February 18, 2026 | Jonathan Bird
There's a saying that you can't live a life with no regrets — but you can choose them. In 12 years of advising retirees and speaking with over 10,000 investors, I've noticed a pattern. People don't regret missing a perfect investment or retiring too early. They regret waiting too long, playing it too safe, and realizing — sometimes too late — that time and health were never guaranteed.
Here's what I've learned from them, and what you can do today so your future self doesn't end up in the same place.
The 5 Regrets of the Dying
Palliative care nurse Bronnie Ware spent years sitting with people at the end of their lives and documented the most common regrets in her book The Five Regrets of the Dying. They've stayed with me ever since.
1. Not living a life true to themselves. For many, this meant staying in a career that no longer fit. For others, it was simply going through life by someone else's expectations rather than their own.
2. Working too hard. Not because they cared too much about their job — but because work became an avoidance tactic. They put status on a pedestal and ignored what actually mattered.
3. Not expressing their feelings. Unspoken words left relationships damaged and family members estranged. Sharing how you feel, even when it's hard, does more for your life than most people realize.
4. Losing touch with friends. Bronnie told the story of a woman named Doris who had four close friends throughout her life. By the time they tried to reconnect, three of them had already passed. Time moves faster than we think.
5. Not choosing happiness. Rosemary — a successful businesswoman hardened by an abusive relationship — sat on her deathbed and said: "We can stop ourselves from being happy because we think we don't deserve it. But we can be whoever we allow ourselves to be. My god, why didn't I work this out sooner? What a waste."
How Retirement Actually Evolves: The Go-Go, Slow-Go, No-Go Framework
Most people assume the body they have at 60 will perform the same way at 75. It won't. As advisors, we plan around three distinct phases:
Go-go years (mid-50s to mid-60s): High energy, full capacity, the time to travel and pursue adventures. Spend more here — it's worth it.
Slow-go years (early to mid-70s): Energy starts to decline. You can still do many of the same things, just with less capacity and more planning required.
No-go years (early 80s and beyond): The body simply isn't the same. My mother-in-law can no longer make the flight from Phoenix to London to see her daughter and grandson — not for lack of will, but lack of capacity. And it didn't happen gradually. It was a sudden shift.
The practical implication: plan to spend more in the first 5–10 years of retirement when you can reliably count on your health. The portfolio can shrink faster early on — that's the point.
The Three Traps That Derail a Good Retirement
1. The Over-Saver Mentality
Jason works at Amazon. He grew up in poverty and spent decades saving aggressively. A few years ago I told him he'd hit $3 million and could stop saving entirely. He said no. Last year he crossed $4 million — clearly oversaved by any measure. It wasn't until recently that he finally agreed to shift to a retirement-ready portfolio.
The habit of saving is powerful. But when saving becomes the goal rather than the means, it starts working against you. There's no finish line feeling, just perpetual scarcity — even when the numbers say otherwise.
2. Assuming Health Will Decline Slowly
One of my fittest clients spent his 50s doing CrossFit, completing events like the Murph — hundreds of pull-ups, push-ups, and squats wearing a weight vest. Then one knee went. Then the other. Then an irregular heartbeat during a pickleball match. Three events in quick succession. He went from elite endurance athlete to two knee replacements and a heart condition — not on a slow curve, but suddenly. Health is not linear.
3. The "One More Year" Trap
Tom handed in his retirement notice. His employer responded with $30,000–$40,000 in stock options to stay one more year. It felt validating — finally being compensated at his real worth. So he stayed. But that year cost him time with his wife and kids that he would have otherwise had. The money was real, but so was the time loss.
Two Tools to Make Better Decisions Now
The Life Calendar
Each box is one week. 90 rows for each year of life, 52 columns for each week. I put one on my wall years ago when I was building up the courage to start my own firm. Every week I'd check off a box. The visual weight of time passing — weeks disappearing one by one — was more motivating than any goal-setting framework I'd ever tried.
The Regret Minimization Framework
Jeff Bezos used this before leaving his hedge fund job to start Amazon. He imagined himself at 90 on his deathbed and asked: what would I regret if I stayed on my current trajectory? The answer was clear — not starting the company. So he did.
You don't need to build Amazon. But the question is worth sitting with. Imagine yourself decades from now, with far less capacity than you have today. What are you regretting? Whatever your gut says first — that may be your next move.
Charlie Munger used to say: "All I want to know is where I'm going to die, so I'll never go there."
You can't avoid death by avoiding your deathbed. But you can identify what you'd regret most, or what would hurt you the most — and then actively build a life that avoids it. Some of those things are obvious. Others, like staying in touch with friends or reaching out to a family member you've drifted from, are easy to keep postponing until it's too late.
