Over the years, I’ve had a lot of conversations with people about their finances. Not just the numbers. More importantly: the feelings, the habits, the stories they tell themselves about money.
One pattern comes up again and again. People who have enough – often more than enough – struggling to actually spend it on the things they say matter to them.
Recently, I’ve been looking at my own spending more granularly than I ever have — building Snoopy forced me to — and I’ve realised this isn’t just something I observed in others. It’s something I’m working through myself. We have a large household income, and yet when I look at where the money actually goes, I’m not sure it reflects what I say I care about. I’m using this article as a forcing function to think out loud about this.
To be clear, this article is for people who are in the privileged position of not being genuinely constrained. And nor am I making an argument against being thoughtful with money. Spending too freely is its own kind of misalignment, and plenty of people struggle with that. This is about a specific pattern on the other side: people with healthy savings, stable incomes, no debt problems, who still can’t bring themselves to book the trip, hire the help, or invest in their health.
The gap between values and behaviour
Most people, when asked, can articulate what they value. Health. Family. Relationships. Learning. Time with people they love.
Or from another perspective: when I ask people what they DON’T want to happen, money isn’t usually the top thing they are worried about.
But when I look at how people actually spend their money, I’ll often find a gap. They’d say health mattered, but they wouldn’t pay for the professional who could help with a persistent problem. They’d say relationships mattered, but they wouldn’t fly to see someone because it felt extravagant. They’d say time mattered, but they’d spend time doing things they didn’t really enjoy to save a modest amount.
The money would just sit there. While the things they said mattered went unfunded.
A lot of people struggle to spend on things they care about. It’s a strange difficulty.
Money as the default priority
One way of thinking about it: if you won’t spend money on something you claim to value, you’re effectively saying the money is more important.
Someone says they value their health, but won’t spend on the physio, the equipment, the quality food. They say they value relationships, but won’t spend on travel, on generous gifts, on experiences together. They say they value time, but won’t pay someone to do the tasks that drain them.
In each case, the money stays in the account but the thing they value goes without.
I don’t think people consciously decide “money matters more than my health.” But the behaviour suggests it.
Patterns I’ve seen
Some patterns I’ve observed:
The moving milestone
“I’ll do it when work calms down.” “When I have more of a buffer.” “When things aren’t so busy.” But the milestone keeps shifting. The trip never gets booked. The help never gets hired. Meanwhile, parents age, kids grow up, bodies get older.
This is the one that struck me most in client conversations. Some things you can defer indefinitely. A new couch can wait. Renovations can wait. But some spending opportunities close. Elderly parents won’t be around forever. Kids grow up. Your body changes. The trip you can easily do at 50 becomes harder at 70 or impossible at 80.
Sometimes, there’s an expiration date on things you can do. There isn’t always next year. Eventually, we all run out of tomorrows.
Identity maintenance
For some people, being careful with money becomes part of who they are. Maybe it’s something they had to do and they’ve internalised this as a core value. It becomes part of their personal narrative. Spending money can start to feel like a betrayal of that identity or the person you are (or were). Often, what served them starts to constrain them. In reality, life has chapters and seasons, and identities and narratives should change.
Families and friends that stay close
Something I’ve noticed is that the families who spend the most time together as the kids and grandkids grow older are often the ones where at least one household has the means to make it happen, and the willingness to use these resources. (It’s often the parents/grandparents, but that’s not always the case.)
Flights. Accommodation. A house big enough to host everyone. The flexibility to travel. The ability to say “I’ll cover it” and mean it, with no strings attached.
I’ve seen this in my own life. My wife’s family were close with their extended family when she was growing up, and they’re still close now. My family wasn’t as close with extended family, and we don’t catch up as much. Money was not necessarily the determining factor. But it was a big one. Money removes friction. Without it, staying connected requires more effort, and effort is finite. Things that require effort happen less.
One of my personal goals is to be the person who makes gathering easier. To have the means to bring people together rather than waiting for someone else to make it happen. With families. But also with friends.
Giving well
The same misalignment shows up with giving. Maybe even more so.
Most people I know who are financially comfortable give something. But if you asked them whether they give enough relative to what they could, most would say no. The reluctance problem applies here too. The money feels safer in the account. There’s always a reason to wait. The identity of being careful wins out.
But if you say you care about the world beyond your own life, at some point the money needs to reflect that. Giving that actually costs you something — that you notice — is different from giving that doesn’t.
I think most people with means could give significantly more than they do. Not recklessly. But meaningfully. It’s the same reluctance pattern showing up in a different context.
When you do give, it’s worth thinking carefully about where it goes. For many of us, we’ll research a new appliance for hours but donate to a charity based on a gut feeling or a compelling story. If we genuinely care about making a difference, it’s worth bringing the same intentionality to giving that we’d bring to any other decision. Where does your dollar go furthest? Which organisations are actually effective? What problems are neglected relative to their scale?
This isn’t about making giving joyless. It’s about taking it seriously — both the amount and the direction.
It’s something I care about enough that I built a dedicated “Giving” section into Snoopy. It’s one of only two categories that I’ve prescribed in the app, which you can’t delete. My view is that generosity matters, and it deserves visibility.
Alignment, not optimisation
The question isn’t “how do I minimise spending?” It’s “how do I use money in ways that serve what I actually care about?”
Sometimes that means spending less on things that don’t matter. But sometimes it means spending more on things that do. Sometimes it means giving more, and giving better.
I think about the families I’ve seen who stay close across generations and distances. Someone usually has the means and the willingness to make it easy — to host, to travel, to say “I’ll cover it.” The money isn’t the relationship. But it removes the friction that makes relationships harder to maintain.
That’s what I want money to do. Not to accumulate. Not to optimise. To make possible the things that actually matter — while there’s still time for them to happen.