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.”

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. Now he draws on his experience to write about wealth building, DIY investing, financial planning, early retirement, and lifestyle design at Can I Retire Yet? Chris has been featured on MarketWatch, Morningstar, U.S. News & World Report, and Business Insider. He is also the primary author of the book Choose FI: Your Blueprint to Financial Independence. You can reach him at]

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