30 Questions to Ask Yourself About Your Life and Choices

Originally published 2015-05-17.

The thirty questions below are prompts for honest self-reflection: about time, values, fear, other people's expectations and what you are ready to let go of. Pick one or two, write your answers down, and come back to them in a few months. The point is not to find the "right" answer but to notice what your answer says about how you are living now.

Good questions work differently from advice. When someone tells us what to do, we tend to argue back. When we answer a question ourselves, the conclusion feels like ours, and we are more likely to act on it. That is why coaches, therapists and teachers lean on questions, and why it is worth turning a few of them on yourself.

How to use these questions well

Psychologists distinguish between two kinds of self-focus. Paul Trapnell and Jennifer Campbell, in a 1999 study, described reflection as curious, open self-exploration, and rumination as anxious, repetitive dwelling on what went wrong. Reflection tends to go with better well-being; rumination with worse. The same question can lead to either, so how you approach it matters.

• Write, don't just think. The psychologist James Pennebaker found in a long series of studies that writing about meaningful experiences for 15 to 20 minutes over a few days helped many people feel better and even visit doctors less. Writing slows thought down and gives it shape.
• Choose one question at a time. Answering all thirty in one sitting turns them into a quiz.
• Make it concrete. Tie each answer to something specific from the past week, such as a conversation, a decision or how you spent an evening.
• Notice when you start going in circles. If a question leaves you stuck in the same painful thought, stop, take a walk, or talk it through with someone you trust.

If reflection brings up deep sadness, hopelessness or old trauma, that is a signal to talk to a doctor or therapist rather than to push on alone.

Questions about time and how you spend it

1. Forget your birth certificate for a moment: how old do you feel?
2. If people only lived to 40, what would you change about how you live this year?
3. Are you merely staying alive, or really living?
4. What did you do today that you will still remember next month?
5. Do your days blur into one repeated day? If so, what one thing could break the pattern?
6. Since your life will end, how do you want to spend it?
7. If the right time is not now, when will it be?

The first question is a version of a line often attributed to the baseball pitcher Satchel Paige, who played in the major leagues into his forties and liked to keep his real age a mystery. The last one echoes the first-century sage Hillel, whose saying in the Jewish collection Pirkei Avot ends: "And if not now, when?" Both questions push in the same direction: time is limited, and waiting for perfect conditions is a choice too.

Palliative-care nurse Bronnie Ware, in her book The Top Five Regrets of the Dying, wrote that the regret she heard most often was not having had the courage to live true to oneself rather than to others' expectations. Questions about time are a gentle way of checking for that regret early.

Questions about values and happiness

8. If happiness were a currency, what would make you wealthy?
9. Which matters more to you: doing the right thing, or doing things the right way?
10. Would you rather be a brilliant person full of worry, or a carefree person who knows less?
11. If you could fix one thing in the world, what would you choose?
12. Why do the things that make you happy leave other people cold?
13. What makes you the person you are, and not someone else?
14. What do you love so much that you would do it unpaid?

These questions are useful because the honest answer is often different from the polite one. Many people discover that what would make them "rich" in happiness is time, health or a few close relationships rather than possessions. Research on well-being, including the long-running Harvard Study of Adult Development, keeps finding that the quality of close relationships predicts a happy, healthy life better than income or status.

Questions about fear, failure and risk

15. Can you be sure something is true if you have never questioned it?
16. Have you ever faced your biggest fear? If not, how do you know it deserves that place?
17. Where do you think creativity ends and madness begins?
18. If mistakes are how we learn, why do we try so hard to avoid them?
19. Which would hurt more in twenty years: having tried and failed, or never having tried?

The last question has a research answer of sorts. Psychologists Thomas Gilovich and Victoria Medvec found that in the short term people regret actions that went badly, but looking back over their lives, they regret the things they never tried far more. Fear often grows in the space where we avoid testing it, which is why naming a fear and taking one small step toward it is a classic technique in anxiety treatment.

Questions about freedom and other people's expectations

20. When your life is over, will you have talked more than you acted?
21. Is your work an expression of what you believe, or a way of getting through the week?
22. How much of your life so far did you actually steer?
23. If you could pass on just one piece of advice, what would it be?
24. Would you trade ten years of life for fame or good looks?
25. Would you choose a lighter workload, or a heavier one doing work you love?
26. What would you do if nobody could judge you for it?
27. Are the choices you are making now really yours, or someone else's?

The advice question is a quiet trick: the advice we would give a stranger is often the advice we most need ourselves. If your answer to the judgment question is very different from your current life, it is worth asking whose approval you are really working for, and whether that person would even notice if you changed.

Questions about letting go

28. Would you rather lose every memory you have, or lose the ability to form new ones?
29. What are you still carrying that it is time to put down?
30. Does something that upset you five years ago still matter today? Why, or why not?

The memory question sounds like a party game, but it reveals whether you value your past or your future more. The last two are practical. Holding on to old grudges, roles or plans takes energy. Sometimes the answer is that an old hurt still matters and needs a conversation or professional help; often it is that the story has already ended and you are free to stop telling it.

Where these questions come from

Several of these prompts were inspired by the question books that became popular in the 1990s, especially If… (Questions for the Game of Life) by Evelyn McFarlane and James Saywell, a collection of hypothetical questions meant to start conversations and self-discovery. The list was later shared widely online, including by I Heart Intelligence. The wording here is our own, grouped by theme so you can go straight to the area of life you most want to think about.

A good way to finish is to choose just one question from this page, write it on a card, and keep it where you will see it this week. One question lived with for seven days usually teaches more than thirty answered in seven minutes.

Sources: Pirkei Avot 1:14 (Sefaria); original list via I Heart Intelligence; Trapnell and Campbell (1999), Journal of Personality and Social Psychology; Gilovich and Medvec (1995), Psychological Review; Bronnie Ware, The Top Five Regrets of the Dying.