[#02] The Problem With Retirement Plans That Look Fine on Paper
When “On Track” Doesn’t Feel Like Progress
The verdict from this year’s review with their financial adviser was handed down: everything’s on-track.
It just didn’t feel that way.
John and Karen, now in their early sixties, have been working with the same adviser for a few years. There was trust, familiarity, and a clear process. Each year brought another set of reports, another walk-through of portfolio performance, another reminder that things were going well.
This year was no different.
Their adviser pointed to the numbers and smiled. The portfolio had delivered slightly above the target their risk profile suggested. The charts were clean. The trend lines reassuring.
“Right where we want to be,” he said.
And on paper, that was true. Their net worth had grown. Everything looked to be in order.
But later that evening, sitting at home, neither of them felt the relief they’d expected.
They weren’t worried. Not exactly. But there was no sense of arrival either — no feeling that this mountain they were climbing had a clear summit.
After dinner, John opened his laptop and pulled up the spreadsheet he’d been quietly maintaining for years. It wasn’t something he’d ever shared with their adviser.
The name of the file is: how much is enough.xlsx
The first tab: when does it run out
While John is no spreadsheet expert, he’s no slouch either. For years he’s used them at work to stress-test decisions and make forecasts. But here, what began as a simple question has quietly turned into a colour-coded beast, dense with formulas, and endlessly tweaked — a private attempt to find certainty where none has been offered.
The only thing it doesn’t provide is confidence.
They certainly have a plan – their adviser has seen to that. And yet John and Karen can’t shake this off: “Why does it still feel like we don’t know how this ends?“
John didn’t have an answer.
But for the first time, he wondered whether the plan they thought they had was actually answering the question they cared about most.
Not “Are we getting good returns?” … but “Will this last as long as we do?”
Nothing was wrong. But something wasn’t right either.
Why the Numbers Don’t Settle the Question
What unsettled John and Karen wasn’t market volatility or poor performance. It was something more basic — and more revealing.
The adviser was measuring one thing. They were worried about another.
Their adviser talked in terms of returns: performance against a number, diversification, risk profiles. The question being answered, year after year, was simple:
Is the portfolio doing what it’s supposed to do?
And by that measure, the answer appears to be ‘yes’.
But John and Karen were quietly asking a different question altogether:
Will this be enough to last as long as we do?
Those two questions sound similar. They are not.
One is about how a pot of money behaves. The other is about whether their lives can be sustained.
What John and Karen had — despite years of reviews, reports, and reassuring charts — was not really a retirement plan at all. It was an investment strategy, wrapped in the language of retirement planning.
That’s why the adviser could point to progress while they felt none.
The plan had depth in one dimension — investment performance — and near silence everywhere else. No clear sense of how much they’ll need. No visibility on how long it will last. No way of knowing whether they were climbing toward a finish line or simply watching numbers move.
So John kept his spreadsheet. Not because he distrusted the adviser, but because the system he was in never answered the question that mattered most.
This is how confidence erodes — quietly, over time.
Not when markets fall. Not when returns disappoint.
But when everything appears to be working, and yet the people living inside the plan still don’t know whether they’re safe.
The unease they felt wasn’t irrational. It was a signal.
A sign that the way success was being measured, and the way their future needed to be understood, were not the same thing.
The Problem Isn’t the Advice — It’s the Starting Point
The reason John and Karen felt this gap has nothing to do with poor advice or bad decisions. It comes from something far more basic.
You see, historically retirement advice has always been built around a single organising idea: how a pot of money should be invested.
Everything flows from that starting point. Risk profiles. Target returns. Asset allocation. Performance reports. Review meetings.
Progress is defined by whether the portfolio behaves as expected relative to a model. And within that frame, the advice John and Karen had was fine.
The problem is that it does nothing to answer their question.
So whereas a portfolio can be judged by performance, a retirement has to be judged by whether it’s going to be enough, in all circumstances.
