How to deal with regrets

“Mistakes are the portals of discovery” wrote the author James Joyce. I recently spoke with a young analyst in Private Equity who wanted to take a pragmatic look into regrets with one qualifier – “not the deathbed kind.” He wondered aloud, what were some common regrets of people ten or twenty years older? And did they deal with the regret? If so, was it with action, acceptance, or self-doubt? I polled a community and aggregated their 100+ responses. The answers spanned relationships (“I married the wrong person”), careers (“not placing riskier, asymmetric bets on myself,”) self-care (“failing to have the difficult conversations with myself”) and hobbies (“Not learning my nana’s language.”)

Are regrets a “failure of imagination?”

I personally don’t have many regrets. Not because I’m special or risk-seeking, but because I see the actions I’ve taken in my life as exactly that: my life.

Should I have left the corporate world earlier? Maybe, but I wouldn’t have had the same perspective and experiences. Should I have investigated my fear of death earlier? Maybe, but I probably wasn’t mature enough to look it directly in the eye.

One of my favorite survey responses was “Regrets feel like a failure of the imagination to see how the past has served us.” Another added that regrets felt like “wasted energy – stories we tell ourselves about the past that take up a lot of time in the present, [blocking us from] whomever or whatever we feel called to be.”

However, there are a few specific regrets which could be paired with action. The most common regret in our survey (by a long shot) was not studying abroad (or living abroad); one that I shared. We’ve still got a window for that regret, in fact, Lisa and I talk about a family gap year when the girls are in middle school. So we’ll see.

My other regret is not having treated certain people with kindness. Let’s just say that my insecurities revealed themselves by seizing on others’ insecurities. Some of these people are in my life and others aren’t – but I have the agency to change (not necessarily atone) my behavior on a go-forward basis.

Regret minimization frameworks

How do other thinkers re-frame and process regrets. Jeff Bezos started Amazon using his own regret minimization framework which is rumored to be inspired by the story of unfulfilled love in Kazuo Ishiguro’s book The Remains of the Day.

“The framework I found, which made the decision incredibly easy, was what I called — which only a nerd would call — a “regret minimization framework.” So I wanted to project myself forward to age 80 and say, “Okay, now I’m looking back on my life. I want to have minimized the number of regrets I have.” I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision.”

Or said differently, “In X years, will I regret not doing this?”

Similarly, super-blogger Tim Urban argues that our regrets stem from the inability to stray from society’s pre-set expectations. In How to Pick a Career (That Actually Fits You) he writes:

Kids in school are kind of like employees of a company where someone else is the CEO. But no one is the CEO of your life in the real world, or of your career path—except you. And you’ve spent your whole life becoming a pro student, leaving you with zero experience as the CEO of anything.

Urban sees regret minimization as an exercise in choosing your own adventure in life, a process he calls “path-making”:

When scientists study people on their deathbed and how they feel about their lives, they usually find that many of them feel some serious regrets. I think a lot of those regrets stem from the fact that most of us aren’t really taught about path-making in our childhoods, and most of us also don’t get much better at path-making as adults, which leaves many people looking back on a life path that didn’t really make sense, given who they are and the world they lived in.

HBS professor (and Rad Awakenings guest) Mihir Desai describes regret through the metaphor of financial leverage. At the corporate level, borrowing allows an organization to amplify its resources and impact in the economy. But it’s not without constraints, such as interest payments and covenants. And the inability to fulfill these commitments comes at a high price: default and bankruptcy.

For an individual, your leverage is the range of your commitments: kids, extended family, careers, education and philanthropic passions. In The Wisdom of Finance, Desai describes how his family has toed this line:

“I often ask myself if we are making the most of our lives by living a highly levered life or simply taking too much at the cost of the people closest to us.”

And maybe the challenge (as the hedge fund Greenlight Capital agitated with Tim Cook and Apple in 2013) is that we as individuals are under-levered:

One of the central facts about corporations and their financing decision maps particularly well to our lives. By most measures, firms are dramatically under-levered. They don’t appear to take the full advantages that the tradeoff theory implies. Many individuals may well be doing the same – they retreat from commitments and obligations, and in the process, they limit what they can do. Studies of regret show that regret mostly arises from commitments avoided – untaken educational opportunities, missed love connections, and the inattention to children.

The List of Regrets

Here’s the categorized excerpts from the survey of regrets organized by family, self-reflection, hobbies, career, and geography. (Here’s the entire Google Doc):



  • 35M Marrying the wrong person. I have two kids that I love with all my heart, so I’m willing to be miserable for their sake, at least until they are adults (only 16+ years to go). But I regret marrying this person, every single day. (Note: If you’re reading this, please know you can email me directly, in full confidence)
  • 21M Not getting closer to my brother earlier
  • 38M Not getting closer to my sister earlier
  • 26M i regret not being closer to my family while we all lived in the same house, can’t change without a time machine
  • 35M Not spending enough time with my family (catching up, planning meetups, etc)
  • 32M Being far away from family




