Labor Day and getting paid what you're owed
A long weekend thought about work and why asking a friend to pay you back doesn't make you petty.
Blog
Notes on lending, borrowing and keeping money friendly.
Page 2 of 7
September 2026
August 2026
The end-of-summer money reset
Summer tends to leave a trail of small IOUs and loose ends. A gentle way to tidy things up before fall starts for real.
Lending money without expecting it back
Some people say you should only lend what you can afford to lose. A few thoughts on the "consider it gone" mindset and when it actually helps.
Why some people never ask to be paid back
Every group has the friend who quietly covers things and never brings it up. A few thoughts on why, and how to make sure they're okay.
Shared subscriptions and the slow leak of small debts
Family plans and shared streaming accounts usually land on one person's card. The monthly amounts are tiny, until you add them up.
When your kid asks to borrow money
A teenager asking for a loan is a small moment with a real lesson tucked inside. Some thoughts on teaching repayment without becoming a bank.
Back to school: setting money rules with new roommates
New roommates, shared groceries and a fridge full of mystery. A few easygoing ways to sort out money before it gets awkward.
July 2026
Talking about money is easier than you think
Money conversations with friends feel scary until you actually have one. Why they usually turn out smaller than we expect.
Concert tickets, group buys and the Venmo gap
When one friend buys tickets for the whole group, getting paid back can drag on for months. How I think about closing that gap.
How to lend to someone who's struggling without making it weird
Helping a friend through a hard stretch is about more than the money. Some thoughts on discretion and keeping repayment flexible.