The Best Money We Almost Didn’t Spend

The thought came into my mind the other morning when drinking coffee in the sunroom. Over the years have you ever prevaricated or had doubts about spending money on specific things, then with the gift of hindsight realised it was a great use of your hard earned cash?

The sunroom in question very nearly didn’t happen. My wife Suzie and I had closed on an old two bedroom house. We could see past the surface state and knew the plot had massive potential for refurbishment and expansion into a great home.

Six months later, with the end of the project in sight and with a considerable amount of cash sunk into the refurbishment, the contractor floated the idea of knocking out another wall and building a large sunroom overlooking the large mature garden. Cash was tight and it would be a considerable extra expense, but after a lot of thought we went ahead. The last minute addition is now the heart and most used space in the whole house.

I don’t have to stretch my memory that hard to find other occasions when doubt and reluctance over purchases have in retrospect been wonderful uses of money. When younger I anguished over taking three months unpaid leave to hike around Australia and parts of South East Asia with my wife Suzie.

The loss of earnings and depletion of savings turned into one of the best experiences imaginable. Unique memories, like trying to hurry a comfort break in the Australian outback when I noticed a twenty foot snake wrapped around the roof beam above my head. Or dining in a pagoda in Java during a tropical rain storm when thousands of bullfrogs unearthed themselves for breeding during the rains. They hopped through the wall-less restaurant looking for frog romance. That money bought us an irreplaceable shared history.

And finally, there’s the memory that surfaces every December: the Lapland Christmas trip. When the kids were still young enough for the magic to be real, we agonized over splurging on a trip for them to go snowboarding and, of course, visit Santa. The expense felt reckless. It was the cost of a new car just for ten days of snow and childhood make-believe.

But that trip wasn’t just a vacation; it was the purchase of a family myth. The memory of learning to snowboard together, the moment we all lay down to make snow angels under the aurora borealis while still clutching ice creams bought two hours earlier—because we knew they’d never melt—and the sight of their faces meeting the “real” Santa, the sheer joy of it all remains vivid. Now that they’re adults, the stories and the photos come out every year. The money is long gone, but the lasting emotional bond and the family legacy we created is priceless.

So now when I’m faced with a decision that makes me hesitate—not because it’s reckless, but because it stretches the budget or disrupts the plan, I try to ask myself a different question. Not “can I afford this?” but “will I regret not doing this?”

The three examples we almost didn’t spend money on—the sunroom, the travel, and the family trip—represent the three pillars of a well-lived life: Comfort, Experience, and Connection. More often than not, the things we agonise over spending money on turn out to be the things we treasure most. Sometimes the best decisions are the ones that almost didn’t happen.