a painting of an island with a rainbow in the sky

Traveling to Neverland

Bob Ewing
November 17, 2023
a painting of an island with a rainbow in the sky

We all relive moments from the past. Including our regrets. We can pretend they don’t exist – or we can learn from their wisdom.

Talking Big Ideas.

“There are two possible situations – one can either do this or that. 
My honest opinion and my friendly advice is this: 
do it or do not do it – you will regret both.” 
~ Soren Kierkegaard

How often do you daydream? 

I recently joined our local Brazilian Jiu-Jitsu gym and it’s made me think back on my wrestling days. Last week, as I biked along the river to class, my mind flashed to a moment from long ago – when our whole wrestling team went to our coach’s old high school for practice: Saint Eds. They had the most dominant wrestling program in the state and one of the best in the country. 

Back in that moment, stepping into the Saint Eds wrestling room, I felt exhilarated and terrified. Clutching my headgear and awkwardly waiting for practice to start, I remember staring at a large quote on the wall that has stuck with me over the years: 

Don’t join The Shoulda Coulda Woulda Club.

Our coach repeated this maxim often. He was a state champion and I imagine it was drilled into him. And that he truly believed it. 

I used to believe it myself. 

The truth, as I’ve come to learn, is that we’re all members of The Shoulda Coulda Woulda Club. We are, without exception, mediocre in most things and have all sorts of regrets. 

We regularly think back to moments in our past and imagine them differently: how we should have acted; how things could have gone; and how they would go now if only we’d get another chance.

According to Jonathan Gottschall, author of The Storytelling Animal, we constantly travel back in time and reimagine our past. He says we “visit Neverland” about 2,000 times every day. If each flashback lasts about 14 seconds, it adds up to almost half our waking lives! 

To what end? 

So we can learn. And make our lives better. 

In The Power of Regret, Dan Pink quotes a sea of famous people – from Ruth Bader Ginsburg to Slash, Angelina Jolie to Bob Dylan – all expressing the same mantra as Saint Eds: live without regrets. My favorite is Scottie P and his hilarious upper chest tattoo in the comedy We’re the Millers:

Pink has a strong response to everyone who disses on regret: 

What the anti-regret brigades are proposing is not a blueprint for a life well lived. What they are proposing is – forgive the terminology, but the next word is carefully chosen – bullshit. 

Regrets are universal to the human condition. Rather than pretend they don’t exist, we can embrace them as they’re steeped in wisdom. If we pay attention, regrets will “lift us up” and improve our lives. 

Pink says that looking backward is vital to moving forward. We should establish a ritual of doing this with intention. Dale Carnegie, the iconic self-help guru, believed this was one of the most powerful ways to make progress in life. 

Carnegie advised a weekly reflection. Sit down in a quiet place and review your past week’s meetings and conversations. Travel in your mind to each of them. Visualize being back there. Consider how you could have done each a little bit better. And then do your best to apply these insights the following week. 

image that vividly illustrates the concept of traveling back in time within ones mind to revisit past memories

During coaching sessions, I always have our clients do self-assessments before I offer any feedback. And whenever they go on stage – be it a formal speech, a media interview, a testimony, a court argument, or even an important c555onversation – I encourage them to do a self-assessment shortly afterward and send it to me.   

I want every client to build the habit of looking backward to move forward. I encourage you to do the same. 

“I made decisions that I regret, and I took them as learning experiences… 
I’m human, not perfect, like anybody else.”
~  Queen Latifah

Revisit your past presentations, conversations, and meetings often. Ask yourself what you could have done better. Capture whatever you come up with. 

Over time these little insights lead to compounding improvements. 

And whenever you daydream about how you shoulda, coulda, woulda done something different, embrace it guilt-free. Relax and enjoy your trips to Neverland. 

Just be sure to take notes and learn while you’re there. 

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