written by
Flavian DeLima

How to overcome regret and not be a ‘cog in the wheel’

self-improvement community 17 min read , July 5, 2021

This article on regret was inspired by Issue 12 of the CFP newsletter.


The theme is regret. I hadn't thought about this topic much before. In the past, my default answer when asked about regrets was, “I don't have any ". I was like the guy in "We’re the Millers". If I told this to President Biden, I bet he’d say, “That’s a bunch of malarkey“.

Everyone has regrets, especially in the short term, which can feel devastating at the time. Short-term regrets become less significant with time. It’s the long-term regrets that linger and fester as we get older and look back on things we wanted to do but never did.

I’ve watched many smart and talented friends admit to me, saying, “I’m a screwup” when something bad happened and they felt completely alone and responsible. I’ve had the same thoughts and said the same words, especially early in my career, when I keep my failures private. Along the way, I learned that saying, “I screwed up” is so much lighter 😌 and allows you to move past a regret instead of replaying the same "I'm a screwup" story in your head. Stop beating yourself up and be kinder to yourself.

One of the biggest regrets people have is about education. They regret not going, not completing, or taking too long to go back to school. This past month has been graduation season with thousands of convocation ceremonies. Congratulations to the Class of 2021!

Regret Don't waste time small talk
Don’t waste time on small talk

Regrets of the Dying

In 2009, Bronnie Ware started a blog. Her fourth post, Regrets of the Dying, was 800 words, which changed her life and has been viewed about 10 million times. The article was based on her 8 years working as a live-in palliative care nurse for terminally ill patients in their final 6 to 12 weeks. She says the conversations were more meaningful because noone had time to waste words on small talk.

Bronnie summed up 8 years of listening to dying patients into 5 main categories of regret. The article became a bestselling book called The Top Five Regrets of the Dying. They were:

  1. Didn't have the courage to live a life true to myself, not the life others expected of me.
  2. Regretting working so hard
  3. Not having the courage to express my feelings.
  4. That I hadn't stayed in touch with my friends.
  5. I wish that I had let myself be happier.

I want to focus on the first regret, which is the most popular one. In April 2018, researchers at Cornell University published a paper called “The Ideal Road Not Taken”. Similar to Bronnie, they found the biggest and most enduring regret people have is:

The failure to live up to your ideal self.
Regret Spend less time on ruminating regret
Spend less time on ruminating regret

The science of regret: what you did vs. what you wish you did

People experience regret in two ways. The first is regret for the actions they took. The second is regret for actions they wanted to take but never did. People often regret something they did in the short term like getting a tattoo. But the big regrets tend to be long-term after people look back on their life at things they didn’t do but wish they did. The number one regret most people have when looking back is not being true to themselves

Social psychologist Amy Summerville runs The Regret Lab at Miami University. She studies how people think about the choices they made or wish they made. It turns out that regret is the second most frequently experienced emotion behind love. Regret is a negative emotion. It occurs when we wonder how a different choice or decision we made could have led to a better outcome. Summerville says these “alternative histories” and the imagined futures create what psychologists call “counterfactual thoughts”. Upward counterfactuals are the negative thoughts that haunt us as we think hard about how life might have gone better. On the other hand, downward counterfactuals make us feel pretty good because we think about how life could have turned out worse. Most of us, especially younger people naturally reflect on different choices that could have led to a better outcome.

Car crash example

The first thing a driver thinks about after getting into a car accident is what they could have done differently to avoid the crash. People obsess over "what if" scenarios and rack their brains with questions like, "Could I have left at a different time?", "Did my phone distract me?" or "Why didn't I pay more attention to the road?" This type of counterfactual thinking keeps you focussed on the negative instead of the positive.

The worst part of regret

The worst part of regret is a process called rumination. It happens when we beat ourselves up, repeatedly replaying a negative event in our heads. It's counterproductive to have ruminating regrets, which has been known to increase a person's depression and anxiety as well as cloud their decision-making in other important areas of life.

