Avoiding Retirement Regrets

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Regret almost always occurs as a result of a decision we made. “If only I’d made this decision, or hadn’t made that one….everything could have been different.”

Regret in block letters

In his book, The Power of Regret, Daniel Pink argues that we should look backwards at our regrets to help us make better decisions moving forward. Our regrets are like a photo negative of the ideal life we picture living.

Many of us ponder two key questions as we contemplate one of the biggest decisions of our lives. Can I retire yet? Should I retire?  

As we consider these questions, it is worth taking time to understand the most common regrets people have. How can you use that information to avoid making a decision you will regret?

What Do People Regret?

In his book, Pink points out that many studies of regret have selection bias. They tend to take samples of convenience. Since, for example, many studies are done on college campuses, studies frequently show people’s biggest regrets relate to education or career path.

Pink attempted to avoid these sampling biases by looking at studies that included diverse populations including people of various ages, cultures, and socioeconomic backgrounds. He also conducted his own World Regret Survey which includes responses from thousands of people from more than 100 countries.

Categorizing Regrets

After analyzing data on regret, he found that regrets could be organized into one of four categories. The categories, with a couple of common examples from each are:

  1. Foundation: “I wish I would have taken my education more seriously.” “I should have started saving when I was younger.” “If only I had taken better care of myself….”
  2. Boldness: “I wish I followed the career path I was interested in instead of focusing on financial implications.” “I should have asked her out.” “ If only I had traveled when I was younger and I had the freedom before having kids….” 
  3. Moral: “I wish I didn’t bully the new kid in school.” “If only I would have been faithful to my spouse, my family could still be together.” “I regret stealing that money.”
  4. Connection: “I regret losing touch with my oldest friend.” “I should have made that phone call.” “If only I had focused more on my family and less on my work….”

Applying Pink’s Regret Categories to the Retirement Decision

As I read The Power of Regret, I couldn’t help but think about my own regrets and how they have motivated my decisions. I also repeatedly thought about conversations and correspondence I’ve had with readers of the blog, and how regrets seem to drive their actions.


Moral regrets are the most rare type. They also tend to be the most powerful and long-lasting. Some of the regrets Pink describes in the book are heart wrenching. 

People suffer with feelings of guilt and shame for decisions they made, sometimes decades earlier, related to actions like bullying, infidelity, and theft. If your biggest regrets fall into this category, I feel for you. But I don’t think these regrets relate to the retirement decision for most people.

The other three categories of regrets are worth examining more closely. They offer a window into past decisions and can help us make better decisions moving forward as we plan for retirement.


I venture to guess that for most people reading this, foundation regrets are relatively rare in frequency and of minor importance. If you are in position to retire early, you likely took your education and career development seriously. You likely started saving and investing relatively early.

As I look at my own life, I do have some regrets about being intimidated by investing and tax planning and not learning about them sooner. Those mistakes cost me over ten thousand dollars per year for about a decade. Compounded over decades, that easily represents a million dollar mistake!

Related: The Worst Investing Advice I Ever Heard…. Everywhere!

Still, I did enough things right that those weren’t crippling mistakes. I’ve managed to turn that negative into a positive, using that experience as motivation to share my story in an effort to educate others and help them do better with their money.

The foundational regrets I hear frequently from this community relate to physical and mental health. Many people driven by career and financial success work long hours, characterized by high stress and lack of prioritization of diet and exercise. They view retirement as an opportunity to start over and right those wrongs.


Boldness regrets are the opposite of foundation regrets. So in a community with few foundation regrets, I would wager that many of us swing too far in the other direction. We often end up with boldness regrets.

My biggest regrets were boldness regrets. I’m not completely risk averse. At a relatively young age, I decided to commit to the love of my life and put all I have into that relationship. We’ve traveled the world and sought adventure, climbing 20,000 foot mountains and traveling half way around the world to dive the Great Barrier Reef.

Those decisions weren’t without second guessing and heartache. I’ve shared struggles in my marriage

We’ve spent months and thousands of dollars on adventure travel that turned out disastrously. There were close calls in the mountains with rock fall, avalanches, and altitude sickness. 

