There is always an underlying emotional reward

What we seek when buying any good or service is an emotional reward, and it is against that that spending decisions should be weighed, measured, and judged

We know what we want, but we don’t know we know when we need to know

Purchases are investments in meeting emotional needs

How do you know when you’re being ripped off? You compare what you thought you were getting with what you got. If the latter doesn’t match the former, you feel cheated. This is at the heart of this book – we think we’re getting the Good Life (why else would we sacrifice our precious resources?) yet because we’re misled into seeing deceptive substitutes for what we really want, the sacrifices of our exhaustible resources are in vain.

Knowing whether something’s worked should be easy – we should just ask ourselves if it worked. But instead, we choose to make it difficult, perhaps fearful of what would happen if we admit we’ve been chasing the same thing forever and haven’t got reliably better at it. If you don’t revel in reviewing your calendar and credit-card statements… why not?

As we saw earlier:

We have an intuitive understanding of what we want – we feel we’re living the Good Life when who we are and who we want to be align. We desperately seek this alignment in all of our actions. Which is precisely why we bugger it up: desperation drives us towards shoddy substitutes.[1]

When we looked at unexamined expenditure we noted that: ‘We clutch at social performance as a substitute for something more meaningful, because we are too distracted and deceived to understand what it is we’re subbing it in for’ and quoted the School of Life: ‘We choose the wrong things because we don’t know ourselves well enough to select what will best work for us.’[2]

What concerns us here is why this happens. Why are we so bad at calibrating our wants? Of course who we are is in flux, but many of us have had decades of trial and error and oodles of individual transactions to learn from. We should be getting better much faster than we are.


Some purchases meet purely functional needs – things we know only on a propositional or procedural level. Most things, however, play a deeper role in our lives – we know them, or rather should know them, on a perspectival and/or participatory level.

We want all purchases to align with our wants: and most of those wants are emotional. Yet when it comes to money we treat everything as if it’s swimming in a shallow pond of isolated events, not the open ocean of human experience.

On some level, the thing we believe we’re buying is rarely what we’re actually buying. The thing is only a symbol for an underlying emotional reward. This is one of the most important concepts in all of financial advice. It’s at the heart of our having-mode / becoming-mode confusion.

If a need is going unmet, and we don’t know why, we’ll continue trying to meet it in the same way, and rather than honing in on the answer, instead get increasingly confused as to why it’s not working. As Mark Manson put it:

People with an overwhelming desire for wealth or fame aren’t motivated by the pure joy of having wealth or fame. No, they have a hole in their psyche that they are trying to fill with enough stuff to not make them feel so inadequate anymore.[i]

There are echoes here of the ‘Object Relations’ theory from psychoanalytic psychology. As described by Lavinia Gomez:

To see oneself and others as thing, object, possession, rather than subjective stream of consciousness and unconsciousness, is to be tied to sensation without meaning.[ii]

People buy things for all sorts of purposes, but to lead a meaningless life isn’t ordinarily one of them. This goes beyond simply swapping material goods with experiences,[3] as Bertrand Russell explains:

Fads and hobbies, however, are in many cases, perhaps most, not a source of fundamental happiness, but a means of escape from reality, of forgetting for the moment some pain too difficult to be faced. Fundamental happiness depends more than anything else upon what may be called a friendly interest in persons and things.[iii]

The whole point of defeating self-deception is to do the opposite: not to escape reality, but to embrace it, and so steer it, rather than living defined by fear of it. This is good news! For it means we’re not materialistic monsters, we’re just a bit misguided. And ‘a friendly interest in persons and things’ is so much easier to save up for than a McMansion. Hear too Alain de Botton from the TED stage, in a passage so good it deserves memorising:

I don't think we are particularly materialistic. I think we live in a society which has simply pegged certain emotional rewards to the acquisition of material goods. It's not the material goods we want; it's the rewards we want [...] The next time you see someone driving a Ferrari, don't think this is somebody who's greedy; think this is someone who is incredibly vulnerable and in need of love. Feel sympathy rather than contempt.[iv]

In summary, and in the words of a man from a domain that both understands and exacerbates our substitution errors, marketer Rory Sutherland, ‘We don’t value things; we value their meaning.’[v] We, deep down, value goods and experiences not because of their price tags, but because of what they add to our narrative; not because we can show others that we ‘have’ them, but because of what they help us become.

