Here’s a question worth sitting with: if 73% of Singaporeans expect to keep working past the official retirement age,1 and among high-income earners, nearly half (48%) say it’s not by choice, working longer out of financial necessity rather than preference2, what does that tell us about how well we’ve actually planned?
It tells us something bigger. Singapore doesn’t just have a retirement savings challenge. It has a retirement confidence challenge.
Increasingly, people aren’t asking, “Will I have enough money?” They’re asking, “How do I know if what I have will actually last?”
That’s the retirement confidence gap. And it’s widening across every income group.
The Retirement Confidence Gap
Recent surveys make this uncomfortably clear.
Together, these numbers paint a clear picture of Singapore’s retirement confidence gap. People aren’t necessarily short of savings. They’re short of certainty. They have CPF. Investments. Insurance. Property. Yet many still don’t know whether those pieces add up to a retirement that can withstand decades of inflation, healthcare costs, and an uncertain future. That’s why confidence remains low, even among people who appear financially comfortable.
Why does this gap exist? Because saving is necessary but not sufficient. What you accumulate matters less than what survives the journey through retirement intact. And that journey is longer, costlier, and more unpredictable than most plans account for.
Why the Gap Exists
Singapore is ageing rapidly. By 2030, one in four citizens will be aged 65 or above. Life expectancy at 65 has risen from 18 years in 2003 to over 21 years today, and that trend continues. A couple retiring together at 65 has a high probability that at least one of them will still be alive at 90.
That’s a 25-year retirement. A quarter-century of expenses, healthcare bills, and inflation stacking on top of each other, with no salary coming in to absorb the shocks.
One in two Singaporeans aged 65 today is projected to need some form of long-term care during their lifetime. Yet most retirement plans don’t price this in at all.3
At the same time, medical costs in Singapore have been rising rapidly, far outpacing general inflation. And housing-asset-rich Singaporeans often find themselves cashflow-poor in retirement: property wealth doesn’t pay the grocery bill or the hospital co-payment.
For many Singaporeans in their 50s and 60s, the financial reality of retirement is arriving faster than their plans expected. The buffer they assumed was there is not. And that’s the soil the confidence gap grows in.
The Five Retirement Risks Create the Gap
When we talk to clients at Havend, the anxiety isn’t usually “I haven’t saved anything.” It’s something more nuanced: “I’ve saved, but I’m not sure it’s enough. I don’t know what I’m not seeing.”
That instinct is correct. Because what erodes retirement isn’t usually a single catastrophic event. It’s the slow, simultaneous pressure of multiple forces working against you at once: inflation quietly shrinking your purchasing power, healthcare costs arriving earlier than expected, markets turning at the worst possible moment, or a spending pattern that felt sustainable until it suddenly wasn’t.
The Sun Life survey found that 49% of high-income respondents cited uncertainty about future expenses as a key barrier to planning for retirement.4 Not lack of savings. Uncertainty. They have the money. They just don’t know if it’s enough, or for how long, or what will eat into it first.
And that uncertainty is precisely what erodes retirement confidence. People don’t lose confidence because they lack assets. They lose confidence because they don’t know how those assets will perform when real life happens.
That uncertainty has a name. Actually, it has five names: five distinct forces that can derail even a well-funded retirement. Longevity. Healthcare costs. Inflation. Poor investment timing. And overspending. Together, they form the invisible architecture of retirement risk, and the engine behind Singapore’s retirement confidence gap. Individually, each is manageable. Together, without a plan that accounts for all of them, they compound.
The research confirms this. Among those who feel most anxious about retirement, it’s rarely one thing. It’s the sense that several things could go wrong at once, and they’re not sure which to worry about first.
The 3Cs Reduce Those Uncertainties
If the retirement confidence gap is caused by uncertainty, then closing that gap isn’t about chasing higher returns. It’s about systematically reducing the biggest sources of uncertainty. That’s where a structured retirement plan makes the difference.
Based on our work with clients across different life stages, and our research and solutioning work over the past year, there are three distinct areas that a retirement plan must get right, and they must be addressed together, not separately.
Cashflow: How your money flows, month by month
Most retirement plans focus on the total number: the lump sum you need at retirement. But what matters in retirement is whether your retirement income reliably covers your expenses each month, especially in the early years before CPF LIFE payouts begin, and in the later years where your CPF LIFE payout might not be sufficient. A robust plan distinguishes between what you must spend (essentials) and what you choose to spend (lifestyle), and ensures the essentials are always covered, regardless of what markets are doing. The 27% who retired earlier than expected due to poor health5 didn’t plan for that cashflow disruption. Most people don’t.
