The most dangerous thing in a retiree's portfolio

Sumit Tiwari · Certified Estate Planner (EPPL) · July 2026 · 4 minute read

The message came in on a Tuesday morning, a little before lunch.

Still going through a lot of financial pressures recently. Thanks for your service all this while. Too bad couldn't do a proper financial planning for myself. Bad luck, and too trusting of friends. Wish you all the best for your future.

I read it twice. Then I put the phone down for a while.

I met this client five years ago. By every measure Singapore uses, he had won. Property fully paid up. A couple of businesses that ran well. Children educated and settled. No debts. The kind of man who sits across from you at the kopitiam and has nothing left to prove to anyone.

When we first sat down, I told him the same thing I tell every successful father. Your money is settled. Your estate is not. You have children who will inherit all of this one day, and inheritance is where harmonious families quietly stop being harmonious. Do the full planning. Wills, structures, everything.

He did the Lasting Power of Attorney and stopped there. My kids are close, he said. They won't fight.

We did get one thing right together. We parked aside a sum purely for his retirement, built to pay him an income for life, so that he would never again depend on his businesses to eat. He liked that idea. A man who has run businesses for thirty years knows better than anyone that businesses have moods.

Then the moods came. One of his businesses hit heavy weather and the losses were serious. He called me wanting to surrender the retirement funds to cover the hole. I told him no, as firmly as I could say it to a man twenty years my senior. Those funds were the floor under him and his wife. Break the floor to save the business, and if the business fails anyway, there is nothing left to stand on. To his credit, he listened. He found another way to cover it.

I thought that was the close call. It was only the rehearsal.

A year later, the same business partner came back to him. Not with a rescue this time, but with an opportunity. A high risk venture, big returns, the kind of deal that gets offered to men who are known to have money. He went in with a seven figure sum.

The partner used it to pay off his own old debts. There was no venture. There never was.

And here is the part that still sits with me. To settle what the banks were owed after that, he had to liquidate everything. The careful structures. The retirement income. The floor. Every piece of planning we had built over five years, dismantled in months to pay for one afternoon of trust.

He was not a foolish man. That is what I need you to understand. He was careful, experienced, and successful, and he was defrauded anyway.

Because the most dangerous thing in a retiree's portfolio is not a scam you can screen for. It is being known to have wealth. Money that is visible attracts opportunities, and opportunities do not arrive labelled as the good kind or the ruinous kind. They arrive through a familiar face, at a friendly dinner, from someone who has sat at your table before.

The planning I do is not really about growing money. It is about building things that cannot be undone in one bad season, by one bad partner, in one moment of misplaced trust.

He replied to say he wished me well for my future. I spend a lot of mine thinking about his.

This is a true account. Identifying details, including the nature of the businesses and the sums involved, have been altered to protect the client and his family. Shared as a caution, with respect.