I Teach This. I Hadn’t Finished It Myself.
This fall, I’m getting my own affairs in order — in public. You’re welcome to walk along.
Last week I pulled out my own Vital Legal Papers Checklist — the one I made for my readers — and did something I’d been putting off longer than I care to admit.
I checked my own work.
The results were mixed.
Starting to Build the System
Some things passed. My will is exactly where it should be — in the safety deposit box at the bank. My passwords are all current, too. I’d love to tell you that’s because I’m disciplined, but the truth is simpler: I use a password manager, and it does the remembering for me. That’s not discipline. That’s a system. (And that difference is going to come up again and again this fall.)
Then it got humbling.
My insurance papers? I have most of them. But “most of them” and “all in one place” are two very different things. Some are filed where they belong. Others are — well, elsewhere. I know it’s somewhere is a phrase I hear from readers all the time. It turns out I say it too.
And then the part I’d been avoiding entirely: the notes for my children. The page that tells them where everything is, who to call, and what they’d need to know if I weren’t here to answer questions.
I haven’t written a word. Not a rough draft. Not a list on the back of an envelope. Nothing.
What’s the Cost of Not Doing
Here’s the thing that struck me as I sat there with my own checklist: my papers are in better shape than my family’s ability to find them. The will exists — but the map to it lives only in my head. If something happened to me tomorrow, my family wouldn’t be starting from nothing. They’d be starting from guessing. And I’m not sure that’s much better.
I know what that guessing costs, because I’ve lived it from the other side. When my mother and my mother-in-law passed, my husband and I served as executors of our parents’ estates — and losing them taught us a lot. I learned firsthand what it means to sort through everything — the papers, the accounts, the decisions — while you’re grieving. It’s a burden I decided long ago my children would not carry.
What? How?
But deciding, it turns out, isn’t the same as finishing.
And since we’re being honest, here’s one more confession. Sitting there with my own checklist, I realized it tells you what to gather — but not how. Where should the originals live, and where should the copies go? What’s fine in a box on a shelf, and what belongs somewhere more secure? What needs to be written down for your family, and how much information is enough? My checklist doesn’t answer those questions yet.
Neither do I. That’s what this fall is for.
As I work through my own checklist, I’ll be asking those questions out loud, figuring out the answers, and adding what I learn — which means the checklist you download today is going to keep getting better as we go. You’re not just watching me get my affairs in order. You’re watching the how get built.
So this fall, I’m finishing — in public. Each week I’ll take one step toward what I call being legacy ready: papers findable, accounts written down, the house a little lighter, the stories saved. I’ll show you exactly what I did, how long it took, what I put off and why, and what I’d tell a friend to do differently.
Not because I enjoy confessing. Because I know from thirty-four years in education that people finish things when someone is doing it alongside them — and almost never when they’re alone at the kitchen table with a stack of folders.
Promises…Promises…
A few promises about what this series will not be.
It won’t be morbid. This is about living with your affairs in order, not dwelling on the end. A folder full of answers makes life lighter, not heavier.
It won’t be overwhelming. One step a week. Some steps take an afternoon. Most take less.
And it won’t require you to be organized already. You can start where you are. Clearly, I did.
If you’d like to walk along with me, start where I started: the Vital Legal Papers Checklist. It’s free, it’s short, and this week your only assignment is the same one I’m giving myself — print it and look it over. Don’t gather a single document yet.
The Real Question
So let me ask you what I had to ask myself: if your family needed your important papers tomorrow, would they know where to look — and could they get to them?
I’d love to hear where you are with this. No shame in the answer. I just told you mine.
Next time: the first step I’m taking — choosing where everything will live.
