Is Being “Good” with Money Making You Miserable?

I used to be basically unaware of my financial standing. My Discover bills and rent were always paid on time, but I couldn’t tell you how much I was saving or what my net worth was. As such, my purchases were relatively low-drama affairs—desire, swipe, and move on, only to be reminded three weeks later when the credit card statement came and I sweatily cross-referenced my checking account balance with the total due. 

Buying $23 weekday lunches and Sephora sample platters is easier when you don’t understand compounding. (In fact, that’s why so much of my own personal finance evangelization emphasizes the power of compounding—to get non-believers on board.) 

Realizing that unspent money can grow is a precious, pivotal moment in any spry young capitalist’s life, and yet, it can also mark the beginning of an emotionally exhausting relationship with your legal tender of choice.

“Realizing that unspent money can grow is a precious, pivotal moment in any spry young capitalist’s life.”

Your calculation for purchase decisions graduates from the realm of second-grade subtraction (is there enough money in my checking account to pay for this?) to future value formulas and exponents (if I don’t spend $23 today and invest it instead, in 40 years it’ll become $Y—do I value that money in an uncertain future more than this plate of baja shrimp tacos?). 

When you begin to think this way, you become too tired from running constant cost-benefit analyses to fully enjoy buying anything (which, I suppose, is a solid strategy if your goal is to spend less). Sometimes I yearn for those more freewheeling days, when I’d sign my bar tab at the end of the night through half-shut eyes and make a run for it before the barkeep could inform me that my card was declined.

Concluding that “it’s about balance!” or that you “should spend money on things you value!” feels insufficient to me, even if the sentiments are true. This particular brand of balance allows maladaptive financial behavior to stick around for as long as it serves a purpose (read: making you richer), then employs category-specific spending like a burn salve. Sure, you’re blistering in the hot sun of your own mental accounting, but at least you’ve got some discretionary aloe to soothe the pain!

Alternating between operating like a human calculator and a selectively wild spender conjures a similar dilemma to the person who discovers the magic of healthy eating and exercise, then quickly descends into extreme dieting—but decides a “cheat” meal will make their restrictive habits more sustainable. 

“‘Value-based spending’ feels like it falls short as a practically useful outlook for money management.”

My approach to responsible money management often looks a lot like the cheat meal framework: As long as I aggressively save and invest most of the time, I’m permitted (encouraged, even) to splurge—but only occasionally, and only on things that I’m certain I value. There’s little room for more experimentation, play, or error, beyond the occasional anomaly. 

On that note, “value-based spending” feels like it falls short as a practically useful outlook for money management, because it’s a lens that’s relevant to a relatively small portion of your financial choices each month. The vast majority of my spending is just the stuff that keeps me (or my family) alive—like our godforsaken PG&E electric bill that charges 52 cents per kWh (jail!) or biweekly bags of groceries. I tallied our April spending to see how much of it was purely discretionary—like buying books, getting haircuts, paying for streaming services, or going to restaurants. The total was 11%. The other 89% of our outgoing funds went to things like car insurance, medication, utilities—stuff I certainly value, but by default. I didn’t have to think very hard about whether or not I would pay for trash pickup or abide by the state of California’s laws around vehicular liability.

If you, like me, find yourself flinching with every purchase or undermining your own joy in even the smallest of indulgences lest they shave $32 off your net worth, is your metaphoric “cheat meal” really having the desired effect? Even if your results are rapid wealth accumulation, is relating to money in that way healthy? After all, you can have a really high net worth and a bad relationship with money at the same time.

I wonder if a better balance might be striving for an attitude that doesn’t analyze every insertion of the chip; maybe a personalized threshold below which you decide not to second-guess your desires. My friend (and COO of Ritholtz Wealth Management) Nick Maggiulli recommends .01% of your net worth—for example, if your net worth is $250,000, it’s a waste of time to think twice about any purchase that costs less than $25.

“What I’m really looking for is a broader orientation for relating to money that’s prosocial, playful, and generative.”

But what I think I’m really looking for is a broader orientation for relating to money that’s prosocial, playful, and generative, as opposed to operating from a defensive crouch. I want to build the muscle of knowing exactly how money can deliver the highest and best use in each moment—even when the highest and best use is ignoring it altogether.

Tonight, I ordered a $31 to-go order of trash sushi (read: deep-fried and stuffed with cream cheese). As I drove home eager to eat it while watching Sex and the City reruns away from other diners who may judge my inability to deftly operate chopsticks like the grungy little couch gremlin I am, I felt a pang of guilt about my purchase. Carrie voice: I couldn’t help but wonder, Do I really value takeout, or could this money have been better allocated? 

Clearly, I still have some work to do.