Questions to Ask Your Younger Self
Twenty questions to put to a specific earlier version of you, at ten or seventeen or twenty-four, for journaling or a long walk. These ask rather than advise, on the theory that the child you were knew things about you that the adult has stopped being able to see.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
How old are you, and where are you sitting while I ask this?
Fix the age and the room before anything else, because a general younger self answers in generalities. A specific kitchen at a specific hour produces detail, and the detail is where everything useful in this exercise lives.
- 2
What are you worried about this week?
Not the big fears, this week's. The weekly worries of a fourteen year old are usually social and immediate, and remembering the actual texture of them is what stops this becoming a sentimental exercise.
- 3
What do you do when nobody is watching?
Unobserved behaviour at that age is the closest thing to an unedited answer about who you were. It often names an interest that later got filed as unserious, which is a hint about what has gone missing since.
- 4
Who is your favourite person right now, and does anyone know?
The secrecy is the interesting half. Whether you could say who mattered to you, and to whom, describes the level of safety in that period more accurately than any general memory of it.
- 5
What are you pretending to like?
Everyone has a list at that age: music, a sport, a group, a subject. Naming yours tells you what you were buying with the pretence, which is nearly always belonging or a particular person's approval.
- 6
What are you pretending not to care about?
The harder direction, and the more revealing. Feigned indifference tends to protect the thing you wanted most, and quite often it is still the thing you want and still the thing you are casual about.
- 7
Who scares you, and what do you do to stay on their good side?
The strategies are the answer: going quiet, being funny, being useful, being early. Most people are still running one of them at work thirty years later without recognising where it came from.
- 8
What do you think adults have figured out?
Answering in the voice of your younger self, honestly, is uncomfortable in a productive way. It shows you the standard you have been quietly failing to meet since, and gives you a chance to notice that nobody meets it.
- 9
What do you think will be easy that I know is not?
Do not answer this one with correction. The value is in seeing which specific piece of confidence you lost and whether losing it was accurate or just the general erosion that happens to everybody.
- 10
What are you good at that nobody has praised yet?
Children usually know. Unpraised aptitude tends to get abandoned rather than developed, and it is common for this question to name something you now pay other people to do.
- 11
What did you stop doing because someone laughed?
There is almost always one, and the person who laughed was often not important. Recovering the specific moment is oddly freeing, largely because the incident turns out to be so small compared to what it cost.
- 12
What are you saving for, and did you ever get it?
A small, concrete question that opens a large one about how you handle wanting things. Note whether you saved and were talked out of it, saved and got it and lost interest, or never saved at all.
- 13
Which grown-up would you call if everything went wrong?
The name matters, and so does an empty answer. If nobody comes to mind, that absence explains a lot about how you now handle needing help and how reluctant you are to ask for it.
- 14
What are you lying about, and to whom?
Adolescent lies are usually about small shames rather than misdeeds. What is worth noticing is who you protected yourself from, since that is generally the person whose voice you still hear when you make a mistake.
- 15
What are you angry about that I have stopped being angry about?
Some of that anger was accurate and got talked out of you. Ask which one it was, because dropped anger about something genuinely unfair often turns into a low grade tiredness you have carried since.
- 16
What do you already know about yourself that you will not say for another ten years?
Most people can answer this instantly, and the speed of the answer is the point. It shows how long the gap was between knowing something and being able to say it, and to whom you eventually said it.
- 17
Would you recognise me?
A blunt question that separates change from drift. Recognition is not really about appearance or achievement, it is about whether the things you cared about at that age would still be visible in a day of your current life.
- 18
Would you like me?
Sit with this one rather than rushing to a verdict. The answer usually turns on one or two specific habits rather than on your whole character, and those are the ones worth taking seriously.
- 19
What did you want that I gave up on without telling you?
Abandoned plans are rarely formally cancelled. Finding the point where a thing quietly stopped being possible is often the most useful minute of this whole exercise, particularly when it turns out to still be possible.
- 20
If you could ask me one question, what would it be?
Give the answer honestly, including the parts that are disappointing. People frequently find that their younger self would not ask about money or status at all, and what they would ask about is who is still around.
Using these questions
Practical guidance for the conversation itself.
Pick one age and stay there
Pick one age and stay there
- Choose an age you have a real, textured memory of rather than a symbolic one. Nine and sixteen usually work better than eighteen.
- Anchor it with a room, a school year, a bedroom wall, a bus route. Physical detail brings back the emotional weather, which is what you are after.
- Answer in that person's vocabulary. Adult phrasing smooths over exactly the parts worth reading later.
- Do a second age another day rather than blending them. Ten and twenty-two give completely different answers and blending them produces neither.
- Photographs help, but old school work, playlists and messages help more, because they are unedited.
When an answer stings
When an answer stings
- Write it down before you explain it. The explanation is what the adult does to make the answer manageable, and it usually removes the information.
- Distinguish regret from grief. Regret suggests something is still open; grief is about something that closed, and the two need different responses.
- If a memory arrives that you cannot hold, stop the exercise. Journaling is not the right tool for everything, and there is no benefit in pushing through it alone.
- Resist apologising to your younger self on the page. It ends the conversation early and it is generally more comfortable for you than useful.
- Leave the page and come back in a week. The second reading is where the pattern shows up.
Turning it into something
Turning it into something
- Look for anything on the page that is still available: a person you could call, a skill you could pick up badly, a place you could visit.
- Pick exactly one and do it within the month. Insight without a small action tends to evaporate by the following weekend.
- Notice repeated names. A person who appears in four answers is the subject of this exercise whether or not you meant them to be.
- Keep the page and date it. Doing this again in two years is considerably more interesting when you can compare.
- If you want a companion exercise, write the same twenty questions addressed forward instead of back, and seal them.