a painting of a man sitting on a cliff overlooking a waterfall

#54: Traveling to Neverland

Bob Ewing
February 4, 2022
a painting of a man sitting on a cliff overlooking a waterfall

Talking Big Ideas.

~ Scottie P’s tattoo, We’re the Millers

On a recent walk with Ollie I flashed back to a moment from high school. My wrestling team had gone to our coach’s old high school for practice: St. Eds. They have the most dominant wrestling program in the state and one of the best in the country.

Back in that moment, stepping into the St. Eds wrestling room, I feel exhilarated and terrified. Holding my headgear, awkwardly waiting for practice to begin, I stare at a large quote on the wall. It sticks with me all these years:

Don’t join The Shoulda Coulda Woulda Club.

I take it to mean I should avoid a mediocre and regrettable life. Our coach repeated this maxim often. He was a state champion from St. Eds, and I imagine it was drilled into him. And that he truly believed it.

I used to believe it myself.

But I’ve come to learn we’re all members of The Shoulda Coulda Woulda Club. We are mediocre in most things. We 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. How they would go now if only we’d get another chance.

According to Jonathan Gottschall, author of the delightful book 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.

As I’m writing this, Dan Pink’s new book showed up at our house. The Power of Regret. The timing is serendipitous.

Pink quotes a sea of famous people – from Ruth Bader Ginsberg to Slash, Angelina Jolie to Bob Dylan – all expressing the same mantra: live without regrets. A more concise version of the St. Eds maxim, to which Pink responds:

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.

He drives home how regret is universal to the human condition. Rather than pretend it doesn’t exist, we should lean into it. Regrets are steeped in wisdom. If we pay attention they 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.

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.

I help people build their public speaking skills. I always have 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, or an important conversation – I encourage them to do a self assessment shortly afterwards 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.

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

Over time these little improvements compound.

And whenever you catch yourself daydreaming 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 while you’re there.



Be a proud and loyal member of The Shoulda Coulda Woulda Club.

Today you will daydream. When you find yourself traveling back to a recent conversation, pay attention to how you wish you had spoken. How specifically you could have been a little more eloquent or effective. Capture the improvements.

See if you can use your new and improved version in another conversation within the next week.


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