Sell Me This Pen: A Lesson In Authenticity

I had just sold my lawn and landscape company and thought, “This is it. I’m finally going to have it all.”

For years I had dreamed of escaping the business I built with my own hands. I was sick of the Florida heat, drenched in sweat and rain day after day. I was done with the sideways glances, the silent judgment from people who looked at me like I needed to “get a real job.”

I didn’t know what was next, but I was certain it had to be better than this.

Within two weeks, I decided: I was going to become a financial advisor. They looked successful. They made money. Their lives seemed polished and easy. Never mind that my own finances were a wreck — that was just a detail they didn’t need to know.

I sent out application after application. Each job posting dangled the dream: “Potential earnings \$250K. No experience required. Will train.”

But instead of opportunity, my inbox filled with rejection emails: “Thank you for applying. Unfortunately…” Over and over. No callbacks. No interviews. Just silence.

So I did what the movies taught me. I started dialing, working my way up the corporate ladders, trying to prove I was hungry enough to make it. I wanted to be the guy who wouldn’t take no for an answer.

Still, nothing.

Finally, out of desperation, I hired a professional resume writer. And wow — that man was worth every penny. He took my ragged history and polished it until even I didn’t recognize myself. I had to Google some of my own “skills” just in case someone asked about them.

But it worked.

I finally got the call. An interview. My shot.

I was electric with excitement. I went straight to Men’s Wearhouse and dropped \$1,000 on 2 suits, shirts, ties, and shoes — more money than I’d ever spent on clothes in my life. For the first time, I wore tailored clothes, and I caught myself in the mirror thinking: I look like a financial advisor. I look like success.

On interview day, I sat in the parking lot and called my wife. My voice was shaking with nerves and hope. This was it — the beginning of the life I’d been dreaming of. A life where money wasn’t an issue. A life where people would finally be impressed when they asked, “So, what do you do?”

Inside, I met the senior partner — distinguished, polished, the kind of man who wore confidence like a second skin. Fancy suit. Expensive watch. Vacation photos that looked like postcards. To my surprise, we even belonged to the same club and knew the same people. My confidence soared. I was sure this was destiny.

The interview lasted almost an hour. We laughed. We connected. I left thinking: I nailed it.

Then came the words I’ll never forget:

“I wish you luck.”

If you’ve ever heard that phrase after an interview, you know it’s code. It means you didn’t get the job.

I was crushed. My head spun. How could this be? I had the suit, the persistence, the connections. I did everything the movies told me to do.

But then he kept talking. He didn’t just dismiss me. He leaned in. He asked me questions:

“Why do you want to be a financial advisor?”

(Don’t say money, don’t say money.)

“What will you bring to this firm?”

(Uh… I’ll work hard? I’ll show up on time?)

And then he said it. The line that burned into my brain:

“Chris, you’re a good guy. You’ve got talent. But you don’t have the fire in the belly.”

I tried to fight back. I told him I’d do whatever it takes. I reminded him I was a hard worker. I even wanted to say: Did you see this suit?!

He didn’t budge. Instead, he handed me his Montblanc pen and said, “Sell me this pen.”

My heart leapt. I’d seen The Wolf of Wall Street three or four times. I knew this scene. I was ready.

I asked him if he signed important documents, ones tied to big money. Of course he did. Perfect — then the pen was worth nothing compared to the value of his deals. He’d have to buy it.

Except he didn’t. He pushed back. He asked again. Over and over, until the room was filled with my frustration and his calm certainty.

And then it was over. I left angry, embarrassed, and confused. I sat in my car gripping the steering wheel, replaying everything. What did I do wrong? Why bring me here just to tear me down? What the hell does “fire in the belly” even mean?

For years, I carried bitterness toward that man. I thought he had dangled my dream in front of me only to rip it away.

But now, looking back, I see it differently.

That man did me a favor. He saved us both from a disaster. He saw something I couldn’t see — that I was chasing an image, not my truth. I would have failed, not because I wasn’t smart or persistent, but because I was trying to live someone else’s life.

And maybe, just maybe… that conversation was the first spark of me finding my own fire.

Here’s what I wish I had understood back then: you can’t borrow passion from a suit, a title, or someone else’s dream. You can fake confidence for a while, but eventually the truth leaks out.

That senior partner was right — I didn’t have the fire in the belly for finance. But I did have a fire. It was just buried under years of chasing approval and trying to fit into boxes that didn’t belong to me.

If you’re reading this and you feel stuck in a role, a job, or even a life that doesn’t feel like yours, ask yourself the same question he asked me:

👉 What truly excites you? What lights you up when no one’s watching?

That’s where the fire is. And when you build your life around that flame, everything changes your work, your relationships, your health, your purpose.

Because the truth is, the fire in the belly isn’t something someone else can give you. It’s something you uncover when you finally decide to live authentically.