How long will this last?
What happens if markets disappoint early?
What if we live longer than expected?
What if the next twenty or thirty years don’t resemble the last twenty?
Those aren’t investment questions. They’re life questions with financial consequences.
But when your entire planning system is built to optimise a single outcome — investment performance — every projection, forecast, and report that follows inherits that limitation.
That’s why John and Karen could be told they were “on track” and still feel unsettled.
“If we’re getting the right return, and we’re paying for professional advice, surely that should be enough.”
But there is something missing: a scaffold that connects good investment outcomes to the thing people actually need in retirement: confidence their life will be sustained, for as long as it lasts, in the face of uncertainty.
Not just a portfolio that performed as expected last year.
Until that distinction is recognised, it’s entirely possible to do everything right and still be left wondering whether any of it will actually hold up over the decades ahead.
That quiet doubt isn’t a failure of trust. It’s what happens when you use tools to solve problems they were never built to solve — a sign that the framework was designed for yesterday’s retirement, not for the one most of us are about to experience.
Where This Leads
When retirement is planned through a framework that can’t answer the question “Will this last as long as we do?”, the consequences are profound.
They don’t arrive all at once. They emerge gradually, often while everything still looks fine on paper.
Unless addressed, most people end up in one of four places …
1. Running Out
This is the most obvious fear, but not the most common starting point.
Running out doesn’t usually come from reckless spending or poor discipline. It comes from plans that underestimate longevity, overestimate certainty, or assume markets will behave politely over decades.
The danger isn’t one bad year. It’s a long sequence of reasonable assumptions quietly compounding in the wrong direction.
2. Blowing Up
When confidence erodes, people look for fixes.
That’s when late-stage mistakes happen: chasing yield, taking bets, timing markets, or reaching for strategies that promise results without risk.
These are rarely born of greed. They’re born of a plan whose destination doesn’t account for uncertainties.
3. Missing Opportunities
The quietest cost of all.
When planning is built around protecting a pot of money rather than supporting a long, active life, people often fail to recognise genuine opportunities when they present themselves.
These ‘opportunity costs’ add up over the years to rival the cost of mistakes.
4. Living Small
This one is easy to miss, because it looks like prudence.
People spend less, travel less, help family less — not because they can’t afford to, but because they don’t know whether they’ll need the money later.
Fear fills the gaps the plan never illuminated.
What gets lost isn’t capital, but life.
A Different Starting Point
If this feels unsettling, it’s not a sign you’ve done something wrong.
On the contrary, it’s a healthy response to using a framework that was never designed for the kind of retirement we now face.
Retirement today is no longer a lump sum funding twenty years of travel that precedes a slow and unpleasant decline.
The retirement we are ageing into is increasingly a long, open-ended chapter shaped by longevity, uncertainty, changing markets, and evolving health. Geopolitical and economic shocks are no longer rare events – they’ve become the background noise of modern life.
Intuitively we can accept that lifespan has changed. We’re living longer than previous generations ever planned for.
We also realise that the rate of medical and biotech innovation are accelerating. The Healthspan dividend is not just longer lives but a better quality of life.
What few of us have been helped to think about is what those two shifts mean for our money.
Not in terms of returns or performance charts, but in terms of whether your financial life can actually endure — whether it can deliver the lifestyle you want while still absorbing the shocks of the new world. That requires a framework which reflects the new reality, not one built on the straight-line forecasts that only work in a simpler, more predictable world.
The fact is that when your decisions rely on tools designed primarily to optimise investment performance, too much is left unseen.
That missing dimension — the relationship between your money and the length, shape, and uncertainty of your life — is what makes the difference between feeling confident about the future … and living with a nagging sense that you simply don’t know.
It’s called your Wealthspan.
In the next essay, I’ll unpack what thinking in terms of Wealthspan actually looks like — and why it changes how you approach retirement in a world defined by longevity, volatility, and uncertainty.