Three Stories of Successful Contractors

Not terribly long ago, most of my friends in technology worked for “big companies.” But ever since the first propaganda about “The Brand Called You” started spewing from the pages of Fast Company in 1997, and ever since the dot-com bust of 2000 and the recessionary moment that followed it, I’ve watched as several friends and colleagues carved out their own independent careers in tech on their own terms. I think about them and watch their progress during this recession because it’s inspiring to see how liberated they feel, taking responsibility for their own survival no matter how choppy the seas. Here are three quick stories.

Working at HomeFriend number one was the first to jump ship, way back in 1999. With his fists full of investors’ money, he set out to create an investment-related dot-com that he had up and running just in time for the dot-com crash. Before he made a single dollar in profit, he was done. Rather than come crawling back to some corporate job, he dusted himself off and transformed the remnants of his little company into a Web design and consulting service. There were lean years for sure, but today, more than ten years later, he’s thriving, and throughout it all he’s been his own boss and now couldn’t imagine ever working under someone’s thumb again.

Friend number two worked as a corporate network manager and analyst, and after a while he realized he was usually the smartest guy in the room. (And he was right!) Figuring that if anyone could succeed as a freelance networking consultant it would be him, he started selling his expertise, using whatever primitive social networking tools were at hand eight or nine years ago. Amazingly enough, he was able to set up a highly sophisticated network server test bed in his rather old and small New York apartment and hasn’t burned the building down… at least not yet. Today he travels coast to coast making what I can only assume is serious money consulting on network security for some gold-plated clients.

Friend number three is the latest success story. A former technology magazine editor like me, he worked in the editorial trenches for more than 20 years until he realized that traditional print journalism was quickly morphing into “content creation.” Frustrated by the cost-cutting edicts of his employers, he took a layoff package, spent two months relaxing at home, and then set out to reinvent himself… quickly. Within weeks — and with the help of a well-paid career coach who prodded him on — he established a content creation and consulting business, set up bank accounts, created a logo, had a website built, lined up a team of writers to help him, and landed his first big technology client. Now he’s working as hard as ever, but for himself.

What have I learned by watching my friends? Well, to update the Fast Company schtick about branding yourself, there is something to be said for understanding that your real career goal shouldn’t be about climbing up to the next title but rather understanding what your skill set is, improving it as diligently as you can, and then selling it, either to your bosses or to anyone else who is willing to pay for it. You might complain that the idea of going out on your own is risky — and let’s not even bring health insurance into this discussion — but I think millions of Americans have seen in the past few years that being employed by a big corporation is pretty darned risky too. Nothing is for sure except the skills you have and know you can sell. It’s worth thinking about.

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