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I have a confession as a financial advisor: Goals are overrated.
When a new client signs on, they get prompted for their goals on a discovery form. Those responses tend to fall into two categories.
1. They provide specifics: time frames, risk/reward, hopeful goal, outcomes to be avoided, etc., OR
2. Something meh that is vague aspiration like:
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I want to retire comfortably (who doesn’t?).
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I want to spend more time with my family (nice but not helpful for planning).
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I want to leave a legacy (such as…?).
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I want to be independent (are you being controlled by another entity right now?).
In my experience, every one of these general goals is admirable in a way, but rarely sufficient to get people to change their behavior. Sometimes I sense the tyranny of routine, or death by autopilot, or an ossification from the familiar.
This ties back to why goals are overrated. The image of success is often too fuzzy to change behaviors. I’ve found that people are often motivated less by the possibility of becoming slightly better than by the possibility of becoming a disappointment.
That idea crystallized for me after more thinking about anticipatory regret—the practice of asking today what your future self is most likely to wish you had done differently. I’ve written about it before. It strikes me as an unexpected definition of wisdom. Wisdom isn’t simply accumulating knowledge. It’s borrowing experience from the past, sometimes not your own, and applying it to a future before we get there.
I’ve spent more than three decades watching people arrive at retirement with wildly different balances in an account that doesn’t appear on any financial statement. Some accumulated joys. Others accumulated regrets. The difference wasn’t usually intelligence or income. More often, it was whether they had acted while there was still time.
We live in an Age of Measurement. Investment management software measures portfolio risk, flags problems, and prompts review. Calendars tell us where we are supposed to be. Our smartphones and smartwatches constantly remind us how much time we spend on our steps, our apps, or just looking at our phones (I spend too much time on mind-numbing card games).
Yet almost nobody has a system that tracks maybe the most important question of all:
If I keep living exactly like this, what am I going to regret?
Regret compounds exactly the way investments do. Small decisions repeated over years eventually become a life.
I’ve imagined for myself a conversation with Future Tom. What if we took that concept a step further and got 60 seconds to call our current selves. I don’t mean a Back to the Future II scenario where you make a fortune betting on sports when you know the outcome. Instead, imagine having one minute to explain what you’ll wish you had done differently.
We’d probably say stuff like,
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“Call your brother.”
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“Take the trip.”
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“Write that book.”
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“Spend more time with your kids and grandchildren.”
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“Get that spot looked at.”
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“Stop assuming there will always be another chance.”
Future regret tracking 101
It’s no secret that fear sells. From advertising to politics, negative effects resonate more than positive outcomes. I am no different. Tell me I’ll be happier if I exercise more and I’ll nod politely. Tell me I’ll regret not being able to hike or swim with my future grandchildren because I ignored my health in my 50’s, and suddenly I’m listening.
So instead of asking only, “What goals do I have?” it may be even more useful to ask, “What regrets do I have now or might I have later, and why do I have those regrets?” That second part is critical because it helps us work backwards to understand how we arrived at an outcome we didn’t want.
You can turn this approach into a practical regret tracker. This isn’t something that needs to be complicated. Once a month, think about asking yourself a handful of uncomfortable questions.
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What will I regret if nothing changes? Identify one likely regret that is becoming more expensive with time.
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Which relationship needs attention? Name one person who deserves a call, apology, visit, or honest conversation.
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What opportunity am I avoiding? Identify one action you keep postponing because of fear, embarrassment, or uncertainty.
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What regret requires acceptance instead of action? Choose something you need to release because it cannot be repaired or no longer deserves your energy.
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What will I place on next month’s calendar? Convert one insight into a specific appointment, deadline, or recurring block of time.
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What repeated behavior produces regret over and over? Look for the weekly habit—not merely the dramatic mistake—that keeps delivering the same disappointing result.
Death by 1,000 regrets
That last question deserves particular attention. Many regrets aren’t dramatic. They’re repetitive. Overeating. Working too much. Spending four hours a day staring down at your phone. Never exercising. Never apologizing. Every individual decision seems insignificant, but eventually those tiny regrets become your biography.
Most future regrets aren’t likely to be surprises. They’re more often plainly forecasted results that we ignore. I’ve come to believe that thinking about future regret is less like a bolt of lightning and more like weather radar. Most of the time, we can see the storm coming, but we simply convince ourselves it won’t hit us. We tell ourselves we’ll start exercising after the next physical, reconnect with our spouse after this busy season, call our sibling next month, or finally write the book once life settles down.
We need to be honest about the lies we tell ourselves.
Here’s an example: I asked a client named Leo where he wanted to retire. He gave me some trite answer about staying home with his wife near his sons until he died. It was clear there was something more behind this.
“What would future Leo regret if he was a widower?” I asked as a follow-up question.
Looking up at the ceiling, Leo said, “I’d regret not seeing the obvious. I don’t have a great relationship with my sons. She does. If I’m by myself, I’ll be lonely as shit because I really don’t talk to them and they really don’t talk to me. And I’d be out in the middle of nowhere.”
That honest look at regret allowed us to get to real planning and for Leo to make some real decisions. We revisited where he might live and when he might move, things that I can help with planning-wise. But Leo also came away with motivation to think more deeply with his wife about family and health.
Adding a “Countdown Calendar”
Lately I’ve been thinking about pairing a Regret Tracker with a Countdown Calendar. If you’re fifty-six like me and actuarial tables suggest you have roughly 35 years remaining, that’s about 420 months.
Suddenly time becomes less abstract. Every month is a box you can check off, never to be reopened. At the end of each month, instead of asking whether we were productive, ask a different question:
Did this month reduce future regret?
Not whether you answered every email. Not whether you cleared your to-do list. Not whether you stayed busy.
Did you become someone your future self will thank?
The more I think about it, the more I realize calendars and regrets belong together. Your calendar doesn’t just reflect your priorities. It can predict our regrets.
Start tracking and get cracking on those regrets
Open next week’s calendar. Where is the appointment to repair a friendship? To spend an uninterrupted afternoon with your spouse? To sit quietly for an hour? To take the hike you’ve been talking about for years? To write the first chapter?
It’s remarkable how often we claim these are our highest priorities while allocating exactly zero time to them. Your calendar isn’t lying.
Part of the challenge, however, is recognizing that not every regret deserves fixing. Once you begin making a regret list, it quickly becomes obvious that you cannot eliminate them all. Some opportunities have passed. Some relationships won’t be restored. Some dreams will remain dreams. Maturity isn’t eliminating regret altogether. It’s learning the difference between the regrets that require action and the regrets that require acceptance.
That may be one of the oldest insights in philosophy. Much of our suffering comes from refusing to let go. Sometimes the healthiest decision isn’t fixing the past. It’s finally putting it down.
Thanks Buddha!
Research consistently finds that later in life people regret the chances they never took more than the mistakes they made. Failure usually teaches us something. Inaction rarely does. Every risk we avoid feels safe today, but many become expensive decades later.
Perhaps that’s why I’m beginning to think every month deserves a Regret Review. Not an annual resolution or another productivity system. Just a simple conversation with your future self.
Because you don’t wake up one morning overwhelmed with regret. You accumulate it quietly—one postponed conversation, one delayed decision, one ignored opportunity, one distracted afternoon at a time.
The encouraging news is that, unlike your past, your future is still editable. The Regret Tracker may not measure your net worth, but it will help you do something even more valuable: measure the distance between the life you’re living today and the one you’ll wish you’d lived tomorrow.