Better money decisions, step by step

The practical steps on your path towards financial enlightenment are an unfolding story of becoming wiser with money, its star’s fate determined by each fork in the road

Money is the great universal. That’s sort of the point of it. This means it gets involved in all sorts of decisions. To do one thing is to not do a million other things. The way your brain works says that how you do anything is how you do everything: every decision is a vote for one version of you over another. Grand stories are told in gradual steps.

By assigning a translatable value to the competing components of each decision, money can save us from paralysing confusion. But it can – and regularly does – go too far. Having a universal converter doesn’t stop an incalculable number of decisions needing to be made. We need mental defaults. But the defaults we’ve ended up with aren’t wise ones. Our common money defaults deceive us, and ruin our decisions.

Doubt is drawn to kicking cans down roads. Yet later is just now with less time to enjoy living with the outcome of whatever decision it is we’re dodging.

This is why a grounding philosophy is so important. Because it wisens up our defaults, linking them to a vision big enough and cool enough to get us to stop and think things through, rather than being blindly swept away by self-deception.

‘Nothing is easier than self-deceit,’ said Demosthenes, ‘For what each man wishes, that he also believes to be true.’[i] And ‘No hell is worse than that in which one lives without knowing it’[ii] wrote Alan Watts, 2,000 or so years later. We’re not great at dissolving this deception. Money may be most prone to expressing these errors, but it also gives us the best starting point for correcting them.

At each moment of decision, our self-deceiving beliefs about money send us down unnecessarily dumb and dangerous paths. Becoming wiser with money steers us instead in the direction of our dreams – towards financial enlightenment.

The aim of this book is to inject a shot of consciousness at each crossroads, to break unhelpful patterns and build better ones in their place.

The three main sources of monetary self-deception are:

  • Believing money is something you have, rather than part of who you are.

  • Believing other people’s money defaults can be valuably adopted as our own.

  • Believing the importance of money lies in numbers, rather than narrative.

The way we cede control to these self-deceptions is subtle; that’s how self-deception works. Mental mirrors can be uncomfortable to look at. Rear-view ones that force us to reflect upon what we’ve done with our lives are all the more so.

But the pain of not confronting them, of remaining trapped by them, far outweighs the discomfort of doing so in a quest for freedom. Financial enlightenment is not a state. It is a process of cultivating a positively reinforcing capacity for making better decisions.

It is your sight, not your soul[1], that needs to change. This is about self-love, not self-control. It calls for clear thinking, not hard-assed discipline. It’s not about learning lessons, but practising them.

The path towards financial enlightenment

Enlightenment is both everyday and ethereal and is a mode of operation of the brain and the body, not the pot of gold at the end of a checklist of circumstances

In any anthropocentric tale, the point of a path is rarely its destination. Humans move along paths to grow; to arrive is to stop moving, to stop growing.

A focus on a destination may start you going somewhere, but maintaining it gets you nowhere. Dreams of a somewhere may ignite a spark, but it’s nurturing the fire within us, not the light on the horizon (or across the bay), that warms our lives.

We need both a zoomed-out view to check we’re on the right path, and to zoom-in on each individual step that keeps us there. The flourishingness or fucked-up-ness of our fate flows like a waterfall from a cascade of droplet-sized decisions. Little lifestyle choices add up to big brainstyle choices.

On the one hand, this is lucky. Money is an ever-present at the forks in our mental roads. It’s the perfect vehicle on which better-decision-making machinery can hitch a ride. On the other hand, this is unlucky. For ten thousand reasons, the paths either side of each fork are not created equal. The bad way is often a highway, with a flood of fancy cars offering lifts, while the right way is overgrown with weeds, barely visible without hours of hacking about with a machete.

Becoming wiser

We want to become wiser with money more than we want to become loaded with it; this requires a process of seeing more clearly, not making more money

To take the path towards financial enlightenment is to participate in a process of becoming wiser with money. It is the becoming wiser, not the being wise, that is important.

It is a participatory process because money isn’t wise by itself, and you cannot be wise with it, without it.

Becoming wiser is to see the right path more clearly, by clearing out the weeds of self-deception, in such a way that we progressively and systematically side-step future self-deception by default. Each step is a choice, between self-deception and its opposite, rationality. Our rationality is our capacity to overcome self-deception in a reliable and systematic manner, so that we may stay on course, take the right next step, and trigger a cascade of insights that levels-up who we are and what we’re capable of.

