The Stoic’s Guide To Buying Happiness

All action is based on prediction.

Every time you do something, its because you or your subconscious brain has predicted that doing so will leave you better off than the alternative.

Decide to stay with your romantic partner? It’s because you predict they’ll make you feel better than being alone or with someone else.

Spend money? It’s because you predict purchasing that object will make you feel better than buying nothing or something else.

Perfect the art of prediction, and no joke, you can take over the world. You’d be able to pick the best romantic partner, best career, best stock portfolio, best education, best everything. No more returns.

In the form of conscious deliberation and subconscious emotion, prediction directs our behavior.

We’re passingly good at it.

We feel that spending time with friends and family will make us happy. So we do it and feel happy.

We deliberate that going for a jog will give us a high. So we do it and feel high.

We deliberate that slacking off at work will get us fired, which in turn will make us feel bad. So we work hard, keep our job, and avoid feeling bad.

But when it comes to money, passingly good becomes pathetically wrong.

Desire distracts.

A college student dreams of becoming a lawyer making a cool $150,000. He’s been told he’s good at arguing and has an eye for detail, he’s hard working and ambitious, and most important of all, he wants that $150,000.

Lawyers are four times more likely to develop depression and two to six times more likely to commit suicide.1,2

Desire distracts – only 4 in 10 lawyers would recommend their career to others (this, from the American Bar Association, not some crackpot researcher with an agenda against the profession). What happened to quality of life?

Why gamble and hope to be one of the 40%?

A yelper has spotted a new Mexican restaurant. It’s got a bad rating, but why not give it a try – it’s got a great looking menu, complete with too good to be true pictures of its food.

Desire distracts – less than 1 in 10 yelp users enjoy their meal at a low rated restaurant.3 What happened to quality of food?

Why gamble and hope to be one of the 10%?

Just because the college student desires to be a lawyer, or the yelper desires to eat at that Mexican restaurant, doesn’t mean that doing so will make them happy.

The strength of your desire DOES NOT EQUAL the amount of happiness lying at the end of the road.

Usually, it does, but when it comes to money, shi*t goes crazy – our desire gets hijacked for purposes not our own.

I’d prefer me and my family to be the ones benefiting from my earning and spending behavior. All too often, I’m not. All too often, we’re not.

Considering how much of our lives revolves around money, that’s a problem. This desire hijacking is the biggest obstacle to our successfully buying happiness.

But there’s a fix – free and easy to implement.

No, not hiding in a cave and trying to avoid the 1,000+ daily desire distorters (also known as marketing messages) thrown our way.

Something much easier.

You wouldn’t believe me if I told you now, so first, more on how money makes your usually intelligent brain go haywire.

  1. Your memory becomes foolish.
  2. Your extrapolations become foolish.
  3. Your desire becomes foolish.

1. Your memory becomes foolish.


I know, you’ve never had a conversation like that in your head. But a lot goes on under the hood, below conscious awareness.

Imagine that you purchased a nice, $80,000 car a few years ago. You enjoyed it. It’s getting old. Now it’s time to buy another – a newer model. If you enjoyed it once, you’ll probably enjoy it again.


Have you ever noticed that other people have an uncanny ability to enjoy expensive purchases, even when you can tell they were blatant mistakes?

I’ve noticed that behavior in myself. I spent $1,000 on a training course a few months ago.

Every time I think back on it, there’s a voice that says, “It was a mistake, you freaking moron!” But that voice is quickly overwhelmed – the idea that I wasted $1,000 feels so bad that I immediately search for justifications – reasons why I didn’t really make a mistake, “Oh, but because of that purchase I learned how to do x, y, and z… that’ll probably come in handy… eventually.”

It’s called cognitive dissonance.

1. It’s psychologically painful to simultaneously hold conflicting beliefs.


2. The brain automatically and without conscious awareness changes one or more of those beliefs to bring them into alignment.


Does this seem like voodoo magic? Nope, it’s real and it happens all the time. Two examples:

Example no. 1: Liberals rarely read the Wallstreet Journal and conversely, conservatives rarely read the New York Times. The information from those other sources conflicts with their preexisting beliefs.


The subconscious answer – avoid reading the conflicting information.


I’m just as guilty as anyone else. I rarely read information from conservative sources.

Example no. 2: The Innocence Project frees prisoners who were wrongfully convicted using newly available DNA technology. So far they’ve only been able to free 302 people, despite thousands of innocent people remaining in prison. It’s not for lack of resources – it’s because the effort receives massive resistance from prosecutors and police.


The subconscious answer – discredit the source of conflicting information.


Cognitive dissonance is real, and it happens all the time – for more, in-depth examples: Mistakes Were Made (But Not by Me): Why We Justify Foolish Beliefs, Bad Decisions, and Hurtful Acts

The larger a purchase, the greater the dissonance when it turns out bad.

The larger a purchase, the more likely we’ll subconsciously convince ourselves we liked it… even when we actually didn’t.

You may be resisting the idea that you dislike your career because you’ve already invested so much time into it.

You may be resisting the idea of making a change – of going somewhere else for vacation this year or buying a different car, laptop, or phone brand because you’ve already invested so much time and money into them.

If you want the best for your money, you’re going to have to deal with cognitive dissonance. Lucky us, we can just sidestep it.

2. Your extrapolations become foolish

You’ve only got $15 to spend on entertainment this week. You’re a TV junkie. It’s either season 7 of Friends or season 2 of Heroes.

