The day I put on the lanyard

Turn your decades of expertise into a premium consulting practice built around the life you want.

_{Issue #20 — May 19, 2026}

They told me they loved my entrepreneurial approach. That’s why they wanted to hire me.

I was running a consulting practice at the time. I’d been doing good work for them across several months, and the offer came at the end of a project debrief.

The CEO followed me to the parking lot and said, “I could really use you on my leadership team to finish what we started here.” A few days later, he slid a number across to me, and the number was better than what I was making on my own.

A steady deposit on the 1st and 15th. Benefits I didn’t have to think about. A title that would mean something to professionals I respected, plus family and friends I’d grown up around in Indiana.

What he said that closed me was simple. “You can keep doing what you’ve been doing. Same approach, just with the resources of the company behind you.”

What could go wrong? I thought. I told myself it was for a couple of years. I told myself I could infuse the entrepreneurial spirit into the work I was doing there and watch people truly blossom.

I took it.

On my first day, the guy in security handed me a badge and lanyard. I put it over my head. The badge settled on my shirt. I looked down at the picture they’d taken twenty minutes earlier, the name underneath it, and I heard something I didn’t expect.

The clink of the steel bars closing.

That’s what it felt like. It was a door closing. I’d had this job for thirty minutes and I already knew I’d made a terrible mistake.

The energy around me changed within the week. People I’d been advising as a consultant started treating me like the help. The calendar was no longer mine. From 8 to 5, I belonged to someone else. The work was the same. 

My positioning was very different.

I settled in. I did the best work I could. And I want you to hear this next part, because it matters a lot.

It wasn’t all bad.

I fell in love with the people. Two genuinely good years in there. People I would never have met otherwise. A few who became friends I still have. And years later I still have people introduce themselves at local events who were positively impacted by my time there.

It felt good to see the deposit hit every other Friday, and I stopped checking my bank account on Sunday nights. The roller coaster I’d been on as a consultant... the income while at the top, the worry at the bottom, the math at the kitchen table after the family was asleep... it all went away.

That alone is what makes the cage so “tolerable.”

Then the politics started. The turf wars. The meeting before the meeting. Bad decisions already made by people who weren’t in the room. The competing agendas and sabotaging of my efforts. My entrepreneurial muscle started to twitch uncontrollably now.

And then...without warning…fired.

For the same reason they hired me.

The same man who’d slid the number across the table sat across from me again, some two years later, and told me I wasn’t a fit. That I was too entrepreneurial. He used those words.

Too entrepreneurial.

The approach he’d called valuable on the way in was the reason on the way out.

Nassim Taleb wrote a line I didn’t read until years later. When I did, I read it three times before I put the book down.

“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.”

I thought about the lanyard. I thought about how I’d told myself I’d be different. I thought about how every smart, accomplished person I know who’s tried to leap has wrestled with this exact same addictive, black-hole-like, gravitational pull.

If you’ve ever stared at an offer and felt the math work on paper while something in your chest said no... you know exactly the gravity I was up against.

Two prospects told me a version of the same thing this month.

The first one, on a discovery call last Tuesday. I asked him what it would mean if nothing changed for him in a year. His answer was twelve words.

“It would mean I need to go back into working the W-2 job.”

He’s twenty-some years into a strong career. He’s built something on his own. The gravitational pull is still there, and he identified it on the call. That’s what makes addictions, addictions.

The second one, the week before, said it more directly. “I’m fighting myself every day... do I go for stability, or where I feel most confident?”

Two consultants. Two industries. Same gravity. Same tempting monthly salary pulling at them the way it pulled at me, years ago, on the day I put on the lanyard.

So the real question is this.

How do you want to live?

Not what should you do. Not what’s smart. Not what would other people think. How do you actually want to live?

I’m not going to answer that for you. You already know.

But I will say this. I’ve watched the version of you that takes the leap because the math is now obvious and the season is right. I’ve also watched the version that stays in the cage on purpose, for a season, because little ones are underfoot or the runway isn’t long enough yet. Both can be right. The wrong move is the one that pretends you’re in a season you’re not.

P.S. The lanyard moment never fully leaves you. And it shouldn’t. It’s the reason I can hear it in someone else’s voice when they say it out loud on a Tuesday call. The cost of caving was real. The lesson it taught me has paid for itself many times over.

Want to dive deeper? Check out these related articles:

👉  The Prosperous Consultant | Issue #19
👉  The Prosperous Consultant | Issue #18

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