The Echoes of Regret and the Lessons from Hindsight

by Jeffery A. Keill, CFP, CIM, FMA, FCSI, CEA

A few years ago, I was sitting with a client who was just shy of 60. He leaned back in his chair and sighed. “If only I’d started investing earlier,“ he said, swirling the last sip of coffee in his mug. I realized his words hung in the air, heavy with the weight of regret and hindsight. A powerful admission that has stuck with me over the years.

It wasn’t the first time I’d heard that consideration, nor will it be the last. In fact, it’s almost a chorus among people in their fifties and early sixties. They’ve built careers, raised families, and carried mortgages - but when they look at their retirement accounts, they see not just numbers, but missed opportunities. The magic of compounding, that quiet miracle of time, feels like a door they should have opened decades ago.

The 60-Year-Old’s Whisper

At 60, his regret is about money left on the table. It often is. Clients imagine what those small investments in their twenties could have become. A few dollars tucked away each month, growing silently, could have blossomed in to financial security. Instead, they’re left calculating how much harder they’ll need to save now to catch up.

His words were not bitter, but truthfully a wistful recognition that time (as well as health) is the most valuable currency we posses in this life. He simply spent it elsewhere and on other wants. To some, there is an element of time wasted.

The 80-Year-Old’s Confession

I’ve heard another refrain very often as I have worked with another segment of my clients, this time from those in their eighties. Their voices are softer, but the message is louder: “I wish I had retired sooner.”

It is perfectly clear to me that it is not about money anymore. For them, it is often about time left unused, just like the 60-year-old. They talk about trips they postpone, hobbies they shelved, and moments with loved ones they thought they’d have “later.”

Later, as we all learn as we age, arrives with slow sneaky steps. Later approaches with a creeping cadence that suddenly appears and passes us by.

The regrets shared by these clients are not financial at the core - they're existential. Both ages realize that while they worked to secure their future, they had sacrificed the present. And now, the present feels too fragile to fully enjoy.

Together, these two voices - one at 60, one at 80 - share a lesson about balance:

• From the 60 year old the lesson is: start sooner.

• From the 80-year old the lesson is: stop sooner.

It’s a paradox, but it is also a roadmap. Start to invest earlier so your money grows while you sleep. Retire earlier so you can enjoy the life you’ve built while you’re strong enough to live it fully. I think about these conversations with clients often. For me it frames the importance of time. These are nuggets of wisdom that, as a Wealth Advisor, I have the privilege of sharing with others. The sigh of the 60-year-old, the quiet confession of the 80-year-old. Both are reminders that the clock is always ticking, and the best time to act is before regret has a chance to speak.

Could the real wisdom in this be: don’t wait to start, and don’t wait to stop?