At the very end of your life, what will you wish you had done with your money?
It is the most important question you will ever be asked about money, and almost nobody asks it of themselves until the answer has stopped being useful.
Not what you should have invested differently. Not what you should have saved more of. Those are the questions a financial planner asks, and they are worth asking, but they are smaller than this one.
What will you wish you had used it for?
Arthur, at eighty-two
Arthur was comfortably situated. Grown children, grandchildren, a working life as a senior accountant behind him. Mortgage paid off by sixty. A pension. A portfolio. His children had been given a sound education.
From the outside, financially competent in every respect. There was nothing he was actively worried about.
He also had two regrets, and both had grown larger as he aged.
The first was that he had not, in his fifties, taken his wife on the long tour of Europe she had asked for. He had thought it extravagant. They had taken three shorter holidays closer to home instead. She died seven years ago, and never saw the cathedrals she had wanted to see.
The second was about timing rather than amount. He had decided to leave his children a larger sum at the end of his life rather than give them some of it in their thirties and forties — the years of small children, large mortgages and exhausting careers.
By the time they received it they would be in their fifties and financially settled, and earlier support may have made a greater difference — depending on where the family was at the time.
He looked at his eldest grandchild, working two jobs against a HELP debt, and felt the peculiar weight of having timed his generosity for his own funeral rather than his family's need.
These are the common ones
Arthur's regrets are not unusual. They are among the most common you encounter in elderly clients at every income level, and they cluster around two themes.
Things we did not spend on while we could still enjoy them.
Things we did not give while the giving would still have changed something.
Notice what is absent. Almost nobody, at eighty, regrets the return they achieved. Nobody wishes they had rebalanced more often, or chosen a fractionally cheaper fund, or timed an entry better. Those things are not nothing — they are the difference between having enough and not — but they do not appear on this list, ever.
The regrets are always about use.
The accumulator's quiet mistake
Money's deepest function is to be used.
The accumulator who dies with far too much has not won the game. In a small and quiet way, he has mistimed his life — spent decades converting hours into a number and then failed to convert the number back into anything.
This is not an argument for spending everything, and the version of this idea that ends in die with zero is too clever by half. Running out of money at eighty-five is a catastrophe of a different and worse kind, and the margin that prevents it is not waste. It is the price of not being a burden, and of not being afraid.
The point is narrower. Past the margin that genuinely buys security, additional accumulation buys progressively less, and the years in which it could have bought the most are being spent right now.
Two questions with better timing
On spending: what is the thing that has a deadline?
Some purchases are available at any age. A better kitchen will be a better kitchen at seventy. But a walking holiday has a window. So does a long trip with a parent who is eighty. So does being the grandparent who is well enough to be on the floor with a four-year-old.
The failure is rarely that people never spend. It is that they spend on the things without deadlines and defer the things with them, because the deadlines are invisible until they have passed.
On giving: when would this actually change something?
A hundred thousand dollars at thirty-five, against a mortgage and small children, is a different substance from the same sum at fifty-five. The first buys years of a life; the second is added to an existing balance.
There is a version of generosity that is really about control — the sum released at the end, when it cannot be misused because it also cannot be used. It is worth being honest with yourself about which one you are practising.
None of this means handing over everything early, and there are real reasons for caution: your own longevity, aged care, a child's relationship you may have doubts about. Those are arguments for structure and for staging, not for waiting.
Ask it now
The question is not morbid. It is the opposite — it is the only version of the question that can still be acted on.
At eighty-two, Arthur could answer it perfectly. He could describe exactly what he would have done differently, with total clarity and in considerable detail.
That clarity was worth a great deal, and it arrived about thirty years late.
You are being asked the same question, at whatever age you are reading this, while the answer can still rearrange the years in front of you.
What will you wish you had used it for?
Client examples in this article are anonymised or composite. Names and identifying details have been changed.
Adapted from The Money Script by Paul Yang. See the books.