Kick Starting a Freelance Business… When You Can’t Afford to Fail



Like so many others before me, I realized long ago that freelancing is the only way to take full advantage of life in a free society. We all want greater control over our own daily schedules and future accomplishments. But while many of us can plainly see the allure of never having to ask a boss if we can go on vacation (or take a nap at 2pm), we often don’t view ourselves as entrepreneurs in the traditional sense… you know, those dynamic people who can make a business hum along profitably whether it’s an ice cream parlor or a rubber band factory?

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Getting Stood Up: Identity and the Freelancer



Folding a regular Internet broadcast into my media empire—which, at the moment, consists of a laptop and two pens which actually work—has increased my visibility as a freelancer. Everything that comes with being a freelance writer is there: the flexibility, the endless reach to bump up against another human soul through art, the second-glass-of-wine buzz of speaking with admired guests. And you know who else came over to play? Rejection and self-consciousness. Hello, old friends.

The show that was rushed into production (after one of the entrants in the Kentucky Derby was euthanized right on the track) was fielding its first guest. Even after such an auspicious beginning, I was terrified, for this was Talking To People, which is horrifying on any level and even worse while still finding my footing as a radio hostess. It would be like recording my very worst cocktail party small talk, then broadcasting it over the World Wide Web.

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