Fixed budget, one choice. Well, you could just download them both illegally, but lets assume you’re not a pirate.

If you’re anything like most people, you decide by going back into your memory and comparing how much you enjoyed each respective series. Whichever one you’ve gotten more pleasure out of, you purchase the next season of.

Common sense. Except things change. The future isn’t always the same as the past.

I should have listened when my friends told me Heroes had gone downhill after season 1. But of course, I like to think I know best.

Usually, I do. But when it comes to spending money, my college degree and latin honors don’t seem to do me much good.

Marketing messages warp our extrapolations.

Let’s say you see an advertisement for axe body spray – you know the kind I’m talking about – a guy sprays himself and then becomes irresistible. If not, a nice refresher:

warning, don’t watch at work or with children around

If you’re a potent man, like me, seeing all of those scantily clad women sparks desire. Here’s where we get tricked, and how marketing companies stay in business

  1. We men get a surge of desire (or not, if we’re married).
  2. We associate that desire with axe body spray.
  3. We predict that if we purchase axe, that desire will be satisfied and make us feel good.

In my experience, rarely does purchasing the right body spray suddenly turn a man into a ladies magnet. And so, the desire unfulfilled, latches onto another product (thanks to a friendly nudge from another well intentioned advertisement).

It’s not just sexual suggestion. There’s an entire category of mischief, in which the object that creates desire has little or even nothing to do with the actual consumption experience.

You finally buy your vacation home, predicting quite moments by the lake… but end up spending all of your time swatting mosquitoes.

You splurge on a trip to Disneyland, predicting many family bonding moments… but end up spending most of your time in line, sweating and increasingly anger prone.

Without actually living the experience, it’s often difficult to make accurate prediction.

Don’t get me wrong – I’m a big fan of Disneyland. But there’s a quick, costless way to double-check, ahead of time, that you too, will enjoy the experience.

3. Your desire becomes foolish.


You smell a cheese pizza. Your desire shoots through the roof. You buy it, you eat it, and for a moment, you feel bliss.

This isn’t an article about health or dieting, so whatever. I consider that example a success. You had desire, you acted on it, you felt good for it.

But all too often, desire has nothing to do with happiness.

The primitive part of your brain doesn’t care about your happiness. To it, happiness is a means to an end, one of many tools it can use to motivate you to act in ways it thinks will help you survive and spread your genes.

Your primitive brain wants you to consume fatty, sugary food. Your motivation? Eating it makes you happy. That way, you go out of your way the next time you’re shopping to buy even more fatty, sugary food.

It works something like this:


That’s your desire and happiness systems in alignment – you desire those things which make you happy.

Sometimes, though, things go a bit wrong:


That’s your desire system out of alignment with your happiness system – all desire and no happiness.

You’d hope that if something didn’t satisfy you, you’d stop desiring it (any exes come to mind?). But you weren’t made to handle the craziness of the modern world.

Among other things, as you become more attractive, you start comparing yourself to ever more beautiful standards (how many ‘ugly’ friends do you have?). The good-looking are just a few percentage points happier than the ugly.4,5,6

That’s okay with your primitive brain – the more attractive your partner, the more attractive your offspring. Win for your genes.

But I suspect the reason you purchased that dieting program is because you wanted to feel happier and more confident, not because you wanted more attractive children.

For you, happiness is the end, not a means.

So, the way to sidestep all of these problems?

Ask those who have already made the purchase how it made them feel.

How was that restaurant? That vacation? That laptop? That movie?

I’m not suggesting you become a clone – obviously we’re all different.

On Yelp you can filter by type of cuisine. On Goodreads by literary subgenre. On IMDb by demographic. On Amazon, they’ve got recommendations based specifically on people similar to you.

When it comes to money, rather than thinking, “I’m different, but sometimes others are similar to me,” I suggest taking the opposite perspective.

“My consumer preferences are similar to others, but sometimes they’re different.”

No. I’m not a communist. Well, if you’re going to call me that, at least call me a happy commi. I’ve found great success in adopting that mindset – fewer bad apples, more shining stars.

Some lawyers are happy with their career. Many are not. Thinking of going into law? I suggest investigating what makes those happy lawyers different, and seeing if you too, are one of the exceptions.

It’s not about justifying yourself to some invisible stoic judge. It’s about getting the most for your time and money.

These websites aren’t perfect – some reviews are fake, some are made by people radically different from you, sometimes the wisdom of the crowd is more the folly of the masses.

But give it a try. You might be surprised. There are lot of people in this world more similar to you than you might think – there’s 7 billion of us, after all.

Two tips for getting more out of reviews.
Jinesh, a big user of review sites, had these tips to offer:

“One of the big problems is placing too much emphasis on negative reviews that may be edge cases or not common for your use case. It’s happened to me time and again where I’ve resisted buying something because of these reviews (for example, speakers that some reviews say aren’t loud enough; yet, when I got them, they’re perfectly loud).”

Takeaway: Try to find out why reviews are negative. If they’re complaining about a feature you don’t care about, you may want to ignore them.

“Online, you can’t tell whether people are like you; hence, you tend to assume that every person who writes a review is like you. It’s why social reviewing/social search is so important – when a friend recommends something, I can say “this person has a weird taste in food, I’m not sure I’ll take her up on a restaurant recommendation”.”

Takeaway: Social reviews > stranger reviews.

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