#103: Don’t worry about playing a game better when there’s a better game to play

5th September, 2022

Welcome to the Idiot Money newsletter. This week, becoming wiser with money by understanding that your money blinkers are more powerful than you think they are, including:

  • A deconstruction of a post from one of the smartest blogs out there.

  • How to beat your hidden money addictions.

  • What to watch out for from even the good financial advisers.

‘Before we set our hearts too much upon anything, let us first examine how happy those are who already possess it.’ – François de La Rochefoucauld

Pretty much everybody lives with money in exactly the same way. Those that worship it and those that renounce it are still playing the same game of using it as a scorecard. Everybody lives in a world where better means more expensive, and done well for themselves means made a ton of money, regardless of the non-measurable costs of doing so. Most play so blindly that when it comes to living better with money, most foolishly focus on playing the same game better, rather than playing a better game.

One of the reasons this newsletter is called Idiot Money is because its mission is quixotically foolish. To a world wanting cheat codes for playing the popular version of the live-action role-play game ‘how to make and spend money’, I’ve spent two years suggesting, and occasionally screaming, ‘play a different game!’

But what, in the context of making more of your money, does ‘play a different game’ even mean?

This week, with the help of a wiser writer than me, we’re going to dance with an attempt at an answer.

What does it mean to play a different personal finance game?

Once upon a time, there was a blog written by someone called The Last Psychiatrist (TLP). It’s difficult to tell, reading TLP’s posts, if they are the work of a crackpot or a generation-level genius, if indeed the two ever exist independently. One thing you could guarantee was that you felt smarter for reading them, even if you were also fairly sure you’d completely misunderstood them.

One such post was this one. It’s about an advert for beauty-product peddlers, Dove. Though of course it’s not really about Dove, or beauty products, or the abstract notion of ‘beauty’, or empowerment, or anything like that.

It’s about you. And the game you’re playing. And the awareness (or not) with which you’re playing it.

It’s therefore also about how you live with money, and how to do so less idiotically.


I encourage you to both read the post, and watch the ad embedded in it. Though for the purposes of this walk through its lessons for making more of your money, you needn’t bother right now.

The first thing to know about the ad is that while it looks like it’s selling beauty products – because it’s advertising a beauty-product-making company – it’s not. You can tell because there aren’t any actual beauty products in the ad. Indeed, the surface-level message of the ad is ‘you don’t need a beauty product to be beautiful.’

So what is it selling? And what relevance does this have for financial advice?

Over to TLP:

A beauty ad operates by creating a gap between you and an ideal: by creating an anxiety that can only be mitigated by the product.

Dove is doing something far more important than selling a product. It’s establishing its authority as the writer of the rules of the ‘beauty’ game. It is telling you what you have a deep existential need to believe – that you don’t need beauty products to be beautiful. In doing so, Dove isn’t making customers; it’s making disciples. Disciples make the best customers, because shopping somewhere else no longer requires merely finding a better product; it requires losing a faith.

It’s the same trick pulled by gurus who’ve amassed millions of followers by telling you that you don’t need to follow a guru.

So far, so basic. But hold this thought; we’ll be building on it.

TLP continues:

Dove is telling you you don't need to do anything to be beautiful, but it knows full well women must do something to themselves to feel good about themselves, and if they don't need makeup then at least a moisturizing soap. All Dove needs to solidify this is to be recognized as an authority on beauty – real beauty, not fake, Photoshopped, eyeliner and pushup bras beauty.

There’s a fundamental overlap here with how financial advice works. Because clients don’t go to financial advisers for wisdom – practical advice on how to live better by paying attention to how to pay attention and so more consciously constructing their ‘self’, and the world, and how the two dance together. That requires challenging their worldview. Clients go to financial advisers for the opposite of challenge. They go for reassurance.

Sure, they want some ‘actions’ and some ‘takeaways’… as long as they’re firmly within the boundaries of their current view. They want cheat codes for the game they’re playing, not to question if the game they’ve been playing their whole lives is entirely sane, or if there may be an alternative.

Is this such a bad thing?

That Dove wants you to think of it as the authority on beauty so it can sell you stuff makes sense, there's nothing underhanded about it and hardly worth the exposition. The question is, why do they think this will work?

The women in the ad, TLP explains, are representatives of ‘a psychological type that transcends age/race/class’. They are:

characterized by a kind of psychological laziness: on the one hand, they don't want to have to conform to society's impossible standards, but on the other hand they don't want the existential terror of NOT conforming to some kind of standard.

Be it the beauty game, or the living with money game, we strive to stand out in the way we play the game, but are driven to fit in via the game we choose to play.

Which would be fine if the game we were choosing afresh each and every time we went to work or opened our wallets were reliably and effectively enriching our lives. However, if this were true, the people playing it the ‘best’ – the ones with the biggest numbers on the scorecard – would be living the best lives. You don’t need to work in face-to-face financial planning to know that they are not.

The people winning not enjoying their prizes is a bit of a hint that the game is a silly one.

But what else is there?

The Dove ad got a lot of criticism, which tended to focus on things like the diversity of the cast. That is, on the content of the ad – the way in which the game is being played.

As TLP points out, when criticism is focused on the content, it is ‘founded on the assumption that ads have the authority to set standards […] not assert the insignificance of ads’ – i.e. it supports Dove’s position as the writer of the rules of the game.

Ok. Cool. Got it. Don’t give them the power. Turn off the TV. Boycott the products.