Coverage: How you protect yourself from costs you can’t predict
Healthcare is the retirement wildcard. It’s the cost that rises fastest, arrives most unpredictably, and can drain savings with brutal speed. A hospital stay, a critical illness diagnosis, or years of long-term care can wipe out a decade of careful saving. The right coverage (the right hospital plan, the right long-term care policy) doesn’t just protect your health. It protects your retirement income from being redirected to medical bills. The goal is simple: transfer the financial risk to an insurer, not absorb it yourself.
Certainty of Income: How you guarantee income that lasts as long as you do
The deepest fear in retirement isn’t dying. It’s running out of money before you do. A 25-year retirement period needs an income stream that is reliable and secure, not just variable and market-dependent. For most Singaporeans, CPF LIFE is the most powerful tool available for this: government-backed, lifelong, and completely immune to sequence-of-returns risk. But CPF LIFE carries its own risks (policy change, and it cannot be surrendered) and limitations, making it less than a one-size-fits-all solution. The real question is how to optimise it and what to build alongside it. Structured carefully, insurance annuities complement CPF LIFE. They provide an additional cashflow layer that does not rely solely on volatile market performance, giving you the peace of mind that your income will last as long as you do.
Putting It Together
The three planning areas above aren’t separate conversations. They are one integrated system. Get cashflow management right, and you sidestep the overspending trap and the damage that bad market timing can cause. Get your coverage right, and healthcare stops being the wildcard that derails everything else. Get your income certainty right, and longevity stops being something to fear, because you can’t outlive a lifelong payout.
Together, these three areas do more than reduce retirement risk. They reinforce retirement confidence. Because confidence doesn’t come from hoping your savings are enough. It comes from understanding how your cashflow, protection, and lifelong income work together, even when markets fall, healthcare costs rise, or you live longer than expected. That’s how the retirement confidence gap is closed: not by eliminating uncertainty entirely, but by planning for it deliberately.
This is not complicated. But it does require clarity, discipline, and the kind of honest assessment that most people put off until they’re uncomfortably close to retirement. The Sun Life survey found that 22% of high-income earners only draw up retirement plans within two years of leaving full-time work.4 And separately, 42% of Singapore respondents planned to leave retirement expense planning until five years or less before retirement.6 Two years. Five years. For a 25-year journey. Better to start early.
RetireSURE Helps Reinforce Retirement Confidence
The three planning areas above (managing your cashflow, protecting yourself with the right coverage, and securing a guaranteed income for life) are what Havend calls the 3Cs framework: Cashflow Management, Coverage Management, and Certainty of Income.
This is the foundation of RetireSURE, Havend’s structured retirement planning service. RetireSURE exists for one purpose: to help Singaporeans close the retirement confidence gap. Using the 3Cs framework, it helps you understand not only whether you’re financially prepared, but why, and shows where the gaps are before they become retirement problems.
Because confidence isn’t something you hope to have when retirement arrives. It’s something you build long before it does.
If you’re not sure which side of the retirement confidence gap you’re on, that’s the right place to start.
This is an original article written by Eddy Cheong, CEO at Havend, a specialised insurance advisory where you don’t have to fear being mis-sold, over-sold, or pressure-sold.
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Sources
| 1 | Sun Life, “Retirement Reimagined: Asia’s Retirement Divide”, February 2026 (Singapore-specific data). As reported in Insurance Business Asia, 25 February 2026: insurancebusinessmag.com |
| 2 | Ibid. 48% of high-income Singapore respondents reported expecting to work longer to maintain income for daily expenses and long-term financial security. |
| 3 | Ministry of Health Singapore / CareShield Life public statistics, 2025. |
| 4 | Sun Life, “Retirement Reimagined: Asia’s Retirement Divide”, February 2026. High-income Singapore respondents: 49% cited expense uncertainty; 22% plan within two years of retirement; 39% feel very confident in their plans. |
| 5 | Sun Life / People Matters Global, February 2026. Singapore respondents. |
| 6 | Sun Life, “Retirement Reimagined: facing the future with confidence”, 2024. Singapore respondents: 42% intended to leave retirement expense planning until 5 years or less before retirement. |