My father died on a Tuesday. The hospital called at 6 a.m., and by the time I got there, he was already gone. I spent the next three months sorting through his things, opening drawers, reading old receipts, trying to piece together the parts of his life he never talked about. I found a safety deposit box key but no idea which bank. A photo of a woman I didn't recognize. A handwritten recipe for something called "Sunday gravy" with no instructions, just ingredients.

He wasn't a secretive person. He just never got around to telling me things. And now I'll never know.

If you want to talk to your kids before death about the things that actually matter, the window is right now. Not when you're sick. Not when it's dramatic. Now, on an ordinary Saturday, over coffee. Here are ten specific conversations worth having.

1. The medical history they'll need but won't think to ask for

Your children will eventually sit in a doctor's office and get asked: "Any family history of heart disease? Cancer? Diabetes?" And they'll stare at the form and realize they have no idea.

Don't make them guess. Sit down and tell them:

What runs in your family. Not just the big diagnoses, but the patterns. "Your grandfather had high blood pressure by 40. So did I. Get yours checked early."
What medications you take and why. They may need this information in an emergency, and they may need it for their own health decisions decades from now.
What you wish you'd known sooner. Maybe you ignored a symptom for years. Maybe you learned something about diet or exercise the hard way. Say it out loud.

Try this: "I want to tell you about our family's health history, because someday a doctor is going to ask you and I want you to have real answers."

2. Where the money is and how it works

This isn't about being wealthy. This is about not leaving your kids to play detective during the worst week of their lives.

I've watched families tear apart over a missing bank account number or an insurance policy nobody knew existed. The money conversation isn't greedy. It's kind.

Tell them:

Where your accounts are. Banks, investment accounts, retirement funds. Write down the institutions and account numbers.
What debts exist. Mortgage, car loan, credit cards. If they don't know about a debt, they can't plan for it.
Who to call. Your financial advisor, your accountant, your insurance agent. Names and phone numbers, not just "I have a guy."
What you want done with what's left. Even if you have a will, say it in your own words. Wills are legal documents. Your kids need to hear your voice behind the legalese.

Try this: "If something happened to me tomorrow, would you know where to find our financial information? Let's fix that."

3. The story of how you became you

Your kids know you as a parent. They don't know you as a scared twenty-two-year-old who moved to a city where you didn't know anyone. They don't know about the job you almost took, the relationship that almost happened, the year everything fell apart and you rebuilt from nothing.

These stories matter. Not because they're dramatic, but because your children are going to face their own versions of them. And when they do, they'll remember that you survived yours.

Tell them about:

A time you failed badly and what it taught you. Not a cute failure. A real one that kept you up at night.
The decision that changed everything. Moving somewhere, marrying someone, quitting something, starting over.
What you were like at their age. Be honest. If you were lost, say so. If you were reckless, say that too. They need to know that uncertainty is normal.

Try this: "I never told you this, but when I was your age..." and then just keep talking.

4. What you believe and why

You don't need to hand your children a worldview wrapped in a bow. But you owe them the honest version of what you believe about the big questions, whether that's God, purpose, what happens when we die, or what makes a life worth living.

Kids absorb beliefs by osmosis for years, but at some point they need to hear you say it plainly. Not as a lecture. As a conversation between two adults.

What gives your life meaning? Not what should, according to some book. What actually does, on a daily basis.
How has your faith or philosophy changed over time? Most people's beliefs at 50 look nothing like their beliefs at 20. That evolution is worth sharing.
What do you hope they'll believe? You can say this without demanding it. "I hope you'll always..." is different from "You must always..."

Try this: "I've been thinking about what I actually believe, not what I was raised to believe, but what I've landed on after all these years. Can I tell you?"

5. The relationships that shaped you

Your kids know your marriage from the inside. They know your friendships from the outside. But they probably don't know the full story of either.

Talk about the people who mattered most and why:

How you and their other parent got together. The real version, not the rehearsed one. Include the doubt, the timing, the luck.
A friendship that saved you. Who showed up during your hardest season? What did they do that made a difference?
A relationship that ended and what you learned. Whether it was a falling out, a breakup, or just a slow drift. Loss teaches things that closeness can't.

Try this: "Let me tell you about someone who changed my life that you've probably never heard of."