Investing in a meaningful life

Making more meaningful choices requires challenging the ones you’re already making

This chapter has, like sunrise over the Great Pacific Garbage Patch, shone a light on waste we’d rather pretend didn’t exist, but that subtly accumulates into a stinking millstone of poor life choices. Every day, we are attempting to turn our resources into a Good Life. Every day these attempts fail because of the self-deceptive beliefs on which they’re based.

The foundations of a Good Life are built by cutting out the crap – training ourselves to play a different game than the unwinnable numbers-based one obsessed with income, ‘more’, and price tags. But if all purchases are investments, and we’re investing in a meaningful life, it would help to identify some positive investment criteria too. How do you buy meaning?

‘Meaning in life,’ wrote Susan Wolf, ‘arises when subjective attraction meets objective attractiveness, and one is able to do something about it or with it.’ When one is living, she continues, ‘in a way that connects positively with objects, people, and activities that have value independent of oneself harmonizes with the fact that one's own perspective and existence have no privileged status in the universe.’[vi]

That is to say: when you align your resources with your wants – what is Good for you – and those wants are in turn aligned with what is Good for the world, then you’re cultivating meaning in your life. If this sounds familiar, it’s because it’s the same aim as outlined in Part One when discussing the goal of phronēsis (practical wisdom): ‘not only how to choose a path to an end, but how to choose the end most consistent with the aim of living well overall.’[4] You don’t need an Ancient Greek to tell you that wanting the ‘right’ things is better than wanting the wrong ones.

Yet want counts as ‘right’? What qualifies as ‘objective attractiveness’? Wolf makes the case, and I agree, that it doesn’t matter. Much like ‘the Good Life’,[5] ‘objective attractiveness’ defies definition… but we know what isn’t it. Even if we could pin it down, who’s to say it wouldn’t change? The world, after all, has a habit of changing.

Our problem is not the lack of an objective measure, but believing that there has to be one, and so filling the void with deceptive bullshit. Like believing ‘more’ is better, or that price is a fair proxy for value.

Dissolving these self-deceptive beliefs means giving up the craving for certainty. It means a shift in worldview from one fixated on fixity to one open to the reality of impermanence. It means reacting to this reality, not with a hypercorrective leap to a nihilistic rejection of everything, but with embracing a process of examination and refinement. The aim is not to have perfect judgment, but to become a better judge.

Where money is involved, it’s an almost universal trait that people seek it to not have to think about what it all means – to forget about the responsibility of using their resources wisely. Yet this not only doesn’t work, it cannot work. More money – more ability – means more responsibility. Plenty have tried, do try, and will continue to try to escape this, but they’ll never escape the niggle… the niggle that says ‘there must be more to life than this…’ that wonders why acquiring the money they sought didn’t weaken the worries they sought it for, and that goes on believing the answer must be that they simply don’t have enough of it yet.

Seeing ‘better judgment’ as a thing to possess, rather than a side-effect of becoming a better judge, is self-defeating. Because it denies the reality that to be a better judge, we must see the world more clearly. Nothing meets with more resistance than admitting that the way we see the world must change. In many aspects of our life – and money is chief among them for countless people – nothing runs deeper. As Wolf explains:

Our initial pretheoretical or intuitive judgments about what is valuable and what is a waste of time are formed in childhood, as a result of a variety of lessons, experiences, and other cultural influences. Being challenged to justify our judgments, being exposed to different ones, broadening our range of experience, and learning about other cultures and ways of life will lead us to revise, and, if all goes well, improve our judgments.[vii]

The core message of the first two parts of this book is that seeing more clearly starts with making peace with your illimitable ignorance… being open to the possibility that the way you’ve known something you’ve interacted with every day of your life – from unconsciously inheriting your parents’ financial demons to your career choices and spending decisions – could be causing you unnecessary admin, angst, or anxiety.

