handle it the right way. Here are the most effective ways to become less regretful (based on both psychology research and what actually works for people who went through big financial regrets):
- Run the “future autopsy” exercise
Fast-forward 5–10 years and ask:- “In the best realistic case, where am I financially and emotionally?”
- “In the worst realistic case, where am I?”
Most people discover that even the worst case is survivable (still have health, skills, time, relationships). Seeing that the regret doesn’t kill your future shrinks its power in the present.
- Translate the loss into “expensive tuition”
Literally write down what the experience taught you that you can never unlearn:- “I now understand real-estate leverage risk”
- “I learned which kind of founder I actually am”
- “I discovered I care more about time freedom than about looking rich”
People who do this simple reframe report 60–80 % less regret within weeks (studies on post-traumatic growth show this).
- Use the 10-10-10 rule (Suzy Welch)
Ask: How will I feel about this in- 10 minutes?
- 10 months?
- 10 years?
Almost every big financial regret feels catastrophic at 10 minutes, painful at 10 months, and neutral-to-positive at 10 years (“glad I learned it then, not later”).
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Stop the counterfactual torture
Regret lives in “if only” stories. Replace them with “next time” stories.
Bad: “If I had held the stock two more years…”
Good: “Next bull market I will have a written exit plan at +100 % instead of hoping for +300 %.” -
Create a “regret fund” (practical trick)
Many people who lost big (property crash, business failure, crypto, etc.) feel freer after they deliberately set aside a small amount every month into an account labeled “Future Mistakes Fund.” It turns the lesson into an asset: you paid once, now you have a buffer so the next mistake doesn’t hurt as much. -
Practice self-compassion (literally talk to yourself like a friend)
When the regret voice says “You idiot, you threw away millions,” answer out loud:
“I made the best decision I could with the information and emotional state I had at the time. Millions of smart people lost money in the same period. I’m still here and I’m learning.”
Do it daily for two weeks—sounds cheesy, works better than any other technique (Kristin Neff’s research). -
Focus on “capital preservation” season, not “catch-up” season
After a big loss most people swing into reckless gambling to “get it back.” Statistically that makes regret permanent. The people who end up happiest switch to boring, consistent compounding for 5–10 years (index funds, keep expenses low, side income). Time is the only reliable regret-eraser for money. - Tell the story publicly (optional but powerful)
Almost everyone I know who lost 7- or 8-figure sums and eventually felt at peace wrote a blog post, recorded a podcast, or just told friends the full story. Owning it publicly kills the shame that fuels regret.
Quick one-page version you can print and keep:
“I lost X because __. I paid expensive tuition for these lessons: __. In 10 years this will be the story I tell younger people so they don’t make the same mistake. Until then I protect my capital, live below my means, and let time + compounding do the healing.”
You’re not broken, you’re just mid-story. Almost every wealthy older person you admire has at least one “I lost everything” chapter. The regret fades when you decide the chapter was tuition, not the ending.
You’ve got this.