#44: A story of lions and loss

19th July, 2021

Welcome to the Idiot Money newsletter. The newsletter that YOLOs, but not like that.

This week: becoming wiser with money by understanding that living in the future is an oxymoron.

You only live once. And sometimes not even that. Remembering this should be a spark to living more consciously, not less.

Of all the clients I ever worked with, one will always have a special place in my heart.


This week’s newsletter is dedicated to him. It’s a sad tale, in more ways than one. I hope that by sharing it, it helps you, or someone you know, sidestep potential sadness of your own.

Choose chuckling

Always engaged. Usually double-breasted. Never late. Roger and his indomitable smile lit up every meeting room and dining room they entered.

Where other clients chuntered away about the injustices of the world (despite being among the richest people to ever have lived in it), Roger chuckled.

Where other clients chose to worry, Roger figured it made more sense not to.

Yes, he’d studied hard, worked hard, and taken the risk of setting up his own firm, for which he’d been rewarded with more than just money. But he knew others had studied, worked, and risked way more, and not got nearly as lucky… Lucky in location, timing, intelligence, relationships, and so on.

He knew it wasn’t the making, but the making the most of, that counted.

Like most clients, Roger wasn’t inherently interested in the intricacies of the investment stuff. That’s part of why he and Maggie had hired someone to deal with it.

But he was smart enough to know that getting over the initial inertia was a great way to leverage the investment he’d made in this advice, to derive greater comfort and confidence than could be got by hoping delegation was the end of confusion, rather than the beginning of understanding.

Besides, it wasn’t like he needed to engage with more than the two basic processes that controlled the flow of lifestyle funding – the investment and withdrawal strategies that helped him and Maggie make the most of their money.

Once in a lifetime

Roger and Maggie aren’t gazilionnaires. They’re not going to be taking a holiday to the moon any time soon. But they’re just as far from the gutter.

A common retired-client scenario is to ask about ‘objectives’ or ‘goals’ and get a typical ‘oh, you know, tick along, continue with our current lifestyles’ as an answer, with maybe a ‘fund the grandchildren’s education’ thrown in here and there.

Ask a silly question, get an unusable answer.

‘Is there anything you’ve dreamed of for so long that you can be pretty sure it’s more than just a passing fancy, or a convenient way to bat away awkward on-the-spot questions about “goals”?’

‘Perhaps something that you’re confident would make the sort of memories that outlive you, but that you haven’t done yet because it feels more like an idle dream rather than an actively possible part of your and other people’s future reality?’

For Roger, the thing he thought would make the most magnificent memories was going on a Lions tour with his sons. New Zealand, Australia, or South Africa, it didn’t matter which. Fly over in comfort. Stay somewhere fun. Go to all the games. By any measure, a better use of the money than the boys inheriting the cash later on.

He lit up just describing it.

Okay… so how much would this cost?

Roger didn’t know. He’d never done the calcs. It was just a dream.

Well, let’s see… the meeting rooms have Internet access…

The next one is in New Zealand (this was about 2015)… business-class flights to New Zealand… hotel rooms for a month… plus a month’s worth of eating, drinking, and bungee-jumping…

You can 100% afford it. Barely a blip on the cash-flow-planning radar.

By the time the New Zealand tour happens you’ll be 77. So realistically you’ve got that, maybe South Africa in 2021, maaaaaaybe Australia in 2025.

So which one will it be?

A lifetime, once

After leaving the world of face-to-face advice, I kept in touch with Roger. Not least because he’s the reason I’m a member of the MCC, and I think about him every time I gambol through the Grace Gate.

I’d often accompany such thoughts by sending a message to thank him.

He always replied.

Or at least he used to.

When one time he didn’t, I asked my old boss – still Roger and Maggie’s adviser – if something were up.

It was.


Did he ever make it out to see the Lions with his boys?

He didn’t.

Are you making immortal memories, or building a live-in mausoleum?

Maybe it won’t be dementia. But something will happen. Heck, such is the current state of the world that the 2021 Lions tour is partway through and they still don’t know if it’s actually on or not.

Opportunities, potential, life… their impermanence is the source of their value, not something to try to remove, be it through hoarding, believing happiness comes from having rather than becoming, or pretending life is lived tomorrow.

And no matter how hard we believe in the pot of gold at the end of the certainty rainbow, the only thing we get by waiting for it to magically appear is decay.

I share Roger’s story not as a wordy substitute for a motivational poster telling you to ‘seize the day’.

You can hypercorrectively leap into YOLO land if you want, of course.

Though it strikes me that if you only live once, then the thing to do is to take more conscious care over your decisions, not less. Remembering, naturally, that conscious care does not mean ‘abundance of caution’.

Equating YOLO with ‘don’t think, just do’ only works in a world where we’re so terrified of thinking through what we really want to do with our lives, that we’re sometimes better off not thinking. Frightened humans gonna make frightful decisions.

It’s undoubtedly true that we regret more what we didn’t do than what we did.

But we often regret what we did too.

We never regret doing what we deep down know we want to do. Regardless of the result.

It’s all too easy to live the high life in a very low mood

Many people believe – for reasons related more to the language their parents used than the size of their bank balance – that they can’t afford things, and deny themselves the realisation of their dreams because of it.

It’s one of the great roles of the financial adviser to persuade them that they can, and hopefully rewrite the unhelpful underlying story in the process.

But there’s a danger here too.

Because ‘buy stuff that makes your life better’ has a strange way of morphing into ‘the way to make your life as good as possible is to aim to spend your last penny on your last day.’ Which is about as idiotic a take on the value of money in a life as it’s possible to have.

Yet proffer this pseudo-profundity to people (and I’ve seen it plenty, especially in a financial-planning context) and they’ll probably nod along in agreement.

I don’t know if you’ve suggested to many people that they spend their money only on things that make their life better. The reaction is rather different.

As I wrote in the very first newsletter, when unpicking Socrates’ assertion that the unexamined life is not worth living:

Socrates is saying that he would rather die than live a life governed by self-deception. He is on trial for seeking wisdom, for trying to understand what is real and living in alignment with it; for seeking to establish a rational basis for what to care about, and what to do. For seeking to express his authentic soul through his societal self.

Aligning what we do with what we (deep down, undistracted and undeceived) care about, rather than with what unreal deceptive influences tell us to care about, is what joins up having resources with living a good life.

It was so important to Socrates that he rather died than be prevented from doing it. So should it be for the rest of us. There’s bugger-all benefit in being rich if you use those riches in a miserably misaligned manner.

If you’re driven by what you can afford, rather than what you care about, you’ll be taken for a ride to places you don’t care to go. And at some point, it’ll be too late to turn around.

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