As CEO of Havend, I have spent more than two decades in financial planning and insurance advisory, and I have reviewed more insurance portfolios than I can count.
But my own insurance journey did not begin with a plan. Like many Singaporeans, it began with a sense of responsibility, but without a clear idea of how to think about protection.
Where It Started: Buying Without a Framework
My first policy was an investment-linked policy (ILP), sold to me by a university friend who had become an insurance agent, shortly after I started working. I did not buy it because I understood how it worked. I bought it because it felt like the responsible thing to do as a young working adult.
From there, the pattern was simple. With every promotion, I would add a little more insurance. My next purchase was a whole life policy (coverage that lasts your entire life) with critical illness coverage. At no point did I ask myself the questions I now ask every client: what risks am I exposed to, how much coverage do I need, and for how long?
I later spent three years in the insurance industry as an agent. It deepened my knowledge of products, but I still did not have a robust framework for thinking about protection.
The Turning Point
Things became clear after I joined Providend, Southeast Asia's first fee-only financial firm, as one of its founding members around 2001. There, we developed a clear insurance philosophy: understand the risks you are exposed to, then cover them sufficiently and efficiently, so that you neither overbuy nor overpay.
The overarching theme is that insurance is a support plan, not the main plan. Its job is to protect your life goals when a crisis strikes, not to be the main goal.
When Havend was born, we carried this insurance DNA over. Today, we structure protection planning around five core pillars in our InsureWell Assessment. You can download a softcopy here.
- Income Loss due to Death
- Income Loss due to Critical Illness
- Income Loss due to Disability
- Increased Expenses due to Hospitalisation
- Increased Expenses due to Severe Disability (Long-Term Care)
The first three protect my income during my working years. The last two protect my savings for the rest of my life.
My Life Stage Today
I am in my mid-fifties, a father of three teenagers with a surviving parent to support. Retirement is no longer a distant idea but something I am actively planning for. That shapes how I think about insurance in each of these pillars.
The Income-Loss Pillars: Built for My Working Years
Pillar 1: Income Loss due to Death
As a parent and a son, my biggest concern is making sure my dependants are adequately provided for if I pass on prematurely. That includes making sure my family keeps a fully paid home and continuity of my income contribution to the household.
The coverage needed for this is large, especially in my earlier years, but it does not need to be expensive. I rely mostly on term policies (coverage for a set number of years) and mortgage policies, rather than whole life or investment-linked policies. They give a high sum assured for a relatively low premium over my working years, and until my children are independent.
Pillar 2: Income Loss due to Critical Illness
What concerns me as much as dying early is surviving a serious illness, such as cancer, and being unable to work for a long stretch.
My critical illness (CI) coverage works in two layers. My whole life policies, which cover advanced-stage CI, stay with me for life. They serve as a buffer for alternative treatments or medical costs that my hospitalisation plan may not fully cover, such as non-standard cancer drugs. On top of that, I added term policies with CI coverage to give me the option to stop work temporarily and focus on recuperating.
I chose not to buy early-stage CI coverage, for two reasons. Firstly, I did not see a strong need for it, since many early-stage conditions are treatable with a relatively short recovery and are unlikely to keep me out of work for long. Such treatments are also likely to be covered under hospital insurance. Secondly, at my age it is expensive, and early-stage CI, which today is more commonly bundled into multi-pay CI, was not available when I was building this coverage in my earlier years.
Pillar 3: Income Loss due to Disability
This is the one pillar I could not put in place. I applied for disability income coverage but was unable to obtain it due to some pre-existing medical conditions.
It is a lesson I now share often: insurability is not guaranteed. The best time to secure coverage is when your health is good, because that window can close without warning. To mitigate this gap, I made sure my critical illness coverage is sufficient to act as a backup if a serious illness keeps me from working.
The Increased-Expense Pillars: Built for a Lifetime
As I plan more seriously for retirement, my priorities have shifted. Income protection matters less when there are fewer working years left to protect. What matters more now is protecting the assets I will be drawing on in retirement. That is why hospitalisation and long-term care are becoming my priorities.
Pillar 4: Increased Expenses due to Hospitalisation
I am covered under a private hospital Integrated Shield Plan, with a rider (an add-on to the policy) that pays my deductible and covers my co-insurance, subject to a co-payment cap.
