Photo by LAUREN GRAY on Unsplash

Dilbert told the Pointy-Haired Boss to take that job and shove it. Here’s what happened next.

David Kimbell
2 min readOct 12, 2021


In 2019, I turned my back on 30 years of engineering in a Dilbert cube, and launched out on my own as a copywriter.

I had a few advantages: Zero debt, low expenses, a wife with a job, and a few friends who’d told me I could write well. Success was assured, right?

Two years later, what’s happened?

Learning is the easy part, UN-learning the hard part

The skills that served me well on one level of the game did NOT serve me well next level up.

A salary is an addiction not cured overnight

Oh boy, does that regular paycheque look attractive sometimes.

Fortunately, I was financially prepared for lean times.

But that didn’t make them easy on the Male Ego.

To get to the promised land, you have to go through the desert

I didn’t really know myself until I launched out on my own.

That’s where my hidden insecurities revealed themselves. And in the desert, I found there was nobody to shield me from my mistakes.

Nobody to tell me the oasis on the horizon was just a mirage.

A few awesome friends make a HUGE difference

I talk to 3 men on a regular basis.

They get the good, the bad, and the ugly.

Without them, I’d have gone back to the Dilbert Cube months ago.

I still earn a fraction of what I used to earn as an engineer.

But it’s a growing fraction. And I have a portfolio and network of extraordinary people I wouldn’t trade for anything.

No regrets. Stay tuned.



David Kimbell

Curiosity. Questions. Simplicity. Principles. Meaning. The Vital Few, not the Trivial Many. Be your own Chief Questions Officer.