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20 January 2026
“There’s a gap between knowing something intellectually and truly believing it. Visualising your spending, your financial projections, or your mood data can close that gap — making abstract knowledge…
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24 January 2025
Lately I've been using AI to help with goal-setting — working on a "living" document that outlines my goals in a way that feels organic. I've included some prompts you can experiment with yourself.
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5 May 2023
AI can get you 90% or 95% of the way through a project surprisingly quickly. Getting the final stretch — the bit that makes it actually ready — is often harder than everything that came before. It's a…
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4 April 2023
Red herrings are things that distract us from what is really important — a bit like bringing up the upcoming movie Superman vs Voldemort during a conversation that is hitting a lull. When it comes to…
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2 April 2023
I've always said my crystal ball broke sometime in my late teens or early twenties. But right now, that feels more true than usual. The emergence of AI has me genuinely uncertain about what comes next…
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16 September 2022
A follow-up to my 2019 “How I money”, showing how my wife and I actually structure our savings, investments, insurance, and spending three years on. Don’t treat this as a guide — it’s illustrative onl…
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8 July 2022
Hurricane Camille hit in 1969 and narrowly missed New Orleans. When Katrina came in 2005, many who had lived through Camille didn't evacuate — and died. They'd learned the wrong lesson. I worry the qu…
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6 May 2022
The secret isn't living without regrets — it's having the right ones. Most important decisions come down to shades of right, not right versus wrong. Embrace the ragrets.
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11 February 2022
When people are thinking about cancelling or reducing their personal insurances because of short-term cash flow pressure, I try to get them to s-l-o-w the decision down. Step back. Think big picture a…
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18 June 2021
It's easy to think you're either spending money or saving it. In reality, financial decisions rarely fall cleanly into one bucket. Businesses "spend" on wages and tools that are really investments in…
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12 March 2021
The idea that there's one specific right way to invest, or manage your financial affairs, is kind of weird. Yes, I give clients specific recommendations — but that's what I'd do in their shoes. In rea…
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4 December 2020
The word "decide" traces back to Latin — "to cut", or to kill. Every decision kills other options you could have taken. Time is scarce. Money is scarce. Even Bill Gates makes trade-offs. It's trade-of…
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25 September 2020
I'm not naturally frugal. I love spending money and buying stuff. I've never gone overboard with spending. Initially that was because it wasn't really an option. But as time has gone on, I've found my…
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28 August 2020
When an expert speaks, parts of your brain shut down. Be wary of experts, gurus, and idols who present themselves as qualitatively better than the rest of us. There are no Supermonkeys. Just monkeys.…
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21 August 2020
Everyone is different. Even identical twins raised in the same household are pretty different once you get to know them. When you meet someone new, you have NO IDEA about who they are. Two takeaways:…
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14 August 2020
I've watched loads of videos on knife skills. Turns out, advanced knife skills only really matter if you're a professional chopping the same things over and over. For the rest of us, paying attention…
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15 May 2020
Many people think they lack financial literacy when what they really lack is financial confidence. In my experience, with clients and with friends and loved ones, the issue is much more often confiden…
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7 May 2020
April 2020 was the S&P 500's best month in over 30 years — the same month tens of millions of Americans claimed unemployment. How? The sharemarket isn't the economy, and more importantly it's a predic…
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21 April 2020
Niceness does not equal goodness. Gavin de Becker's line has stuck with me. How often do we trust people on a gut read of "nice" or "credible"? Con-artists and psychopaths tend to be charming — that's…
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14 April 2020
When we look at our expenditure, it's easy to mix up day-to-day costs with capital expenses. It's common to make this distinction in business (Opex versus Capex) but it's valuable when it comes to our…
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14 February 2020
If you engage a financial adviser, you might think the decision will leave you better off financially. Not necessarily. I often encourage clients to spend more, or point out they can afford to earn le…
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24 January 2020
Money is emotional, and rarely talked about candidly — which is a recipe for disaster. Borrowing from the sex-positivity frame: who cares what's "normal"? If someone's spending gives them pleasure, do…
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13 December 2019
A personal allegory. On the surface it's about my long-running desire to own a Porsche Cayman. Underneath it's about having a clear-eyed perspective on your goals — the real, annualised cost of the th…
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29 November 2019
When it comes to the things that really matter, focus on what you can control. Checking your KiwiSaver balance every week isn't one of them — and yes, I'm a hypocrite about this when it comes to Trump…
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1 November 2019
Ethical investing sounds simple: invest in line with your values. In practice it's a minefield. What counts as ethical varies wildly from person to person, the labels on funds often don't mean what yo…
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25 October 2019
Ethics in the abstract makes people roll their eyes, but "what's the right thing to do" is one of the most engaging conversations you can have. What often gets overlooked in Ethics 101 is how much sit…
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11 October 2019
I love books that swing for the fences. The Last Safe Investment is one — a personal development book with a strong financial focus. I disagree with chunks of it, and the authors strawman mainstream a…
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12 July 2019
I have clients worth tens of thousands of dollars, and clients worth tens of millions of dollars. I find it much easier to advise clients with millions rather than thousands. As a general rule, the we…
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28 June 2019
