Fail forward: an origin story

It was the winter of 1983. I was a senior in high school. I had told my parents that I didn’t plan to go to college that fall. So I didn’t apply to any schools.

As a parent today, the thought of this terrifies me. A college degree is a ticket to lifelong opportunities. So I can only imagine what my parents were thinking at the time. I was in a private, all-boys high school known for graduating 98% of its students to college. And I had enough ability to do the same.

But the reality was a bit different than that first principle of “thou must go to college if you can”. I was suffering from years of depression, my grades had deteriorated in my junior and senior years, I was soul-searching for who I was. I didn’t feel ready to continue the shitty academic experience I’d been having by continuing on to college.

So my dad did something surreptitiously. Knowing he and my mom were about to move back to Nova Scotia from New Hampshire to be closer to my ailing sister, he called the dean of admissions at Acadia University in Nova Scotia.

Somehow my dad got me in over the phone. He must have been a pretty good salesperson, because Acadia has been ranking in the top 3 schools in Canada for decades, often ranking #1. And it was weeks past the application deadline.

My dad came to me afterwards and basically said, “write your application and essay and you’re in”. For reasons I can’t recall or are buried in my psyche, I went along with it.

The first years at Acadia were a continuation of my struggle. But somehow I stuck with it and gradually became engaged as a student. I graduated with mediocre grades but at least I had that piece of paper. The thing that opened the door to future opportunity.

Parlaying that degree into career opportunity back in the United States wasn’t easy, but we’ll save it for another story.

There’s multiple lessons to be taken from this story in my opinion.

First, even in the times of struggle and failure, an opportunity exists if you choose to take it.

Second, we can fight ourselves over seizing opportunity. Perhaps because of limits to our own self-esteem.

Third, there are always people in your life who are willing to help you and give you that opportunity. Bob Stead was the Dean of Admissions at Acadia. He had no reason to admit me. But for some reason he did. I am forever thankful.

Have you ever met the type of person who was a class valedictorian? The one who was both gifted and driven? Who got into Stanford, or Harvard, or Princeton? Who got hired at Bain or Goldman Sachs? I know some of these people, and I’m not one of them. Never been.

So if you’re not that “achiever” persona how do you succeed?

Fail forward.

“Failing forward” for me is a metaphor for seizing opportunities when they are there, risk-taking, and learning from failure. In my case, I don’t have that valedictorian pedigree. So to the extent I have built a successful career, it’s been from a series of fail-forward events, originating all the way back to high school.

Only as I get older and wiser do I see the outright merits to embracing this idea and accepting it as a blueprint for success.

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