After traveling all the way to Australia, I got so sea sick I couldn’t dive the Great Barrier Reef. I couldn’t stop puking long enough to get a wetsuit and oxygen tank on.

But I never regretted any of the things I’ve tried. My biggest regrets have always been the things I didn’t have the courage to do….the risks I wasn’t willing to take.

So when I reached a fork in the road as I approached financial independence, I chose to be more bold. I left my job and career completely. We moved our family across the country to start over. 

Some things have gone better than planned. Others have been far harder than anticipated.

Related: Does FIRE Make Life Harder?

At the end of the day, I don’t regret decisions I’ve made. Had I not taken those chances, I think it would have forever gnawed at me. I’d have been left wondering, What if….?


Other regrets I have, and which I assume are common in this community, are connection regrets. Much as it is easy to neglect our health in the pursuit of success, relationships can become casualties of lifestyles focused too much on work, careers, and financial success.

In The Power of Regret, Pink describes how hard it is for many of us to reach out to others. He emphasizes that it can be especially awkward when we want to reconnect when there was no rift, and instead we’ve just drifted apart over time. 

He recommends that when in doubt, always choose to reach out to the other person. There’s so much upside with virtually no risk. I love this idea.

Again, retirement is seen as a time for a reset. It can be a time to reestablish old connections and create new relationships. 

However, it can be easy to over romanticize the idea that retirement is the time to change and connect with others. It’s vital to be honest with yourself as you think about why you have connection regrets and how you’ll establish connections after leaving the workforce.

Relationships are the outcome of two (or more) people’s actions. Just because you are ready to create time and prioritize relationships, it doesn’t mean others are. 

A substantial amount of research has shown that loneliness, feelings of isolation, and depression are common in retirement. It’s important to have a plan and take action on it to create the connections you desire.

If you think connection will magically happen because you have more time in retirement, you may end up even more lonely….and regret your decision to retire.

Related: 5 Lessons From 3 Years of Early Retirement

It’s Not All or None

I’ve been reflecting on my decisions after reading The Power of Regret. With the benefit of hindsight and the insights of Pink’s book, I realize that some of my best decisions were avoiding all or nothing decisions that may leave me with regret.

We tend to see the world in black and white. The retirement decision is often viewed this way.

You can choose more money, security, and prestige that come with staying in a career. But you risk sacrificing health, relationships, and other dreams.

On the other hand, you can choose a life of boldness and connection. But your future self may regret not having more money and the options money can provide. And it may be too late to do a lot about it because of earlier decisions.

Either argument has validity. Maybe instead of choosing black or white decisions that are diametrically opposed and can leave us with regrets, we need to learn to appreciate the different shades of gray. 

Instead of asking “Can I Retire Yet?,” we should ask better questions. What degree of financial independence do you already have? How can you start using that today to build a life that you won’t regret?

Related: The Fundamental Problem With Retirement Planning

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[Chris Mamula used principles of traditional retirement planning, combined with creative lifestyle design, to retire from a career as a physical therapist at age 41. After poor experiences with the financial industry early in his professional life, he educated himself on investing and tax planning. After achieving financial independence, Chris began writing about wealth building, DIY investing, financial planning, early retirement, and lifestyle design at Can I Retire Yet? He is also the primary author of the book Choose FI: Your Blueprint to Financial Independence. Chris also does financial planning with individuals and couples at Abundo Wealth, a low-cost, advice-only financial planning firm with the mission of making quality financial advice available to populations for whom it was previously inaccessible. Chris has been featured on MarketWatch, Morningstar, U.S. News & World Report, and Business Insider. He has spoken at events including the Bogleheads and the American Institute of Certified Public Accountants annual conferences. Blog inquiries can be sent to chris@caniretireyet.com. Financial planning inquiries can be sent to chris@abundowealth.com]

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  1. This might be the most powerful 1,500-word essay I have ever read in my life.

    Thank you, Chris!

