Do you have enough money already?

Posted by TEBI on July 18, 2023

Do you have enough money already?
Robin writes:

Have you considered whether you might now have enough money — so you can afford to move from earning for the future to enjoying the future? If so, what might that future involve? Is it about the absence of work, or do you want to move to different and more meaningful work?

If you’re one of those people, then our new podcast series, Second Lives, presented by JONATHAN HOLLOW, is specifically designed for you. In the first episode. Jonathan spoke to author Andrew Hallam about the pursuit of happiness and how to lead the life you really want, and to Alex Davis, who worked for many years in a family business, then decided, in her 40s, to go to university and study ancient history and literature. In the third episode, he talks to BRIAN PORTNOY, an expert on the psychology of contentment and wealth. 

Brian has so many interesting things to say about the difference between riches and wealth, and the dividing line between fear and aspiration, that he will provide ample food for thought for anyone considering a change of direction.


TEBI would like to thank the London-based financial planning firm Mulberry Bow for collaborating with us on this series.
As well as Spotify, you’ll find The TEBI Podcast on all the major podcast platforms, including





Episode 42: How to follow your dreams in your 40s

Episode 41: How to live a life of purpose



The transcript below has been lightly edited for clarity and length.

Please note, the copyright on this interview belongs to The Evidence-Based Investor. If you wish to quote any of it, you are required to attribute it to TEBI. We also request that you include a hyperlink to this article. We regularly monitor the internet for breaches of copyright, and any such infringements are dealt with appropriately.


Jonathan Hollow: You said to me that you are on, I think, your fifth career, and you described your life as a series of midlife crises. One of your crises gave birth to your first book, ‘The Investor’s Paradox’. So tell me about that switch. 

Brian Portnoy: Yeah, sure. Thirty-plus years ago, I started my career in politics. Then I decided to go to graduate school and do a doctorate in politics and economics. I decided not to be a professor; I decided to go into investments and finance and, over the course of close to 15 years, did investment research, managed portfolios, worked with clients, did due diligence on complex investments, a variety of different things.

And you know, there was a moment in 2010, 2011 or so – I think it really was a midlife crisis. Like .. what the hell am I doing with my life? I wasn’t particularly happy in the job that I was at for whatever the specific reasons were at the time. And you know, I just began to write and journal and think and talk to friends. At the time I was probably right around 40 years old – give or take – and part of that journey was just beginning to read somewhat randomly in the psychology literature, the psychology of money. Some pretty big light bulbs went off: oh, okay, here’s depth that I hadn’t fully appreciated on the way we are wired, how our minds work, how we get along with others, how we make decisions. I enjoyed that so much that I began to write a book. I published a book in 2014 called ‘The Investor’s Paradox’. 

There’s something in social psychology known as the paradox of choice, which says that we very much cherish or love the choices that we have in life because it’s indicative of us having freedom and opportunity, and things that are very meaningful.

But at the same time – in modern society, we have so many choices across so many domains. It could be very overwhelming to the point where it is depressing – clinically depressing. To the extent that any of the listeners are like, “Yeah, some days I just feel overwhelmed with how much stuff there is.” 

It was a book about becoming rich. It was about making better decisions, so that you could have more money. It wasn’t until my second book that I went broader and deeper on rich versus wealthy, and what it means to be wealthy as distinct from rich

Jonathan Hollow: And that’s why you say ‘The Investor’s Paradox’ was the right book, but in the wrong order – because you started at the tactics end, rather than the reasons and purposes end.

Brian Portnoy: Yeah, I joke that ‘The Geometry of Wealth’ is a prequel to ‘The Investor’s Paradox’. But I couldn’t have written that book – I couldn’t have written ‘The Geometry of Wealth’ until I chopped the wood I needed to in ‘The Investor’s Paradox’: coming to terms with the relatively narrow topic of decision making and cognitive science, and how we sort through all of the noise. 

Hardly a narrow topic, but it’s not as broad as the question: what is the good life? 

