I'm thinking it's genetic. My brother's an entrepreneur, too. And when you look at our childhood, it's not hard to see why.
When I was five (1986) my father left his job as an IT big-wig, bought a Macintosh computer, and started a graphics design company with my artistically inclined mother. I asked him "Why?" for a project in 6th grade. His reply? "So I could see you get off the school bus every day."
I grew up stapling blank invoices to manila folders for a penny a piece.
In middle school, I started running my own business doing "over printing." This was before digital printing came along. My parents would create a shell brochure for companies with multiple offices. My brother and I would collect orders from individual offices and carefully feed the glossy paper through a bubble-jet printer, set it on the floor to dry, run it through a folding machine, and ship it out. My father and I still laugh about my mishaps with the (really finicky!) folding machine.
By early high school, my parents had merged their business with a pre-press and printing company. I came up with the name and tagline — Proximus; Next generation printing — by opening my Latin dictionary. That was my first foray into copywriting and I'll never forget the thrill of seeing my idea scattered all over signs and stationary.
At the age of 24, I quit my job in sales because of an ethical belief. When I became frustrated in the job search, my parents bought me a laptop, desk, and a copy of Quickbooks. Within a month I had landed three clients. For three years I finessed my skills and made my living as a freelance copywriter. I started a blog. Capital One read it, a recruiter called me out-of-the-blue and asked me to come write for them.
That was two and a half years ago.
For a while, I really enjoyed the steady paycheck, vacation pay, sick days, and 40-hour work weeks. These were luxuries I never had when I worked on commission or freelanced. The first week, my manager would have to remind me to go home at 5:00. I didn't know what to do with myself. Compared to the 14-hour days I was used to, I essentially felt like I was leaving at lunchtime.
I got a bonus and flew to Australia. I won the 3-legged race at the Brand Olympics. I went to some kick-ass conferences. But I also stopped blogging, watched my inspiration slowly fizzle, and became daunted by corporate politics.
Then, last September, I bumped into one of my best friends from high-school at our 10-year reunion. He owned a software company and needed marketing help. The next day we sat by the pool and dreamed about offering copywriting and coding services to designers. In November, I became a Partner in Corgibytes. Two weeks later, we had our first client. In March, he proposed — at the same spot where we dreamed up our business plan (I said yes). Today we're living that dream.
I suppose for some people, the itch to be an entrepreneur is just inherent. You do it because you don't want to do anything else. Because you'd rather work for yourself 14 hours a day than work for somebody else for 8. And because life seems more fun after you dove in than it ever did watching from the dock.