Rationality isn’t about not feeling. It’s about a more refined appraisal of inputs into our predictive model of our place in the world – and feelings are very much part of these inputs. But behaviour-changing protocols that rely only on exciting emotional responses are not reliable if the excitement fades before the habit highway forms.

Intelligence, rationality, and wisdom

The time to dive more deeply into the cognitive science of wisdom, and how it relates to being better with money is at the end of Part Two. Here and now, it’s worth being clear on the differences between intelligence, rationality, and wisdom.[2]

Intelligence is your capacity for being a general problem solver. It is your intelligence that allows you to pick things up with your mind, play with them, manipulate them, and use thereby use them to make sense of the world. Intelligence is not possessing knowledge; it is zeroing in on the most relevant information in a noisy universe to better work out what is going on, and what to do. This zeroing-in is not logicality, i.e. it is not checking every option (and combination of options) and rejecting all the duff ones.[3] That’s impossible. Not even chess computers work like that. It’s a capacity for ignoring all the duff ones.

Rationality is your ability to deal with self-deception. Your self-deception arises inevitably from the same machinery you use to solve problems. Because it cannot be logical, your brain solves problems by using shortcuts. Self-deceptions, as we’ll see in the next section, are shortcuts gone awry – substituting a tempting easy answer that looks and feels right, for one that actually is right.

Intelligence and rationality are therefore quite different things. In the way we make and use money, we often jump to conclusions driven by believing we’re being intelligent (or will be seen as intelligent)… jumps that are often inspired by self-deceptive, self-destructive beliefs. However, the hallmark of rationality is valuing the process, not being fixated on the belief and the conclusion.[iii]

As cognitive science has demonstrated, sometimes the processes that cause you to be intelligent also cause you to be irrational. The distinction is vital for training yourself to become wiser with money. Intelligence is necessary but insufficient for making you rational. Intelligence is a capacity. Rationality is an ability. This is important. Because: a) there’s not a huge amount you can do to become more intelligent, but you can become more rational; and b) becoming more rational is more important than becoming more intelligent anyway.

In the words of John Vervaeke: ‘Intelligence is not a synonym for being rational. And what you should ultimately care about is not how intelligent you are but how rational you can become.’[iv] As with life, so with money… For when it comes to money, we worry far too much about the ‘intelligent’ or ‘logical’ problem-solving ‘answer’, when a wiser, more rational approach would remember the emotional human life story that those ‘answers’ should be serving.

It’s hard to define wisdom in an especially helpful way. Because it is more a characteristic of a way of living than it is a definition of static state, choice, or even series of choices. It’s the cultivation of a dynamical system for countering the equally dynamical system of self-deception, and consequently for affording a flowing, flourishing, meaningful life.

‘Wisdom,’ wrote Socrates, ‘begins in wonder.’ The sort of wonder that opens you up to the possibility that aspects of your worldview, however well-engrained, and however well-enforced by internal and external guardians, could be bullshit. The sort of wonder that upon being open like this is motivated to challenge previously jumped-to conclusions, and, when they’re found wanting, to aspire to find a better way.

Right now, going beyond that isn’t important. Which is why we’ll return to it later.

The becoming mode v the having mode

If you misidentify the needs you are trying to meet, you’ll only ever meet them by accident, causing more frustration than flourishing; most misidentification comes from seeing ‘having’ solutions for ‘becoming’ needs

Money misleads us into believing it will bring us what we want, when in reality it is only a well-disguised substitute. ‘As a man is, so he sees,’ wrote William Blake.[v] If we are to stop being mislead by money, we need to start living in a different mode.

At the very roots of our language we find two verbs: ‘to be’ and ‘to have.’ These words have become so absorbed into our unthinking everyday discourse that their primordial meaning has been lost. However, they denote two of the most fundamental dimensions of our existence: those of having and being. These two dimensions reveal two distinct attitudes towards life. In terms of having, life is experienced as a horizontal expanse precipitating towards ever receding horizons; in terms of being, life is felt in its vertical depths as awesome, foreboding and slightly mysterious.[vi]

Some wants are met by having something. We relate to them in a subject-object fashion. There is ‘I’, and there is ‘it’. ‘I’ owns ‘it’. ‘It’ can be controlled by ‘I’ in service of solving problems. ‘It’ is replaceable. There are many ‘its’, and each one is a good-enough substitute for all the others.