The most valuable thing I do as a financial adviser isn't running numbers. It's having conversations. The right questions uncover what a client actually cares about, which is usually the hardest and m…
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19 April 2019
"To be happy, buy experiences, not things." It's a compelling slogan and I've repeated it myself. But the more I think about it, the more I question it. Experiences aren't all equally rewarding, and s…
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22 February 2019
Warren Buffett is endlessly quoted about investing, but his most important lesson isn't about money. In a 2001 speech at the University of Georgia he said you measure success in life by how many of th…
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15 February 2019
My son is starting to get into video games. In many games, you can choose between "easy mode" and "hard mode". Sometimes I think we unnecessarily put our lives on hard mode, when we'd lead much more m…
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14 September 2018
Paying off the mortgage ASAP is usually the smartest move — a guaranteed, tax-free, risk-free return. But I often recommend clients also put some excess income into investments: it builds liquid asset…
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3 September 2018
A friend's cancer diagnosis sent me back to Stephen Jay Gould's essay on being told his own disease had a median survival of eight months. Most people would read that as "I'll be dead in eight months"…
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13 August 2018
Geoffrey Miller's book *Spent* has probably saved me thousands of dollars. Its central point — "the fundamental consumerist delusion" — is that other people care less about the products we display tha…
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11 April 2018
How do people respond when the unthinkable happens? How should we respond? Amanda Ripley's terrific book The Unthinkable looks at extreme circumstances and how people actually act — with guidance for…
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8 February 2018
The NZ news media keeps warning of "frightening" long-term consequences when people use KiwiSaver to buy a first home. This is a false dilemma. Owning a mortgage-free home by retirement is one of the…
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26 September 2017
Innovation doesn't need to be revolutionary or technological. When people think "innovation" they think iPhones — but iterative change counts, and so does doing things differently. I'm allergic to bus…
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7 August 2017
Approaching 20, I asked myself a stark question: would I rather have $1 billion in the bank, or a fantastic relationship with a fantastic woman? The answer reshaped my priorities. I spent years workin…
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17 June 2017
My wife and I own a wonderful house. We could have bought one for half the cost, halved the mortgage, and been financially independent years earlier. We made the decision with open eyes — we were prep…
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11 June 2017
We can organise our lives to make good luck more likely and bad luck less costly. Invert the standard risk-management moves — eliminate, reduce, transfer, retain — and you get a framework for opportun…
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15 May 2017
Many people don't think they have a financial plan. They're wrong. Even without clear goals or articulated strategy, you're acting as if you have one — maybe spending more than you earn, maybe skippin…
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5 May 2017
Money can buy happiness — we're just usually bad at spending it in ways that deliver. There's research identifying eight principles for spending in ways that actually make you happier: buy experiences…
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12 April 2017
In most of life, the best things go to those who hustle. Spend more, get more. Investing is the inversion: the riches go to those who wait, and performance and fees are inversely related. You’re rewar…
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9 April 2017
Next time you're facing a decision with uncertain outcomes, imagine 100 versions of yourself splitting into parallel universes. Which decision leads to good outcomes across the widest slice of them?
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27 March 2017
If you pick stocks, you aren't playing in a Little League. You're playing against the best full-time professionals in the world — the equivalent of stepping onto a tennis court with Federer, or a rugb…
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1 August 2016
I'm both attracted and repelled by the self-improvement genre. We should get better at things as we go through life — but a lot of the popular stuff astonishes me. Puett and Gross-Loh offer a useful c…
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24 January 2016
Paul Graham, having sold a startup and become wealthy, started paying attention to how fortunes are actually lost. Not through excessive expenditure — it’s hard to blow a fortune on luxuries without n…
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23 January 2016
It's easy to think of ourselves and others as moral or ethical people — as if it's an internal trait, largely independent of context. But what if circumstances play a significant role in our actions a…
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9 September 2015
The things most likely to kill us aren't swashbuckling. Turbulence and close calls get the heart racing, but heart disease is the leading cause of death — and the risks driving it are sitting on the c…
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23 July 2015
One of the best ways of knowing whether you'll enjoy something is to look to the experience of others. There's a difference between wanting something and enjoying it. Take supercars. I fully empathise…
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14 July 2015
Ask most educated people what the leading cause of death is in a developed country and they'll say heart disease. But a provocative Ralph Keeney paper reframes this: the real leading cause of death is…
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18 February 2015
Some rules I've cultivated over the years for dressing better while spending less time and money on clothes. Focus on fit and colour, not fabric or style. When something works, buy multiples. Orient y…
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16 December 2014
The world we live in was not inevitable. But it can feel like it is. One of the ways I like to draw attention to this is by looking at movies that could have been cast very differently — Cary Grant as…
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4 December 2014
David Myers' Intuition: Its Powers and Perils shaped how I think about probability. Big hearts and hard heads can come wrapped in the same skin — being wise means asking to see the numbers, even when…
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15 May 2010
My favourite chapter of Michael Lewis' Moneyball is "Field of Ignorance", where Bill James points out that you cannot tell a .300 hitter from a .275 hitter by watching — the difference is one hit ever…
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2 May 2007
Daniel Gilbert hasn't written a prescription for how to be happy. He's written a description of the psychological stumbling blocks we face in pursuing it. We're unique among animals in our ability to…