This policy has served me well, funding several hospital treatments, including surgery on both shoulders for rotator cuff injuries, as well as endoscopies. These treatments were expensive, amounting to more than $100,000. Each time, I have been grateful to have this coverage in place, and it is one area where I have truly felt the value of insurance.
A note for readers: the Ministry of Health (MOH) has changed the rules for riders. From 1 April 2026, new riders are no longer allowed to cover the minimum deductible, and the annual co-payment cap has been raised to at least $6,000. My rider was bought well before this change and is not affected by the new ruling. Anyone buying a new rider today should expect to pay the deductible and a higher share of the bill, in exchange for lower premiums.
The concern with my existing rider is that its premium keeps rising, and it is now more expensive than the new riders, which offer less coverage. When it becomes too expensive to be meaningful, my likely path is to downgrade the rider first and keep my private coverage, and only downgrade to a public hospital plan when the premium becomes unsustainable.
At what point would the premium become unsustainable? It is a subjective question, because it depends on your resources, your healthcare expectations, and the likelihood and frequency of claims, such as needing multiple treatments for pre-existing conditions. For me, if the premium costs more than 10% of my retirement spending, it starts to lose its appeal. It will not be an easy adjustment to make, but it is a necessary one to plan for.
Pillar 5: Increased Expenses due to Severe Disability (Long-Term Care)
According to MOH, 1 in 2 healthy Singaporeans aged 65 could become severely disabled and need long-term care in their lifetime. That is not a remote risk.
I started with ElderShield and later converted to the new CareShield Life. On its own, this national scheme only serves as a base and is unlikely to cover caregiving costs, which average about $3,000 a month, according to the Singlife Long-Term Care Study 2024. Hiring a dedicated helper as a caregiver, or a place in a nursing home, will cost even more.
So over the years, I have progressively added supplement coverage, on three occasions, to strengthen my long-term care safety net.
Having sufficient long-term care coverage gives me assurance on two fronts. It helps pay for caregiving costs, and it protects my retirement assets from being depleted if I need that care for many years. Just as importantly, I want the financial means to choose the kind of care I receive.
Beyond the 5 Pillars: From Working to Retirement
Retirement income sits outside the five pillars of protection, but it is an essential part of retirement planning, and it is where insurance, in the form of an annuity, plays an important role.
In my forties, I bought an insurance annuity that will provide me with a monthly payout from age 60. It will complement my CPF LIFE payouts.
For most of my working life, I was accumulating wealth and protecting my ability to keep accumulating. Now I am transitioning towards drawing that wealth down in retirement. At Havend, annuities are a key component of RetireSURE, our retirement planning approach. Annuities provide certainty of income, either for a fixed period or for life, that investments alone cannot guarantee. My annuity also bridges the years between 60 and when my CPF LIFE payouts begin.
What I Put in Place for My Children
For my children, I have bought an Integrated Shield Plan and a multi-pay critical illness policy. The hospitalisation plan protects against large medical bills. The critical illness policy serves two purposes. It locks in their insurability while they are young and healthy, and if one of them ever suffers a critical illness, it gives my wife or me the financial room to slow down or stop working to care for them.
When they start working, my personal rule is that they will take over paying the premiums. But if they would rather buy their own policies than take over these, that is fine with me. Once their own policies are in place, I will gladly terminate these and put the savings towards my own retirement.
On Term Policies That Expire Without a Claim
I expect many of my term policies will expire without a single claim, and I am completely at peace with that. That is in fact a good outcome. That money did not go down the drain. It did exactly what it was meant to do: protect my family from the unknowns during the years they depended on me most.
A Final Thought
As for that first ILP, I terminated it shortly after I understood its shortcomings as a protection tool. It is better to unbundle the investment and insurance components. A term policy plus a separate investment portfolio can do a better job, with lower charges and better access to the universe of investment funds. It was an early lesson in buying something without knowing what it was for.
Looking back, my journey has moved from buying out of instinct to planning with a framework. The framework did not make my decisions for me, but it tells me what each policy is meant for, where the protection gaps are, and which coverage is excessive or unnecessary.
My main plan has always been to stay healthy. Insurance is my backup plan, and I hope never to need most of it. But if I do, I know it is there, and that is the whole point.
This article was written by Havend's CEO, Eddy Cheong.