Other wants are met only by being, or rather becoming something. Like wanting to be in love, or wanting to become mature. We deceive ourselves into thinking becoming mature can be met by owning a house, or being in love can be met by having sex, but not only does this never work, but because we are deceived, we remain puzzled as to why it didn’t work, and end up blindly trying the same thing again. And again. No second house has ever met the need its prospective owner believed it would.

‘Becoming’ wants are about a relationship, between you and the world, or you and another person, or you and yourself. They relate not to solving isolated problems, but to the very meaning of your existence. Relationships are expressions: they do not fall into neat categories; and finding adequate substitutes is not easy.

In the words of Erich Fromm, whose landmark book To Have, Or to Be? set out the distinction, being and having[4] ‘do not refer to certain separate qualities of a subject as illustrated in such statements as “I have a car” or “I am white” or “I am happy.” ’ They refer, rather, ‘to two fundamental modes of existence, to two different kinds of orientation toward self and the world, to two different kinds of character structure the respective predominance of which determines the totality of a person’s thinking, feeling, and acting.’[vii]

It would be a mistake to think of one mode as good, and the other bad; they each have their place. What is very bad indeed though is when we try to meet being mode wants with having mode answers. Unfortunately, inciting this confusion is the foundation of marketing, and marketers have got awfully good at it. Want love? Want maturity? Have sex! Own a Ferrari! Have sex in your Ferrari!

‘In the having mode of existence,’ wrote Fromm, ‘my relationship to the world is one of possessing and owning, one in which I want to make everybody and everything, including myself, my property.’[viii] We believe that if we ‘own’ the answer to our wants, we will be somehow secure. It’s a tempting illusion. Sadly, it’s bollocks.

Haves will only take us so far. And when we use having something as a substitute to becoming something, where it takes us is far away from where we want to be. When Prince Siddhartha Gautama left his palace – where he allegedly ‘had’ everything – on his way to becoming the awakened, enlightened one (the ‘Buddha’) this is what he came to realise.

If anything feels more like something you have rather than something you are in the process of becoming, it will never feel real. Consider the difference between ‘having’ health versus living healthily, or a job title versus being the competent creator of value for others. In all cases, becoming who you want makes having what you want happen by accident. The reverse is not true.

Faking it really can make it, as dreams of a having a six-pack can kick-start a journey to living healthily. But it can also end with a life in service of a metric, rather than a metric in service of a life. In a choice between fundamental modes of existence, metrics are signs of things to be forcefully done, rather than expressions of a way of living. And chores always eventually go undone.

Thinking v unthinking

In existential-anxiety-driven desperation we grab at anything that saves us from thinking; sometimes this is wise, but given how well it is woven into the fabric of our lives, making money decisions unthinkingly is unparalleled idiocy

When the bad way is the highway it doesn’t take a lot of effort to zoom along down it. In many instances, it takes no effort at all. When defaults go bad, inertia carries us to places we don’t really want to be. It is less a path, and more a conveyor belt.

Jumping into a car simply because it’s chaffeur-driven isn’t always wise. Where we’re going is important. How we experience getting there is more important still. You can’t climb a mountain in a mobility scooter, and even if you could, you’d feel worse than if you’d hiked up instead. The more we hike, the easier and more enjoyable it gets. But to keep it enjoyable, we don’t keep it easy. We seek new challenges. A baby doesn’t take its first steps, think it’s nailed it and put its feet up. It learns to run.

When it comes to the forks in the road on our path to financial enlightenment, we need to see thinking in the same way. The conveyor belt of unthinking will always be tempting, but that doesn’t mean we want to hop on.

Unthinking is unquestioning. Often we allow ourselves to be ruled – and ruined – by beliefs that wouldn’t survive the slightest scrutiny… if we bothered to subject them to any.

The inaction of unthinking inertia is broken by thinking. This doesn’t happen automatically. We need to train our vision for mental triggers – thoughts, words, phrases, and concepts we know we’ll encounter that we can use as reminders to confirm the consciousness of our actions. That remind us to pause and think before blindly going off course.

Do this often enough, and you soon start to dance through your financial life not with discomfort and confusion, but with effortless effort. Doing without feeling like it’s a chore. Fighting without feeling like it’s a fight.

