If you’re a career changer who’s recently started down the path of self-employment, you’re probably discovering what we veteran self-bossers have learned from experience. Most of the time, being your own boss is everything it’s cracked up to be, offering autonomy, decision-making power, unlimited learning and earning potential, flexible hours, dress code, office environment, yada yada yada. But not every day is like that. Some days, there’s just a little too much “self” in “self-employment”; some days, you need a little outside support, perspective, and inspiration — preferably from someone who’s been there, survived that. Some days, you need a little Barbara Winter.
I first discovered Barbara at a seminar called “Making A Living Without a Job” at the Boston Center for Adult Education, oh, about 7 or 8 years ago when I was newly self-employed. Beyond providing the obligatory useful information, which I appreciated, what distinguished Barbara was the way she talked about running a business: as if she had no doubt whatsoever that it was the absolute most fun thing you could spend your time doing. She talked about self-employment as an outlet for creativity and self-expression, an opportunity to make a contribution, and a way to be more successful financially than you might be in a J.O.B. (her term for work that delivers a paycheck but none of those other things, preferably a temporary pursuit.) The message: Not only is it possible to be “joyfully jobless” but you can earn a living doing it.
If you’ve been in corporate for as long as I had, it’s hard to imagine those two concepts coexisting. But Barbara made a convincing argument; not only that, I thought she was “just a hoot” (one of many Barbara-isms that always make me chuckle.) Even if I didn’t care to learn about self-bossing, I would have wanted to listen just for the enjoyment of it. Check out this example of her writing to see what I mean. Since then, in devouring pretty much every piece of content Barbara’s produced (book, seminars, newsletters, tapes, blog, tweets), I’ve found it uncanny how she always seems to strike just the right note on just the most relevant aspect of my self-employed life at any given moment.
In conclusion, shifting back from groupie to financial planner… New self-bossers, veterans who could use an infusion of inspiration, anyone trying to make a living without a J.O.B.: do yourself — and your bottom line — a favor, and get the book.