So yeah, by the time I got to the final chapter – both figuratively and literally – of ‘The Investor’s Paradox’; I just began to ask myself, who the hell cares? Investing, for the most part, is a solved problem. Most people, most of the time, should not struggle on how to build the right portfolio for their purposes, which isn’t to say that people don’t make mistakes and advisers don’t put adviser clients into the wrong portfolios. That’s a kind of a separate conversation – as the line goes, simple doesn’t mean easy.

Jonathan Hollow: You run a platform called Shaping Wealth. It’s really been built up from the impact of a phrase, from ‘The Geometry of Wealth’, and that phrase is “funded contentment”. You say that funded contentment is true wealth, and you contrast it with being merely rich. 

Brian Portnoy: So, rich versus wealthy … as I think about it, rich is a number. Rich is a search for more. 

It’s something that’s quantifiable. So if you have a million dollars and then you have $2 million, you’ve become richer. But you haven’t necessarily become wealthier. So this idea of funded contentment is true wealth, or as I define it, the ability to underwrite a life that is meaningful to you

And so the book takes deep thinking about a life well lived, and then introduces the money piece to it. Can you underwrite that life that you want? Can you afford a meaningful life? It’s a little bit of an awkward question. 

But that is “wealthy”, to me. 

And I think that, for most of us, who thankfully have a roof over our heads and food on the table and live safely – that search for wealth is ever present and ongoing.

Jonathan Hollow: You train financial advisers from all over the world through this platform in the psychology of money, and more importantly in the evidence and the elements of a happy life. How radical is your thinking compared to the backdrop of technical qualifications that advisers are used to? 

Brian Portnoy: I wouldn’t call it radical. It fills out the whole. I mean, if we take a step back, and we just think about the financial planning profession over the last generation – there’s been a pretty dramatic transformation from this being a transactions-oriented business, to a relationships-oriented business. 

Along the way, there are a lot of technical skills on the planning side – not just on building the right portfolios, but engaging with the right types of insurance, structuring estates in ways that are appropriate, tax optimisation, legacy planning. There’s a whole variety of what I would consider “technical” skills that are designed towards solving engineering problems.

But they don’t in any way touch on the deeper things that we tend to desire when it comes to our lives generally, and our money lives specifically. 

So, the platform that I started a few years ago – well, the book that I wrote, ‘The Geometry of Wealth’, and then the platform that it inspired – are really designed to help advisers and advisory platforms engage the other half of their brain. So if we’ve got these left-brain quantitative, analytic engineering problems; well, we also have right-brain challenges – with understanding ourselves, understanding others, building deep relationships, helping others. 

We now have decades’ worth of insight from behavioural science on how to communicate better, how to listen better, how to engage people more deeply – and so we’re bringing that to bear. 

Jonathan Hollow: And what kind of forces are drawing people towards that service that you offer?

Brian Portnoy: In some ways ChatGPT is the best thing that could have happened to my business. I mean, it sort of came out of the blue, right? Not AI. AI’s been around since the late 1940s. But ChatGPT and some of these easy-to-access AI engines now have everybody wondering, “Huh! I, as a knowledge worker … can I be outsourced? What does it mean to show up as a real human being and not as a robot?” 

And so we’re seeing just a ton of interest in humans becoming even more human … whatever that might mean. 

Jonathan Hollow: How much does the evidence about happiness or its application differ across the world? 

Brian Portnoy: I don’t think it differs at all. I think people are people. 

That’s not to say that there aren’t different cultural attitudes and approaches towards something called happiness; but the model that I put forth in ‘The Geometry of Wealth’ (and, you know, there’s an old line that all models are wrong, but some are useful), I think the model that I put forth in the book, and what we now leverage from a training point of view, is very useful. 

I talk, in some detail – my team coaches in some detail – on the four sources of deep contentment. What I call the four Cs: connection, control, competence, and context. So: what really matters to us – and it doesn’t matter if you are in the UK, or in the US, or in Argentina, or in New Zealand – these are universal. They are timeless. 

Jonathan Hollow: Connection, control, competence, and context. These are the elements of your theory of happiness, I suppose, and central to ‘The Geometry of Wealth’. 

Set them out for us. 

