Over the course of my career, I’ve become increasingly comfortable with—and, in fact, proud of—being in sales. (I would go so far as to say salespeople actually run the world. Happy to argue that with you over coffee.)
Sales is the act of turning a zero into a one (I’m reclaiming that from Peter Thiel). Taking something that doesn’t exist and making it real. It’s not finger guns and used cars. It’s the exercise of bringing people into something meaningful and exciting.
As you get better at sales, you start to realize that what you’re selling is largely irrelevant. There’s a reason why people say they work “in sales” rather than telling you what they sell. It kind of doesn’t matter. The skill is the skill.
My 30-year, work-in-progress understanding how and why people make decisions drives my fascination with the “sell me this pen” exercise. It isolates the act of selling from everything else: who you’re talking to, what you’re talking about, its features, its benefits, its competitive positioning. It strips everything away and focuses on the one thing that actually matters—the act of bringing someone along with you.
As you can imagine, I’ve given a lot of thought to how I would do it. And partially for fun, partially for ego, here’s my take.
“Sell me this pen.”
I love this exercise. Have you done it before? What did you focus on?
I’ve been thinking about this one for a while. I was a kid who grew up with computers. I learned to type before I ever really learned to write by hand. All my communication was digital. I found pens to be annoying, slow. I also wasn’t any good at drawing. Pens and paper always seemed to just get in the way of what I was trying to accomplish.
But—while I was still very young, 19—I met my wife. Because I was 19, I was at the start of a lot of different journeys—professional, social, romantic. And, through her, I met my now father-in-law. Who 30 years later is one of the most significant role models in my life.
He’s an accomplished entrepreneur. Started several businesses: travel agencies, real estate, and a building supply empire. He’s invested in his community, employed people right out of high school. His name is above the door at the local hospital. He’s had an interesting career and a meaningful life. And while I don’t agree with all of his choices, it’s been instructive and deeply meaningful for me to learn from this man and watch how he operates.
One day, I was grabbing something from his office at his farmhouse and I noticed he had a wall—really, a windowsill—full of these stunning Montblanc pens. An entire row of them.
My first reaction was: why does he need dozens of these pens? What’s wrong with one? And why do they need to cost $500?
So I asked him.
And he told me that one of those pens was in his hand when he signed the each of the important documents in his life. The first loan for his startup, the first big deal he closed, the donation to the hospital, being the executor of his father’s will, establishing his legacy for his own children. Each pen represented a moment. Honored it and gave it weight.
That gave me an entirely new lens—not only on what a pen could represent, but on the idea of legacy, a life well lived. What it means to build things. What it means to both make and to mark consequential decisions. What it meant to be a man who was proud of his life, reflected on his choices, and tried to leave things better than he found them.
And, interestingly enough, it’s a fascination my wife inherited from her father. She’s an entrepreneur, as well, and owns several beautiful pens. They gift them to each other at major moments. It represents a unique bond between the two of them—around their entrepreneurial efforts, around the experiences they’ve shared, and around the moments that matter enough to mark.
Geoffrey MacDougall 