Some decisions do not fit neatly into a spreadsheet. Should you leave a stable job to start something of your own? Take an overseas posting? Go back to school at 35? Move your family to a new country? The regret minimisation framework is a simple thinking tool for exactly these moments, when the numbers are close, the stakes are personal and the usual pros and cons list keeps ending in a tie.
The idea is often credited to Amazon founder Jeff Bezos, who described using it when deciding whether to leave a secure finance job to start an online bookshop. He imagined himself at 80, looking back on his life, and asked which choice he would regret more. He concluded he would not regret trying and failing, but he might regret never trying. That question is the heart of the framework.
How the Regret Minimisation Framework Works
At its simplest, the framework asks you to shift your point of view from today to a distant future self. Instead of asking “What do I want right now?” or “What is safest this year?”, you ask “Looking back from the end of my life, which choice will I be most at peace with?”
A practical version has four steps:
- Name the decision clearly. Write it as a choice between specific options, for example “Accept the regional role in Shanghai” versus “Stay in my current team in Singapore”.
- Project forward. Picture yourself at 80, or at least 20 years from now. Be concrete: where are you, who is around you, what matters to you then?
- Ask the regret question for each option. If I take this path and it goes badly, how much will I regret it? If I skip this path, how much will I regret never knowing?
- Check the downside. Make sure the option you favour has a survivable worst case. Regret minimisation is not a licence to gamble everything.
The framework works because short-term emotions, such as fear of embarrassment or the discomfort of change, tend to fade with time. Long-term regrets, research on regret suggests, more often centre on things people did not do than on things they tried. Projecting forward helps you see past the noise of the moment.
Action Regret Versus Inaction Regret
A useful distinction is between two kinds of regret:
- Action regret is the sting of “I wish I hadn’t done that”. It is often intense at first but tends to soften, because you learn from it and can usually explain why you acted.
- Inaction regret is the quieter ache of “I wish I had tried”. It can grow over time, because the untaken path stays idealised and you never get the information that would settle the question.
This does not mean you should always choose the bolder option. Some actions carry regrets that do not fade, such as harming relationships or taking on debt you cannot repay. The point is to weigh both kinds honestly rather than letting fear of action regret decide by default.
| Situation | Likely action regret | Likely inaction regret |
|---|---|---|
| Leaving a stable job to start a business | Lost savings and income for a period | Always wondering if the idea would have worked |
| Turning down an overseas posting | Little, if family needs come first | Missing a career step or new experiences |
| Going back to study mid-career | Time and money spent, temporary stress | Feeling stuck in a field you have outgrown |
| Staying in a relationship or friendship out of habit | Years spent in something unfulfilling | Rarely, if the bond is genuinely healthy |
Applying It to Career Decisions
Career choices are where many people first reach for this framework. A few prompts help keep it grounded:
- Separate the decision from the timing. Sometimes the regret is not about whether to do something but about doing it now. You may decide you would regret never running your own business, but also that starting after you have built six months of savings is wiser.
- Write a “letter from 80”. Draft a short note from your older self describing what they are glad you did in your 30s or 40s. It often surfaces values you had not put into words.
- Look for reversible versions. Can you test the path before fully committing? A side project, a short course, a secondment or a conversation with someone already doing the job can turn a huge leap into a series of smaller steps. If you are weighing a reskilling move, our guide to the SkillsFuture and WSQ framework explains how many people trial a new field through short courses.
- Factor in obligations. In Singapore, many people carry commitments such as a home loan, support for ageing parents or children’s schooling. Your future self will also regret letting those people down, so include them in the picture.
Applying It to Life Decisions Beyond Work
The same thinking applies to choices about family, relationships, health and where you live:
- Relocation. Moving countries, or moving back home, is a classic case. Ask whether your older self would regret not having lived somewhere new, and also whether they would regret time away from parents in their later years.
- Relationships. Would you regret not reconnecting with an estranged sibling? Not proposing? Not ending something that has quietly run its course?
- Personal projects. Learning an instrument or writing a book rarely feels urgent, which is why such projects become “I always meant to” regrets.
- Health. Choices about rest, exercise and check-ups look small week to week but loom large decades later.
When a choice involves major life upheaval, pair the framework with support for the transition itself. Our piece on how to cope with big life changes covers the emotional side.
Where the Framework Falls Short
Regret minimisation is a lens, not a full decision system. Be aware of its limits:
- It favours dramatic choices. Imagining your 80 year old self can make bold moves look romantic. Always run the worst case check.
- Your future self is a guess. Values change. What seems vital now may matter little later, and the reverse.
- It can feed anxiety. If you tend to ruminate, constantly asking “Will I regret this?” about small decisions is exhausting. Save the framework for the handful of choices each decade that genuinely shape your life.
- It does not replace facts. You still need to research salaries, costs, visa rules, health implications or whatever applies. The framework helps you weigh information, not skip gathering it.
A good habit is to combine it with other tools. Use structured reasoning from how to make better decisions for the facts, then use the regret question as a final tiebreaker. Recording your reasoning in a decision journal also lets you look back later and see how well your predictions about regret held up.
A Quick Worked Example
Imagine Wei Ling, 33, is offered a role at a smaller firm with more responsibility but less job security. Her current employer is stable and comfortable.
- Option A, stay. Worst case: she stays comfortable but feels she plateaued. At 80, she suspects she would wonder “what if”.
- Option B, move. Worst case: the firm struggles and she job hunts within two years. She has savings to cover several months and a network in her industry.
Her worst case for B is uncomfortable but survivable, and her imagined 80 year old self is more troubled by A. She takes the new role, but negotiates a start date that lets her finish a key project and leave on good terms. That last step is the framework at its best: bold where it matters, careful where it counts.
Making Peace With Whatever You Choose
No framework guarantees you will never feel regret. What the regret minimisation framework offers is a way to choose deliberately, guided by what you value most over a lifetime rather than what feels easiest this month. When you know why you chose, regret tends to lose much of its power, and you can move forward with the path you are actually on.
Further reading: The Premortem Technique for Better Decisions · How to Make Hard Choices When Both Options Are Good