two people riding horses in a field with mountains in the background

A New Year for Regrets and Courage

Bob Ewing
January 5, 2024
two people riding horses in a field with mountains in the background

Talking Big Ideas.

“Life is too short to be living somebody else’s dream.”
Hugh Hefner

I started rock climbing almost twenty years ago.  

It happened by chance. I made a couple of friends who were climbers and joined them one day. I caught the bug and soon we were traveling the country on epic adventures. Being in the mountains was all I wanted to do. 

“I’m moving to the Rockies,” I’d say. For years, I told people this. 

And for years, I didn’t do it. 

I had a stable job. That’s what was expected of me. Of course, I couldn’t just quit and head west. “Maybe next year I’ll move.”

Another year would pass and I’d regret how little time I spent in the Rockies. I was destined, it seemed, to live in the city and pine for the mountains.

Then I met Maryrose. 

We’d go on walks together and discuss our lives. I’d talk about living out west one day and being an entrepreneur. She’d push me, “what would it take for you to actually do this?” 

Conversations turned to plans. And then, together, we made it happen. 

Maryrose is excellent at encouraging people to grow rather than settle for the status quo. Without her I’d likely have had this regret on my deathbed: “I wish I moved to the Rockies and started my own company doing something I love.” 

Deathbed regrets are real. 

There was a nurse named Bronnie who comforted people at the end of their lives. Her patients would talk about their regrets. Over the years Bronnie noticed common themes and published them in a viral post called Regrets of the Dying

She expanded her post into a book where she tells the story of a little old lady named Grace. Days from death, Grace opened up to Bronnie about her regrets in life. 

Grace admitted to living a life that was expected of her. She got married, had kids, and supported her family. And while she adored her children and grandchildren, she regretted silently enduring abuse from her husband for half a century. 

She dreamed of traveling and being happy. 

But Grace’s illness, caused by inhaling second-hand smoke from her husband, confined her to a bed. By the time he died and she was free, she was too sick to enjoy her independence. 

“Why didn’t I just do what I wanted? Why did I let him rule me? Why wasn’t I strong enough?” she lamented.

Bronnie says that Grace was not alone in having this regret. It was repeated by people from all different backgrounds and walks of life. In fact, Bronnie says this was the most common regret of all: 

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

The author Dan Pink calls this The Mega Regret. He says it shows up all over the world. Put succinctly: I regret living someone else’s life, not my own. 

Pink created a World Regret Survey for his book The Power of Regret. He’s combed through tens of thousands of regrets. His research shows four primary types: 

We discussed in November how regret is universal to the human condition. Regrets help us see the values we hold dear but are afraid to embrace. Like anxieties, they can be giant blinking lights telling us to pay attention to what really matters so we can correct course. 

Pink says if we muster our courage, regrets will direct us to lift ourselves up and improve our lives. This is why we encourage our clients to often revisit their past presentations, conversations, and meetings. To ask themselves what they could have done better and capture whatever they discover. 

Over time these little insights lead to compounding improvements. 

I’ve written before about Leo Tolstoy’s advice to “read less, study less, but think more.” If our minds are always filled with other people’s ideas, we don’t have space for our own ideas to emerge. Likewise, if all our time is spent doing what other people expect of us, we end up not living our own lives. 

The same principle holds for our writings and speeches. 

The first time I ran a workshop on public speaking, I showed up with my boss’s notes. I gave his presentation with his stories, anecdotes, and thoughts.  

Effective speakers do the opposite. They have the clarity and confidence to share their own thoughts and feelings. And bring their own stories, insights, and values to life.  

Having the courage to be ourselves in something we all understand. There’s a viral video of a little boy and an old man talking about life. Toward the end they give each other their best advice: 

Do the things you like doing that make you feel good . . . act normal . . . don’t let other people tell you what you should be . . . just be as you are.

Shortly before Grace died, with tears in her eyes, she asked Bronnie for a favor: 

Promise this dying woman that you will always be true to yourself, that you will be brave enough to live the way you want to, regardless of what other people say. 

Bronnie held Grace’s hand and said that she would. 

I promise you this: 2024 will be filled with regrets. They are universal. The only question is, will you have the courage to learn from them and grow? 

As you start this new year I encourage you to channel your inner Grace by reflecting honestly on your regrets. Imagine you have someone like Maryrose encouraging you to learn from them and take action. Ask yourself this:

If I truly had the courage this year to live my life on my own terms, and speak my mind in an authentic way, what would I do and say? 

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