Living at Your Values, Not Just Your Means

There’s an argument worth making about money that doesn’t get aired often enough: living below your means is a sin worse than living above them. Money that just sits in your accounts isn’t doing the job money is supposed to do. The Casio watch and the aging Highlander aren’t badges of virtue. They’re just habits.

I see this often enough that I’ve stopped being surprised by it. A widow in her sixties with seven figures in the brokerage account and an honest fear of spending a dollar of it. A retired engineer who tracks every grocery receipt out of habits formed when he was twenty-six and broke. A business owner who’s spent thirty years deferring everything into the future, and now the future is here and he doesn’t know how to give himself permission. The math says they can. The internal accountant says no.

The truth that gets buried in most personal finance writing is this: people don’t regret the money they spent. They regret the money they didn’t. The trips not taken. The experiences postponed indefinitely. The home that stayed half-finished because the renovation was always going to happen “next year.” Those are the actual regrets. Not the BMW.

So I’d agree with the diagnosis: a meaningful number of financially healthy people are leaving real life on the table. Spend the money. Live a bigger life.

Where I’d push, gently, is on the frame.

“Live at your means” is still measuring the wrong thing.

It’s better than living below your means, and certainly better than living above them. But “your means” is still a dollar figure. It still anchors the question to capacity rather than meaning. And what I see, over and over, is that people who give themselves permission to “live at their means” often end up spending up to that line in ways that don’t actually make them happier. The BMW is fine if you love driving. The BMW is a bad purchase if you bought it because someone told you that’s what your bank account justifies.

The better question isn’t “How much can I afford?” It’s “What is this money for?”

That sounds soft, but it isn’t. It’s the most concrete question in financial planning, and most people have never actually been asked it. They’ve been asked about retirement age, risk tolerance, withdrawal rates, asset allocation. Useful questions, all of them. But none of them answer the prior question: what is the money in service of?

When you can really answer that, in specifics rather than generalities, the spending decisions get simpler. The trip to see your sister isn’t a splurge; it’s the point. The renovation that turns the kitchen into the room your family actually wants to be in isn’t an indulgence; it’s exactly what the money was for. The second home in a place that matters to you isn’t a status purchase. It’s an instrument.

And conversely: the watch you bought because somebody implied a person with your assets ought to own one is a worse purchase than the Casio. Not because it’s expensive. Because it isn’t yours.

This matters more in transition than at any other time.

Most of the work I do with widows, divorcées, retirees, and business owners after a sale involves money that arrives or shifts during a period when the person hasn’t yet figured out who they are on the other side of the change. The natural impulse is either to lock everything down (don’t spend, don’t move, don’t decide) or to spend impulsively in ways that don’t fit. Both responses are about avoiding the harder question that most financial conversations skip past: what do you actually want this chapter of your life to look like?

That work can’t be rushed. There’s a reason the financial transitions framework starts with “make the client safe” before anything else. You don’t make big values-driven spending decisions in the first ninety days after losing a spouse, or the first six months after a business sale. But you do, eventually, need to make them. And when that moment comes, the question isn’t whether you’ve earned the right to spend. The question is what you’d like to spend on.

A note on the floor.

None of this argues for ignoring the math. Risk of ruin still matters. Sequence-of-returns risk in the first years of retirement is real. The point isn’t that values-based planning lets you off the hook for the engineering. It’s that the engineering exists to serve the values, not the other way around.

Once the floor is set, the rest of the conversation gets to be about something more interesting than your means.

The question worth carrying.

The people who reach the end of their lives most at peace are not the ones who maximized the balance sheet. They’re the ones who put the money to work in the service of a life they actually wanted.

So sure, get the car if you love the car. Stay in the $600 hotel. Take the trip. But the prior question is the one that matters: what is this money for?

That’s a question worth answering before you spend, and worth re-answering every few years. The answer changes. So should the spending.

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