The Long Game
The psychological shift from saving to spending is harder than it sounds — and more important than most people realise.
There is a particular irony that shows up in retirement research, and in the conversations we’ve had: the people who were most disciplined about saving often find it hardest to spend. The habits and instincts that built the nest egg — caution, restraint, the ability to defer gratification — don’t automatically switch off when the need for them has passed.
The result is a quieter problem than running out of money, but a real one: people with sufficient resources underspending on the experiences, connections, and quality of life that their savings were always meant to fund. Living cautiously through the years when caution is no longer necessary.
Before we go further, one important note: this post is for people who have enough. Singapore has real elderly poverty, and for those who are financially stretched, the challenge is different and the resources are different — ComCare, Silver Support Scheme, and community assistance are the right starting points. What follows is for those whose hesitation is psychological, not mathematical.
What freedom from financial anxiety actually looks like
Ben describes something that many people spend their whole careers hoping for but never quite reach: the ability to spend on something that brings joy, without the accompanying calculation about whether it’s justified.
“If I decide to buy something, I buy it. I don’t think, do I need to buy this? I say, no, it makes me happy, I buy it. Of course, I’m practical — I don’t buy things I don’t use. But I’m not afraid to spend money if I want to, because I know I have sufficient to tide me through the rest of my years.”
— Ben (not his real name), retired at 65
He is not spending recklessly. He is spending without fear — which is a different thing entirely. The confidence comes not from having an exceptional sum, but from having done the planning: he knows his income streams, he knows his monthly needs, and he knows the numbers work. That clarity is what makes the spending feel like freedom rather than risk.
The Smile Curve of retirement spending
One of the most useful — and least widely known — findings in retirement research is that spending in retirement doesn’t follow a straight line. It follows a curve. And understanding that shape changes how you think about using your money.
Research on actual retirement spending patterns shows three distinct phases:
The Smile Curve of retirement spending — higher at the start, lower in the middle, rising again at the end.
Phase 1 — The active years (60s and early 70s). Spending is highest. Travel, experiences, family, hobbies, eating well. This is the window for the things that require energy, mobility, and vitality. Die With Zero calls these your “go-go years” — the period when you have both the means and the physical capacity to do the things you planned for.
Phase 2 — The quieter years (mid to late 70s). Spending naturally declines. Travel becomes less ambitious, social life more local, lifestyle simpler. Many retirees describe this phase as deeply contented — less about doing and more about being. The spending drop is not a sign of financial trouble; it is a natural shift in what brings satisfaction.
Phase 3 — The care years (80s and beyond). Spending rises again — but now it is healthcare, medical treatment, home help, or residential care. This is the spike that most people fear, and rightly so: long-term care costs in Singapore can be substantial. But here is the key: this spike should be covered by insurance and structured income streams, not by the nest egg you were hoarding for experiences you never had.
The key insight: insurance covers the spike, not your nest egg
This is where the Smile Curve becomes liberating rather than frightening. If the late-life healthcare spike is covered by:
CareShield Life — the mandatory long-term care insurance that pays out if you become severely disabled and need help with daily activities. Covers the baseline.
Integrated Shield Plans and critical illness coverage — supplementary insurance that covers hospitalisation, specialist care, and lump-sum payouts for major illnesses. If these are in place and adequately sized, the healthcare spike is largely absorbed.
CPF LIFE — the lifetime annuity that pays monthly regardless of how long you live. This is your income floor for the care years, regardless of what happens to your investments or portfolio.
Then your capital — your investment portfolio, your savings, your property equity — does not need to be held in reserve for a healthcare emergency. It can be used for its intended purpose: funding the life you designed.
This is exactly what Bill Perkins argues in Die With Zero: hoarding a large nest egg to fund an uncertain future is, in practice, hoarding it forever. The uncertainty never fully resolves. The right response is not to spend without a plan — it is to build the plan (insurance, CPF LIFE, structured income) that allows you to spend the rest without fear.
A practical note: review your coverage at this stage
ST, who has been thinking carefully about her financial architecture in the lead-up to full retirement, described doing exactly this — reviewing her insurance policies to ensure she was appropriately covered without being over-insured. She moved from late-stage critical illness coverage to early-stage, recognising that early detection and treatment is where the real financial exposure sits.
It may be worth asking yourself some questions at this stage. Are there policies you’ve been paying for since your 30s that were designed for a life situation you no longer have — dependants, a mortgage, a particular income to protect? Are there gaps that have opened up as you’ve aged, particularly around hospitalisation or long-term care? These are not rhetorical questions with obvious answers — everyone’s situation is different, and what’s right for one person isn’t right for another. But they’re worth sitting with before assuming the coverage you have is the coverage you need.
As always, we are not financial advisers. These are frameworks for thinking, not personalised advice. For specific decisions about your coverage and drawdown strategy, please consult a qualified financial adviser.
A question to sit with
What is the experience, trip, or version of generosity that you’ve been deferring — and what, honestly, are you waiting for?
Is the hesitation mathematical — a genuine gap in the numbers? Or is it psychological — the savings instinct running past its useful life?
If the plan is in place, the waiting is the cost.
The Long Game
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