TL;DR: Most of my decisions, big and small, start with a vibe check and get tested against the data. For tougher questions like forks in a road, I add one more question: can I explain why I made this choice to myself in the future? This article dives into my thought process behind making decisions in situations of high uncertainty and ends with an AI prompt you can use to build and turn your own regret minimization method into a reusable skill.
What regret minimization is
Regret minimization is a way to make decisions when there’s not a clear answer. Instead of asking “which option is best right now?”, I ask:
Do I have all the information I need to understand why I won’t regret the choice I make today when reflecting back on this in the future?
Jeff Bezos popularized the idea when he explained how he decided to leave his job on Wall Street to start Amazon. He pictured himself at 80 and asked which choice he’d regret more. He figured he could live with trying and failing, but not with never trying.
Both his version and mine work because they change the time frame, which helps you see the bigger picture. In the moment, a decision is full of fear, short-term cost and what other people will think. From far enough out, most of that shrinks, and you’re left with the reasons behind your choice, and whether you made it with the best information you had at the time.
Regret means different things to different people
There isn’t one official way to do this, and people use the word “regret” differently. Here are three versions:
- The 80-year-old test. This is the Bezos version. Picture yourself at the end of your life and ask which choice you’d regret more. It’s about the big picture and what you’d wish you had tried.
- The worst-case version. Decision theory has a formal cousin called minimax regret. For each option, you imagine the worst outcome and how much you’d regret it, then pick the option where that worst regret is smallest.
- The informed-at-the-time version. This one is mine. I’m okay with a decision, and I don’t regret it, as long as I know why I made it at the time and what limited information I had in the moment. The outcome can turn out badly and I still don’t regret the decision, because I understand I made the best decision for me at the time. I don’t believe in controlling anything except myself (will have a future article about this), so I do believe sometimes things I wish wouldn’t happen do because it is meant to be, and I have no way of preventing it.
Because these point in different directions, it helps to know yourself first. Do you regret bad outcomes, or only choices you couldn’t explain? What does a decision you can live with look like to you? If you haven’t answered that yet, “which choice will I regret least?” doesn’t have a clear answer.
I only use regret minimization when there’s no clear right or wrong answer at the moment I decide. Do I sell this stock? Do I move to USC? Do I marry this person? Nobody can tell you the answer in advance, and the data only gets you so far.
My version starts with a vibe check
Before I get to the data or the regret, I sense the vibe of the decision. That’s the INFJ in me (see my personality results). I believe life is meant to be easy, and that moving toward the things you’re meant to do is supposed to feel easy. That doesn’t mean the actual work is easy. It means the vibes should be right.
Pushing through is almost always possible. It just fails the vibe check for me.
After the vibe check, I make sure the data/numbers check out (if applicable), and regret minimization is how I make the final call when the data doesn’t decide for me. I cover the first two checks in how I make most decisions, on vibes and data.
Why it works for me
I’m a Gemini, the twin sign horoscope, so I always sound like I’m contradicting myself. It works because I hold the yin and yang together instead of picking one.
I’m a big data person and love to model my world on equations, but regret minimization and the vibe check matter just as much to how I decide. A spreadsheet only counts what you can put a number on, and the cost of not doing something rarely shows up in one. Regret is how I put a price on that missing column.
It also helps me make contrarian calls with a clear head. When I understand why I’m choosing something, I’m comfortable going against what most people would do, because I’m not trying to win the argument. I’m trying to be able to look back and say I understood the trade-off and made it on purpose.
I trust this approach because it doesn’t depend on how things turn out. Even if I’m proven wrong later, I won’t regret the decision as long as I know why I made it with the information I had.
Example 1: Leaving a full scholarship for USC
This was a decision that looked wrong on paper and sounded crazy to my friends, but it was a no brainer to me. After my first year of undergrad, I gave up a full scholarship at Cooper Union (where I studied Civil Engineering) to transfer to USC. I took on student loans and still graduated with the same degree, because I wanted the life experience that came with it.
I went to Stuyvesant High School in NYC. When I decided to study engineering in college, the Cooper Union in downtown NYC at first made a lot of sense and seemed to fit my value-oriented profile. A full 4-year scholarship to an engineering school with a good reputation seemed like a great fit.
