20 Life Story Writing Prompts, and What Each One Is For
Most prompt lists give you a hundred questions and no idea which ones are worth your Sunday. These twenty each do a specific job.
There is no shortage of prompt lists. Most of them are a hundred questions long, which sounds generous and is actually the problem: a hundred undifferentiated prompts gives you no way to tell which one is worth the only free hour you have this week.
These twenty are chosen because each one reliably produces a page rather than a sentence. Under each is what it is designed to reach and how to answer it so the writing actually goes somewhere.
Prompts for the beginning
1. Describe the house you grew up in, room by room.
Why it works. A guided tour has a built-in structure and a built-in ending, which is why it produces pages when a general childhood prompt produces a paragraph.
How to ask it. Walk through in a fixed order, front door inwards. Say who was usually in each room.
What it opens up. The family, the era and the daily routine, all arriving without being asked for.
2. What did your parents argue about?
Why it works. It reaches the actual economics and pressures of the household, which the sentimental version of a childhood leaves out entirely.
How to ask it. Write what you overheard, not what you understood at the time.
What it opens up. Money, family, work, and what you learned to worry about.
3. Who outside your family paid attention to you?
Why it works. There is almost always a teacher, neighbour or coach, and they are systematically missing from family records because nobody else knew them.
How to ask it. Describe what they actually did, not what it meant.
What it opens up. A person who changed your direction and has never been written down anywhere.
4. What were you afraid of as a child, and when did it stop?
Why it works. The second half turns a static memory into a story with a shape.
How to ask it. Be specific about the fear. Vague fears produce vague writing.
What it opens up. The interior life of a child, which adults reliably forget.
Prompts for the years nobody knows about
5. Describe the first place you lived that was yours.
Why it works. First homes are unusually vivid because everything in them was chosen or endured for the first time.
How to ask it. Start with what was broken and what you could not afford to fix.
What it opens up. The job, the money, the roommates and the neighbourhood.
6. Write about a job you were bad at.
Why it works. Failure is far easier to write honestly than success and it produces better pages almost every time.
How to ask it. Include what you told people at the time about why you left.
What it opens up. What you learned about yourself, and who was kind to you.
7. What is a decision you almost made and did not?
Why it works. The strongest prompt in this list. Everyone has a fork they still think about and almost nobody has written it down.
How to ask it. Write both branches. What you did, and the life you can still picture.
What it opens up. The shape of your life as a set of choices rather than a sequence of events.
8. Who did you lose touch with, and how did it happen?
Why it works. It reaches people who mattered enormously and left no trace in the family record, which is most of them.
How to ask it. Write the last time you saw them, if you can find it.
What it opens up. A period of your life that is otherwise undocumented.
9. What did you own that you loved?
Why it works. Objects unlock everything: the money to buy it, the place you kept it, who else touched it.
How to ask it. Describe the object physically before you say anything about why it mattered.
What it opens up. A whole era, arriving attached to one thing.
Prompts for the middle
10. What was the hardest year, and what ended it?
Why it works. The second half makes it possible to write. A hard year alone is a wall; a hard year that ended is a story.
How to ask it. Name the person who helped, even if it was a small help.
What it opens up. Resilience described concretely rather than claimed.
11. What did you believe then that you do not believe now?
Why it works. It gets at the actual shape of a life, which is a series of revisions.
How to ask it. Stay in the past tense and describe the belief generously.
What it opens up. How your mind changed, and the specific thing that changed it.
12. Describe a normal working day when you were forty.
Why it works. Nobody thinks the middle of their life is worth writing about, and it is the part their children will most want.
How to ask it. Start at waking and go through in order. Include the boring parts on purpose.
What it opens up. The texture of an adult life, which vanishes completely from memory.
13. What were you proud of that nobody noticed?
Why it works. Everyone has one, and the fact that nobody noticed is precisely why it has never been recorded.
How to ask it. Write what you did, not how it felt to be overlooked.
What it opens up. Something quietly significant that would otherwise die with you.
14. What did you get wrong about somebody?
Why it works. It produces honest writing because it costs a little to write, and that cost is what makes it readable.
How to ask it. Say what you thought, what was true, and how you found out.
What it opens up. Judgement, revision, and often a real reconciliation.
Prompts for the whole thing
15. What has changed in the world that you find hardest to explain?
Why it works. It positions you as a witness to a period, which is a comfortable and generous role.
How to ask it. Explain it to somebody who was not there. Assume they know nothing.
What it opens up. Historical texture that a grandchild genuinely cannot get anywhere else.
16. What advice did you ignore, and were you right to?
Why it works. The second half saves it from being a moral. Sometimes you were right, and saying so is more useful than a lesson.
How to ask it. Name who gave it and what they were worried about.
What it opens up. Your own judgement, examined rather than asserted.
17. What are you better at than people realize?
Why it works. It invites you to claim something, which the direct question about pride does not.
How to ask it. Give an example rather than a description.
What it opens up. A competence your family has taken for granted for decades.
18. What do you miss that no longer exists?
Why it works. It is elegiac without being sad, and it captures a vanished world precisely.
How to ask it. Pick something small and physical. A shop, a sound, a way of doing something.
What it opens up. The disappeared everyday, which is the part history books never carry.
19. What would you do with another twenty years?
Why it works. Forward-facing, which stops the whole project from becoming purely retrospective.
How to ask it. Answer practically rather than aspirationally.
What it opens up. Who you still are, as opposed to who you were.
20. What do you want your grandchildren to know about you?
Why it works. The right last prompt. It stops being an exercise and becomes a statement addressed to somebody specific.
How to ask it. Write it to one named person. Addressing one reader produces far better writing than addressing everybody.
What it opens up. Whatever you most want kept, which belongs at the front of the finished book.
How to use these
One a week, in any order, for twenty weeks. Do not do them in sequence and do not do several in a burst. Space is what makes the answers good, because you will think about next week's question while doing something else, and arrive already knowing what you want to say.