We use money like numbers. Make, save, spend, repeat. But if you look deeper, money is never actually about numbers. It’s about meaning. Each purchase is a attempt to buy not only a thing, but a feeling — security, status, comfort, belonging, joy.
The paradox? We’re generally terrible at predicting if those feelings will last. A bag we buy for confidence is hung in the back of the closet, dust-gathering. A dinner we almost skipped becomes a story we tell for years. The real cost of indulging isn’t financial — it’s emotional. And the real question isn’t “Can I afford this?” but “Will this be worth it when the moment has passed?
Why We Overspend on Some Things and Spend Too Little on Others
Psychologists call it affective forecasting: our tendency to overestimate the length of time a purchase will give us pleasure.
Take such luxuries. I used to buy an expensive coat because I thought it would transform my self-assurance. And yes — for a week, I walked differently, shoulders squared, thinking folks were noticing. But by the second month, it was hanging in my apartment, like just another item, seldom seen, often begrudged. Hedonic adaptation had gotten there and done its work.
Put that alongside a $200 journey I used to hesitate taking to visit an old friend. The journey wasn’t flashy-we slept in her small flat, prepared our own meals, took long walks. But to this day, years later, I still refer back to that memory. Morgan Housel describes this as a memory dividend-a dividend that pays dividends again and again every time you recall it.
And then there’s identity. We don’t buy stuff just for utility. We buy for the story it tells about who we are — or, at least, who we aspire to be. Sometimes this is deep: shelling out for a degree or a health program can feel like a deposit on future us. But sometimes it rings hollow, like swiping a credit card for a name that promises to lend us some borrowed confidence. When the gap between the buy and who we really are is too large, regret comes fast.
The Two Ledgers of Spending
Every purchase has two ledgers:
The Financial Ledger — what you see on your bank statement.
The Emotional Ledger — the lingering aftertaste the purchase leaves.
The emotional ledger is where the truth lies.
I once spent $50 on a sloppy takeout dinner following a long day. The food wasn’t even that wonderful, and I felt bad the moment I discarded the box. Then again, there was the evening when I spent the same $50 at a quaint family restaurant with an old friend I hadn’t met in years. We hung around for hours, laughing over candlelight. That $50 keeps coming back to me. Same dollar value, completely different return.
If you genuinely care to know whether something’s “worth it,” you have to compare both ledgers — not the one that’s seen with the eye.
The Formula for “Worth It”
After decades, I’ve found four questions cut through the noise:
Future Self Test: One year from now, will I be happy I invested this? (A coding course I almost didn’t take has shaped my career in ways a dozen on-the-spur impulse buys never could.)
Frequency vs. Flash: Am I gonna be using it every day, or is it a one-day high? (The $500 cell phone upgrade that I use daily is way more valuable than the $80 outfit that I wore once.)
Value Alignment: Does the buy confirm the life I profess to desire — health, growth, relationships — or take me off track? (A gym membership I originally considered “too expensive” turned out to be one of the best investments in my energy and focus.)
Emotional Residue: After I’ve made the purchase, do I regret, feel guilty, or take pride? (The shame of helping perpetuate fast fashion is deafening. The pride in helping support a local artist or ethical brand is lasting.)
After you sift through these questions, you begin to see a pattern: the most “costly” spending isn’t what drains your bank account — it’s what makes you feel more drained afterwards.
The Deeper Question: What Are You Really Buying?
Spending is fundamentally a form of narrative. You’re saying to yourself:
“I deserve this.”
“This makes me somebody who belongs.”
“This will make me feel secure.”
But narratives can be deceptions. If you continue to purchase for a sensation that never lingers, perhaps it’s not the buy that’s flawed — it’s the story.
Such as: when I spent more money than I should have on an expensive designer handbag, I was certain that I was buying confidence. What I really bought was a story that confidence has to be outside of me. The handbag did not fix it. But when I paid for a cooking workshop, I felt like I was buying education — but what I really bought was a sense of belonging, self-expression, and a new dimension of my identity. That caught on.
Philosophers distinguish between instrumental value (usefulness) and intrinsic value (worth in and of itself). Most things we buy have instrumental value — they get us somewhere. But the best buys — learning, travel, dining with others, therapy, time with loved ones — have intrinsic value. They don’t just get us somewhere. They are the somewhere.
The Philosophy of Enough
The hardest part of money isn’t creating it. It’s deciding what “enough” is. Without that, every purchase feels like a must. Every sell feels urgent. Every desire feels like necessity.
But when you decide “enough” — whether it’s the clothes you really wear, the tech that really enhances your life, or the level of savings that keeps you secure — spending shifts. It no longer is about escape and is now about alignment.
Because in the end, ROI on cash isn’t monetary. It’s living. It’s the life it enables you to have.
Final Thought
Every dollar you give is buying something other than a product. It’s buying an experience and an emotion. The trick is to spend on the things that bloom — memories, growth, health, connection — rather than the things that disappear the moment the receipt is thrown away.
The question isn’t “Was it expensive?” but “Does it leave me richer than before?”