Hold on. Remember that denunciation is still attachment. Remember that those most wedded to the typical way of living with money are those that chase it AND those that make a point of not chasing it. Boycotting a product (which is different to simply not buying it, like you unconsciously don’t buy basically everything but a teeny tiny selection of the world’s goods) is a fine way to say that you believe that particular product has the power to shape your decisions.

‘The important point,’ TLP writes:

is not that you believe this to be true, the point is that you want this to be true. You want it to be true that advertising sets the standard of beauty because in the insane calculus of your psychology you have a better chance of changing Dove than you have of changing yourself.

You can’t get enough of the sweet, sweet, satisfying certainty that money promises. You want money to be the answer to everything. You want price tags to indicate value. You want financial advice to be scary and complicated. You want your net worth to signal your self worth. You want your salary, and your job title to say more about you than your character. You ‘want’ money to not have to think about money. You want a lack of consciousness in making a decision to be the hallmark of making a wise one. You want accumulation of stuff to determine quality of life more than the alignment of that stuff with your soul. And so on.

I use ‘want’ here in the way that a smackhead ‘wants’ a fix, or somebody that’s spun themselves a story about having a ‘sweet tooth’ believes their body wants a cake. That is to say, entirely inappropriately.

These aren’t wants. They’re addictions. To see them as such is to see the flaws in the typical game and maybe, just maybe, start to question if there might not be a better way.

Addiction is blindness, not helplessness

Addictions, as we’ve seen, are about narrow visions, not compulsive desires. Which is why pointing out to an addict that there are alternative ways to live never works. Especially an addict who – because of their narrow vision – doesn’t even see themselves as an addict (which is just about everyone failing to make the most of their money).

So what do we do about this?

We pretend.

We test our truths.

If they pass, fantastic. Nothing changes and the old beliefs are now held more confidently.

If they fail, also fantastic. Because you were believing something you now know to be bullshit, and now (one hopes) you aren’t.

There are all sorts of ways to do this. Living an examined life can happen everywhere, not only the psychiatrist’s coach.

One of the easiest places is your language.

Catch yourself saying ‘better’. Do you mean ‘better’, as in ‘makes my life better’? Or do you mean merely ‘more expensive’?

When you say ‘success’ do you mean ‘living well’ (and how do you know?) or do you mean merely ‘earns a lot of money’ or ‘owns a lot of things’?

And so on.

This should be so simple that to point it out sounds insane. But money hijacks our attention to the extent that the whole world, upon hearing ‘what do you do’ automatically fills in the ‘for money’ bit without troubling a neuron.

In the same way, borrowing from Bertrand Russell, we’ve often had cause to ask: ‘What is the use of making everybody rich if the rich themselves are miserable?’

Most people who pursue being rich do so as a proxy for living non-miserably. Living non-miserably is obviously a better goal than being rich. But we can’t measure it, can’t pursue it directly, so we pursue money instead. Even when it doesn’t work.

Yet you’re allowed to aspire towards things that can’t be measured! In fact, they’re the only things you should aspire towards. Character, courage, wisdom, love, truth, beauty, goodness.

You’re also allowed, when somebody suggests that cravings aren’t helping you, to see beyond the simplistic compartmentalised view of craving – ‘oh, it’s fine, I don’t want a yacht, or a mansion, or a fancy handbag’ – to the whole framework of grasping after things… any things… at all. It’s not about the ‘what’ you crave, but the way in which you live. (And if you think to not crave is to not aspire, and thus lead a joyless, actionless existence, then come back when you’ve read these.)

Beware the advisory industry

Finally, a short note on how this applies to the financial-advisory industry.

How to manage your money is an important game to understand. Not understanding it is likely to be the costliest mistake you can ever make, whether that’s because of ignorance-induced panic-selling, panic-buying, or how investment fees inflate and compound in a way that breaks free of most people’s ability to grasp the consequences.

There are therefore plenty of fine reasons to pay someone to help you live better with money. However, paying someone on an ongoing basis to understand technical investment stuff for you is not one of them.

A great adviser would leverage their unparalleled knowledge, from being inside the heads of its winners, of the ultimately unrewarding game you’re playing, and coach you to play a better one – eventually making themselves redundant.

Most advisers don’t do this, of course. Because it means challenge, which means risking getting fired long before they get to make themselves redundant. And it means not playing the silly version of the game themselves. You struggle to find many advisers that don’t strongly substitute having more expensive things for becoming better people.

To return to our Dove ad. Even those advisers that say it’s not about the money do so mostly to build trust to sell you the product. It’s just a looser definition of ‘product’ than the one used by old-school life insurance salesmen hunting commission. Telling you that the product isn’t as important as the process behind the product, or the purpose behind the process is a great way to establish the sort of authority that dictates that whatever you’re buying – and you need to buy something – you’ll buy it from them. They’re not trying to make themselves redundant; they’re doing the opposite: they’re providing a means for needing them for life. Personal finance remains scary and complicated, but it’s okay, because you’ve got a repeat prescription for reassurance. It’s opium for the mass affluent.

But what if the stuff that really mattered – that you really wanted – couldn’t be bought?

What if the mark of an adviser worth listening to wasn’t saying the things that sustained the system, but the ones that aimed at making themselves redundant? That focused not on protecting and growing assets, but strengthening minds and cultivating character? That played the role not of guru to be followed, but momentary mentor in your heroic journey? The sort of figure whose wise counsel pops into your head at just the right time to remind you (in the sense of sati) who you are, such that it helped you become that.

Wouldn’t that be a better game?

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