Brian Portnoy: Number one: connection. Our sense of belonging, belonging to a group, sort of our deep tribal nature defines who we are. This is the way that we’re born. 

At the same time, we value control or autonomy. We want freedom, liberty, we want to be able to do what we want. We want to be able to determine our own destiny, and tell our own story. 

The third c: competence is finding meaning in the things that you do – so, when you go to a party and you meet somebody new and they say, “Well, what do you do?” … spoiler alert, they don’t care what you do! They just want a window into who you are. Our work, to some extent, defines us. 

So with connection, control, competence; the fourth c is context. This is the idea that we want to be attached to a broader context, to a broader sense of purpose and – historically – that has been faith or place. 

And not just religion per se, but spirituality. We all have one story or another that connects us to the cosmos of where we fit into this vast and incomprehensible, to some extent, universe of ours. And then secondly, whether it’s our patriotism or our hometown pride, many of us are very much defined by where we come from.

Last thing I’ll say here – we could certainly go into whatever detail you want – on the country by country front; I just want to make a distinction between a happy life and a meaningful life. We’re talking about a meaningful life. 

Jonathan Hollow: And you call that “reflective happiness”.

Brian Portnoy: When we talk about reflective happiness, that deeper sense that life is good, it is attached to a reflective sense of, “Okay, those, those four things are important … and they are going well or not well.” 

It’s not a scorecard. The idea isn’t that each is on a scale from one to 10 and, if you could score a 40, you’re leading a super meaningful life. 

It doesn’t work that way.

In fact, part of the coaching exercises that we do with advisers, who in turn use this with their clients, is to write your life story, through the lens of those four sources of contentment.

Jonathan Hollow: So going back to ‘The Geometry of Wealth’, we talked about the four Cs that you linked to purpose, and then there’s a section on setting priorities. 

You started setting priorities with protection, and I get the impression you think this is really quite deep-rooted in our evolutionary origins. 

Yet I think a lot of people would start with aspiration or ambition.

Brian Portnoy: What I call – and probably others call – the “evolutionary two-step” is just the idea that we want to survive and then thrive.

Our job is to survive. What our genes are here to do is to propagate, and they can’t propagate if we are dead. 

So our number one instinct that has been wired into us over millions and millions of years of evolution is to stay alive. It is not to achieve. It is not to reach goals. It’s not to have a great time. It’s not to go out with your friends. It is to stay alive so that you can move forward and your genes can move forward. 

We only get one ticket for the ride, so on any given day, you have to survive, but you don’t necessarily have to thrive. And this isn’t sort of a one-stop thing, it’s a never-ending thing every day. 

We are incredibly sensitively hardwired, so precisely to perceive danger around us. Physical danger, but also psychological danger. The psychological danger is not something unimportant or ephemeral. I’m sitting comfortably in my home office, as are you. I doubt either of us is feeling physically endangered. I hope not! I feel okay. You seem fine?

Jonathan Hollow: No, I’m good!

Brian Portnoy: You good? Okay. Good, good! We’re good!

But then the psychological safety piece is also critical. We don’t want to feel emotionally unstable or threatened or captured in some way. We are always taking stock of our environment and sussing out whether there’s any sort of danger. It’s only on the back of that that we really can and want to think about thriving, and aspiration, and achieving our goals, and living the good life. 

When you attach all of this to the financial planning process, it means that job one – absolutely, job one – is: make sure that you’re okay. 

I’ve met tens of thousands of end investors over the years; the number one question that you get in one way or another is, “Am I going to be okay? Are my loved ones going to be okay?” Not, “How do I afford the next Ferrari, or go on the next luxury vacation?”, or anything like that. Deep down, we are wired to constantly ask the question: am I going to be okay? 

And so, through the lens of planning, that is making sure that we have satisfied our basic needs. It is making sure that maybe we have a little extra cash in the bank in the event of emergencies. It makes sure that we have thought about insurance in a general and constructive way. 

Jonathan Hollow: A lot of the times when you read books on behavioural finance, people will be saying that loss aversion is a psychological trap that you need to – at times and places – overcome, in order to succeed. 

