What Should I Ask My Parents While I Still Can?
What I'd Want to Ask My Parents
Most of what we wish we had asked, we realize too late to ask. These fourteen questions are a way to ask on purpose while there is still time, in a real conversation, at whatever pace feels right. You can ask one at a time over months or sit down together for an afternoon.
Why ask now rather than later?
Because the window closes without announcing itself. The questions people most regret are almost never dramatic ones. They are small and specific: what the move was really about, why they stayed at that job, what they thought of the person you married before they knew them properly.
Those answers exist in exactly one place. When that person is gone, so is the answer, and no amount of family records will reconstruct it.
How to use this
- Ask in whatever order feels natural. Skip anything that does not fit today.
- Write down what they say soon after, in their words if you can.
- There is no deadline. A few honest answers beat a rushed full set.
These are questions to bring to your parent or parents, not questions to answer yourself.
What I'd Want to Ask My Parents is also a free printable guide you can take with you, with room to write down what they say. Nothing to sign up for.
Download the free guide (PDF)Where they started
- What is a moment from your childhood that you think about most?
- What did your family have plenty of, and what did it go without?
- What is something you believed as a kid that turned out to be wrong?
How they decided
- What is the hardest decision you ever made, and how did you actually make it?
- What is something you almost did but did not, and how do you feel about that now?
- What is a mistake you made that you are glad you made?
- If you could redo one decision with what you know now, which one, and why?
What they actually believe
- What do you want me to understand about money that no one explained to you?
- What is something you value that most people around you do not seem to?
- What is a rule you live by that you have never actually said out loud?
What they hope for me
- What do you hope is true about my life ten years from now?
- What is something you hope I never have to learn the hard way?
- What do you want me to know about you that I might not find out otherwise?
- If you were not here to say it in person, what is the one thing you would want me to hear?
Once you have asked these
Keep what they tell you. Write it down while it is still fresh, and come back to it.
There is no wrong way to have done this. The only mistake is never asking.
If the conversation turns practical, and it often does, If Something Happens to Me is the one page a family needs first, and The Beneficiary Check-In covers the designations that quietly override a will.
If this mattered to you
This is a smaller, self-guided version of something we help families do more fully. The Legacy Vault preserves a parent’s own voice, values, and wishes, in their words, built through the conversations they already have with their advisor.
If you would rather someone else asked the questions, The First Chapter is one guided conversation, recorded and kept, with the questions prepared around their life beforehand.
Quick answers
- What is this guide for?
- It is a short set of questions to bring to your parent, so the things you would regret not asking get asked while they can still answer. These are questions to ask them, not questions to answer yourself.
- What if my parent does not want to talk about this?
- Start with one question, not fourteen, and pick an easy one. Most people who resist the idea of a big conversation are happy to answer a single specific question about their own life. If they stop, stop.
- Should I record the answers?
- If they are comfortable with it, yes. If not, write down what they said soon after, in their words where you can. A story loses less than you would think, but it does lose something.
- Do I have to ask all fourteen?
- No. Ask in whatever order feels natural and skip anything that does not fit today. There is no deadline, and a few honest answers beat a rushed full set.