Entrepreneurship

I have a 21-year old personal trainer, Scott, whom I've been working with for about two years. He is a good trainer who knows his stuff. But frankly, that's not why I see him two to three times a week. I use him because he is a natural marketer who happens to be marketing himself.

At a birthday dinner last week with Scott and a group of his clients, talk turned to how all of us, well into our 30s and 40s and established in our careers, could learn a lot about career management by watching our young trainer. And it has nothing to do with his use of technology or some of the other ways we think young people are succeeding today.  It’s pure old-fashioned business smarts.

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I can’t go a day without talking to someone about how to get started as a freelancer, consultant or entrepreneur. Some folks are going solo by necessity; others are betting on themselves over employers in a market where jobs are no more stable than gigs. I spent the weekend with my cousin and her fiance who had both been laid off from jobs in adventure travel. We brainstormed about how they could build careers as entrepreneurs or consultants.

A few days later I had lunch with a colleague who is in the midst of a negotiation with her boss about moving from employee to consultant because she thinks she’d have more opportunities if she diversified her client base rather than remain at one company.

Those conversations came in handy this morning when I was interviewed by Tory Johnson on how to break into freelancing for a video series promoting her new book, Fired to Hired, which will be published in early August.

Here's a summary of our chat:

Dip into freelancing while keeping your job. Start by quietly spreading the word that you are available for projects and taking on assignments that don't present a conflict with your current job. The goal is to test the waters to see whether your services are in demand and to have at least one or two clients lined up once you're completely out on your own.

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I was raised with business in the background and the foreground. When I was in middle school, my parents bought their first motel -- a small beachfront property on the Jersey Shore -- and moved our family into an apartment on the second floor. We lived like that, alongside my parents' work, for the rest of my teen years until I went off to college. Working for yourself feels natural to me, so it's not all that surprising that I followed their path. But the model of self-employment I’ve chosen is worlds apart from theirs. They ran a physical business with employees and property. I work entirely on my own, with a laptop, a phone, a virtual assistant and a rotating group of colleagues and clients.

Like it or not, more people are going to be joining the ranks of the self-employed whether they do it in my parents’ style, in mine, or in some other way altogether.

If you didn’t grow up with entrepreneurship in your DNA, one way to catch up is to study at the heels of Pamela Slim, a consultant, life coach and blogger whose new book, Escape from Cubicle Nation, is a roadmap to self-employment. I chatted with Slim about how the current economy is affecting people striking out on their own, how to launch a business on the side, and whether it’s possible to warm to self-employment when it’s not your natural inclination. Read More »