You learned the ropes of selling when you were first hired at IBM at 25. How did that experience shape the way you do and teach sales?

I got my MBA before it got trendy in the late ‘70s. Getting a master's degree back then was quite rare, but I had this feeling my life would be a little different from my peers. After six years of university, I had to learn to sell at IBM — and I had zero sales skills. I had an MBA in business and a degree in marketing, but I had nothing in practical skills.

To get into sales at IBM, you had to go on a two-week residential class. So even if you lived in Toronto, you had to go to a hotel. It was 16 to 18 hours a day for two weeks solid. They figured if they made it really hard at the training, when you get loose into the customer environment, then it would be easy. But I barely scraped through because it's so formulaic how they want to teach you. And it wasn’t until I figured out how to make sales my own — by being curious and caring, by asking questions and saying as little as I had to — that I found the secret to my success.

That was over 45 years ago, yet business students still graduate without an appreciation for sales skills. It’s really a crime.

That’s why I tell my students I teach life skills — the skill of influence, persuasion, negotiation and how to deal with people. I think I can help you and if you don't want my help, fine. But I do care, I do my best and I encourage my students.

After three decades spent working different sales jobs in Europe, in the early 2000s, you moved to rural Ottawa and owned a garden centre and farm. How did that come to be and what did you learn from that experience?

I was in tech for most of my life and then — I blame it on the internet — I moved to the country and I started a garden centre and a hobby farm. I mean, talk about going from high-tech to low-tech.

I was 48 when I did that, so it's a shock to your system. I'd never worked in a greenhouse, I'd never worked at a garden centre; I just had a green thumb. I love plants, so I thought: How hard can it be?

But it just goes to say, you can do whatever you want. Restarting my life at 55, coming back to Toronto after 30 years away — it's not easy, but it's doable.

You’ve made so many pivots in your life, hopped from place to place, career to career. How have you found the courage and ambition to make those pivots possible?

The only way to make a dream reality is to flesh it out.

I'm currently teaching a life-design class for graduating students. It's a new one, an open elective. It’s like, “You're going to graduate, so what are you going to do now?” I'm sort of forcing them to make decisions and figure out what they're going to do with their life. So, you want to be a digital nomad — well what's your business? Do you have the money? You can't just sort of take a one-way ticket somewhere and go, “Okay, now what?”

At the age of 25, I decided to live a life without regrets. I literally took the money, left everything behind in Canada and did it. And when I left IBM, they were saying,  “Oh, you're going to the competition,” because I was an up-and-comer. I said, “No, I'm taking a year off to travel,” and they went, “I wish I could do that.” It was just my own fear of regrets, of not doing it and living to regret it. So, that's been driving my life.

This interview was edited and condensed for clarity.