Regret: Write your book
Write your book: page 70

John the banker: TIFU my whole life

At some point, we all behave like a version of John or know someone like him. John wrote a Reddit post in 2015, titled, "TIFU my whole life. My regrets as a 46 year old, and advice to others at a crossroad". It's worth a full read because you get the feeling he really wants to help others not make the same mistakes he made. Passages of his post are below.

I need to get my life off my chest. .. I'm a 46 year old banker and I have been living my whole life the opposite of how I wanted. All my dreams, my passion, gone. In a steady 9-7 job. 6 days a week. For 26 years. I repeatedly chose the safe path for everything, which eventually changed who I was.
Today, I found out my wife has been cheating on me for the last 10 years. My son feels nothing for me. I realised I missed my father's funeral FOR NOTHING. I didn't complete my novel, travelling the world, helping the homeless.
Let's start with a description of me when I was 20. It seemed only yesterday when I was sure I was going to change the world. People loved me, and I loved people. I was innovative, creative, spontaneous, risk-taking and great with people. I had two dreams. The first, was writing a utopic/dystopic book. The second, was travelling the world and helping the poor and homeless.
I had been dating my wife for four years by then. Young love. She loved my spontaneity, my energy, my ability to make people laugh and feel loved. I knew my book was going to change the world... I was 70 pages through when I was 20. I am still 70 pages in, at 46. By 20, I had backpacking around New Zealand and the Phillipines. I planned to do all of Asia, then Europe, then America (I live in Australia by the way). To date, I have only been to New Zealand and the Phillipines.
Now, we get to where it all went wrong. My biggest regrets. I was 20. I was the only child. I needed to be stable. I needed to take that graduate job, which would dictate my whole life. To devote my entire life in a 9-7 job. What was I thinking? How could I live, when the job was my life? After coming home, I would eat dinner, prepare my work for the following day, and sleep at 10pm, to wake up at 6am the following day. God, I can't remember the last time I've made love to my wife.
Rationalizing everything, making excuses to put things off. Excuses. Procrastination. It all leads to one thing, nothing. I rationalized that financial security was the most important thing. I now know, that it definitely is not.
I regret doing nothing with my energy, when I had it. My passions. My youth. I regret letting my job take over my life. I regret being an awful husband, a money-making machine. I regret not finishing my novel, not travelling the world. Not being emotionally there for my son. Being a damn emotionless wallet.
If you're reading this, and you have a whole life ahead of you, please. Don't procrastinate. Don't leave your dreams for later. Relish in your energy, your passions. Don't stay on the internet with all your spare time (unless your passion needs it). Please, do something with your life while your young. DO NOT settle down at 20. DO NOT forget your friends, your family. Yourself. Do NOT waste your life. Your ambitions. Like I did mine. Do not be like me.
TL:DR I realised I let procrastination and money stop me from pursuing my passions when I was younger, and now I am dead inside, old and tired.
Despair and regret: Tomorrow will be just like today

I think John’s post went viral because he was honest, unedited and it felt like for the first time, he did "get his life off his chest". The 4,000 people who responded to John offered support and started sharing their life regrets.

The bronze-medal mindset

Winning a medal at the Olympics or in any sport is not supposed to make you feel like a failure. Researchers discovered since studying the 1992 Barcelona Olympics that bronze medal winners are consistently happier than silver medalists. Silver medalists tend to practice counterfactual thinking and repeatedly tell themselves, "if only I did a little better, I could have won the gold". Bronze medalists are happier because they compare themselves to everyone who didn't win a medal. In the 2012 London Olympics, Olympic swimmer and silver medalist Ryan Lochte said he was disappointed because he was "just short of gold". In the same race, Brendan Hansen, the bronze medalist said,

“[I] swam my own race. And knew I had a lane, and had an opportunity, and I went for it. It worked out... it's just awesome that I get to go on the podium tonight."
Bronze model less regret than silver

Ryan was fixated on the regret of the loss and unable to see past it. Brendan's response was about his future. He saw the race as one performance, celebrated it, and knew how he could do better at future competitions.

