The most difficult money move is the one that pays you back nothing.
I'm good with money. I'm terrible at giving it away.
Here's the part I'm embarrassed to admit. When a wedding rolls around and I think about a $100 gift, I don't see $100.
I see the $760 it could've become in 30 years.
I do this with everything. There's a number stuck in my head: 25.
Every yearly expense gets multiplied by it. A $50/year subscription isn't $50 — it's $1,250 I "need" invested to cover it forever.
It's the math behind early retirement.
And it's quietly drained the joy out of giving.
And recently I figured out why giving is so hard for me:
It's the only expense that breaks the spreadsheet.
Think about it. Everything else, I can justify. Index funds compound. A good mattress is "health." A vacation "recharges me for work." They're all moving me closer to that goal.
But a gift? No ROI. Nothing compounds. Nothing comes back and the second you expect it to, it stops being a gift.
And that's exactly why it matters.
Funny thing — the research agrees. Spending money on other people makes you happier than spending it on yourself, and it shows up across dozens of countries.
Here's my problem though: I can't think my way out of this. The 25x brain always wins the argument.
And that's the reason it's important to manage your finances as a team. I want to be more generous. It's something I'm actively working towards.
My wife is the one who reminds me when I need it.
Whether it's buying dinner for our friends, taking people out for their birthday, surprising someone with a book they like, or just offering to pay for coffee…
None of it happens without her.
Interestingly enough, some of my best memories and best relationships have come from these small gestures.
It's a bit like having a gym buddy. Left to yourself, you may skip the workout. But when someone's in it with you, you show up and you're always glad you did. That's what she is for our giving.
—Jake