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How to feel less anxious about money you're owed

June 23, 2026 · 3 min read

A woman sitting quietly on a window sill
Photo: Kelly Sikkema / Unsplash

It’s 1:40 in the morning, and I’m lying in bed mentally drafting a text to someone who owes me $220.

Not sending it. Just drafting. Rewording. Imagining the reply, and then imagining myself being very calm and mature about a much worse one. I’ve done this, conservatively, a few hundred times in my life, and I’ve never once actually sent the text at 1:40 in the morning.

If you’ve ever been owed money by someone you like, you probably know this exact feeling. It’s not really about the money, most of the time. $220 isn’t going to sink me. It’s the open loop. It’s the low background hum of something unresolved, like a browser tab you can’t find that’s playing music somewhere.

I’ve gotten a lot better at this over the last couple of years, and I think it comes down to a handful of small shifts more than any clever trick.

What helps me most is getting the facts out of my head and onto something. Anything. When it lives only in my head, it gets bigger, and the details start to fuzz. Did they pay me back $50 that one time, or am I thinking of someone else? Did I say “no rush”? (I did. I always do. I wrote a whole post last month about why that’s a mistake.) When I sit down and write out who owes what and what we actually said about it, the anxiety usually drops by about half.

It sounds too simple to work. But anxiety loves vagueness. It’s a bit like hearing a weird noise in the house at night. As long as you don’t know what it is, it could be anything. Turn on the light and it’s the ice maker.

Having a plan helps too, even a tiny one. Rumination, as far as I can tell, is what happens when your brain keeps trying to solve something you haven’t decided to solve. So decide. Am I going to ask, and if so, how? Once I’ve picked even a rough answer, something like “I’ll text her Saturday morning and keep it light,” my brain seems to relax. It’s like it was waiting for permission to stop holding the thought.

Sometimes the plan is to not ask. That’s allowed. If I decide the friendship matters more than the $220, or that this person is having a genuinely rough time, I can choose to let it go on purpose. That’s a real decision, and it’s very different from avoiding the question forever. One is peace. The other is a 1:40 a.m. habit.

If I do ask, I keep the message plain and kind. The amount and what it was for. That’s usually enough.

Hey Tasha, hope your week’s going okay. I’ve still got $220 down for the cabin weekend in April, whenever you’re able. Zelle’s easiest for me. Thanks!

Then I put the phone down. This is the part I used to skip.

The piece I’m still worst at is letting it rest once I’ve done my part. After I’ve sent a friendly message, the ball is in their court. I can’t make someone pay me by thinking about it harder. I’ve tested this extensively. It does not work.

What helps me let go is giving myself a check-in point instead of a constant vigil. I’ll look again in a couple of weeks, and if nothing’s happened I’ll send one more light nudge. Until then the matter is officially closed in my head, filed away in the note on my phone where it belongs. I don’t need to guard it at night. The note’s guarding it.

It also helps to remember that most people who owe you money aren’t ignoring you on purpose. They forgot, or they’re waiting until they can send the whole amount instead of dribbling it out in pieces. Assuming the worst about someone you like is exhausting, and in my experience it’s usually wrong.

Tasha, for the record, paid me the next afternoon. She’d thought she’d already sent it. She texted me a screenshot of the Zelle with about nine crying-laughing emojis, and I slept fine that night.

Well. Until I remembered the $40 my brother owes me.

The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.

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