Why don’t we give ourselves a break?

Brene Brown in Rising Strong writes about Andrew who is the project cost estimator and liaises between the creative and business teams at his job in an advertising agency. He sees himself as a perfectionist. They were bidding on a client project that everyone really wanted. The team worked over sixty hours for two months which led up to a disastrous second stage presentation. The client was rude to someone on Andrew’s team during the presentation and Andrew didn’t do anything.

During the entire trip home, the team didn’t speak and Andrew ruminated on these same thoughts:

I’m a screwup. I didn’t protect my people. I didn’t do my job. I’m a screwup. I failed. I’ve lost their trust. The tape was on a constant loop in my head. ...When I woke up the next morning, my first thought was, I’m a failure and a screwup. My second thought was, I need to get out of this. I need to make this work. I need an easy fix. Who else is to blame? Who else was responsible for this mess?

Brown says that when our stories wrap around shame, perfectionism, or comparison, we will feel isolated and “less than”. She recommends two strategies to rise above feeling “less than”:

  1. Talk to yourself the way you would talk to someone you love.
  2. Reach out to someone you trust - someone who can hear your story and is able to respond with empathy.

When we keep our stories of regret secret, silent, and judgemental, they fester on shame and self-loathing. If it is hard to speak to a kinder “you”, establish trust with friends and listen with care to each other’s stories. The community you nurture is the community that is there for you when you need them most.

Regret:Talk to a friend in your community
Talk to a friend in your community

Andrew chose to phone a close friend and share what happened. His friend listened and then said:

I get it. And I think you might have screwed up. But you make a hundred judgment calls every day. Do you think you’re going to make the right call every time? Does making a bad call make you a failure?

After the conversation, Andrew was relieved because he was able to see he “screwed up” instead of being “a screwup”. Andrew met his team and let them know he screwed up and made a mistake. He apologized and said he hoped to regain their trust. The team responded that they trusted him and together they chose to discontinue bidding on the project.

Brown writes that regret, courage, and growth need to go together if we are to react well:

If you have no regrets, or you intentionally set out to live without regrets , I think you’re missing the very value of regret. ... [R]egret can be the birthplace of empathy. When I think of the times when I wasn’t being kind or generous—when I chose being liked over defending someone or something that deserved defending—I feel deep regret, but I’ve also learned something: Regret is what taught me that living outside of my values is not tenable for me. Regrets about not taking chances have made me braver.

Chadwick Boseman on Purpose

Every person pursues their best version of themself differently and on their own terms (or on someone else’s terms). Chadwick Boseman, who died of cancer on August 28, 2020, was someone who lived strongly with purpose. He recounted an early experience in his career as a struggling actor in his 2018 commencement address to Howard University. Executives brought him into the studio to do more episodes for the soap opera, All My Children. He was fired from the show soon after voicing questions to producers about the racist stereotypes in the script.

Regret and Purpose: Chadwick Boseman's Howard University 2018 Commencement Speech
Chadwick Boseman's Howard University 2018 Commencement Speech

When Chadwick asked what happened to his character's father and mother, execs answered:

Chadwick: Question number one:Where is my father?
Execs: “Well, he left when you were younger.”
Chadwick: Of course. Okay. Okay. Question number two: In this script, it alluded to my mother not being equipped to operate as a good parent, so why exactly did my little brother and I have to go into foster care?
Execs: “Well, of course she is on heroin”.

At the time of his firing, he was conflicted about his need to "speak truth to power" versus being a busy working actor. He made the choice to have agency over his career to play positive characters who had made a difference and aligned with his ideals and beliefs. This delayed his success because his breakout role came later at age 35 when he played Jackie Robinson in the film “42”.