Brian Portnoy: Well, there’s just a very straightforward logic that comes out of evolutionary psychology, which is that if gains were more pleasurable than losses were painful, we would be taking excessive risk – and the future of the species would be imperilled. 

It’s the opposite. We take care of ourselves, we protect ourselves – losses are much more painful, and so we go out of our way to anticipate and avoid those losses, and when the losses happen, we do what we can to mitigate their damage. And then the good stuff comes later. 

So I would say that loss aversion is an absolute centrepiece of what defines being human. 

Jonathan Hollow: Another couple of themes that really interested me in the later parts of ‘The Geometry of Wealth’ were your focus on adaptation, and also creative destruction.

Brian Portnoy: What happens in any capitalist industry is that someone builds something, they sell it for a profit, other people see those profits, and they jump into the fray and try to do something better, or cheaper, or different. 

And change is inevitable. 

I grew up in Pittsburgh, Pennsylvania – the seat of heavy steel manufacturing for a century; and at a certain point, the industry disappeared and a lot of people lost their careers forever. In its wake, Pittsburgh has become a global hub for artificial intelligence and robotics and medical technology. This is the nature of change. Capitalism destroys everything in its wake over time and things replace it. That’s not to say that everyone gets retrained, from a steel worker to an expert in robotics – it doesn’t work that way. There are lots of losers in the process.

But this idea of creative destruction is that the world happens, things change, and we have to respond or we can respond if we want. So that’s the connection in your question between creative destruction and adaptation. The world is predictably unpredictable, and we need to assess the situation we’re in and decide to go left, right, up, down, forwards, backwards in order to survive. 

Jonathan Hollow: The other thing that the later part of the book made me think about is a favourite little anecdote of mine about the writer Joseph Heller, who wrote a novel called ‘Catch-22’. 

It made a lot of money, it made him a lot of esteem, and one day he and his friend, the writer Kurt Vonnegut, were at a party given by a billionaire. 

Vonnegut said to Heller, “Did you know that our host, who is a hedge fund manager, has made more money in a single day than you ever made from Catch-22 since it was published a few decades ago?” 

And Heller replied, “Yes, but I have something he will never have.” 

Vonnegut said, “What on earth could that be, Joe?” 

And Heller replied, “Enough“.

Brian Portnoy: This is the topic on many people’s minds. After 12, 14 years of being in the wealth management space now and just listening to what people are asking, trying to figure out what they care about, there’s really two questions that are on people’s minds: 

Number one: am I going to be okay? 

And number two: how much is enough? 

From a genetic wiring point of view, we’ve got this little neurotransmitter in our brain that sloshes around called dopamine. There’s a really good book called ‘The Molecule of More’ … we’re hardwired to want more. 

We’ve talked a lot about survival; now let’s talk about thriving. We are goal-oriented: the psychology of goals and goals formation teaches us that a life without goals is kind of an empty, not fun life. So we’re always striving towards something, whether it be in the moment or over a multi-decade view – we’re all pushing towards something. And where the dopamine comes in is that the anticipation of achieving that goal floods our little noggins with this chemical bath: “Oh, it feels kind of good. I’m about to achieve that and I’m moving toward the goal. I’m going to win the game, I’m going to get the promotion, I’m going to date that attractive man or woman. I’m going to do the things that I want to do,” 

But then we have another psychological principle called hedonic adaptation (why not throw some more jargon into the mix?!). We have this thing called hedonic adaptation: there’s enough dopamine to make us feel good about striving toward this goal but, when we achieve it, the pleasant feeling more or less disappears relatively quickly.

We could talk about it all day long. We could understand the science and history of it all – but the fact is that we’re not very good at assessing how good we’re going to feel when we achieve that goal. And usually the intensity and duration of that good feeling is much less than what we think it’s going to be. 

There’s an evolutionary argument for why that’s true, which is that – if the reward was so overwhelmingly good – we wouldn’t be pushing for more. So our bodies are actually built in a way that we are chronically disappointed. 

At Shaping Wealth, we do a whole coaching program on sort of thinking through what is enough. 

