The five-year runway – what pre-retirees should start doing

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 transition. Now, I find myself on the runway, watching it shorten.

I do not think of 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.

1. Get your wealth in order

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, across the next 30 to 40 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 (IP) riders a long time ago and have barely looked at them since. That is no longer safe. From Apr 1, 2026, all seven IP insurers have rolled out new riders which are about 30 per cent cheaper in premium, but they no longer cover the deductible and the co-payment cap has been raised from S$3,000 to S$6,000.

Insurers have also used this moment to revise the premiums of their base plans and older riders. The question is no longer simply whether to switch. It is whether your total lifetime premium – across base plan and rider – is something you can comfortably pay in 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.

2. Start living the next phase before you enter it

I have written about Pam Hixon, the retired hospice director whose story, told by her son Tony, still haunts me. She 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 (reason for being) decision must be made first. 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. 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.

3. Focus on your health span

Having wealth and purpose without good health is a cruel situation. The goal is not simply to live long, but 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 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 the 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 inside your retirement plan. Over the past two years, I have been more intentional in caring for my health.

In short, the final five years before retirement are not meant for cruising. They are meant for preparing – with the same intentionality you once gave your career. Get your wealth in order. Rehearse the life. Protect the health.

The writer is CEO of Providend, South-east Asia’s first fee-only comprehensive wealth advisory firm