How to overcome regret and not be a cog in the wheel of life

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 who says the conversations were more meaningful because they didn’t have the time to waste words on small talk.

  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.
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

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 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 knowns 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 same mistakes he made. Passages of his post are below.

Despair and regret: Tomorrow will be just like today

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,

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 spent worked over sixty hours for two months which led to a disastrous second stage presenting. The client was rude to someone on Andrew’s team during the presentation and Andrew didn’t do anything.

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

Chadwick Boseman on Purpose

Every person pursues their best self, best life differently and on their own 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

It takes a village

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
Minimize regrets before getting old

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:

Regret: Top To-Do List
Top To-Do List
  1. Don’t ignore your dreams;
  2. Don’t work too much;
  3. Say what you think;
  4. Cultivate friendships;
  5. Be happy.



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Flavian DeLima

Flavian DeLima

Marketer. Strategist. Consultant. Collaborator. Tinker on the edges…fandoms, creators, entertainment, community, collab & authenticity. Play @collab4purpose