The immediate danger of challenging any long-held belief is rebounding into something equally silly. Lost a faith? Find another! Beaten an addiction? Watch another rush in to fill the void. As Jung explained: ‘You can take away a man's gods, but only to give him others in return.’[viii] Or, as H.L. Mencken put it: ‘A convert to a good idea is simply a man who confesses that he was formerly an ass – and is probably one still.’[ix]

Price tells us we needn’t bother with the hard graft of thinking about what to do with our money – there’s an objective answer, and it’s written in language your wallet can understand. Considering subjective value, on the contrary, causes us to think about what we actually give a crap about. You can give a crap about lots of things, and too easily fix on the less-meaningful ones because you believe that as long as you’re not starting from the price tag, you’re doing it ‘right’… even though the faulty mechanism of searching for the easy, eternal, answer hasn’t changed. The underlying emotional rewards we’re really after are not objective, or even subjective. They’re transjective. Time for another short philosophical detour.

Beyond objective and subjective: introducing transjectivity

Money no more has objective meaning than language does; it both expresses and shapes your life, as a part of that life, not as an external, objective tool

To best understand transjectivity, recall our four ways of knowing something.[6] To recap:

1. Propositional knowing – This concerns statements of fact. It is knowing what stuff is, usually in the form of ‘I know that…’ You find propositions in textbooks.

2. Procedural knowing – This concerns technical skill; pragmatic, practical know-how. It is how stuff works, not just what stuff is. It is about competence and mastery – it is deeper than propositions that can be learned from a textbook.

3. Perspectival knowing – This concerns awareness and perception in context. It is knowing what is relevant right now. To know money perspectivally is to know what it is like to be a person that has some.

4. Participatory knowing – This concerns a shared, symbiotic, identity-based knowing. There is an inherent degree of internalisation (rather than mere ownership) of object by subject. You and your money, to some extent become one. Our participatory relationship with money is incessant. Our interactions with it are constantly shaping our identity and the environment in which that identity is finding its way. And the money-environment in turn shapes us.

It is in our participatory knowing of money that we discover how to turn money into meaning. How we understand the money in our lives as an interactive narrative, rather than an incidental series of numbers. How we see it not as an isolated something to have, but as something that is part of our whole human life, and that, used wisely, can help us in our never-ending, gloriously destination-less journey of becoming the sort of human we want to become.

Cognition – the sort of conscious thinking that can steer us along this journey, rather than leaving the whole thing up to chance – happens mostly in interaction between subject and object.

The fact that there’s no such thing as objective attractiveness doesn’t matter. Because that’s not what we want. We want a transjective relationship with the world – the life we are trying to make Good exists as a part of the world, not alongside it. If we want meaningful lives, we want to live in conditions that enable meaning making. We want to live in an environment that affords – i.e. has qualities that make it clear how something should be used, like a door handle that encourages you to push it and pull it in certain directions – meaning making. We want, to borrow once again from Vervaeke, to realise (in both the sense of understand and bring about) what is relevant.

Relevance is a product neither of objectivity or subjectivity. […] Relevance is transjective – a real relationship between an organism and its environment. Not projected or detected. It is realised (objective sense: to make real; subjective sense: coming into awareness).[x]

This is torture to minds dead-set[7] on grasping for certainty. Those minds crave an environment where nothing has to be made, because everything is already perfect and will remain that way forever, while also magically never becoming stagnant. They are short-sighted, narrow, minds… addicted to analysis within categories, but blind to the fact those categories are only ever a veil to help with understanding a whole life; they are not the life itself.

Importantly, we not only want to live in environments that afford the chance for meaning making, we want to care about creating them. Because to do so is to care about being human… about living a Good Life. ‘The process of meaning making,’ said Vervaeke, ‘is the process of being a person. [It’s] why being connected to other people is so important to meaning in life.’[xi]


That, of course, all sounds wonderful. But what does it mean in practice? How does one create such an environment, such a life? How does one create the conditions for living a different way, when it is likely only by living in that different way that one understands what it even looks like?