But I do like to anchor it on the genetic and the evolutionary. 

I think it allows us to show ourselves a little bit of grace because, you know, I’m comfortable, you’re comfortable, everybody listening to this podcast, I’m sure, is quite comfortable – in the grand historic sense. They’re not living in abject poverty. But we still struggle: with wanting that next thing, wanting to move forward – getting the things that we want, but not being as happy as we thought we’d be once we achieved it.

Jonathan Hollow: I like to ask all my guests about how they planned for their current success. And you have an interesting metaphor for your own life planning process, because you talk about firing the arrows first, then drawing the bullseyes around them. Can you expand on that? 

Brian Portnoy: Yeah, I don’t know what the hell I’m doing. I never have, I don’t think I ever fully will! We’re shooting arrows and we don’t know where they’re necessarily going to go. We don’t always know where we want them to go. We venture forth and, “Hmm, let’s see how this works out.” Well, you know, sometimes you shoot that arrow and you’re like, “Hey, I ended up in a good place.” 

Well, then you paint the bullseye afterwards. “Hey, look! I nailed it! I wrote a bestselling book that’s translated into a bunch of languages – I achieved my goal!”

Was that really my goal? No, not really, but I can certainly tell a story about how I hit the bullseye.

Jonathan Hollow: And do you personally feel like you fire a lot of arrows? Or do you suddenly swerve from one direction to another, through instinct? 

Brian Portnoy: That’s a good question. I haven’t thought about that. 

I’ve shot a lot of arrows, in the sense that I am on my fifth career. As I mentioned earlier: politics, then academia, then investing, then writing, now I’m an entrepreneur. There’s a through line. I mean, there is a bullseye that I’ve painted – so I can tell a very coherent story, but it’s a coherent story looking backwards. 

On a going forward basis, it makes absolutely no sense. I might look like an idiot. It’s like, okay, one thing after another. 

At the same time, there are people who take on a job at age 22, and, at age 62, they’re still in that same vocation and they’ve had a great time and they’ve had success and they’ve made great money, and they have a sense of accomplishment. There’s no one right way to do this. 

So I think, relative to others, I’ve shot a lot more arrows because at each step along the way, I’ve said, “Okay, great, I think I hit that bullseye, but now I want the next archery tournament. I’m going to move on.” So, I got a PhD from the University of Chicago – it’s not a small accomplishment. I got the doctorate and I quit. And I moved on to a low paying job at a local investment firm. Why? Because I wanted to do the next thing. I didn’t want to do what I was on the path toward doing. Even at the time, but certainly in retrospect, I’m very proud of that. Because I gained the courage to make a decision that some people thought was insane. 

But I knew instinctively that it might be a good path for me. 

I’m thinking out loud about this question … I actually think I’ve shot a lot of arrows, and I still am because, in my early fifties, I started my own company for the first time and it’s like – boy, I don’t know – this is sort of a young man’s game! But here I am and, okay, we’ll see how it goes. Maybe we’ll get back on the horn in a year or three, and I can tell you about the bullseye I’ve painted. 

Jonathan Hollow: Thank you. I’d love to do that. And thank you for your candour. I think it’s an inspiration, actually. 

Brian Portnoy: I don’t like bulshitting people. It’s like, let’s talk about what we’re really talking about, or let’s not talk at all. I don’t really have time for the nonsense. 

Jonathan Hollow: Well, before we go, I will link to ‘The Geometry of Wealth’ in the podcast notes, but could you just give listeners a final little summary of what you think the book can do for them? 

Brian Portnoy: Yeah. So I can just relay what others have shared with me, which is that it has facilitated much more productive thinking in one’s own head, but also many more productive conversations with loved ones about what a truly wealthy life looks like – and how you might go about achieving it. 



How to Fund the Life You Want by TEBI founder Robin Powell and Jonathan Hollow is published by Bloomsbury. It was unanimously adjudged Work and Life Book of the Year at the Business Book Awards 2023. Although primarily aimed at a UK audience, it contains valuable lessons for readers everywhere.

Buy the book here on Amazon, or, if your prefer, here on


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