Reflections on two years of writing a personal finance weekly newsletter

Welcome to the two-year anniversary edition of the Idiot Money newsletter.

This week:

• My most important puzzle in personal finance.
• How to reverse the (literal) brain damage at the heart of how you relate to money.
• And a thought I’d like to leave you with as I take a break from writing this.

But first, an announcement: I’ve been publishing Idiot Money every week for two years. I’m not going to publish it (at least not on a regular weekly schedule) for at least the next six months.

While I believe this newsletter has a ton to offer those who grace it with their attention, I believe a book (a restructured, slimmed-down, version of the one that lives here) would offer more. And it’s a book that’s not getting written, partly because Idiot Money is. So I’m switching my focus for a bit.

I’ll probably publish the odd issue here and there (and will post quicker thoughts on LinkedIn), but it won’t be every week.

In the meantime, please act as if I’ve written here whatever words would encourage you to read McGilchrist (I recommended The Master and his Emissary first, then The Matter with Things) and watch Vervaeke (specifically his Awakening from the Meaning Crisis lecture series). When it comes to becoming wiser, I know of nothing more instantly and enduringly rewarding (I say this as someone who’s probably read what you may be considering reading instead). If you want directly related investment stuff to read, I recommend Matt Levine’s Money Stuff. It won’t help you much with the money in your life, but if you like to understand meme-stock news and are drawn to dramas that star Elon Musk, then it’s great.

I also encourage you to read the Idiot Money archive. There’s something like 150,000 words in there, and frankly I think most of them are excellent. Some are even in excellent order. The menu page gives some ideas where to begin if starting at the beginning feels too passé.

A huge, heartful, thank you to all those that have been reading since the beginning, that have joined along the way, that have liked, shared, commented, and e-mailed. Given my insistence on writing only what I think is worth saying, and that others aren’t in as good a position to say, I realise that I’m more demanding of your attention than most, so thank you for playing along.

Please do feel free to continue to e-mail me with your comments and questions. I always reply. It’s great not only to hear about the times something I’ve written has made you, or someone you’ve shared a post with, pause and (re)consider how you pay attention to the money in your life, but also to hear how your experience clashes with what I’ve written.

Reflections on two years writing about money idiocy: the problem of treating addictions that appear to not exist, escaping the straitjacket of classical planning beliefs, and a wildly optimistic hope for a better way.

Like a challenge

Of all the puzzles of personal finance, one is perhaps particularly striking.

Money choices are life choices. People are pretty proud of their life choices, on the whole. Or at least appear to be.

Yet suggest that the accounting records of those life choices – the tax returns, the credit-card statements, the supermarket receipts, and so on – were made publicly available, and just about everybody will react as if you’ve invited them to engage in bestial acts on national television.

For similar reasons, millions of people will review and recommend books about motivation and habits and whatnot long before those books have actually transformed their way of living. And long, long, before they share what their current life – the life the book is supposedly shaping – actually looks and feels like.

In that atomically teeny observation swirls a galaxy-sized storm of bullshit that hints at how money promises so much, yet leads us so far astray from the stuff that makes those promises so enthralling.

As I wrote in Idiot Money 23:

Universally in financial planning, of all the pieces in the initial information jigsaw that marks the start of a new adviser-client relationship, the expenditure breakdown is always the last one to be slotted in – if indeed it’s not declared eaten by the dog and gleefully abandoned altogether. It’s not the homework, but what it reveals that’s unwelcome. I learnt the hard way that asking someone to contemplate what their spending says about their life inspires more terror than asking them to contemplate their or their partner’s possible death.

Assuming you actually traded money for things that made your life better, wouldn’t reliving those moments bring you joy? And if they didn’t, wouldn’t reflecting on that help you make a better decision next time?

This, however, is at odds with the game most people are playing when it comes to money; a game that says the purpose of money is to waste it. The game says that. Clearly the people playing it do not. Which is part of the reason why they never think to play a better game.

