Category Archives: Stories

On limitations

Watching a video recommended by a CoCo member, I came across this gem. It’s David Heinemeier Hansson, inventor of Ruby on Rails and partner at 37 Signals, talking about starting businesses that are not necessarily designed not to “go viral” and take over the world, or to be sold for gazillions … but simply to solve a problem that needs solving or to do something better than how it’s being done.

At 21:20 in the video, he talks about the conditions under which Basecamp, 37 Signals’ flagship project management software was built. If you don’t know the story, Basecamp was the side project for people doing other stuff, built with limited hours. Disadvantage? Quite the opposite, according to Hansson.

Of course these days, with an estimated annual revenue of $19MM, Basecamp is a bit more than a side project.

How I made the leap

Not me. For metaphoric purposes only.

Not me. For metaphoric purposes only.

I can remember the day I made the jump from employment to self-employment. I’d like to say it was a dignified moment of clear headedness. But truth be told, I lost my temper. During a less-than-favorable performance review at my first and only corporate job…I quit.

Looking back, that was not a surprising outcome. I grew up always hearing my dad say, “The best thing is to be your own boss.” So, the minute I met my newest cubicle mate, Daniel, who had just come off of a stint as a freelance writer, I knew what I had to do. The disappointing job review was simply an excuse to make the jump and feel fully justified. “I’ll show them!”

What followed was a hit-and-miss but eventually successful freelance career. But until now, I’ve never really given a thought to why I took the path I did, other than the occasional flippant remark about my having severe hangups with authority (which I do). Looking back, I think it was no small amount of pride that motivated me and my bruised ego to leave the cubicle. And it was pride that pushed me to endure the difficulties of establishing myself as a freelancer.

But there was a moment when it became about something more than an ego trip. About two years into my freelance practice, things were going so well that I no longer had a life. Client work dominated my every waking minute. When I complained about it to a friend who was himself a successful entrepreneur, he said I should think about hiring employees and getting a proper office.

“That’s a huge commitment,” I objected.

“How could you be any more committed than you are,” he said. “And becoming a business owner is something that will define your life in a way that few things will.”

My friend made me realize that being my own boss was a big adventure – like going on a jungle expedition. You might come back. You might not. But it won’t be dull! So, that’s what I did. I got an office downtown, I started hiring, and within a couple years I was running a strong writing practice with a handful of employees.

Looking back, it’s been the adventure that has kept me in the game. In the spirit of full disclosure, I have to admit that several years later I got tired of managing my writing practice, shut it down and went to work for my best client. But it wasn’t too long before I was craving the thrill and risk of the adventure again. More on all that down the road!

Photo Credit: mikelo via Compfight cc