100 Questions to Ask Your Future Self
Twenty questions to put to yourself a year, five years or ten years from now, in a letter, a sealed envelope or a file dated ahead. Written to be answered by the person you turn into, on work, money, health, the people around you, and what you hope has fallen away by then.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
What are you doing on an ordinary Tuesday?
Start here rather than with achievements. A future you can describe an ordinary weekday is a future you have actually imagined, and the answer you write now becomes a fair test of whether the plan was ever about daily life or only about milestones.
- 2
Who did you have breakfast with this week?
A specific, unimpressive question that catches drift. Names change slowly and without announcement, and reading this back is often the first time people notice who left.
- 3
What am I worried about right now that turned out not to matter?
You are recording the worry so your future self can measure it. The value is not the reassurance, it is finding out which category of worry you overweight, since most people repeat the same one for decades.
- 4
What am I ignoring that you wish I had dealt with immediately?
Write your current three avoidances underneath, in a sealed line, so the answer can be checked rather than remembered. Avoided things almost never resolve themselves, and naming them dates the delay precisely.
- 5
What do you spend money on now that would surprise me?
Spending shifts faster than identity does, and the surprise usually points to a change you have not admitted yet. If nothing surprises you, that is its own finding about how much has moved.
- 6
Which friendships survived, and which ended without anyone deciding to end them?
Most friendships do not break, they lapse. Listing four or five names now gives your future self something to check against, and the ones that lapsed usually did so in a year you could point to.
- 7
What did I stop doing, and was that a decision or a drift?
The distinction matters more than the loss. A dropped hobby chosen on purpose costs nothing; one that slid away without notice tends to be the thing people say they miss most.
- 8
How is my body, and what did I do to it in between?
Ask it bluntly so the answer cannot be flattering. Include the specifics you would rather not write down now, because vague health questions get vague answers and this one is only useful if it is concrete.
- 9
What did I get wrong about the work I am chasing?
Almost everyone is wrong about a job before they have it, usually about the day-to-day rather than the status. Whatever your future self answers here is the piece of information that would have saved you the most time.
- 10
What did you keep from the place I am living now?
Objects survive moves for reasons that are never obvious in advance. The list is short, it is rarely the expensive things, and it tells you what you actually valued about this period.
- 11
Am I still in contact with the person I am angriest at today?
Name them privately. Grudges look permanent from inside them, and this question reliably produces one of two useful answers: that it healed and you cannot remember why, or that it cost you someone.
- 12
What was the largest amount of money that passed through my hands, and where did it go?
Not what you earned, what passed through. It catches the years where a lot arrived and nothing accumulated, which is a pattern people usually only spot in hindsight.
- 13
What am I proud of now that you find embarrassing?
Expect this one to sting. It measures how much your standards moved, and if nothing on the list embarrasses your future self, you have probably stopped growing rather than got it right first time.
- 14
What did I do this year that turned out to matter far more than it seemed at the time?
The turning points are usually small and boring: an email sent, a class started, a conversation. Your future self can name them and you cannot, which is the entire reason to write this down.
- 15
Who did I lose, and did I say what I needed to say first?
Write it calmly. The point is not to make yourself anxious about people dying, it is that the answer is usually about visits and calls you could still make in the next month.
- 16
What did I put off until it was no longer possible?
Deadlines that are invisible now become obvious later: a parent's memory, a knee, a friend's move abroad. This is the question that most often changes what someone does the week after writing it.
- 17
Whose advice did I ignore, and what did they say exactly?
Record the advice and the name now, word for word if you can. Ignored advice tends to be forgotten rather than disproved, and the record stops you rewriting the story in your own favour later.
- 18
What do you know now that would have taken the fear out of this year?
You are asking for the fact, not the encouragement. Future selves are unhelpful when they say it worked out, and useful when they say the specific thing that was never worth the anxiety.
- 19
If you could send me one instruction, what is it?
Keep it to one line and make it an action rather than a mood. When you eventually answer this, notice whether the instruction is one you have already been given by somebody else.
- 20
Are you happier, and if not, when did that start?
The closer, and the only one with a follow-up built in. The date matters more than the verdict, because a decline that can be traced to a year, a job or a move is one you can do something about.
Writing and answering it
Practical guidance for the conversation itself.
How to actually do this
How to actually do this
- 1Pick the date first and put it in a calendar, not just on the envelope. Letters with no delivery date are read within a fortnight or never.
- 2One year is long enough for circumstances to change and short enough that you will still care. Five and ten years are worth doing as separate, shorter letters.
- 3Write your answers to the current-facts questions in full: names, figures, job title, where you live, who you saw this week. The letter is only useful as a record if it is specific.
- 4Say what you predict will have happened. Predictions are the part people find most revealing on rereading, and vague hopes give you nothing to compare against.
- 5Store it somewhere retrievable in a year: a scheduled email to yourself, a dated file, a physical envelope with somebody reliable.
Getting the tone right
Getting the tone right
- Write to a person, not to posterity. Second person keeps it readable; grand statements about life age badly within months.
- Do not set targets you would be ashamed to miss. A letter that reads as a list of failures on opening gets thrown away, and you lose the record.
- Include one or two mundane details you assume you will remember: the coffee you buy, the walk you take, what the flat sounds like. These are the lines that hit hardest later.
- Leave the self-criticism out. You are collecting evidence, and evidence collected in a bad mood is unreliable.
When it arrives
When it arrives
- Answer it in writing rather than reading it and moving on. The comparison is the whole exercise and it disappears if you only skim.
- Mark which predictions were wrong before you explain why. The explanation always sounds reasonable and it is the error rate that is informative.
- Look for anything that appears on both lists: the same avoidance, the same worry, the same person. Repeats across letters are the things worth acting on.
- Write the next one the same day, while you can still remember what you wish this letter had asked.