The Regret We Get Wrong

Fritz here, sending this from a library in Northern Ohio as we enter the final week of our month-long RV trip through the Midwest.  It’s been a great trip, and we’re enjoying the break from our retirement routine.

While I’m traveling, I wanted to share my favorite article from last month.

It was written by Jordan Grumet, who is one of the more interesting people I’ve met in the retirement planning space.  After years as a medical doctor, he scaled back to focus on hospice work.  His work with folks in their final days gives him a perspective that few of us have.  It’s influenced his work as a podcaster, author, and speaker.  He’s written numerous books, and I’m proud to call him a friend.  I encourage you to follow him on his Substack channel.  His work has a perspective few can match.

In today’s guest post (originally published here), he shares his thoughts on regrets, based on what he’s witnessed through his hospice work. Here’s a quote from the article:


“And one thing I’ve noticed is this: what people think they’re going to regret is very different from what they actually do.”


Why was it the best article I read last month?  Because it offers a perspective very few of us can ever achieve—insight from a hospice doctor on what people really regret in their final days. 

There’s a lesson here for all of us. 

It’s a powerful post.


The Regret We Get Wrong

I’ve been thinking a lot about regret lately.

That’s not unusual for me. I’m a hospice doctor. I have spent many days sitting with people at the end of their lives, and when you do that long enough, you start to notice patterns. Not just in illness or decline, but in what people say when everything else falls away.

And one thing I’ve noticed is this: what people think they’re going to regret is very different from what they actually do.

Most of us walk around with a quiet fear in the background. It usually sounds something like this: I won’t have enough. Not enough money. Not enough time. Not enough security to eventually do the things that matter.

So we organize our lives around those fears.

We work a little more. Save a little more. Delay a little more.

But sitting at the bedside of the dying, I don’t hear those regrets.

Not once has someone grabbed my hand and said, “I wish I had made two million instead of one.”

No one tells me, “I should have worked more nights. I should have spent more weekends at the office.”

It just doesn’t happen.


Let’s start with money, because it’s the one we tend to obsess over the most.

There’s this belief that we’ll never quite have enough…that no matter how much we earn, it won’t be sufficient to create the life we want. And yet, after years of studying financial independence and watching people pursue it, I’ve come to a different conclusion.

For most people, financial independence is actually possible.

Not for everyone. There are real structural barriers and circumstances that make it incredibly difficult for some. But for many, it’s not out of reach. I’ve seen people with modest incomes build lives of freedom through intentional choices over time.

More importantly, I’ve come to believe that money isn’t the thing we think it is.

We like to imagine it as the end goal—as the thing that will finally make us feel secure, happy, fulfilled. But the data—and more importantly, the stories—don’t really support that. I often think about the Harvard Study of Adult Development, which has followed people for decades and keeps coming back to the same conclusion: what matters most are relationships. Connection. Community.

Not net worth.

And when people are dying, that’s exactly what they talk about. The people they loved. The relationships they nurtured, or didn’t. The moments they shared.

Money barely enters the conversation.


Then there’s time.

This is the other big one. The feeling that life is rushing past us, that we’re too busy, too overwhelmed, too stretched to actually do the things that matter.

We tell ourselves we’ll get to it later. When things calm down. When work is less demanding. When the kids are older. When we finally have space.

But here’s what’s interesting.

If you look at the data, the average person actually has several hours of leisure time a day. It doesn’t always feel that way, but it’s there. And over the course of a lifetime—78, 80, maybe 85 years—that adds up to an enormous amount of time.

More than enough, in fact, to do something meaningful.

The problem isn’t usually that we don’t have time. It’s that we don’t use the time we have in ways that align with what we say is important.

And maybe that’s because something else is getting in the way.


So if it’s not money, and it’s not time…what is it?

When I sit with people at the end of their lives, the regret I hear most often is much quieter. But it’s also much more painful.

It sounds like this:

“I didn’t have the courage.”

The courage to be who I wanted to be.

The courage to say what I needed to say.

The courage to pursue the thing that mattered most to me.

That’s the regret.

Not that they couldn’t.

But that they didn’t.


Courage is a strange thing.

We tend to think of it in big, dramatic terms like heroic acts, bold decisions, life-changing risks. But the kind of courage I hear about at the end of life is usually much smaller. And much more personal.

It’s the courage to have a difficult conversation.

To change careers when something feels off.

To start writing, even if no one reads it.

To prioritize a relationship instead of numbing out in distraction.

It’s the courage to face yourself honestly.

And that’s hard.

Because it means confronting the possibility of failure. Of rejection. Of discomfort. It means letting go of the safety that comes from staying where you are—even if where you are isn’t really working.

In many ways, it’s easier to tell ourselves we don’t have enough time or money. Those are socially acceptable barriers. They make sense. They let us off the hook.

Courage doesn’t.


When I think about my own life, I see this clearly.

The things that have mattered most to me like writing, communicating, and connecting, weren’t limited by money or time. They were limited by my willingness to step into them. To claim them. To risk being bad at them, or misunderstood, or ignored.

And that’s true for most people.

Your thing might not be writing. It might be a relationship, a creative pursuit, a career shift, a way of living that feels more aligned with who you are. I can’t tell you what that is.

But I can tell you this: if you don’t move toward it, it probably won’t be because you lacked time or money.

It will be because it required a kind of courage you weren’t ready to access.


The good news is that courage isn’t fixed.

It’s not something you either have or you don’t. It’s something you build. Slowly. Uncomfortably. Through small, consistent acts of showing up in ways that feel just a little bit scary.