However, after a few months in freshman year, I felt that I was limiting my world and growth opportunities by staying close to home for college. The school itself was small, so there weren’t a lot of options for electives. I had already done the daily commute to the city during my time at Stuy, and I felt like I was missing the opportunity to learn more about myself and what’s outside of NYC in a low stake environment as a college student.
There wasn’t a particular school I was interested in, but I landed on University of Southern California (USC) because I knew exactly one person who was going there- one of my best friends from middle school who had moved out West after the first year of high school. This was the part of the decision that just felt like it was meant to be, so I didn’t dwell on it too much.
I applied, got in, and transferred over for my sophomore year. I never looked back. My intuition was right- I ended up learning so much more about myself and gained confidence in those 3 years. That’s priceless.
But of course, it doesn’t mean the price didn’t matter. When going through the financial aid process, I was pleasantly surprised by how affordable the experience was. I learned at that point not to trust generalizations that deserve a deeper look. Just because something is known to be expensive doesn’t mean you can’t figure out a way to experience it for less. I truly learned so many valuable lessons from my time at USC, because I put myself in a position to have to learn.
A few weeks before I moved to Los Angeles, I started dating my now husband. I did not factor in a long distance relationship to my USC transfer decision, and the cost of roundtrip flights home added up, but my lack of financial resources made me very resourceful and started me on my journey of travel hacking and playing the credit card points game.
I am forever grateful to my younger self for feeling that unhappiness at Cooper Union, leaning into it to figure out what bothered me, and listening to the world to pursue a transfer to USC. I knew why I was choosing it, so the flight costs never changed my answer. Absolutely no regrets there.
Example 2: Career moves
My career has not gone in a straight line. I went from construction project management to a web development bootcamp, back to construction, then to an MBA, real estate asset management and now customer success. Looking at it from the outside, it can seem like I keep changing my mind.
The career move that best shows the regret minimization framework is the one I didn’t make. After the coding bootcamp, I considered taking a software engineering job. I did multiple rounds of interviews and got an offer. But I couldn’t bring myself to take it. I just knew myself to be someone who needed more big picture and strategy work. I enjoyed coding and could do it, but I felt it was not what I was meant to do. So I turned down the offer and went back to my job at Turner Construction.
I didn’t consider the bootcamp a waste of time at all, because my interest in doing it was primarily for the learning. I gained a lot of knowledge on how software development works and saw a lot of parallels in how project management works. Now with AI, I feel super validated in my gut feeling that my time is not best spent on computer programming. AI is a much better fit as a software developer than I am.
The move into customer success looked like a stretch on paper, since I had no formal customer-facing background. When I interviewed at Juniper Square, though, I wasn’t asking myself whether I was qualified. I was asking whether the job fit my life and what I wanted to learn. As a new mom, I wanted the flexibility of remote work. I also have a genuine interest in the private markets, and I felt I could learn a lot from the customers I would get to work with. Those two reasons were enough for me, and I never actually wondered if I was qualified to work in CS.
Six years later, I am still at Juniper Square in Customer Success and I am really enjoying my time here, especially as my role evolves into Customer Success Operations with AI, which feels like the ultimate fit for me. I have learned and grown so much in my time at Juniper Square. I am so glad I took the job and was not worried about not being able to perform.
What the pivots have in common is that I could explain the trade-off each time. I wasn’t chasing a title, I was choosing which regret I could live with.
Example 3: Selling and holding stocks
Investing shows my definition of regret better than anything else, because the outcome is easy to measure and hindsight is brutal.
When Facebook (now Meta) went public, I bought about $5,000 of FB shares. I was quite new to investing, so once the stock doubled, I sold, because I was scared to lose my paper profits and had to lock it in. Objectively, that was a really dumb decision (“only” locked in 100% gains instead of 1,508%), but I don’t beat myself up about it, because I know why I did it.
I was raised to be conservative. I grew up with Hong Kong TVB shows that always showed people losing everything they had in the stock market, so my mom never invested and always told me not to “play” the market. It was also drilled into my head to not be greedy. I didn’t grow up around family or friends who talked about investing, so I didn’t know what a long-term horizon was.
Even though I “missed out” on additional gains, I am actually quite thankful for the experience. $FB was one of the first stock purchases I ever made. Opportunities to make money in the market is always there. Being able to act on it was a big step that helped me get comfortable with more purchases.