This returns us to our discussion of the symbol.[8] When seeking answers to questions we don’t yet know how to ask appropriately, we need to see symbolically. A symbol brings together the subjective and the objective. The clue’s in the name… trans–. Symbols help us bring the objective into the subjective. They give us glimpses of an alternative vision. They are whatever makes us stop and ask ‘What if…?’ ‘Does that have to be true?’ ‘What if it weren’t?’ They allow us to experiment with the answers, in the process of living a truly examined life.

We’ve seen how ever since Buddha and the Greeks (at least) we’ve known that the Good Life emerges as a result, ultimately, of paying attention to the right things. But as we saw with the flaws in the ‘spotlight’ metaphor of attention, paying attention is ‘less the concentrated snapshot of a spotlight and more a process of continually renewing your interest, and refreshing your intention. It is a tuning in not a concentration on.’[9]

In other words, the Good Life happens not by ‘willing’ it into existence, but as a side-effect of mindfully engaging in other activities… similar to the way Susan Wolf described basketball in the previous section.[10] As Wolf concluded: ‘If we want to live meaningful lives, we cannot try too hard or focus too much on doing so.’ We’ll look more at the importance of side-effect living in the next chapter.


In George Lakoff and Mark Johnson’s landmark book, Metaphors We Live By, they do a wonderful job of explaining the importance of transjectivity in how we live in worlds constructed by language, and specifically metaphor:

What the myths of objectivism and subjectivism both miss is the way we understand the world through our interactions with it. What objectivism misses is the fact understanding, and therefore truth, is necessarily relative to our cultural conceptual systems and that it cannot be framed in any absolute or neutral conceptual system. Objectivism also misses the fact that human conceptual systems are metaphorical in nature and involve an imaginative understanding of one kind of thing in terms of another. What subjectivism specifically misses is that our understanding, even our most imaginative understanding, is given in terms of a conceptual system that is grounded in our successful functioning in our physical and cultural environments.

Which is to say meaning cannot be separated from those that experience it, and the context in which they experience it. That context is constructed by language, and the metaphors that give that language structure – our collective system of understanding one thing in terms of another, for example relationships as journeys (‘it isn’t going anywhere’). Communication, as Lakoff and Johnson wrote, is a participatory, culturally contextual act: ‘sentences do not have inherent, objectively given meanings, and communication cannot be merely the transmission of such meanings.’

The inescapable conclusion of how we exist in a world shaped by metaphor is the same as that that emerges when you really know your relationship with money on all four levels: much as we may treat language, or money, as some sort of isolated, objective, thing that we dip into as necessary to facilitate life, this isn’t how it works. They are part of life: they both express and shape who we are. In the words of Lakoff and Johnson: ‘you cannot function within the environment without changing it or being changed by it.’

The upshot of this is that you cannot improve the role of money in your life by seeking to improve it in some sort of ‘objective’ way.

Rewarding retirement

No one wants to ‘retire’. Discovering the underlying emotional rewards masked by the label of ‘retirement’ can save people from blindly sacrificing sources of meaning

Retirement, we saw earlier, is a terrible goal. [11] But, being both a terrible goal and a popular one, it’s a great example of how a clearer appreciation of underlying emotional rewards can lead to better life choices.

I explored this one day with a client we’ll call Hugh. I’d not met him before, but his adviser of many years graciously let me sit in.

Of all the fascinating facets of the lives of the wealthy folk I’ve known, one question stood out: what kept so many working when they didn’t need to? It wasn’t like these people loved their jobs. Some, it is true, didn’t fully appreciate that they didn’t need to earn another penny from their time, so likely were their investments to earn what they needed for them (though this was still no great excuse to not bother doing the maths). But Hugh, like Nigel we met earlier, was not one of these.

Hugh knew that his insurance business had already provided him with enough savings to live on, before considering its potential sale, his huge pension pot, or even that his death’s-door dad was twice as wealthy again. Each time Hugh came in, however – always a flying visit between the sort of demands on his time he’d allegedly set up a business to be more in control of – he spent most of the meeting complaining about work and all the other things it was preventing him from doing. So why bother continuing? What did work give back that made it worthwhile?

