Why I Took the Ladder Less Climbed.
I had a word with management this morning.
It did not go well.
Management has been making some questionable decisions lately. Taking on too much. Worrying about things that haven’t happened. Treating every unanswered email like a referendum on the company’s future.
I suggested management get a grip.
Management suggested I stick to my knitting.
We haven’t spoken since.
This is one of the great indignities of owning a small business. You can identify the problem with remarkable precision and still have absolutely no one to blame.
You are the visionary, the salesperson, the customer service department, the person who notices the toilet paper is running low, and the idiot who scheduled three meetings during lunch.
You are also HR, which makes filing a complaint against yourself unusually complicated.
And the truly ridiculous part?
I chose this.
Nobody forced me to work for myself.
I could have pursued a corporate career. A respectable title. An organizational chart. A steady paycheck. A boss whose decisions I could question from the safety of a conference room.
Instead, I decided to become the person making the questionable decisions.
Apparently, I wanted the freedom to disagree with management so badly that I became management.
And now I have to live with him.
I’ve wondered why I never took the corporate route.
It almost certainly would have been easier on my marriage.
It’s not that I dislike corporations. Some of my favorite people are CEOs. I love spending time with founders, innovators, entrepreneurs, and people who lead organizations much larger than anything I’ve built. That describes a good deal of my clientele.
But there’s a particular kind of person I’m drawn to.
The CEO who doesn’t act like a CEO.
The founder who built something remarkable and is still curious about what it could become.
The executive who knows the official story isn’t quite the whole story.
The maverick who got far enough inside the system to realize the system could use a little rearranging.
People who color outside the lines, even when they’re responsible for drawing them.
Those are my people.
And perhaps that’s why I never felt compelled to climb a corporate ladder.
I was too busy wondering who built the ladder, why it was leaning against that particular wall, and whether we might be better off installing an elevator. Or a transporter.
Also, I’m not especially good at pretending to agree with someone because their name is higher on the organizational chart.
This is not always an endearing quality.
Especially when you work for yourself.
Because then every disagreement with management becomes an internal conflict.
And there is no one to mediate.
Except HR.
Who, no matter how you slice it, is Hersh Rephun.
Of course, there’s another part of the performance.
Because while all of this is happening, you’re supposed to project confidence.
A prospective client asks how things are going.
“Fantastic!”
Your accountant asks how things are going.
“Define fantastic.”
Your mother asks how things are going with “whatever it is you do.”
“I help people explain what they do so even their mothers can understand it.”
“That’s a business?”
Here’s what I’ve come to appreciate about people who build businesses, whether they’re running a one-person operation or an institution with thousands of employees.
Most of us aren’t nearly as certain as we appear.
We’re making consequential decisions with incomplete information, trying to distinguish intuition from indigestion, and occasionally discovering that the brilliant idea we had at 2 a.m. was actually just a reason to be awake at 2 a.m.
And yet we keep showing up.
Not because we’re fearless.
Because something matters enough to us that we’re willing to be seen trying.
And here’s where it gets interesting.
The people I admire most aren’t necessarily the ones who have figured everything out.
They’re the ones who have achieved enough to be comfortable and remain just uncomfortable enough to keep asking questions.
They’ve built the business.
Earned the title.
Won the awards.
Acquired the impressive office furniture.
And somewhere along the way, they look around and think:
Is this really what I meant to build?
Or perhaps:
This is exactly what I meant to build. So why does it feel like there’s something more?
I love that moment.
Not because something is wrong. Because something is alive.
Curiosity survives success. The person inside the title can still surprise themselves.
We work so hard to appear finished that we forget how interesting the unfinished version can be. Sometimes the person saying “I’m figuring this out” is the only one telling the truth.
Of course, nobody wants their contractor exploring his relationship with load-bearing walls.
Competence matters. So does admitting when we’ve been looking at something wrong.
Which brings me back to management.
I’ve decided not to fire the CEO.
He confuses activity with progress, but he cares, he learns, and occasionally sees what others miss.
Maybe that’s why I love unconventional CEOs. I recognize the stubborn creature who wants to build something meaningful without losing himself in the process.
Here’s to those who color outside the lines, even when they’re holding the crayons.
We may not have all the answers.
But we know who’s responsible.