[#13] The Other Retirement Crisis

Nobody wants to talk about the other retirement crisis. Not really.

It’s one that just about everyone my age feels but never quite names.

Me? Late fifties. And although it’s been well over three decades now that I’ve been helping successful people navigate the financial dimensions of a long life, it’s only been somewhere in the last several years — I cannot pinpoint exactly when — something shifted in how I understood the work I was doing.

It didn’t arrive as an epiphany.

It sort of grew as a feeling that I sort of started to notice from time to time. I realise now that this is the same feeling I recognise in almost every serious conversation I have with clients in their fifties and sixties.

And it’s this: time isn’t the abstract concept it once was.

Perhaps you’re starting to notice it too? You see it first in the people around you — friends, colleagues, people you have known for decades — who are beginning to carry their own quiet troubles: health scares, marriages under strain, children in difficulty, careers that have peaked or stalled.

That the moments you value — really value, the ones spent with people you love or doing things that genuinely matter — are more fleeting than you once assumed, and that you have been too busy to fully inhabit them.

With age comes something that younger people do not yet have and cannot quite be told: a ruthless, lived clarity about what actually matters. And with it, a growing impatience for everything that does not.

Unnecessary noise. Conceit. Time wasters and their win-at-all-costs ambition. And the low-grade duplicity that passes for normal in professional life.

In case you’re worrying that you’re becoming old and cynical, let me offer you a counter-point: perhaps some clarity has arisen, too. There is not enough time left for pretence. There is barely enough for what is real.

Consider this …

You and I each have 168 hours a week. That is the whole of it — for everyone, regardless of wealth, status, or ambition. When you subtract what you must do — sleep, eat, commute, the ten thousand little things that keep a life functioning — you are left with somewhere between 50 and 70 hours. Call it 60.

Sixty hours a week that are genuinely yours. These sixty determine, more than anything else, the experienced quality of your life.

Not your net worth. Not your career achievements. Not the portfolio’s performance last quarter. These might be smile moments, for sure, but the quality of your life is held in those 60 hours.

The question that has quietly reorganised everything for me — professionally and personally — is this: what are you doing with them?

If you are spending them doing low priority, low payoff, low value activities then that is the lived experience of your days, week in, week out.

If you are spending the bulk of them engaged in activities you truly value, causes you believe deeply in, endeavours you’re passionate about, with people you care about … that will be your lived experience.

Being very clear on what’s important is crucial, and that’s particularly so when it comes to money.

So here’s a mental audit: if you habitually ‘invest’ time in financial management activities that someone more qualified, better connected, properly equipped could do for you – and do better -- someone utterly reliable who you can genuinely trust … then you are not making a financial decision. You are making a life decision. And the cost is not measured in basis points. It is measured in the hours themselves.

———

I want to introduce you to two people. I have changed one of the names, the other told me not to bother.

So meet David.

David recently had a health scare that had, in his words, “rearranged his priorities somewhat.” He was 58. Materially comfortable, professionally respected, and quietly uncertain about his new planning horizon.

The health event had done something specific to his sense of time. He had revised his life expectancy downward — sharply, in his own mind — and concluded that his window was shorter than he had assumed. He should plan accordingly.

When I gently challenged this —what if he spends big now in the expectation of not making it into his 70s … and it turns out he’s wrong? David’s current plan gave him plenty of opportunity to ‘live big’, he had no need to be frugal. But his push back about planning for a longer timeline wasn’t about spending it all, it was more about him feeling like the rug had been pulled out from under, taking a sense of purpose with it.

I have sat with that observation many times since. David was not being irrational. He was protecting himself from a problem that is, in its way, harder than any financial problem I work with.

The gamble is an unnecessary one. If the years don’t come abruptly to an early end – and for our generation and the future we’re all ageing into – they almost certainly will extend longer and better than any previous generation in history — and you have no clear sense of what they are for, the problem has no spreadsheet.

David was not afraid of dying young. He was afraid of living without a properly financed purpose.

Next, let me introduce Chris and Leoni.

Chris and Leoni are, by any conventional measure, doing everything right. They’re both intelligent, well disciplined, and genuinely on top of their game. Their investable net worth recently pipped over into an eight figure sum.

Chris likes spreadsheets. They run into dozens of tabs. The formulas are sophisticated — strong, self-taught, the work of a man who applies serious intellectual effort to serious problems. He collates data obsessively, builds briefing packages, models scenarios, runs projections. He is, in the language of financial self-management, diligent.

And he is, I would gently argue, not optimising his sixty hours.

Not because he is doing a bad job. He is doing it rather well, for an amateur. The question I keep returning to is not whether he can do this. He can. He is!

The question is whether he should.

Don’t get me wrong – I don’t begrudge anyone an activity they find intellectually stimulating and personally satisfying. Fill your boots, great investment.

But Chris and I have spent some time interrogating what’s truly important to him, and financial management simply didn’t come up. What did come up is just how clear he is on the importance of being mentally and physically healthy -- he’s seen first-hand how fragile health can be.

He and Leoni are also very active in their community, real leaders in many respects, because “seeing the difference you can make in the lives of others makes it all worthwhile”. Hear them talk about their efforts in this space is inspiring.

The spreadsheets come at a cost. And at the end of the day, I really think Chris doesn’t do them because he loves them. He does them because he believes he has no choice.