Thinking is not the same as believing. We commonly say ‘think’ to describe a process involving precisely zero thinking. I caught myself doing this at least a thousand times in writing this book. Questioning what we have really thought through and what we’ve unthinkingly reacted to is a non-negotiable when initiating any behaviour change.

The narrative path v the numbers path

The objectivity of numbers isn’t an antidote to anxiety associated with the uncertainty of a human life, it’s an enabler of it; an exploitative deception that rather than removing the difficulty inherent in human complexity, removes the human from it

Money’s role in our stories seems like it should be super simple. It’s odd how it doesn’t work out that way. Why do those with money not live reliably better than those without it?

Odd, that is, until you realise that not only does it not work this way, but it cannot work this way.

This isn’t because money cannot buy ‘happiness’[5]. Because it can. Just not the way we believe it can (N.B. this isn’t about ‘buying experiences’ either).

We deceive ourselves when we believe money’s role in our lives is about inanimate numbers that decorate the narrative, rather than being a living, breathing part of the narrative itself. Money is integral and instrumental, not merely incidental, to the story we tell ourselves about ourselves.

At each fork in the decision-making road, our options can appear daunting. As we constantly encounter new forks, there is no way to forecast where each explosion of possible path combinations will lead. It would be like trying to calculate every combination of chess moves. Not even the biggest, baddest, computers come close to doing that. Instead, they filter. So should we.

All forks are defined by seeing money as either a mere number, or as part of our narrative. To see the distinction more clearly requires unlocking overlooked ways of knowing.

We will look later[6] at the different ways of knowing something, from propositional (facts), to procedural (technical skill), to perspectival (relevance in context), to finally participatory (how we interact with something – how it changes us, how we change it, and how a meaning emerges that belongs to neither it, nor us, but to the interaction).

By necessity, we know money in a participatory way. Yet when it comes to money, we ignore this type of knowing, keeping this apparently inanimate, functional medium of exchange firmly in the first two categories, with perhaps an occasional peek into the third when for a brief moment a Mastercard advert reminds us that there are some things money can’t buy, before we nod sagely and go shopping for ‘everything else’.

We shall also look at how, when considering the classic pictorial timeline of evolution – where knuckles cease to drag, and everything gets rather less hairy – we must dress the figure at the end, so integral are our clothes to who we are. And how outside of a proportion of people that rounds to nothing, we must also give this tip of the evolutionary chain some money (and companionship to share its story with).


Your life is not a number. It’s a narrative. So why chase a number as the way to enrich your story? Why try to become what you want by having something as a substitute, when the having never works? Why trust to the impersonal luck of unthinking, when the personal judgment of thinking is always available? Why settle for anything less than becoming wiser with each step?

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[1] ‘Soul’ should be read as analogous for ‘what you want, deep down at the core of your being’. ‘Soul’ may be a bit of a tricky term, because it is inherently impossible to ‘pin down’. That is a feature of its import, not a bug. There is nothing more important in our actions than authenticity. We all know on some level that fleeing from the full actualisation of our potential feels so shitty because it feels so inauthentic. There’s no better guide to authenticity than the body… once we’ve learned to listen to it amid the noise of all the crap both within and without of it. The drive to oversimplify, to narrow a vision that our innate humanity wants to expand, to pin everything down, is at the heart of the self-deceptions that mess us up, as we’ll see in the next section.

[2] In outlining both definitions and applications, I am indebted, once again, to the work of John Vervaeke.

[3] The combination part is very important. However well it works in isolation, a solution to a problem isn’t intelligent if it harms your ability to solve future problems (for example by wiring you to be closed-minded in relation to a particular issue).

[4] Fromm uses ‘being’ rather than ‘becoming’; I prefer ‘becoming’, though the distinction is not hugely important, and in referring to modes of existence, they are interchangeable.

[5] We’ll discuss definitions of ‘happiness’ and related terms in Part 1, Section 3.4.

[6] Part 1, Section 3.2.


[i] Demosthenes, quoted in Peter Bevelin, Seeking Wisdom

[ii] Alan Watts, Become Who You Are

[ii] As explained by John Vervaeke, Awakening from the Meaning Crisis, ep. 27

[iv] John Vervaeke, Awakening from the Meaning Crisis, ep. 27

[v] William Blake, Letter to Reverend John Trusler August 16, 1799

[vi] Stephen Batchelor, Alone With Others

[vii] Erich Fromm, To Have, Or to Be?

[viii] Erich Fromm, To Have, Or to Be?