Today I hold Google. As I write this, $GOOGL is about 30% below its all-time high and I’m not selling, because I still believe in the company. If I’m proven wrong, I won’t regret it, because I know why I’m holding with the information I have right now.
That’s the test I use. Not “did it work out?” but “can I explain why I made this call, given what I knew?” None of this is investment advice. It’s just how I think about my own decisions.
Run it yourself
Start by deciding what regret means to you, as covered above. Then you can run this on any tough decision in about ten minutes. Here are the steps:
- Name the decision and the options in one sentence each.
- Do a vibe check. Notice how each option feels before you analyze it, and which one feels like a fight from the start.
- Gather the data you can. Cost, time, and how hard it is to undo.
- Pick a future point such as five years out, ten years out, or age 80.
- For each option, write what you would regret if you looked back from that point.
- Choose the regret you can live with, and write down why so you can check it later.
If you’d like AI to be your thinking partner, paste this prompt into a chat and answer honestly:
I'm making a decision and want to define my regret minimization method. Start by asking me what regret means to me, such as whether I regret bad outcomes or only decisions I can't explain.
Interview me one question at a time. First ask me what the decision is and what my options are. Then ask how each option feels to me before we look at any data, and what feels easy or off about it. Then ask what data I have, such as cost, time and how reversible each option is. Then ask me to picture myself 10 years from now and tell you what I would regret under each option.
Don't give me advice until you've asked at least 8 questions. Then summarize which regret I seem least able to live with, point out anything I said that doesn't fit, and flag what you're unsure about.
Finally, turn the method we just used into a reusable skill I can run on future decisions. Write it as a saved set of instructions with a name, a description of when to use it, the steps and questions in order, and the format of the final summary. Base it on how I actually answered, not a generic template, and keep it short enough that I'll reuse it.The last part of the prompt matters. Asking AI to point out what doesn’t fit keeps it from just agreeing with you. The final sentence of the prompt is what makes this a system and not a one-off. Instead of one answer to one decision, you end up with a skill you can reuse and improve every time you decide something. I keep mine in my Obsidian context vault.
Where it falls short
I don’t think regret minimization is a perfect tool, and I’d rather tell you where it breaks.
We’re not great at predicting how we’ll feel. Research on forecasting our own emotions suggests we tend to overestimate how strongly and how long we’ll feel something. A choice that feels like it will haunt you may fade faster than you expect.
It can justify impulsive choices. “I’ll regret not doing it” is also what a bad idea says when it’s well disguised. That’s why I look at the data first. If the numbers say a decision could seriously hurt my family, regret doesn’t get to overrule them.
It leans toward action. Research suggests that over the long run people tend to regret what they didn’t do more than what they did, which can nudge you to say yes too often. I try to check whether I’m choosing action because it’s right or because it’s exciting.
A vibe check can mislead. Hard and wrong can feel the same in the moment, even though they aren’t the same. That’s why the vibe check starts my process instead of ending it.
So I treat regret as one input, not a verdict. Vibe first, then data, regret as the tie-breaker, and a written reason I can check later.
FAQ
It’s a way to make decisions when there’s no clear right answer. Instead of asking which option looks best right now, you ask whether you’ll be able to explain, in the future, why you chose what you chose with the information you had.
When there’s no clear right or wrong answer at the moment you decide, like whether to sell a stock, move for school or marry someone. If the answer is clear, the data or a quick vibe check is usually enough.
Jeff Bezos popularized the name when he explained how he decided to leave his job to start Amazon. He imagined himself at 80 and asked which choice he’d regret more.
Name your options, do a vibe check, gather the data you can, picture a future point such as ten years out, write what you’d regret under each option, and choose the regret you can live with.
A pros and cons list weighs what you can already see. Regret minimization adds the cost of not acting, which rarely shows up on a list.
It’s a useful input but not a complete method. It works best after you’ve looked at the data, and it can be biased toward action, so check that you’re choosing for good reasons.
Yes. Ask it to interview you one question at a time and to point out anything in your answers that doesn’t fit, so it challenges you instead of agreeing with you.
It’s noticing how each option feels before you analyze it. If one option feels like a fight from the start, I treat that as a reason to look closer, not as a final answer.
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