His parting words to graduates is a masterclass on living with purpose. He reminds us how to use the time we are given and not surrender. Nobody knew but for his immediate family that Chadwick had battled stage III colon cancer since 2016 and continued working at peak performance through chemotherapy and many surgeries.

Graduating class, hear me well on this day. This day, when you have reached the hill top and you are deciding on next jobs, next steps, careers, further education, you would rather find purpose than a job or career. Purpose crosses disciplines. Purpose is an essential element of you. It is the reason you are on the planet at this particular time in history. Your very existence is wrapped up in the things you are here to fulfill. Whatever you choose for a career path, remember, the struggles along the way are only meant to shape you for your purpose. When I dared to challenge the system that would relegate us to victims and stereotypes with no clear historical backgrounds, no hopes or talents, when I questioned that method of portrayal, a different path opened up for me, the path to my destiny.
As you commence to your paths, press on with pride and press on with purpose. God bless you. I love you, Howard. Howard forever!” — Chadwick Boseman

It takes a village

Like anyone starting their career, Chadwick initially saw losing the part as a regret. Ultimately, being fired early in his career became a stepping stone that helped him understand his purpose in relation to what he would agree and not agree to do.

Few people know Chadwick and his classmates were accepted to study but could not afford tuition at the British American Drama Academy in Oxford, England. Phylicia Rashad taught the class and reached out to a friend, Denzel Washington, who paid the tuition for Chadwick and 9 other students. Chadwick would later say in this interview,

There's no Black Panther without Denzel.

Coming full circle, in May 2021, Howard University announced it would rename the College of Fine Arts to the Chadwick A. Boseman College of Fine Arts in honor of the actor and alumnus.

Jeff Bezos on Regret

A self-admitted nerd, Jeff Bezos created his own Regret Minimization Framework in his 20s, so he could make better decisions. It has four simple steps designed to minimize regret and over-analysis when making a tough decision:

  1. Project yourself forward into the future.
  2. Look back on the decision.
  3. Ask "Will I regret not doing this?"
  4. Act accordingly.
Regret: Minimize regrets before getting old
Imagine now what you will think when you’re 80

Jeff explains how he made the decision to start Amazon to sell books online at age 30 and leave a well-paying job at a hedge fund:

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. And, I think that’s very good.
If you can project yourself out to age 80 and sort of think, “What will I think at that time?” It gets you away from some of the daily pieces of confusion. You know, I left this Wall Street firm in the middle of the year. When you do that, you walk away from your annual bonus. That’s the kind of thing that in the short-term can confuse you, but if you think about the long-term, then you can really make good life decisions that you won’t regret later.

Top 5 To-Do List

Returning to Bronnie's 5 Regrets of the Dying article, Paul Graham noticed that 4 of the 5 regrets were mistakes and errors by omission. People had neglected them. He wrote:

You forget your dreams, ignore your family, suppress your feelings, neglect your friends, and forget to be happy. Errors of omission are a particularly dangerous type of mistake because you make them by default. As long as these mistakes happen by default, you probably have to be reminded not to make them.
Regret: Top To-Do List
Today’s List

Graham thinks the top 5 regrets can be summarized into one piece of advice:

Don’t be a cog.

A cog is a person who performs a lesser role in a group or organization. Day in and day out, they perform their duties seemingly with no end in sight.

Graham re-wrote her Top 5 Regrets as a Top 5 To-Do List. This way, when you feel you're moving further away from them, look at the list and take action:

  1. Don't ignore your dreams;
  2. Don't work too much;
  3. Say what you think;
  4. Cultivate friendships;
  5. Be happy.

Steve Jobs in his commencement address at Stanford in 2005, reminds us about the need to find the courage to follow your inner voice because everything else is secondary.

Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma — which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.

Subscribe to our newsletter here for great examples of collaboration and community building.

regret courage short term long term less than