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The Boring Newsletter, 10/25/2026

Why I Didn’t Get My Insurance Photos Done

Hi Friendos,

It’s been two weeks since I confessed two pending items on my personal financial checklist this fall:

  • Transition from two-factor authentication to passkeys and/or security hardware for my investment accounts.
  • Update photos of our home and belongings for insurance purposes, so we have some record of things in case of fire, flood, or other adverse event.

This is all still pending. The truth is that I’ve failed to take insurance photos for more than three years. Three years! But I do have some progress to report. When I take insurance photos, I don’t take out specific items to capture them individually, I just open up a cabinet or drawer or closet and let the camera capture what it can see. Like several years ago I photographed the only drawer in our tiny kitchen:

If we had a fire and lost everything, I might not be able to give a perfect count of how many forks we had, but this photo would get me pretty close, and I can photograph my whole home this way in under an hour. It’s not as if I’m generating an actual home inventory, but it’s far better than nothing. Combined with purchase receipts that I scan and save for larger purchases and other records I keep in the normal course, I think this makes me prepared enough without spending too much time on something tedious. I hope you’ll comment with whatever approach you use for this!

I know that part of why I’ve procrastinated on taking recent insurance photos is because my home office is a mess and I have a number of items I want to get rid of. When I imagined myself taking time to photograph or video items I might not keep, I felt like a sucker so of course I didn’t do it.

I also have a disorganized closet where I stuffed a bunch of things from my parents’ house after my mom died in late 2023. For a long time it felt too hard to touch those items, so the closet stayed too messy to photograph.

So I have this one closet that has been overstuffed since my mom died, and therefore can’t be photographed to show the items inside, and therefore I delayed my annual updating of our insurance photographs. To me, updating these photos is a personal finance chore because they would help me better recover if I needed to file an insurance claim, and they are another example of emotional issues directly impacting personal finance. It’s not “just math.”

When I was finally ready to tackle the closet, I realized that it really needs another shelf installed for proper organization. After months/years of telling myself this was something I could DIY, I have to admit that I have not actually installed a shelf, so it was time to budget for some outsourcing. And tomorrow we have someone coming to install a shelf! I am counting this as progress on my fall checklist and I’ll provide an update in a few weeks to keep myself accountable. I hope you are chipping away at any pending items on your own list.

-Stephanie