People will say their salary doesn’t define them, while being reluctant to talk about it, and lying about it if they do (and yes, that goes for those in the top fraction of 1% of earners too).

At one end, people will say stuff like ‘it wasn’t cheap, but…’ or ‘it better be, given how much it cost’ as a proxy for how well something functions or contributes to their existence. At the other, people will justify a purchase based on it being a ‘bargain’ more readily than because it is beautiful. All these sayings are saying the same thing, of course: the measure of this thing is money, and by extension, it’s the measure of the person owning the thing too.

What we do for money is so much a part of who we think we are that ‘what do you do?’ simply assumes the ‘for money’ bit. What we do with money doubles down on this by acting in large part as a means of bragging about our income while feeling like we’re neither a braggart nor so vulgar as to judge people based on their income.

So far, so trite. As ever, it’s not the specific examples that are important to understand, but what they point to: the picture they paint of the water in which we’re all swimming, but which we are almost incapable of attending to. Problems you can see are way less problematic than ones you can’t… or rather won’t.

No one wants to be unhealthy. And yet look. No one wants to be a stressy mess. And yet look. No one wants to waste their resources, money or otherwise. And yet look. Most people struggling with these things aren’t stupid. They’re not lacking better tactics. And they’re by and large among the wealthiest people that have ever lived. They’ve just been sold on a solution that doesn’t work and become so hooked on it that they can’t see an alternative. They’re addicts stuck playing a silly game.

Spending money in ways you’re not proud of has all the hallmarks of addiction, yet suggest to someone without a crack habit that they’re an addict – that their decisions are based on a form of blindness – and they’ll think you’re being facetious, if not downright insulting.

A chasm between your choices and the consciousness with which they’re made isn’t a sign of living well, it’s a recipe for depression.

Which is why your philosophy (and specifically your financial philosophy) is so important.

All philosophy worthy of the name is about living more authentically. Existential trouble emerges from rejecting rather than embracing the challenge of living an examined life in a bid to combat the inherently human problem of self-deceptive, self-destructive behaviour (or ‘bad faith’ if you prefer your diagnoses of psychological maladies to come dressed in a black turtle neck and smoking a pipe). Money sells us such rejection as a good thing, but it’s also the best tool we have for the embracing.

All roads to doing something about this lead to your attention.

Busyness is laziness

You don’t ask an addict what they ‘want’, because they’ll say a fix.

You don’t ask someone with jaundice what colour something is.

And you don’t ask someone with brain damage anything at all.

This is a right bugger for financial advice. Because even when it’s talking a great game about a plan being more important than a product, and planning being more important than a plan, and purpose being more important than planning, it’s basically built upon enabling people to pursue the shoddy synthetic substitutes that their brain-damaged worldview gets fixated on, rather than fixing the vision first.

In the context of how you attend to money, you are brain-damaged. You don’t believe this, of course. Because one of the primary symptoms of this form of brain damage is not seeing the damage. That makes it more urgent to do something about it, not less.

Nowhere is this more obvious than the pursuit of ‘goal’ of retirement, which, in the form most ‘retirement planning’ aims at, is a joy for a spreadsheet, but an absolute disaster for a human.

In The Matter with Things, McGilchrist shares a story that exemplifies the problems touched on above of tying money to identity, wasting resources to justify what we sacrificed to earn them, and generally living – voluntarily – in ‘bad faith’:

In the German philosopher Josef Pieper’s lectures, delivered just after the Second World War, and later published as Leisure: the Basis of Culture, he wrote: ‘there can only be leisure, when man is at one with himself.’ We tend to overwork, he pointed out, as a means of self-escape, as a way of trying to justify our existence. Busy-ness, he contended, was the true laziness, a failure to engage fully and responsibly with oneself and the world.

Why the bloody hell, you may ask, have I spent two years writing this newsletter?

It’s not about cash, of course. It costs money and time to produce, and the pricing policy of the odd bits of work I’ve got on the back of it has been to bully people into donating to an effective charity.