  • 55F Always looking for a “perfect” life, marriage, kids, jobs, vacation, greener pasture and not living the moment.
  • 25M continuously failing to have the difficult conversations with myself and others
  • 33F Not dealing with my trauma, stretching and teaching myself to breathe properly earlier in life.
  • 33M Letting other people make critical decisions for me instead of trusting myself
  • 30F Aiming too low because I didn’t believe enough in myself
  • 31F Failing to enjoy the “in the moment” beauty around me during periods of my life like living with roommates, spending time with my grandparents, and being young and broke in a bit city because I’m too preoccupied focused on planning for “the next thing”
  • 31F Regret not having learned how to take negative feedback earlier on
  • 29F Not trusting myself enough
  • 20M Allocating too much time to making others happy, not focusing on what makes me happy
  • 43M Never accomplishing anything professionally that I feel has been worth a damn
  • 23F Getting the MMR vaccine right after a concussion ( result of chronic nerve pain) – trying to heal it
  • 35M focusing on one thing at a time
  • 24F Regret being so anxious everyday up and worrying that I’m not good enough; regret not intentionally choose my path and passively going about it because it was the laid out path for me; regret being so risk averse; regret not practicing good habits
  • 29F I regret not living louder, allowing fear or social / cultural expectations to influence my choices. Yes, I have the capacity to change it.




  • 35M Not making the most of potential music career in my twenties. Still have capacity to create and perform.
  • 32M Not having played hockey at more competitive level when I could’ve
  • 38M Not continuing to play musical instruments
  • 24M Wished I learned my Nana’s language




  • 38F Not trusting myself enough to start a business earlier in life
  • 45M Not pursuing new career interests and staying in a stable, boring job
  • 38M stopping too early with start up projects
  • 21F Not majoring in computer science because I thought the intro class was too difficult
  • 43M Not sticking with difficult job placements earlier in my career, leaving instead of fighting gets easier…
  • 47F Not joining the Peace Corp when I was younger
  • 74M Not going to Viet Nam to fight.
  • 22M Choosing a profitable career path instead of following what makes me happy
  • 32M Hedging my bets when younger rather than swinging for the fences with my personal goals
  • 30F Not taking more risks in my twenties
  • 29F Regrets being to scary all my life to believe in myself more and start an interesting project. Regret being not capable to make my career growing. Regret not loving myself enough. Regret not to start traveling earlier and not try a student program Work and Travel USA. Passed that age and possibility
  • 37M not prioritizing academics and learning earlier in my life. I am now “catching up” to make up for lost time, but I lost a lot over the last 15 years…(too busy with work)
  • 37M Wasting too much time partying in college/business school instead of actually learning new and interesting things when I had the opportunity to
  • 30 Not investing in my growth and entrepreneurial career early enough and ingredients required for the same.  Another thing is not getting a mentor before 20.
  • 22M Not keeping up with good habits earlier; I can see the compounding
  • 32M Not placing riskier (asymmetric) bets on myself (job, investments, relationships, etc.)
  • 23F Not applying to better schools- maybe masters/PhD
  • 35M Not waiting out the recession to land a solid job at a great firm and instead joining a mediocre company, which had longer term consequences (following job was not as good, etc.) making it harder to catch up
  • 31F Regret mostly skidding through life on “almost best” (because everything came easy to me), never really learning how to give something 150% of myself and be truly “best” or deliver “the best” [outcome]; Regret not risking more in my 20s – mostly just about not having started a business when I had no obligations (kids, mortgage, reputation, etc.) – this I’m trying to fix as I write this
  • 24F Being too scared and lacking confidence to study and work on what I’m truly interested in. Playing it safe in schooling and not nurturing my ability to take risks and recuperate if I fail. As I’m typing it out, it doesn’t seem that impossible to achieve…
  • 26M I regret not taking a longer break between jobs the two times that i’ve switched (only 1 week between each), still plenty of opportunity to optimize for some sort of 4-6 week break even if it’s not between jobs; cheating by adding two…




  • 32F Not doing a semester in France or living there
  • 37M Not coming to United States earlier
  • 29F Moved to the United States for work and regret it (wasted my twenties in the US / Protestant work ethic hellish workaholic culture)
  • 45M; (2) I try to live with “no regrets,” but I’ve never lived anywhere except Chicago and the surrounding area, and (3) I have the capacity to change it as my husband and I are planning to move to Portland, Oregon within the next 18 months and it is scary as f**k.
  • 33M Not studying abroad in college
  • 32M Not moving to Germany when I had the chance. It was a crazy opportunity I should have forced myself into even though it made no sense at the time.
  • 23F Going to a university in nyc vs. a campus (wanting to grow up too quickly and not getting the « college experience »), can’t change
  • 30M never moving to NYC


Regret and Fear: The twin thieves

“Regret and fear are twin thieves who would rob us of today” wrote Robert Hastings in his poem The Station. Let’s return to the well-documented Regrets of the Dying:


  • I wish I’d had the courage to live a life true to myself, not the life others expected of me.
  • I wish I hadn’t worked so hard.
  • I wish I’d had the courage to express my feelings.
  • I wish I had stayed in touch with my friends.
  • I wish that I had let myself be happier.


Regrets challenge us to strike the delicate balance between past and future; our willingness and ability to commit; and ultimately life and death. In the book Immortality: The quest to live forever and how it drives civilization, Stephen Cave highlights this balance:

“Live so you will have no regrets if you die tomorrow but also no regrets if you don’t. The first part might prompt you to quit the job you hate, but the second should stop you from punching your boss on the way out.”

I work with entrepreneurs and executives on their own ‘regret minimization frameworks.’ If we should be chatting, hit me at: khe [at] radreads [dot] co

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