6. The practical stuff nobody wants to talk about

If you died tonight, would your children know your wishes for a funeral? Would they know if you want to be buried or cremated? Would they know where your will is, who your attorney is, whether you have life insurance?

Most people don't. A recent survey found that more than half of American adults don't have a will. And of those who do, many haven't told their families where to find it.

Write it down and tell your kids:

Your wishes for your body. Burial, cremation, donation to science. Say it clearly.
What kind of service you want, if any. Music, readings, location. Or say you don't care and let them decide.
Where the important documents are. Will, power of attorney, insurance policies, deed to the house. One folder, one location, clearly labeled.
Passwords and digital accounts. Email, bank accounts, social media. This is the modern equivalent of the safety deposit box key.

Try this: "I know this is uncomfortable, but I'd rather have this conversation now than leave you guessing."

7. The apology you've been avoiding

If you have something to apologize for, do it while you're alive. Deathbed apologies make for good movies but lousy healing. Your kids deserve time to process, to ask questions, to be angry, and then to choose forgiveness on their own timeline.

This isn't about dredging up every mistake. It's about the ones that left a mark.

Name what you did. Don't say "I'm sorry if I ever..." Say "I'm sorry I missed your recital because I was working. I know that hurt you."
Don't explain it away. The reasons might matter to you. They don't matter as much to the person you hurt.
Ask what they need. Sometimes the apology is enough. Sometimes they need to tell you how it affected them. Let them.

Try this: "There's something I've wanted to say to you for a long time, and I keep putting it off."

8. What you want them to know about love

Your children are going to build their own relationships based partly on what they saw in yours. That's a heavy inheritance, and it's worth being honest about.

Tell them:

What you got right. What worked in your marriage or partnerships? What would you do the same way?
What you got wrong. Where did you fall short? What do you wish you'd understood sooner about loving another person?
What love actually looks like on a Tuesday. Not grand gestures. The daily, boring, choosing-each-other-again kind.

Try this: "Here's what I wish someone had told me about relationships before I learned it the hard way."

9. The family secrets that shouldn't die with you

Every family has them. The adoption nobody mentions. The estranged sibling. The reason grandma never talked about her childhood. The real story behind the divorce.

You don't have to tell your kids everything. But consider what they deserve to know, the things that would help them understand their own family, their own patterns, their own story.

A friend of mine discovered after both parents died that she had a half-brother. Her parents had known for decades. She found out from a DNA test at age 45. She told me she wasn't angry about the secret itself. She was angry that they chose to leave her alone with the discovery.

What would help them understand the family better? History that explains behavior, grudges that have a backstory, context they're missing.
What are they likely to discover anyway? DNA tests, old letters, a relative who talks. Better they hear it from you, with your context and your compassion.

Try this: "There's some family history I think you're old enough to hear, and I'd rather you hear it from me."

10. How proud you are, in specific terms

"I'm proud of you" is good. But "I'm proud of the way you stood up for your friend when everyone else looked away" is something your child will carry forever.

Be specific. Be concrete. Tell them what you see in them that they might not see in themselves.

Name a quality, not an achievement. "You're kind to people who can't do anything for you" matters more than "You got into a good school."
Tell them about a moment you noticed. Something small that stuck with you. The way they treated a waiter, the way they handled a disappointment, the way they showed up for someone.
Say what you hope for them. Not what career you want them to have. What kind of life. What kind of person.

Try this: "I've been meaning to tell you something I noticed about you..."

You don't have to say it all at once

Ten conversations can feel like a lot. You don't need a family summit. You don't need to sit everyone down with a PowerPoint presentation.

Some of these happen best on a long car ride. Some over a meal. Some in a letter that you write now and give later. The format matters less than the honesty.

The only thing worse than having these conversations awkwardly is never having them at all. Your children won't remember the awkwardness. They'll remember that you cared enough to try.

And if you're thinking "my kids don't want to hear this," you're probably wrong. In my experience, children of all ages are hungry for their parents to be real with them. They just don't know how to ask.

Start with one. Pick the conversation that feels most urgent, or most overdue, and begin there. You can keep it short. You can keep it casual. But start.

If you want help organizing these conversations, or if you want a place to write down the things you're not ready to say out loud yet, When I Die Files gives you a simple, private way to capture what matters most for the people you love.