
The choices people most often regret ten years later are rarely single dramatic mistakes. They are quiet patterns: living to please others, letting someone else define your goals, staying in draining company, putting yourself ahead of everyone, refusing to change, quitting too early, trying to control everything, settling, postponing, and drifting. Research on regret backs up a simple idea behind all ten: over the long run, the things we never tried tend to haunt us more than the things we tried and got wrong.
Below, each choice is explained with the reasoning behind it and a practical way to steer clear of it. The list is adapted from an essay by Marc Chernoff and Angel Chernoff of the blog Marc and Angel Hack Life, with added context from psychology research on what people actually look back on with regret.
What research says about long-term regret
Most of us know the feeling of "if only." Psychologists have studied it closely, and three findings are worth keeping in mind as you read.
Inaction stings longer. In a well-known 1995 paper, Thomas Gilovich and Victoria Medvec found that regrets about things people did tend to hurt more in the short term, while regrets about things they failed to do grow stronger over the years. The class you never took or the move you never made tends to linger longer than an embarrassing mistake.
Opportunity drives regret. A 2005 review led by Neal Roese, pooling nine studies, found that people most often regret choices about education, followed by career, romance and parenting. The explanation offered is that these are areas where people feel they could still have acted differently, so the missed chance feels real.
Ideals matter more than duties. Shai Davidai and Gilovich reported in 2018 that people more often regret failing to become their ideal selves than failing to meet obligations. That echoes the most quoted line from palliative care nurse Bronnie Ware's account of what her dying patients said: "I wish I'd had the courage to live a life true to myself, not the life others expected of me." Her observations are personal rather than scientific, but they fit the research remarkably well.
Living by someone else's script
1. Wearing a mask to win approval
Constantly shaping yourself around what others think can leave you unsure who you are underneath. The fix is not to stop caring about people, but to stop handing them a veto over your identity. You do not need to be flawless to earn respect; people are often more moved by how honestly you handle your imperfections than by any polished image.
2. Letting others choose your dreams
Working out what you actually want is hard enough. Accepting it, especially when it differs from what parents, partners or peers expected, is harder. Disagreement from others is not proof you are wrong; sometimes it is proof you are thinking for yourself. A useful clue: the work that makes you lose track of time is often closer to your real path than the work that earns the most applause. Tim Ferriss's The 4-Hour Workweek is one popular book on designing work around the life you want, though its specific tactics suit some careers far better than others.
The company you keep, and the person you become
3. Staying close to constant negativity
Moods spread. Spending most of your time with people who complain, belittle or stir up drama makes it harder to stay calm and hopeful yourself. Recognizing that your social circle is partly a choice gives you room to spend more time with people who are kind, generous and patient. You can be compassionate towards a negative person without letting them set the tone of your days.
4. Living only for yourself
Selfishness feels efficient in the moment and empty in hindsight. What people remember about us is mostly how we treated them. Kindness, generosity and a reputation for good character outlast anything we accumulate purely for ourselves, which is why so many reflections on a good life come back to relationships rather than achievements.
Growth, effort and timing
5. Resisting change
Your current circumstances reflect past habits; your future will reflect the habits you build now. Holding on to old routines because they are familiar can quietly block progress. Charles Duhigg's The Power of Habit explains the cue, routine and reward loop behind many habits and how people reshape it, which makes it a practical companion to this point.
6. Quitting when it gets hard
Setbacks are information, not verdicts. Most meaningful achievements come from small steps repeated long after the excitement fades. When things go wrong, take the lesson, adjust the plan and keep moving. Persistence does not mean never changing course; it means not abandoning a worthwhile goal just because the middle part is uncomfortable.
7. Putting things off until "someday"
We almost always assume we have more time than we do. Ten years from now you will either have made progress on the things that matter to you or have a set of reasons why not. Computer science professor Randy Pausch, writing with journalist Jeffrey Zaslow after a terminal cancer diagnosis, turned this idea into The Last Lecture, a book about living fully with the time you have.
8. Drifting instead of deciding
Waiting for life to arrange itself, or for someone else to take charge, is one of the most common sources of long-term regret. Taking responsibility does not require grand gestures. It starts with small, deliberate actions: one application sent, one honest conversation, one hour a week on the project you keep postponing. You matter, and what you contribute is needed now rather than at some vague later date.
Control and standards
9. Trying to micromanage everything
Gripping every detail tightly tends to produce anxiety, not better results. Sometimes the wiser move is to loosen your hold, breathe, and wait until the situation is clearer before taking the next step. You do not need a complete map to move in a good direction. The original essay goes further and suggests that everything is already in perfect order; you do not have to believe that to benefit from easing up on control.
10. Settling for less than you deserve
Whether in relationships, work or friendships, accepting treatment that diminishes you is easy to slide into and hard to undo. It takes strength to walk away and patience to wait for something better. Difficult periods can also clarify what you really want, so a low point is sometimes where better standards begin.
Turning regret into a useful tool
Regret has a bad reputation, but in moderation it is useful. It points to what you value and nudges you to act differently. A few ways to use it well:
- Run a ten-year test. When facing a decision, ask which option your future self is more likely to wish you had tried. Because inaction regrets tend to grow, lean towards the attempt when the downside is manageable.
- Separate regret from rumination. Learning from a mistake is healthy; replaying it endlessly is not. If you find yourself stuck, write down the lesson and one action, then close the loop.
- Act on the regrets you can still fix. Education, relationships and career shifts often remain open longer than people think, which is partly why they top the regret lists.
- Forgive the past version of you. You made choices with the information and maturity you had at the time.
A life without any regrets is probably a life without much risk. The aim is not to avoid every "if only," but to make sure the big ones are not about chances you never took.
Sources: Original essay by Marc and Angel Chernoff, "10 Choices You Will Regret in 10 Years", Marc and Angel Hack Life, shared via Why Don't You Try This; photo by J.T. Noriega; research summary from Wikipedia: Regret.
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