It is not really about the spreadsheets. It is about trust. About the private, unspoken conviction that nobody else will care as much, work as hard, or get it as right as he will. That the person he needs — utterly reliable, completely trustworthy, technically capable, someone who has his back — probably doesn’t exist.

He is not wrong to want that person. He is wrong, I think, to have concluded he or isn’t out there.

And so Chris never quite comes up for air. Never quite steps back far enough to ask the larger question: what is all this financial precision actually in service of? What is the life it is meant to support? What would he do with those hours if he trusted someone else with the work?

He does not yet have an answer. Which means he keeps doing the work himself, because the work, at least, has a clear purpose.

———

I said earlier that something shifted for me. Let me try to be more specific about what it was.

It was not a single moment. It was more like a gradual reprioritisation — of what I noticed, what I valued, what I found I had no patience for anymore. The things that seemed important at 35 and still important at 45 began, somewhere in my fifties, to look different. Smaller, in some cases. Beside the point, in others.

What came into focus instead: simplicity. Clarity. Honesty. The particular quality of trust that exists between people who have known each other long enough to stop performing. Time spent doing things that are genuinely absorbing. Conversations that go somewhere meaningful. The people who, when something goes wrong, you want in the room.

These are not complicated values. They are also, I have found, surprisingly hard to protect. The noise of professional life is loud and constant, and it has a way of filling whatever space you allow it. The 60 hours evaporate if you do not defend them.

What I discovered — what I think Chris eventually discovered, and what David was wise enough to seek out before the question became urgent — is that clarity about the life you are designing is not a luxury you add once the financial plan is settled. It is the foundation the financial plan is built on.

WealthSpan — the capacity of your wealth to support your life across the full arc of the years ahead — cannot be properly calibrated without knowing what life it is meant to serve. The how much follows from the what for. That ordering matters. Most planning gets it backwards.

———

There is something else worth naming. Something specific to the generation five years either side of 60 that makes all of this more urgent than it has ever been.

The retirement our parents experienced is not the one we are heading toward.

They had a mental model of late life as gradual contraction — a slow narrowing of capacity that made the question of purpose somewhat self-resolving. The later years were less demanding because the person living them was less capable.

Living small was inevitable. As were the aches and pains. All towards an endpoint of sitting in front of the tv in your mid-80s, ‘God’s great waiting room’.

That picture is increasingly wrong for us.

The world we are ageing into — shaped by advances in medicine, diagnostics, geroscience, and preventive care that have no historical precedent — is compressing serious decline into a narrower window at the very end of life, while extending the years of genuine vitality well into the early nineties and beyond. The person at 75 today bears little resemblance to the person at 75 a generation ago. And the person at 75 in fifteen years will likely be sharper, more capable, and more physically functional than any previous generation at that age.

This is not speculation. It is the direction of travel.

What it means is that the years after full-time work are not a wind-down. For most people reading this, they are a second life — one that will probably be longer and better than anything their planning frameworks were built to anticipate. The identity question — who will I be, what will I do, what is the life actually for? — is not a soft add-on to the financial plan.

It is the most important question on the table.

And the cost of not answering it is not abstract. It is paid in those 60 hours, week by week, in a life that is busy but not quite inhabited.

———

I want to return to David, because his story has an ending worth sharing.

Over several conversations — some in the office, some less formal — he came to examine the assumption he had quietly made: that a shorter life was easier to plan for because it meant he did not have to answer the larger question.

The larger question, once he was willing to sit with it, turned out to be less frightening than he had imagined. He had always wanted to mentor young people in his industry — not as a consultant billing by the hour, but as someone genuinely invested in their development. He had been thinking, vaguely, about a small foundation. About writing. None of these were grand ambitions. They were specific, personal, and entirely feasible. He had simply never given himself permission to take them seriously while there was still a career to maintain.

The last time I saw him, he was 61. Healthier than his health event had any right to leave him. Still working, but differently — with a clarity about what came next that had made the work itself feel more purposeful, not less.

He no longer planned for 70 as a ceiling. He planned for 90 as a midpoint and structured everything accordingly.

That shift did not come from a revised actuarial table.

It came from having an answer to the question he had been avoiding.

———

The financial industry has become very good at answering the question how much.

It is considerably less practised at helping people answer what for.

In a retirement that might run 30 or 40 years (or more) — which is no longer an outlier but an increasingly likely outcome for people in good health at 60 — the second question is not secondary. It is foundational.

There is a version of this gap that was more forgivable in our parents’ generation. When retirement was short and decline was relatively swift, the identity question had less room to do damage. You could muddle through on golf and grandchildren for a decade and the stakes were manageable.

That forgiveness no longer applies.

The person who retires at 62 today, in reasonable health, is looking at a very real possibility of twenty-five to thirty-five years of genuine capability before any serious limitation arrives. Over a quarter of a century of being sharp, experienced, capable, and — if they have planned well — financially unconstrained.

These are not years to be managed. They are years to be used.

Squandering them — whether through David’s avoidance, or Chris’s beautiful, exhausting, misdirected industry — is not a soft failure.

It is the costliest mistake available to a person in their fifties.

Not because of what it does to their finances.

Because of what it does to the years.

———

The WealthSpan Letter is published for people who want to think clearly about the financial dimensions of a long life. If you found this useful, consider forwarding it to someone who is asking the right questions — even if they haven’t quite finished asking them yet.