My daughter was born in 2024. By the time she turned two, my wife and I had taken about 10,000 photos and videos of her.

Every one of them was safely backed up to my home NAS. And every one of them was, in practice, lost.

Not lost like deleted. Lost like a box in the attic you keep meaning to open. The files were there — I just could never find the ones I wanted, because they were mixed in with screenshots, receipts, memes, and every other photo two adults take in two years. “Backed up” had quietly become “buried.”

The Difference Nobody Warns You About

Backup software is very good at one job: making sure you don’t lose a file. It is terrible at a second job that turns out to matter just as much: making the files usable.

My phone backs up thousands of images a year into a folder. My wife’s phone does the same into another folder. So the safe version of my daughter’s life looked like this:

  • Two giant folders, one per phone
  • Thousands of files each, in the order the camera saved them
  • Her first steps sitting three files away from a screenshot of a bus schedule

You cannot hand that to a grandmother. You cannot even hand it to yourself. A backup is an insurance policy, not a photo album.

Two Years of Good Intentions

I knew what I wanted: my daughter’s photos and videos, hers only, sorted by month, easy to watch. I just kept not doing it, and the reasons were always sensible at the time:

  • There were too many. Ten thousand files is not an evening’s work. Every time I started, I quit.
  • I didn’t want to touch the backup. Sorting means moving and deleting, and these were my only copies. Editing inside the one safe folder felt dangerous. (It was. More on that later in this series.)
  • I kept waiting for the “right” tool. I thought AI would just sort them for me. It couldn’t — my daughter’s face changed every few months, and the models lost her. (That’s its own post.)

So the backlog grew. Every month I added hundreds of new files to a pile I was already avoiding. The safer everything got, the less usable it became.

The Thing That Finally Broke the Loop

What changed was not more discipline. It was one idea, which I’ll give a whole post to because it’s the heart of this series: stop working inside the backup.

For two years I’d been trying to sort photos in the folder that held my only copies. That’s why it always felt risky and why I always stopped. The fix was to copy new files onto a separate, disposable “cutting board” folder, do all the messy sorting there, and leave the backup untouched. Once I stopped guarding the backup with every click, the work got easy.

Three weeks later, two years of backlog was sorted into clean year-and-month folders, and — this is the part that still surprises me — new photos now flow in and get sorted almost on their own.

Why I’m Telling It This Way

I could have written this series as “here’s my cool pipeline.” But the real story isn’t the code. It’s that I let something precious sit unusable for two years because I was afraid to touch my own backup, and because I kept waiting for a perfect tool.

If you have your own version of that box in the attic — years of your kids, safely backed up and never seen — the rest of this series is how I finally opened mine. It cost $0 a month and about three weeks of evenings.

(My daughter’s face is blurred in every screenshot. This is a family archive, not a public one.)