Comparing something to nothing is harder than comparing something to something similar. So for starters, if being self-employed hadn’t provided the anticipated control over his time because the nature of the business meant his clients were still calling the shots, did he still prefer it to being an employee; and if so, what did he prefer the most?

After some stumbling and mumbling indicative of never having asked himself that question, it transpired it was how people treated him when we has the boss. Something about respect and relevance and the other classic stuff that when retirement robs people of it they end up unexpectedly deflated, having been unaware of how much it had filled them up in the first place. Business-minded men and women are great at succession planning to replace what they did for their work, but not for what their work did for them.

‘Is there anything else you do that inspires the same feelings?’ I asked Hugh. He took his time, which wasn’t something that came easily to a chap prepared for a quick update on his investments, not amateur career counselling. To Hugh, he made the money, and we, as far as investments at least, told him what to do with it. It wasn’t the place of someone he’d never met before to ask about his life outside the suit.

Asking such questions is always fraught with rear-view-mirror danger. It’s telling how many respond defensively, as if they are being attacked with the suggestion that they’ve been living the consequences of some poor life choices for the last few decades… even though that suggestion only comes from themselves. This danger only grows when someone’s expecting unqualified praise for their unquestioned “success”. It’s hard for something to feel unquestioned when you’re being asked questions about alternatives.

When I’d asked Hugh how he’d got into his career, how he’d transitioned to going it alone, or his plans for the future, he couldn’t wait to tell me. Yet when I asked him what it continued to add to his life, he reacted, as so many do, as if I’d insulted his mother’s virtue or the way he’d chosen to raise his children… he obviously didn’t care more about the appearance of objective success in his job more than the reality of subjective success in his life… but he did act like it. Why?

‘Actually,’ replied Hugh, ‘I’d not thought about it in those terms, but yes… I get a similar buzz from my role in the hockey club, albeit I wear a tracksuit rather than this thing,’ he said smoothing down his lapels while silently screaming for me to notice the cut.

‘Hockey’s a lot less hassle. Though of course it’s a lot less money too. Are you telling me to quit and become a hockey coach?’

‘Haha. No. Whereas on the one hand, if you are thinking of quitting your job, the science is quite clear that you should, advice that jumps to “quit your job” – as opposed to “ask yourself these questions about your career” – is less advice and more a projection of someone else’s prejudices. Being aware of what it is about a job that you like, what alternative sources you have for those things, and whether the job is, all things considered, still the best use of your time and energy to get them, is far more important than “quit or don’t quit”.’

Just as we’re blinded by salespeople to see the alternatives to one house or holiday being only a different house or a different holiday, we’re blinded by the monetary rewards of a job to the extent that even when we do consider the other ways what we do with the majority of our waking life actually contributes to that life, these considerations are secondary… even when – and sometimes especially when – the money is likely to prove of interest only to the inheritance-tax collector.

Dreams of retirement can turn into nightmares when we view the expenditure of time leading up to retirement in price, rather than value, terms – i.e. when we prioritise the world’s judgment of our time and energy based on its demand and supply over and above our judgment of it, based on whatever needs it is meeting, and how well it’s meeting them. Once again, a fixation on the fixity of price shuts down the very thinking that enables us to make better life choices.

It also makes us forget that we are coalitions of competing and conflicting stories. The importance of seeing our ‘self’ as our centre of narrative gravity[12] lies less in the simple fact that your life is constructed as a story, and more in the fact that your brain is constantly spinning a thousand draft stories, and continually reconstructing and reconfiguring the ‘one’ it settles on each moment as the best representation of ‘who’ ‘you’ ‘are’. Our memories are focused not on the past, but the future: which narrative of past events best sets me up to deal with future ones?[xii]

The point, if there is one, seems to be that fulfilment of potential outranks a mere feeling of fulfilment. Living in price world (whether it relates to what one does to earn money, or how they spend it) is to chase having ‘fulfilment’. Living in value world is to focus instead on becoming what one has the potential to become. To remember this is to stop grasping for the ‘one true path’ – and then becoming so attached to it that it becomes almost impossible to consider alternatives, let alone pursue them, however potentially beneficial it would be to do so.


