You Can Go Your Own Way

Thinking About Tomorrow: Reinventing Yourself at Midlife
by Susan Crandell

(Page 3 of 11)

"My boss is an asshole, but I can work with him because I know him so well." That's the self-deprecating joke Portland, Oregon, native Steve Weiner cracks, describing his feelings about becoming his own boss after twenty-two years of corporate life. But he's utterly serious about the satisfaction of being a small-business owner. The freedom and control are intoxicating, he says; he could never, ever go back.

Steve speaks for a big share of our generation. For us, the urge to launch a business and call our own shots is a powerful motivator. An AARP study found that men and women over age fifty make up 25 percent of the total workforce, but a whopping 40 percent of the self-employed. Among the self-employed one out of three took the plunge after turning fifty. It stands to reason that the urge to be our own bosses should sharpen as we mature and grow accustomed to holding the reins, whether it's bringing up children or taking on more authority at a corporate job. We've tested our ability as decision makers. At midlife, we approach a solo venture with a heightened degree of confidence. Most of us have ridden our share of rough road, and our judgment has been honed by our failures as well as our successes.

Some, like me, may be surprised to find themselves thriving as captain of their own ship. I vowed I would never own a small business, having watched my dad run a company that sold travel trailers and camping supplies with reasonable success but no real joy. By his late fifties, he was so burned out, he retired happily to a series of what he called "nothing jobs" - working on the loading dock of a newspaper company or in the parts department of an automobile dealership - relieved to finally shed the stress of running Crandell Sales.

As a child, seeing him struggle with the anxieties and pressure of business ownership, I knew I wasn't cut out to be an entrepreneur. As an adult, I was grateful for the paycheck that arrived every other week, whether business was good or bad, and I appreciated the corporate health plan and the 401(k) with company-matched contributions. If you had asked me when I was in my thirties whether I'd ever work for myself, I would have said "Hell, no." Then at fifty-two, I became the sole proprietor of another Crandell Sales, with just one product to market - me. Two qualities I share with many of my boomer peers made this improbable shift possible: personal growth and a sizable network of contacts. By my early fifties, I had worked at half a dozen magazines and knew lots of editors to whom I could pitch article ideas. By the same token, I was confident that as a freelance writer, I understood what editors want, having sat so long on the other side of the desk assigning articles.

The intersection of those two priceless commodities - contacts and seasoning - can be a boon to midlifers who are launching businesses in the same arena. Becoming a consultant in your industry is a lot easier than making the leap to a completely different line of work. Even if you're entering a new field, your background can be important. Louisiana resident George Oldenburg is one of the Life Entrepreneurs profiled in this chapter. At first blush, his transition from bank executive to zoo owner at forty-five seems about as radical as a career change can get. But George credits his financial background with helping him manage the annual budget for a highly cyclical business, when the lion's share of revenues flow in during just a few high-season months.

So we come at new occupations with special qualities that help us succeed. Often midlife is the first time we have the wherewithal to start a business, whether it's from an inheritance, a severance package, or a plump 401(k) we're willing to bust. Of course, we're gambling with our futures, and the stakes are higher because we can see the potential infirmities of old age ahead. The new-business owners I've talked with don't deny the risks, but they don't dwell on them either. Like Steve Weiner, they're too busy glorying in being the boss.

Calling a Time-Out

Sometimes job burnout hits so hard, there's nothing to do but remove yourself from the workforce for a while. Once regarded as career suicide, this is now an increasingly common strategy for catching your breath. Some people use their time-out to explore a new path, while others rediscover a passion for their job. The lucky ones work for a company like Nike or Intel that offers paid sabbaticals, or a firm such as Procter & Gamble, which grants the time unpaid. According to a 2005 study from the Society for Human Resource Management, 17 percent of all US companies were offering some kind of extended leave.

In her midforties, Mary Lou Quinlan took a five-week sabbatical from her job running one of the top advertising agencies in New York, and ended up leaving her high-powered position to launch her own boutique ad agency, Just Ask a Woman. She wrote about what she called "my walkabout" for us at More, published a book on the subject of sabbaticals, Time Off for Good Behavior, and appears as a judge on the reality show American Inventor. Another article we published, "Leaving at the Top," profiled powerful women who'd become disenchanted enough to quit. Some of them walked away from the workplace, but most simply took some contemplative time to figure out their next career move. Ann Fudge famously left a top post at Kraft Foods, then two years later returned to the fray as CEO of Young & Rubicam Brands.

For one of the couples I interviewed, Kirk and Colleen Kvetko of Naples, Florida, one sabbatical led to another. Kirk was the first to bail out of a job, leaving a twenty-three-year career at FedEx, worn out from being on call 24/7. He wanted to climb a mountain, compete in triathlons, and play lots and lots of golf. It was four years before someone offered him a position enticing enough to draw him back into the workforce. No sooner was he behind a desk again than Colleen called her own time-out, quitting a big-deal bank job to clear her mind and discover a new path. When she started her sabbatical, her husband wrote Colleen a letter telling her to "Smell the roses, listen to the birds, relax and do what you enjoy."

Not everybody can afford a long stretch without pay, and many may find the risk of job hunting without a current job too high a price to pay. But sometimes a valued employee can negotiate some unpaid time away, even at a company without a formal policy. It's worth looking into if you crave a break in the routine but can't afford to jeopardize your job.

Copyright © 2007 by Susan Crandell

About the Author

I got my first job after college not because I was the smartest applicant - I wasn't - but because I was the only one with a pilot's license. I'll be grateful forever to Bob Parke for hiring me at Flying magazine because that's where I met the love of my life, Stephan Wilkinson (the author of two wonderful books, The Gold-Plated Porsche and Man and Machine). Thirty years later, Steve and I are still working together, both freelance writers with offices in our little Hudson Valley farmhouse. Our daughter Brook, who's an editor at Conde Nast Traveler, is the only one with a real job.