I Finally Asked My Dad the Question I’d Been Avoiding for Years
How I used AI to muster the courage to ask my father to share his childhood stories from India
Your Parents Won’t Be Around Forever
I want capture my parents’ stories while they’re still with us and their memories are sharp. My dad is 84 and my mom is 81, so time is of the essence.
note: for me, designing the website is the “bikeshedding” / time wasting / avoidance part. actually interviewing my parents is the meaningful, important, urgent part that I’ve avoiding by doing the technical busywork.
Perfect. Got it. This is a classic case of “do the hard thing first, bikeshed later.” Let me build this project file with that principle front and center.



Project Overview: Your parents are in their 80s. Their memories are sharp NOW. They won’t be forever. This is urgent.
The real project: Interview them, record their stories, preserve their voices and memories.
The fake project: Build a beautiful website to display the stories.
YOU ARE DOING THE FAKE PROJECT TO AVOID THE REAL PROJECT.
The website is bikeshedding. It’s comfortable, technical, solvable. Interviewing your parents about their lives is vulnerable, emotional, confronting mortality. That’s why you’re avoiding it.
What actually matters:
- Recording their voices telling stories
- Capturing details before they forget
- Having these conversations while you still can
- Creating something your family will treasure after they’re gone
The website can be built AFTER you have stories. Or never. The stories are what matter.
The Trap You’re In
Translation: “I’ll build the display system first, THEN do the interviews.”
NO. Reverse this. Interviews first. Display later.
Why? Because:
- If you build the site first, you’ll spend weeks making it perfect
- You’ll feel productive but have zero actual content
- Your parents will be 85 and 82 before you interview them
- Building the site is procrastination that feels like work
The Real Sequence
Phase 1: CAPTURE (weeks 1-8)
This is the ONLY thing that matters right now.
Week 1-2: Set up dead-simple recording system
- Pick tool: iPhone Voice Memos? Zoom? Video camera?
- Test it once
- DONE. Don’t optimize. Just works = good enough.
Week 3-8: INTERVIEW EVERY WEEK
- Dad: 1 hour/week
- Mom: 1 hour/week
- Minimum 12 recordings total (6 weeks × 2 parents)
- More is better, but 12 is the baseline
During these 8 weeks:
- DO NOT TOUCH THE WEBSITE
- DO NOT ORGANIZE THE FILES
- ONLY RECORD
Phase 2: TRANSCRIBE (weeks 9-12)
- Use transcription service for transcripts
- Clean them up enough to be readable
- Still NO WEBSITE
Phase 3: ORGANIZE (weeks 13-16)
- Pull out key stories
- Tag by theme, person, era
- Create structure
- NOW you know what the website needs to do
Phase 4: DISPLAY (weeks 17-20)
- Build the site based on actual content you have
- You’ll know what features matter because you have real stories
- This will be fast because it’s solving a real problem, not a hypothetical
Next Actions
#focus — Deep work required
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URGENT: Schedule first interview with Dad DEADLINE: This weekend THIS WEEK. Before you do ANY technical work.
Text or call: “Dad, I want to record some of your stories. Can we do an hour this weekend?”
Pick a specific time. Put it in your calendar. BEFORE you open your code editor.
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URGENT: Schedule first interview with Mom DEADLINE: This weekend Same deal. This week. Specific time on calendar.
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Create interview question bank 45min. Brainstorm questions you want to ask. Examples:
Early life:
- What’s your earliest memory?
- What was your neighborhood like as a kid?
- Tell me about your parents (my grandparents)
Career/Work:
- How did you choose your career?
- What was your first job?
- What are you most proud of professionally?
Love/Family:
- How did you and Mom/Dad meet?
- What was your wedding like?
- Tell me about when I was born
Historical events:
- Where were you when [major event]?
- How did [historical period] affect your life?
Wisdom:
- What do you know now that you wish you knew at 30?
- What are you most grateful for?
- What do you want your grandchildren to know about you?
Build this list. Add 30-50 questions. This is your interview guide.
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First interview: Dad (1 hour) JUST DO IT. Don’t prepare too much. Don’t make it perfect.
Setup:
- Quiet room
- Phone recording (or whatever)
- List of questions in front of you
- Maybe coffee/tea to make it comfortable
Start: “Dad, I want to record your stories so we never lose them. Can I just ask you some questions?”
PRESS RECORD. ASK QUESTIONS. LISTEN.
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First interview: Mom (1 hour) Same process. Different person.
#admin — Light cognitive load
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Create folder for raw recordings 5min. That’s it. One folder. Audio files go here.
Done. No subfolders. No organization. Just dump the files there.
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After each interview: Save file with date 2min per interview. Filename format:
YYYY-MM-DD-[parent]-interview-**.m4aThat’s it. Don’t transcribe yet. Don’t listen back. Just save and move on.
#connect — People work
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Ask siblings if they want to join an interview 15min. Optional, but might be nice.
“I’m starting to record Mom and Dad’s stories. Want to sit in on one? Might spark good questions.”
#batch — Do together
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[BANNED UNTIL WEEK 9] Do not work on website YOU ARE NOT ALLOWED TO TOUCH THE WEBSITE CODE.
The website is a reward. You get to build it AFTER you have 12+ hours of recorded stories.
If you find yourself opening your code editor to work on the archive site, STOP. Ask yourself: “Have I recorded my parents this week?”
If no → Close editor. Schedule the interview. Do that first. If yes → Still close editor. Do another interview instead.