You don’t wake up one day and suddenly become fearless.

You practice.

You say the thing you’ve been avoiding. You take the first step instead of waiting for the perfect moment. You choose intention over autopilot, even when it’s inconvenient.

And over time, that changes you.


Conclusion

If you want to have fewer regrets at the end of your life, I don’t think the answer is to chase more money or somehow find more time.

I think the answer is to build courage. To get better at doing hard things. To get more comfortable being uncomfortable. To become the kind of person who acts on what matters, even when it’s inconvenient or uncertain.

Because in the end, that’s what people wish they had done.

Not more.

Just braver.

22 comments

  1. Wow thanks for sharing, I will be sharing this with those I love. I hope it spawns conversation.

  2. This is the absolute truth.
    I am a former hospice nurse.
    The real regret is the things you were not brave enough to do.
    Be brave, be happy.
    Be true to yourself.

  3. Great article. The part about hiding behind excuses seems real. And small practices can lead to big improvements!

  4. Really wise article on the courage to face our fears (of failure, rejection, and change). Fear of change and keeping the status quo is a core human trait. Change is hard, painful, and involves loss. Nobody wants to face grief, but it is inevitable. So we must find peace with acceptance of what we cannot change. This is wisdom. It’s the serenity prayer.

  5. Beautifully said. As a recently retired medical professional and after sitting with my own mom in hospice I’ve heard the regrets often . My moms last regret was ” I wished I had spent more of my money on experiences with you kids and the grandkids” ! Those words have made me more intentional in living “my best life “.

  6. Wow, what a great perspective. To me the important things have been family connections. But, somehow I delayed actually trying to build them. Always thought I’d have more time.

    Finally, when my parents were elderly, I overcame the easy way out and we talked about things I know were bothering them for decades. It was uncomfortable. The first step is the hardest. But after that, in my parents last years, I knew they were happy we discussed things. In a way, it was the best years of our lives.

  7. Excellent article, thanks so much for sharing your experience and observations. This really has gotten me thinking.

  8. Great perspective, thanks for sharing. I think , foe me, it’s The Serenity Prayer….give me the courage to change the things I can, & the wisdom to know the difference.

  9. I regret not spending some of my money when I was younger and enjoying it. Now that I’m retired and I have plenty of money that I will most likely not be able to spend all of it in retirement, I wish I would have bought the bigger house that I wanted, or bought new cars rather than used ones. I’m not a materialistic person, but soon after my retirement, I went and bought myself a brand new luxury car. I no longer want the bigger house, but as my mom would always say, when you get older and now that you have some money in the bank, there isn’t much I want anymore. I’m living that now.

    1. If you say you’re not materialistic and that is a trait you’ve always had, then you would not have enjoyed the spendthrift life. It gives you a little dopamine hit and then the bills and stress of those possessions arrive. Do not underestimate the security and satisfaction of a well-funded retirement; you have none of the struggles that a profligate lifestyle would have produced. Instead, look at this FOMO you’re having, and understand where it is coming from. That is where the problem lies — not regret for past actions.

      1. I got into the market at age 26 and my dopamine hit was my portfolio balance, so I’m confident I would have never been stressed out with bills. I don’t ever take for granted my current financial situation, but I made sacrifices to get where I am today, nothing was handed to me. I honestly don’t have any FOMO (I had to look that up lol), but I do believe I could have found more of a balance in life while accumulating wealth to enjoy what my money could buy rather than waiting to enjoy the security that my money now provides me in retirement. I didn’t have a miserable life, far from it, and I love my life now, but I will always ask myself if I sacrificed too much to have security in the last 20-25 years of my life. Thanks for your reply.

  10. Throughout most of my career, I regretted taking a job close to home and not having the courage to move to Silicon Valley and try to get a job with Apple. But as I am older and retired early, I now regret not having the courage so leave my Fortune 500 tech job earlier to pursue my own interests. Had I paid more attention to my retirement plans at a younger age, I could have left the workforce much earlier than I did.

  11. I know that the decisions that resulted in the most joy have always been the ones that required the most courage. I didn’t think of them that way at the time, but i did see them that way after the decision was made. It takes support to make those courageous decisions. Thanks for sharing this!

  12. Fantastic article and so true for me. I am trying to pull my trigger to ‘retire’ or least sub out my book of business but I am waffling on how to best leave a lifetime of self-employment hustling. I struggle with the thoughts of regrets and now I need to muster the courage to enter a new phase of life.

  13. really clear, concise article. and very meaningful…and true….thank you

  14. It has been well researched that, on their deathbed, people express more regret over what they didn’t do than what they did. As a nurse, I have seen this as well. What I love that this article is that it takes that one step further and explains what was lacking… courage. Great guest post with lots of take-a-ways for us!

  15. So I appreciate the advice. My personally had a very full life. I moved 9 times in the last 11 years of my career. I’ve lived in Europe for four years of those years and in a dozen cities in the US. My mother grew up living within the same area, not more than 25 miles from where she was born. I was always encourage to travel and explore, etc., and so forth. I loved a life at exploration and discovery and most importantly Growth. But over the last few years we’ve kind of stagnated. I’m ready to fully retire at the age of 55. Really I prefer to spend more time traveling throughout Southeast Asia. There’ll be a time when we can’t physically do it anymore but right now we can do it both physically and financially. In fact, it’s actually less expensive to live in a couple of southeastern Asian countries. Realize what you can do today and what you might not be able to do tomorrow. Let that inform your decision-making.

Comments are closed.