[#03] Why Traditional Retirement Planning Breaks Down as Lifespans Lengthen
If you’ve been following this series, you don’t need to be convinced that something has shifted.
You already know that retirement is lasting longer, that uncertainty is now the new normal, and that being told “your portfolio is performing” doesn’t give any assurance you’re going to land where you want to land. None of this feels theoretical anymore. It feels lived.
What matters now is understanding why that unease persists — even when nothing appears to be going wrong.
The answer isn’t that markets are broken, or that advisers are incompetent, or that you’ve failed to plan properly.
It’s that what we used to call ‘retirement planning’ isn’t really fit for purpose in the world we’re actually ageing into and starting to experience.
What Retirement Planning Is Really Built To Do
At its core, modern retirement planning has become an exercise in investment management.
It asks how a pool of capital should be invested, how much risk feels comfortable, and whether the portfolio is behaving as expected relative to a model. Progress is measured by performance, tracking error, and risk tolerance.
This made sense when retirement was 20 years’ long, health fails in your mid-80s, and one could assume the future will look broadly like the past.
Within those conditions, the system works well. It is disciplined, measurable, and defensible.
But optimisation is only useful when the goal is clear and stable. And that’s where the mismatch begins.
‘Retirement’ No Longer Has an Easy-to-Predict End Date
Traditional retirement planning assumes a three-act story ...
The show starts with work ending and there’s maybe 20 years of freedom and travel. This leads into a second act which is characterised by a slowing down, closing in your early to mid-80s. This leads into the final act, a steep decline as health fails and spending stops.
And it’s the same for everyone.
This assumption is no longer safe.
For many people, retirement is becoming a new, fulfilling chapter with a much more open end, rather than an all-too-short stage of life with an abrupt ending. Work doesn’t stop cleanly. Health doesn’t decline predictably. Spending doesn’t follow a neat curve. Purpose, contribution, and responsibility keep evolving.
When the length and shape of retirement are uncertain, planning can no longer be about arriving at a single destination. It has to be about remaining viable across a wide range of futures.
Optimisation starts to matter less than endurance.
When Short-Term Performance Replaces Long-Term Success
As retirement planning became increasingly institutionalised, it specialised around investment management, and investment returns soon became a sign of success.
If the portfolio performs, the plan must be working. If returns are within expectations, confidence is supposed to follow.
This logic is seductive — but incomplete.
Performance tells you how your money looks in the rear-view mirror. It does not tell you whether your life, as it unfolds over in the decades ahead, is actually sustainable.
You can have strong returns and still be unsure whether you can spend freely, help family confidently, adapt to change, or absorb shocks without later regret. You can be “on track” and still not know whether the track leads somewhere solid.
That disconnect is not emotional weakness. It’s a signal that the measure of success is misaligned with the lived objective.
Retirement is not about winning. It’s about lasting.
Risk, From Two Very Different Perspectives
In finance, risk is usually defined as volatility — how much values fluctuate and how uncomfortable that movement might feel.
This definition is tidy and measurable. It works well when the primary concern is short-term behaviour.
But that is not how risk shows up in retirement.
In real life, risk looks like running out of money, missing opportunities, discovering poor decisions too late, or quietly shrinking your spending because you’re unsure what lies ahead.
A plan can manage volatility perfectly and still fail on those dimensions.
What many people experience as unease is the gap between these two definitions — a plan that addresses market risk comprehensively while leaving life risk largely unspoken.
Prediction vs Preparedness
Most retirement plans are built around a single projected future, based on long term averages.
Assumptions vary, scenarios are tested, but the structure still implies a path — a best estimate of how things will unfold if reasonable conditions hold.
This is called ‘The Flaw of Averages’ because real lives don’t work that way.
They arrive unevenly. Sometimes better than expected, sometimes worse, often out of sequence. The future doesn’t show up as a forecast. It shows up within bounds.
In a world defined by longevity and uncertainty, planning cannot be about predicting correctly. It has to be about being prepared when predictions are wrong.
This is a subtle but profound shift — from precision to resilience.
From Investing to Stewardship
Over time, retirement planning has narrowed its focus.
What began as broad financial stewardship has increasingly centred on the portfolio — the visible, reportable “money shot” of returns.
But investing is only one part of a financial life.
Structure matters. Cashflow matters. Legal and tax foundations matter. Protection, governance, contingencies, and plain-English Plan Bs matter — especially when life happens.
A portfolio can be elegant while the rest of the financial house is fragile.
Strong returns don’t compensate for weak foundations. And many of the risks that most disrupt long retirements — incapacity, family complexity, cyber-crime, structural inflexibility — have little to do with markets at all.
If the goal is to sustain a life over decades, planning has to incorporate much more than mere investment performance, and steward the whole financial house that supports us.
A Different Question Entirely
At this point, it should be clear that what’s changed is not the quality of the tools available to us.
The charts still work. The models still run. The data still matters.
What’s changed is the question those tools are being made to answer.
Seen side by side, the shift looks something like this:
What’s changed is not the tools — it’s the question being asked
Traditional retirement planning
Straight-line forecasts built around a single expected future
Retirement framed as work ending, followed by a decade or two of spending, tapering into decline
Planning narrowly defined as investment selection and portfolio construction
Success measured primarily by investment returns
Plans anchored to risk tolerance and comfort with volatility
Increasing investment complexity in pursuit of marginal gains
Technical language (alpha, beta, Sharpe ratios, correlations)
WealthSpan thinking (emerging)
Outcome ranges designed — and stress-tested — for how the real world actually behaves
A long, open-ended financial life, potentially punctuated by reinvention, uneven spending, capital injections, or even a sudden end rather than a gentle fade
Whole-of-life financial stewardship, incorporating every part of the financial house — not just investable assets
Success measured by endurance: how long the financial life can reliably sustain the life being lived
Plans anchored to resilience and durability across shocks, change, and longevity
Relentless focus on the one question that actually matters
Plain-English confidence: “How sure are we this will last until you’re 102?”
None of the planning tools disappeared. They’re simply serving a larger worldview.
When you look at it this way, the quiet unease many people feel makes sense.
They’re using capable tools, competently applied — but inside a framework that was never designed for a long, uncertain, evolving financial life.
Once that becomes visible, continuing to refine the old map no longer feels reassuring. It feels misdirected.
If retirement is no longer a short, predictable phase — but a long condition shaped by longevity, uncertainty, and change — then planning has to start from a different place. Not with performance, but with whether a financial life can hold together across whatever the future brings.
WealthSpan thinking isn’t about restraint. It’s about enabling a fuller life because uncertainty has been accounted for, not ignored.
In the next essay, I’ll show how this way of thinking allows financial decisions to support longer, more uncertain lives — without sacrificing purpose, freedom, or abundance along the way.