Work provides many things we want from life, like respect, and relevance, and belonging. But not all work is created equal. Just because work can provide meaning, it doesn’t mean it does, or that one type of work does it as well as the next. The value of a job is a coalition of need-fulfilment opportunities; it’s a complex web of trade-offs made for and by a complex changing human.

The conundrum of retirement is that we’re led to believe retirement (or ‘making working optional’) is a universally desirable long-term goal, but because we view it in numbers terms (because we don’t analyse the coalition) when that goal is ‘won’, all-too-many find that the victory was terribly – and sometimes tragically – Pyrrhic.

Failure to make the most of an opportunity that’s open only to a tiny proportion of people for an even tinier sliver of time is a distinctly first-world problem.[13] However, that doesn’t diminish the value of the analysis. Because ‘retirement’ remains a crappy goal.

The person that discovers how to derive daily Goodness from a means of providing objective value to the world in a way the world is happy to reward them for will always be doing better than a retiree who was blinded by price both on the way up and on the way back down.


When we know what reward we’re really after, we can take a closer look at whether the way we’ve chosen to get it is the best way. Just as it is daft to spend more resources for the same output (be that efficiency of movement, business operations, or living a Good Life), it’s daft to dedicate one’s working time to rewards that could be reaped with a more effective routine.

As Morgan Housel wrote about stuff, but which could apply equally to jobs:

Almost no one actually enjoys flaunting expensive stuff. What they enjoy is the respect and admiration that they assume flaunting expensive stuff will bring them. And they're often wrong about it. Humility may bring you more respect than vanity, but it's so hard to accept that.

A job choice, like an expenditure choice, is a way of shaping and expressing an identity, of meeting a need, of getting an emotional reward; it’s just a more complex one.

page2.2.3.4: Selling style over substance

I hope you found this useful. If you did, sign up to get regular insights in your inbox. If you didn't, sign up to get extra content as redress.

Have something to say? Go here. Witty comments welcomed. Insightful ones win prizes. Reading guaranteed. Replying not.


[1] Part 1, Section 2.2.1.

[2] Part 1, Section 2.1.2.

[3] Recall too ‘How not to buy experiences’ from Part 2, Section 2.1.2.

[4] Part 1, Section 3.3.

[5] As per Part 1, Section 3.4.

[6] Part 1, Section 3.2.

[7] Very deliberate phrasing.

[8] Part 1, Section 2.4, ‘Do you see money through the eyes of a child, an adult, or a sage?’

[9] Part 1, Section 4.4, ‘How does money fit into meditation?’

[10] ‘Even if basketball, removed or abstracted from its now established place in our culture, is not an objectively valuable activity in itself, it provides an opportunity for much that is of value…’

[11] Part 1, Section 1.2.

[12] Part 1, Section 1.2, ‘Who or what is your ‘self’?’

[13] Recall that the typical retirement age has been meaningfully lower than life expectancy for barely a handful of decades, and that the vast majority of people have next to nothing in retirement savings.


[i] Mark Manson, ‘5 Steps to Becoming Insanely, Spectacularly, Wildly Successful… or Whatever’ https://markmanson.net/how-to-be-insanely-successful

[ii] Lavinia Gomez, Object Relations

[iii] Bertrand Russell, The Conquest of Happiness

[iv] Alain de Botton, TED talk https://www.youtube.com/watch?v=MtSE4rglxbY

[v] Rory Sutherland, Alchemy

[vi] Susan Wolf, Meaning in Life and Why it Matters

[vii] Susan Wolf, Meaning in Life and Why it Matters

[viii] Carl Jung, The Undiscovered Self

[ix] H.L. Mencken, On Religion

[x] John Vervaeke, Awakening from the Meaning Crisis, ep. 31

[xi] John Vervaeke, Awakening from the Meaning Crisis, ep. 38

[xii] See Tomaso Vecchi and Daniele Gatti, Memory as Prediction

Last updated