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Labor Day and getting paid what you're owed

My grandfather worked at a tire plant in Ohio for thirty-one years, and the man could not stand being shorted. Not by the company, and definitely not by his brother-in-law, who once borrowed $60 for a fishing trip in 1987 and apparently never heard the end of it. I used to think that was kind of funny. A little grumpy, sure. But the older I get, the more I think he was onto something.
Labor Day always makes me think of him. It’s supposed to be a holiday about work, about people who fought for a fair day’s pay, and somewhere between the burgers and the back-to-school sales that idea gets a bit lost. I’m not going to pretend I have anything profound to say about labor history. I don’t. What I do have is a slightly uncomfortable observation about how a lot of us treat our own money once it leaves our hands.
We’ll fight for a paycheck but not for $45
Here’s what I mean. Most people I know would never let an employer skip a payday. If your direct deposit came up $45 short, you’d email HR before lunch and you wouldn’t feel weird about it at all. It’s your money. You earned it.
But lend that same $45 to a friend for concert tickets? Suddenly it gets fuzzy. You wait a couple of weeks. Then a month. You start telling yourself that bringing it up would make you seem cheap, or that maybe they forgot and that’s fine, really, it’s fine. And it sort of sits there in the back of your head like a sock you can feel bunching up in your shoe.
I did this for years. My college roommate Luis borrowed money from me constantly, nothing huge, just $20 here and $30 there for groceries or gas. He always meant to pay me back. I genuinely believe that. But I never kept track and I never asked, and by senior year I honestly couldn’t have told you if he owed me $80 or $300. Probably closer to the second number, if I’m being honest with myself.
I didn’t resent Luis. I resented me, a little, for acting like my money was somehow less real than everyone else’s.
The guilt part
I think a lot of the hesitation comes from a feeling that asking for money back is greedy, or that it means you care more about cash than about the friendship. That framing seems totally backwards to me now. You traded hours of your life for that money. Somebody sat in traffic for it, or answered emails until their eyes hurt. That somebody was you.
Valuing that isn’t greed. It’s just being honest about what the money actually represents.
My grandfather would put it more bluntly. He’d say something like, “I didn’t break my back so Frank could go fishing.” Which, okay, harsh. But the core of it was respect for his own effort, not stinginess. He was one of the most generous people I’ve known when he chose to be. He’d pick up the whole check at a diner without blinking. The difference was that he chose it. Nobody chose it for him by quietly forgetting.
That’s sort of the line I try to hold now. If I want to give someone money, I’ll give it, and I won’t keep score. If I lend it, I expect it back, and I’m allowed to say so without wrapping it in six layers of apology.
What asking actually looks like
It doesn’t have to be dramatic. Most of the time it’s one text, sent in a normal voice, the way you’d ask someone to return a book. Something like this:
Hey, just circling back on the $45 for the Saturday tickets. Venmo whenever works for you. Thanks again for driving!
That’s it. No essay and no deadline. Just the amount and what it was for, because people really do forget, and it’s a lot easier to pay a specific thing than a vague “that money from a while ago.”
The first few times I sent something like that, my heart was pounding like I was asking for a raise. Which, in a way, maybe I was? Asking to be treated fairly with my own earnings, at least. Nobody got mad. One friend actually said, “Oh my gosh, thank you for reminding me, I was sure I’d already sent it.” That was the whole drama.
I think the long weekend is a decent time to sit with this stuff. You’re off work with a little breathing room, and you might notice the small tabs floating around in your life that you’ve been pretending not to see. Not to go collect on everybody like a loan shark. Just to admit, quietly, that your time had value and the money it turned into does too.
My grandfather never did get that $60 back from Frank, by the way. He brought it up at Frank’s retirement party. Frank laughed and handed him a twenty and said he’d owe him the rest. Grandpa kept that twenty folded in his wallet for years and never spent it. When my grandmother asked why, he said he was still waiting on the other forty.
The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.