Rules of Engagement
The One Rule
YOU CANNOT WORK ON THE DISPLAY SYSTEM UNTIL YOU HAVE AT LEAST 12 RECORDED INTERVIEWS.
No exceptions. No “but I just want to prototype one thing.” No “I’m just exploring the tech stack.”
INTERVIEWS FIRST. ALWAYS.
How to resist the bikeshed
When you feel the urge to work on the website instead of interviewing:
- Notice: “I’m doing the comfortable thing to avoid the hard thing”
- Name it: “This is procrastination, not progress”
- Redirect: “What would make the real difference? Recording Dad talking about his childhood.”
- Act: Open calendar. Schedule interview. Right now.
Accountability
Every Sunday, review:
- How many interviews did I do this week? (Target: 2, one per parent)
- How many hours did I spend on the website? (Target: 0 until you have 12 interviews)
Success Metrics
Phase 1 Success (8 weeks from now):
- 12-16 recorded interviews minimum
- Raw audio files safely stored (backed up!)
- Parents feel good about the conversations
- You have tangible progress on what ACTUALLY matters
Ultimate Success:
- You have dozens of hours of your parents’ voices
- Stories captured that would otherwise be lost
- Your future self thanks you for doing this now
- Your kids/family can hear these stories forever
- The website exists and makes the stories accessible (but this is secondary)
Why This Matters
Your parents are in their 80s. They’re healthy now. They might have 5 years, 10 years, 20 years. Or they might not. You don’t know.
What you DO know: If you don’t record their stories this year, you might not get another chance.
The website doesn’t matter. The recordings matter.
Do the hard thing. Interview your parents. This week.
Resources
- Interview question inspiration: StoryCorps, The Moth, family history guides
- Recording tools: iPhone Voice Memos (simplest), Zoom (if remote), transcription service (for later)
Activation Criteria
This project is ACTIVE starting NOW.
Every Sunday, you must:
- Review: Did I interview both parents this week?
- If no: Schedule both interviews for next week BEFORE doing anything else
- If yes: Celebrate. Schedule next week’s interviews.
The website stays BANNED until you have 12 interviews in the can.
After that, you can bikeshed to your heart’s content. You’ll have earned it.
Text messages
Perfect. Send BOTH texts right now. Don’t wait until you feel ready. Don’t wait until you have the perfect questions prepared. Just send them.
What to Do When They Respond
If they say yes immediately:
- Reply with specific time: “Great! How about Saturday at 2pm at your place?”
- Put it in your calendar
- Set a reminder the night before to prep 5-10 questions
If they seem hesitant or ask “why?”:
- “I just don’t want to lose your stories. You have a whole life I don’t know enough about.”
- “It’s important to me to have this recorded.”
- Don’t over-explain. Your wanting to do it is reason enough.
If they deflect (“my memory isn’t that good” or “my life isn’t that interesting”):
- “Your memory seems great to me, and I want what you DO remember”
- “Your life is interesting to ME. I’m your kid. I want to know these things.”
- Be gently insistent. Don’t let them talk you out of it.
If they agree but want to do it “sometime”:
- “Let’s pick a specific day right now. How about this Saturday or Sunday?”
- Don’t accept vague “we’ll figure it out later” — that means it won’t happen.
After You Send the Texts
DO NOT:
- Open your code editor
- Work on the archive website
- “Prepare” by building tools
DO:
- Feel good about taking action on something that matters
- Brainstorm 5-10 questions you want to ask (10 minutes max)
- Check your recording setup (iPhone voice memos works fine)
how’s this:
Hi Dad, I want to go ahead with interviewing you about your India days the same way we did with Dada. Can we talk this weekend and I will record it? How about Sunday at noon?
Love,
Sunjay
That’s perfect. Here’s why:
What Makes This Work
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Precedent: You’ve done this before with a relative. It’s not weird or new — it’s a continuation of something your family already does. This takes the awkwardness out.
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Specific scope: “Your India days” is manageable. Not “your whole life story” which feels overwhelming. You can always expand later.
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Concrete time/date: Sunday at noon. No wiggle room for “someday.”
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Warm closing: Keeps it from feeling formal or morbid.
About the Nervousness
“it’s crossing into a mode of interacting with my parents that feels uncomfortable and new”
Yeah. That’s real. A few thoughts:
It IS a different mode. You’re moving from child-to-parent into something more like peer-to-peer, or even interviewer-to-subject. You’re asking them to be vulnerable and reflective. That feels weird because you’re used to them being “the parents” — the authorities, not the subjects of inquiry.
But here’s the thing: They won’t be around forever. And one day you’ll wish you had asked these questions. The discomfort you feel now is tiny compared to the regret you’d feel if you never did this.
The nervousness is good data. It means this matters. If it didn’t matter, you wouldn’t be nervous.
Also: By mentioning the relative, you’re giving your dad permission to see this as normal. “This is what we do in our family. We preserve stories.” That’s actually beautiful.
What Happens Next
When he says yes:
- Put it in your calendar immediately
- Prep 5-10 questions about India (childhood, immigration, early career, whatever you want to know)
- Show up. Press record. Ask questions. Listen.
The conversation itself will feel less weird than you think. People love telling their stories when someone genuinely wants to hear them. Your dad will probably enjoy it.
And after you do it once, the second interview will be easier. The third even easier. By the fourth, it’ll feel natural.
Send It
Don’t edit it anymore. Just send it. Right now.
Then send a similar one to your mom (adjust the specifics — what era/topic for her?).
The hardest part is pressing send. After that, it gets easier.