Ten years ago today, I played golf with a guy who was working in the corporate world. He had a degree in math and an MBA, but he also had a newborn son at home and wanted to find a way to spend more time with his family. He was fed up with the corporate culture and had done well enough to make a career change without worrying about finances for a while.
Teaching, he had decided, was the way to go. He had always wanted to be a teacher, and he loved the idea that when his son was on vacation, he would be, too.
“No more working until 7:00 and missing dinner or all day on Saturdays,” he said.
Once he discovered that I was a teacher, he immediately began asking me question after question about the profession, including the fastest way to earn a teaching certificate. I explained the ARC program to him, a three-month process by which college graduates can become teachers in specific areas of need throughout the state, including math.
“You could start the program in June and be teaching in September,” I said. “One of my friends did exactly that. He left the corporate world in June and was teaching math in Hartford in September.”
The man was enthusiastic about the process and asked about a dozen follow-up questions as we walked the course together. With each step, his enthusiasm seemed to increase.
As we made our final putts of the afternoon and headed back to the clubhouse, he thanked me for the information. “That program sounds great,” he said. “It’s still a little pie in the sky for me, but I think it’ll make it part of my five-year plan.”
“Five-year plan?” I thought. “Really? Five years? Do you have any idea what can happen in five years?”
I don’t understand people who talk about five-year plans. That’s 1,825 days. Thinking you can plan that far ahead is crazy.
Five years ago, we were in the midst of a pandemic. I had just met a woman named Masha who was working at Slack and wanted my help crafting stories for their product. Other than that single corporate job, all of my coaching and consulting was with storytellers, authors, and small business owners.
Not much of it, either. At the time, consulting was occasional, unpredictable, and didn’t pay exceptionally well. It amounted to found money and little more.
A career in corporate consulting and keynoting — one lucrative enough to allow me to leave teaching five years later — seemed impossible.
It wasn’t even on my radar.
I had published one nonfiction book on storytelling that had sold marginally well, but I couldn’t imagine publishing a second or third. None of the ideas that inspired those books had yet come to me.
I also didn’t know that my first nonfiction — “Storyworthy” — would begin selling more and more, year after year, once the corporate world found the book and began seeing its value to their business.
Soon after, companies began calling to seek my help. Microsoft, Google, Amazon, Johnson & Johnson, Pfizer, and Adobe soon became clients, as did biotechs, advertising firms, banks, manufacturers, holding companies, universities, and even the FBI.
Was any of this on my BINGO card five years ago?
Of course not.
A lot can change in five years.
Instead of a five-year plan, how about a one-year plan?
Or a six-month plan?
How about a three-month plan?
In five years, this guy’s son would be entering kindergarten. He might have more children, planned or otherwise. His company could declare bankruptcy. The United States could be at war with Canada.
Five years is a long time. If this man was serious about making a change in his life, spending more time with his family, and finding a way to make a difference in the world, why wait five years? Having an intimate and personal understanding of how short life can be, I wanted to tell this guy to ditch the stupid five-year plan, go home, and sign up for the damn program today.
I didn’t.
In the end, this guy seemed too invested in this five-year plan to be deterred by my few nuggets of wisdom. More likely, he was afraid. Change is hard. The unknown can be frightening. People dream about brighter futures, but are too afraid to step into the light of that future to take their first step.
But I was left wondering where he would be in five years.
Ten years later, I wonder where he is today?
Is he the teacher that he wanted to be?
Is he spending more time with his family?
Did he escape the corporate culture that he so despises?
I hope so, but my heart says no. My heart says that five-year plans rarely work out.
You either want something or you don’t.
You either dream about it or you chase it.
You make plans as time slips through your fingers.
Five-year plans allow you to do nothing for a very long time, which is almost always disastrous.



