Over the past 10 or 11 years I’ve had more jobs than I can count on both hands. My longest and last full-time job lasted a year-and-a-half, and that in of itself was a miracle. It was during that last job that I built up enough work on the side to quit and start my own web development business, which is alive and well today.
At the time I had been married for close to 5 years, had a house and a dog, and had gotten out from under somewhere around $30,000 in credit card debt (thanks to my wife and her financial savvy, something I lack).
I was very excited to be back on my own, and doing something I loved and truly enjoyed doing. And though I was working like crazy to build a business, I once again fully owned my accomplishments.
Start – Fail – Repeat A Bunch – Win
The reason I started my first business, the one that landed me $30k in debt after 9/11 and the sniper incident in DC (where we lived at the time) brought business to a halt, was that I had a boss that told me to stay at client sites longer because I was moving too quickly from place to place, reducing the number of billable hours. For me it wasn’t an issue of slowing down, it was a matter of him finding more clients for me to service. But that really ground on me until, after speaking with my wife, I jumped ship and went off on my own. A few years later after trying everything I could think of and the first economic country-level shit storm of my life, I found myself getting a full-time job, in Florida. Fast forward a few years and I was back off on my own, after going back and forth between a few jobs and working for myself, until finally I could again gain the freedom that I knew I needed.
I’ve work for myself ever since.
The reason I never lasted long at a job wasn’t that I didn’t work hard or try to make money for my employer. It was that I’ve always felt I could do more than any job would ever let me do. I always felt somehow held back, and never given the chance to truly shine, or fall on my face learning. It wasn’t the recognition I was after – all that comes from inside. It was that I wanted to prove that I could do it.
Welcome To The Factory
The workplace of today is set up like a factory, with colleges feeding the system. Now don’t get my wrong, I’m a big proponent of school. My 2-year-old daughter is in school. I was in school for 10 freaking years! Rather, I feel that the job situation today sucks, and I don’t just mean the employment numbers. I mean that employees are treated like cogs in a machine. Believe me I know, I have an MBA and sat through the classes, knowing that I didn’t really fit in. And you have to be either super specialized (boring) or know a lot about a lot (overwhelming).
Exit Stage Left
My father went to college, then law school, and then worked for a single employer for 31 years before retiring. And as much as I love my Dad, he is still trying to accept the fact that no matter how bad thing get, I refuse to again get a full-time job. Believe me I’ve tried – no one will hire me. I’m what a friend calls “risky.” But what’s more risky – hiring an employee that might kick ass for your company for a year, or not hiring that person and losing all of the benefit you could have gained?
Either way, I’ve taken myself out of that pool. And no matter how many hours I put in a week, I am happier. Why?
I get to see my wife and daughter every day.
I get to meet and work with new, awesome people, every day.
I get to go outside and take a break without worrying, every day.
I get to own my failures and successes, every day.
I get to help other people find the same freedom that I have, every day.
And for that, I am grateful.





This is hit right to the heart, great post. Freelancing or self employment has positives in giving you minor wins that you own daily.
And that’s one of the things that can really keep freelancers going – all of those minor wins. What is success? Every day I stay self-employed.
You really hit the nail on the head with this post. I think for me that inherent risk is what wakes me up in the morning and motivates me to keep trying to get better at this craft. When I was checking into the cubicle every day the biggest risk was running into Clyde at the water cooler, that guy was super annoying.
The risk keeps me going too – there is no failure, only success. And we can own both the risks we take and the success taking those risks brings. Of course, we can be smart about it to. Clyde is unavoidable.
Robert,
You’re right on the money. It’s about how you can create your own future when they future offered by the so-called system doesn’t fit the bill. But it’s also about the little successes that you get every day that you can stay in the game. These little wins are hugely important, because you earn them as you go, rather than having to wait until your 65 (if you’re lucky) to cash in.
You know, this seems to be part of a bigger phenomenon, in which people are rejecting conventional wisdom (aka the rat race) and taking control of their lives. And since you mentioned education, take a look at the trailer for this new documentary “Race to Nowhere” (which we hope to screen at CoCo): http://www.youtube.com/watch?v=Uem73imvn9Y
Thanks for flying the flag of freedom, Robert!
I knew this one would get you Don! Thanks for your comment.
Your point of the little daily successes is so spot on. We don’t have to wait for the cash to be rolling in to be experiencing success. Awesome point.
I’ll check out the trailer thanks for the link.