  2. This is so difficult because I do fall in the so called “black or white” category.
    Just before 2022, I was positive that I can retire, but now I’m not so sure because of the war in Ukraine. If I was born in the US I don’t think I would be over analyzing and I would still retire perhaps, but I emigrated from the ex-USSR and my family/friends still live there (not in Ukraine, but very close to it), so I’m overcome with a lot of difficult feelings and regrets nowadays, one of which is whether to continue working in order to save money to help my family. I never included a potential war and what resources would be needed for such a situation. Since I don’t like my job anymore, this makes even more psychologically difficult.

    1. S&M,

      Thank you for sharing. It is a sad and scary time, particularly for anyone with direct ties to that area.

      You never know what the future holds. Best wishes as you navigate these challenging times.


  3. The ”moral” regret category really hit home for me. I am 62 years old and still struggle with how terribly I bullied classmates when I was in grade school. Also,…I stole a few things from local department stores when I was younger. To be fair (to myself),I came from a horribly dysfunctional family,..and,…was left alone to raise myself.I often say that I would have turned out better being raised by a pack of wolves. My childhood was a complete disaster. I wish I could go back and apologize to everyone,…or,…have a complete do-over,…unfortunately, I can’t.

    1. Steven,

      I’m sorry if this post stirred up any negative emotions and memories in you. As I noted in the post, reading that portion of the book was gut wrenching. You are not alone in having those regrets. I hope you can find solace in having made the best of the situation. While you can never go back and undo the past, you can certainly create a better future.

      All my best,

    2. It’s not too early to apologize! I apologized to one kid about my actions when I was in the fourth grade. Go back and apologize. It is cathartic and everybody will feel good.

  4. I’m not sure if my other comment went through or not. But thanks for sharing this review and post. Regret is something that has driven me for a very long time.

    One of my biggest regrets was not asking out this girl that I really liked. So since then, I’ve always tried to be as bold as possible with the people I enjoy hanging out with.

    My other regret was living in San Francisco during the.com boom and not doing anything to participate in the Internet boom. I was working in finance for 13 years and saw innovation after innovation and so many companies go public, by my own company.

    So the good thing about fearing regret is that it encourages you to take action to not feel regret. So now, I feel pretty good because I’ve done almost everything I’ve wanted to do.

    Regret was the same decision I had two years ago when an editor at Penguin Random House contacted me on whether to join them and write a book or not. I didn’t really want to do it because I had already written a book that took a long time to write. But I felt I would regret not having tried.



    1. And I have some mild regrets about working in the SF dot com boom.

      There were way more companies that dot-busted than dot-boomed. When holding two job offers, it was impossible to divine which was likely to be years(s) of 60 hour weeks, cramped offices, 24/7 phone calls and exhaustion followed by the payback of an IPO. And which were likely to be years(s) of 60 hour weeks, cramped offices, 24/7 phone calls and exhaustion followed by your paycheck bouncing and no cramped office to go to the next week. I slogged down the latter of those two paths. FWIW I was in A arch for 30 years and those were two of the most miserable of those years with no financial reward for me.

      It was really really hard to tell beforehand which slim minority of companies would make it and which vast majority would crash and burn. We all want to think we’d make the best choice. I didn’t, and I was in the industry.

  5. Coincidentally, The Power of Regret is sitting on my nightstand, but it’s the 3rd or 4th book down in the queue. This post was an excellent preview. About a year ago, I read an AARP article entitled, “Live Longer, Stronger and Better.” I don’t recall anything else about the article, but I did throw this tidbit in my inspiration file . . . “Keep a ‘no regrets checklist.’ Write down a list of all the things you’ve had to put off over the years because of work or raising a family. Then make a timeline for how you’ll revisit these goals. Regret is largely avoidable with a little reflection and mindful focus.” I don’t believe that regret is largely avoidable because it’s a product of hindsight. But I do think that revisiting a list of pursuits or relationships that fell by the wayside in the past is an excellent way to mitigate regrets later in life. I can also see how doing so might make the transition to retirement more fulfilling, especially for anyone who didn’t specifically have something to retire “to.” Thanks for a thought provoking article, Chris!

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