I am 56 this year. If all goes to plan, Providend should have a new management team in another five to seven years. It is a thought I hold with both anticipation and unease. For most of my working life, I have been the one helping others plan their transitions. Now, I find myself on the runway, watching the ground approach.
I do not describe this phase as “retirement” because I am not sure I will ever fully retire. But I am clearly a pre-retiree: someone with five years or fewer before a significant change in their working life. Through my own preparations and many conversations with clients at this stage, I have come to believe that the final five years before the transition are the most important. It is when your financial, life, and health plans must all be stress-tested, and when the life you want next must start becoming real.
Here is what I believe every pre-retiree should begin doing now.
Get Your Wealth in Order: Spending Plan and Protection
For decades, our industry has trained people to ask, “How much do I need to retire?” It is, at best, an incomplete question. A lump sum means little without a plan for how it will be drawn down to produce a reliable income for the rest of your life.
The withdrawal phase of retirement is far more complex than the accumulation phase. Retirees face longevity, inflation, healthcare, investment, and overspending risks all at once. A single bad sequence of market returns in the early years of retirement can do irreversible damage to a portfolio that looked perfectly adequate on paper.
This is why, at Providend, we designed RetireWell®, which distributes a retiree’s assets across different buckets with different purposes. The nearest five years of income sit in very secure instruments: annuities, direct bonds, and cash-like assets. Money needed later is invested for longer, in portfolios with higher expected returns. A reserve bucket cushions the plan against periods of muted returns. The goal is not to maximise returns; it is to ensure that, regardless of what markets do, you have a safe retirement income floor for life. Start now: map out what you will actually spend, adjusted for inflation, over the next thirty to forty years, and test whether your resources can reliably fund that plan.
A good spending plan can be undone by a single uninsured claim. So, the second piece of wealth planning is protection. Most pre-retirees bought their Integrated Shield Plan riders a long time ago and have barely looked at them since. That is no longer safe. From 1 April 2026, all seven IP insurers have rolled out new riders in line with the Ministry of Health’s revised requirements. The new riders are about 30 per cent cheaper in premiums, but they no longer cover the deductible, and the co-payment cap has been raised from $3,000 to $6,000. Insurers have also used this moment to revise their base plans and older riders, many with price increases. The question is no longer simply whether to switch; it is whether your total lifetime premium, across the base plan and rider, is something you can comfortably pay deep into retirement, when income has stopped but premiums have not.
Equally important, and too often ignored, is long-term care. The real risk in later years is not dying; it is living for a long time while dependent on others for daily living. CareShield Life provides only a modest floor of payouts, nowhere near enough to fund a helper, a nursing home, or home nursing care over a decade or more. Review your CareShield Life supplements, and if you do not have an appropriate long-term care plan, get one in place before your health changes and you are no longer insurable. This is also the time to review your life and disability cover. Some policies bought to protect a young family may no longer be needed. Sit down with a trusted adviser and go through every policy.
Start Living the Next Phase Before You Enter It
I have written before about Pam Hixon, the retired hospice director whose story, told by her son Tony, still haunts me. Pam retired with more than enough money, but she had no detailed plan for her days. The ideal she had built in her mind — leisurely mornings, hobbies, time with loved ones — could not fill a week, let alone a decade. She lost her purpose, sank into depression, and took her own life.
Money is only ever an enabler. Before a financial decision is made, an ikigai decision must be made. What is the good life you want to live in the next phase? Where do you want to live it? Who do you want to live it with? What “work”, paid or unpaid, will give meaning to your days?
I encourage pre-retirees to do what the army calls a dry run: a rehearsal as close as possible to the real thing. So, if practical, take a sabbatical, a break, or extended leave, and live as closely as you can to the life you are planning for. Do the “work” you imagine doing. See if it fits. If not, you still have time to adjust.
I am doing some of these myself. I have been preparing for years to become a life coach. I have started building a blog to write down my reflections. My wife and I are also travelling more to experience what it feels like to have the time and space to travel the way one might in retirement. By the time my successor takes over, I want the next chapter to already feel familiar.
Focus on Your Health Span
Having wealth and purpose without good health is a cruel situation to be in. The goal is not simply to live long; it is to have a long health span — the portion of life in which you are cognitively sharp, physically capable, and emotionally strong.
Four chronic conditions account for most of the decline we fear: cardiovascular disease, cancer, neurodegenerative disease, and metabolic disease. We cannot stop ageing, but evidence shows that we can push the onset of these illnesses later and compress the period of poor health at the end of life.
Start with a properly designed health screening, not a standard package. Speak to your doctor about your family history and your goals. From there, build a plan across five areas: exercise (both cardio and strength training), nutrition, sleep, emotional health, and, only where appropriate, medicines and supplements. Budget for it. Personal trainers, nutritionists, and thorough screenings cost money, and that money needs to sit within your retirement plan. Over the past two years, I have been more intentional in caring for my health.
A Final Word
The final five years before retirement are not meant for cruising. They are meant for preparation, with the same intentionality you once gave your career. Get your wealth in order. Rehearse the life. Protect your health.
Man proposes, God disposes. But to use that as an excuse not to plan is unwise. Start now, while you still have the runway.
The writer, Christopher Tan, is Chief Executive Officer of Providend Ltd, Southeast Asia’s first fee-only comprehensive wealth advisory firm and author of the book “Money Wisdom: Simple Truths for Financial Wellness“. He is also a Certified Ikigai Tribe Coach.
For more related resources, check out:
1. 4% Rule, Dividend Investing, RetireWell™ – Which Spending Strategy Is Best for Retirees?
2. Why Chasing a 100% Retirement Success Rate May Cost You More Than You Think
3. Beyond Finances: Are You Really Prepared for Retirement?
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