How To Wring Lasting Happiness From Your Dollars

A guide To breaking free of the pleasure trap (mostly).

That sinking feeling.

Maybe it hit a week after you brought the thing home, or two years later when you spotted it gathering dust in the closet. But it was probably subtler. A few hours, weeks, or months after the purchase, you were no happier than before.

This is how most of us spend our lives. We’re chained to hedonic treadmills, running faster and faster after happiness but rarely getting very far.

The raise, the marriage, the new car — we want so many things, but how much happier are we a year after getting them? Often not much.

Life drills the truth home again and again if we pay attention: each purchase or accomplishment spikes our pleasure, only to revert to baseline way faster than expected. It’s enough to make us despair. Much of what we seek is pointless, and never moves the needle on happiness.

Only a handful of “acquisitions,” increase long-term happiness, and the sooner we acknowledge our happiness delusions, the sooner we start on a saner path.

Today I want to focus on the “buying stuff” side of this problem and how we can bring sanity to it.

By this point, everyone has heard the raft of research showing that it’s better to buy experiences than things. So I’m going to go beyond that.

The One-Month Purchase Plan

We need it! Or at least we want it, right? The electronic device, gym membership, or whatever’s caught our eye. Something whispers how awesome it’ll be to have. Sometimes our delusions are grandiose — this will change my life!

And yet…all those clothes in the closet that go unworn. The underutilized memberships. The junk in the attic that once seemed so critical. How could we have been so wrong?

I know of no foolproof buying litmus test, but I have a strategy that cuts down on mistakes. Anytime I’m tempted to buy something that’s not critical, I delay for one month. Two weeks is not enough.

Example: Last month I told myself I needed an e-ink tablet to read obscure, out-of-print Latin pdfs that I refuse to read on my laptop. The logic seemed sound. It wasn’t completely delusional. I wanted to pounce and get one, but forced myself to wait.

I spent three weeks reading reviews, looking for used versions on Facebook Marketplace, and thinking about what I’d do with it. But by the time I hit 30 days, my lust was gone.

I may need one eventually, but now? It’s not even tempting. Last month’s strong desire seems almost inexplicable.

If the desire returns next year, when I’m a bit further along with my Latin abilities, I’ll give it a month and see. In the meantime, I’ve saved $500 and kept myself a bit saner.

Anticipation Trumps Consummation

I enjoy travel, and I’ve lived all over the world. As great as these experiences are, more than half haven’t lived up to my brain’s hype, let alone the overblown societal mythology of travel. Material purchase satisfaction is probably more hit or miss.

There’s a lesson buried here — we should milk anticipation for all its worth, since it’s often better — and usually longer-lasting — than consummation pleasure. And it’s free!

At least when it comes to anticipating experiential purchases, the evidence points to increased happiness from contemplating and waiting for an experience¹.

What follows from this:

• Don’t eat out regularly. If you make most of your meals, eating out once or twice a month feels like a luxury with an outsized hedonic impact. Set a date with a friend or loved ones well in advance and consider how you’ll enjoy the meal/experience/conversation as it approaches.

• Taking a vacation? Book it months or a year in advance and think about what it will be like.

• Since many experiences are free or cheap, build your recreation around them and anticipate their arrival.

None of this means we should spend our days daydreaming. We live in the here and now, and that’s where our power lies. But having a good thing on the horizon can be a pleasure, a little beacon to savor as we move through rough days.

Incremental Pleasures:

If you’re going to experience pleasure, it’s usually better to experience it more times than fewer times, within the limits of moderation. What follows from this?

Say a room in your home needs work. You could remodel it all at once and buy a whole new set of furniture to fill it, but this will give you only a single burst of pleasure that quickly fades to nothing.

It’s far wiser to incrementally upgrade, causing fresh bursts of pleasure for you to savor. First, you paint the room. A few months later you buy a new lamp. Next year you add a table, then replace the old creeky window, then add a comfortable chair.

Home decorators will rebel at the incongruity of piecemeal acquisitions, but they have other priorities. Let every purchase bring the room more into congruity with your vision while it adds another hit of pleasure. This also tends to be the financially saner approach as well.

The Pleasures of Handymanning It

I’m not a particularly handy person. I certainly didn’t grow up fixing things or mastering useful crafts.

But coopting spending for the mastery of physical reality creates long-lasting pleasure loops you can’t get from hiring workers to make problems disappear. Besides the pleasure of whatever fix or upgrade you execute, satisfaction stems from understanding how reality can be bent to your will. Each little skill you claim provides the perhaps-deluded feeling of bringing order to a small corner of the universe. It extends your mastery of physical reality, and it just feels great.

My own skills are modest, but years after I did the work, I still experience satisfaction opening the closet doors I installed and using the garbage disposal and above-range microwave I replaced. I sometimes look at the work of professional room painters and think — Man, I did a way better job in my place. Look at all those spots they missed!

Doing things yourself has a learning curve, and you’ll make mistakes. It’s frustrating and slow. But if you want long-term satisfaction, it’s usually the better option.

The Weirdest Buying Skill

Socrates thought wisdom was a skill to be learned and applied rather than something possessed by those with the most facts or the correct dogma. Wise people aren’t passive drones, but active participants in life. To be wise, we ask the right questions, look for contradictions in our thinking and actions, and strive to correct ourselves when we go wrong.

As we get better at the skill of wisdom, its execution provides a pleasure somewhat akin to the handyman advantage, but greater and more encompassing. The ancient Greeks called it eudaimonia. Money and spending are major areas in which we apply wisdom and reap happiness not just from the things we get, but from living a flourishing life of applied wisdom. If our buying is unsound, so too will our life be.

Socrates wandered around the agora of Athens, looking at the goods imported from across the Mediterranean. “How many things I can do without!²” he would say to himself as he browsed.

There’s a JOMO — joy of missing out — here. It doesn’t come naturally to most people. It’s best to drill it in by purposefully using disgust and perspective on our desires until we inculcate a gut reaction acknowledging these things won’t make us happier.

How to Escape FOMO and Jealousy With Horace's Wedge

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1. A. Kumar, et al. Waiting for Merlot: Anticipatory Consumption of Experiential and Material Purchases. Psychological Science, 2014; DOI:

2. Diogenes Laertius, The Lives of Eminent Philosophers.