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The end-of-summer money reset
There’s still sand in my car from the Fourth of July. Yesterday I found a crumpled parking receipt from a beach town under the passenger seat, along with a single flip-flop that I’m fairly sure isn’t mine.
Summer does this. It’s the most fun season and also the messiest, at least where money’s concerned. Everything’s a little looser. You’re splitting rental houses and bar tabs, covering a friend here, getting covered there, telling everyone “we’ll sort it out later.” And then it’s late August, the evenings are getting shorter, and “later” has quietly shown up.
A few years ago I got into the habit of what I think of as an end-of-summer reset. Nothing fancy. Just one evening, usually the last weekend before Labor Day, when I sit down with a glass of iced tea and try to tidy up whatever financial loose ends the summer left behind.
Start with what you owe
I always start with my own debts, not other people’s. Partly because it feels good to clear those first, and partly because it puts me in a more generous frame of mind before I start thinking about who owes me.
This summer, I owed my friend Caroline $70 for half a kayak rental I’d completely forgotten about until I scrolled back through our texts. I also owed my neighbor for some groceries she grabbed when I was sick. Small stuff. The kind of thing that’s easy to let drift for months because no one’s going to make a fuss about it.
I paid both that night. Caroline sent back a string of kayak emojis, which I didn’t know existed. It took maybe ten minutes total, and I felt noticeably lighter afterward. There’s something about not owing anyone anything that makes the start of fall feel cleaner, like climbing into a freshly made bed.
Then look at who owes you
This part’s a little harder, because it means bringing stuff up. But I think late summer is actually a great time to do it, since everyone’s in that same back-to-routine headspace. A message right now doesn’t feel random. It feels like part of the season wrapping up.
I go back through whatever I’ve got (texts, payment app history, the occasional note on my phone) and figure out what’s still open. Then I send short, friendly messages. Nothing heavy. Something along the lines of:
Hey! Doing my end-of-summer money cleanup and realized I still have you down for $45 from the lake weekend in June. Whenever works, no pressure.
Framing it as my own tidy-up project seems to make it feel less personal. I’m not chasing you. I’m just cleaning out my metaphorical junk drawer, and your $45 happens to be in there with the dead batteries and the takeout menus.
Most people pay right away. A couple might need more time, and that’s fine.
Let some things go
The last part of the reset, and maybe the one that matters most, is deciding what to let go of. Not everything needs to be collected. If a friend owes you $8 from a coffee run in June and they’ve had a rough summer, maybe that one just quietly disappears. That’s not being a pushover. That’s being a person.
I wrote a little while back about lending without expecting it back, and the end of summer feels like a good moment to make those calls on purpose instead of letting them linger by default. Tell your friend “don’t worry about the coffee,” and then actually stop thinking about it.
What I’ve noticed, doing this a few years in a row now, is that the reset turns out to be less about the dollars than I expected. Okay, it’s a little about the dollars. Mostly, though, it’s about walking into fall without a bunch of small, nagging things rattling around in the back of my head. Fall already comes with plenty, between school schedules and the sudden, inexplicable urge to buy a new sweater. I’d rather not add “wait, did I ever pay Caroline back?” to the pile.
If you try it, pour yourself something cold first. It helps more than it should.
I’m still not sure whose flip-flop that is, though. If it’s yours, I owe you a shoe.
The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.