The content certainly isn’t optimised for clicks. Though if anyone knows how to both encourage challenging a potentially screwy worldview and play the popularity game, do let me know; it feels like that’d be a handy skill.

In short, I write about this stuff for much the same reason I left one-on-one advice: I see something horrible happening, and I want to try to help stop it.

‘I feel it is the duty,’ wrote your friend and mine, Carl Jung, ‘of one who goes his own way, to inform society of what he finds on his voyage of discovery.’

I believe the best way of doing this is to shine a light on how ‘money’ (in a grand, amorphous way, inextricably intertwined with how we each relate to it on individual and societal levels) has got ideas way, way, above its station, how we’re all culpable for enabling this, and how we can go about putting it back in its place.

If I didn’t see friends and acquaintances of all ages and from all possible starting points sleepwalking (perhaps decades in advance) towards the same disappointing dead ends that my former clients had drifted before them, only to discover that it was possible to ‘have everything’ and yet still feel like something was missing…

If I didn’t see more people asking ‘how much do I need?’ or ‘where’s the best place to buy property?’ or ‘which fund should I pick?’ than I see questioning how such answers could possibly point towards anything other than an unhelpful craving for certainty…

If I didn’t see such an imbalance between making money, and making something of it…

…then I wouldn’t’ve written a word about this, let alone a quarter of a million and counting.

How do you go about steering a somnambulist in a more conscious direction? It’s hard enough when you’re working with them one on one and they’re paying you tens of thousands a year for the privilege. In a series of 1,000-word weekly missives, it’s harder still. A bunch of tips, tricks, and tactics, or a takeaway step-by-step guide is great for changing a tyre, but a worldview isn’t a tyre. It requires a timeless shift in your mode of paying attention, not a shift in the direction of your existing attention for a limited time.

Final thoughts

As I step away for a while, I’d like to leave you with this thought:

We think about money all the time.

But we don’t think about how we think about money.

We cannot help but pay attention to something all the time.

But we don’t pay attention to how we pay attention.

The world is not short of ambition.

But it is short of aspiration.

There’s an important difference.

Ambition works from an assumed set of values. A set that’s inherited, and unchallenged. Because they work from this assumed value set, ambitions are about having ‘things’ (which could be material things, but could also be, say, a job title) more than they are about becoming someone. Ambitions use external changes as a proxy for internal ones.

Aspiration works towards values you do not yet possess, but have an inkling would be good for you if you did. ‘Aspiration,’ in the words of Agnes Callard, ‘is rational, purposive value-acquisition.’ Aspiration isn’t about having something, but ‘the method by which you work to become your true self.’

‘The aspirant,’ writes Callard, ‘brings herself to a different view as to what matters in life and comes to appreciate what she once did not […] At the end of the process, she will be able to say, truthfully, “Now I see what I was after all along!” ’

Aspiration looks like madness to a left-hemisphere-dominant worldview (and therefore a worldview as it’s typically shaped by money). Because what sort of crazy person pursues something that not only can’t be measured, but which they can’t even really explain what it is that’s valuable about it (because they won’t know until they possess it)?

To a brain hijacked by money, ambition is clearly saner:

An ambitious agent aims, usually over many years, to achieve something difficult and perhaps important. Nonetheless, the pursuit is not, with respect to value, a learning experience: she is not, as she proceeds, coming to a better and better grasp of why she is doing what she is doing. An ambitious agent’s behavior is directed at a form of success whose value she is fully capable grasping in advance of achieving it. Hence ambition is often directed at those goods—wealth, power, fame—that can be well appreciated even by those who do not have them.

Just like the left- and right-hemisphere’s ways of paying attention to the world, both ambition and aspiration have their place. Where human living is concerned, it’s crucial to know those places, and to keep each in their respective, rightful ones.

My ambition is to help people aspire. To see a different way of playing requires a different way of seeing. When you’re stuck with an addict’s narrow vision, you need something external to show that just maybe there are alternatives after all. And just maybe they’re worth paying attention to.