I wish I'd had the courage to live a life true to myself, not the life others expected of me.

In the last few weeks of your life, you’ll look back on years passed with crystal clarity of how things turned out. What will you remember?

This was the most common regret of the dying as recorded by a palliative care nurse. Knowing that dreams were left unfulfilled due to the actions and choices you made is a devastatingly sad way to spend your final moments. 

As a self-proclaimed “good” decision-maker, with a little life experience to back it up, I always freeze when it comes to one part of the decision-making equation: regret. The fear of experiencing regret in the future paralyzes me. 

But what if you could eliminate the possibility of experiencing major regret later in life? Decision-making is a skill that can be developed – learning to manage regret is simply part of honing your ability to make good decisions.

Just like smart investors minimize the probability of an investment losing money, we can study those who encountered regret to ensure we escape its pity and fully experience our lives.

Brace For Impact: Say Goodbye To Your Life

One January afternoon in 2009, a routine flight headed to Charlotte departed from NYC. That flight turned out to be an odds-defying miracle and a spectacular case study on regret.

After a flock of birds caused the plane to lose all engine power, Captain Sully managed to land the plane in the Hudson River saving everyone on board from what appeared to be certain death. 

In the moments before crashing, Sully announced three simple words… “brace for impact.” This gave passengers 90 seconds to say goodbye to their lives. Ric Elias, a passenger certain he was facing death, encountered three waves of regret during what he thought would be his final moments. 

Wave 1: “There’s no going back and there’s no turning back.”

• The things he did not get to.

• The people he needed to ask for forgiveness from.

• The people he needed to hug again and say “I love you” one more time.

Wave 2: Regret about his ego.

• “Wow, I’ve lived my life in a very wasteful way because so much of my energy has been spent on things that did not matter.”

• He allowed his ego to become very active in his life. 

• So much time spent focusing on being wronged by people.

• So much time spent trying to be “right” vs. choosing to be happy.

Wave 3: Regret that he had not focused on the things that matter most.

• For Ric, this was his kids.

• His most important responsibility was to make sure his kids were the best versions of themselves and he had completely delegated that to his wife in a very unfair way.

Dying was not scary, it was tremendously sad.

Performing a Post-Mortem: Earn Your Life

Ric often says he was given the ultimate gift that day. To believe you’re going to die, experience what you thought to be your final moments, then be given a second chance.

Encountering the tail end of life only for it to be drenched in regret spurred Ric to change how he lived – he began judging his life with one question: “Did I earn my gift?”

Principles of Regret Management

Focus on What Matters

We spend far too much time complaining about traffic, thinking about those who “wronged us” (this is usually a story we tell ourselves), and whining about the weather. It’s a tough paradigm to escape when you’re in the grind of everyday life.

The solution? Expand the gap. Between every external stimulus and your response, there’s a gap. For most people, it doesn’t exist – they reactively snap back at every situation without thought. If you learn to expand that gap, through practices like mindful meditation, you become empowered with choices.

Use that gap to prioritize the things that matter and shrug off everything else. 

Do Not Postpone Anything

“For all of the most important things, the timing always sucks. Conditions are never perfect. "Someday" is a disease that will take your dreams to the grave with you. If it's important to you and you want to do it "eventually," just do it and correct course along the way.” ¹

― Timothy Ferriss, The 4-Hour Workweek

Do not fool yourself. “Someday” is an illusion we tell ourselves to avoid the necessary but often uncomfortable actions required to create the life we desire. Take action now and correct course as you go.

Do Not Deal with Negative Energy

If the people in your life aren’t adding something positive, they’re actively stealing your limited time. Be ruthless in cutting people out of your life. 

Fight and Argue Less 

“I ask for forgiveness not because I may have done something wrong, but because someone was offended by what I did. I choose to be happy, not righteous.” – Ric Elias 

The compulsion to always be right is something I certainly suffer. Although it can be very beneficial in some settings – the truth matters – it can also be damaging to personal relationships. 

There are three sides to an argument: your perspective, the other person’s perspective, and the truth. Practice seeing all three for what they are and sympathizing with the other person even when they’re wrong.

And, as always, please give me feedback. What did you like? What do you want more or less of? Other suggestions? Let me know! Just hit reply to this email or send a tweet to @jackrossdixon.

Stay safe and have fun out there. 

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​Much love,

Jack