The Siren Call of Starting Over

After a long-anticipated Brazilian vacation in February 2009, Sean Ogle had a hard time returning to his stable—if unexciting—job as a financial analyst in Portland, Oregon. For years he’d had two main goals: to travel the world and to become his own boss. Now he saw with new clarity that he wasn’t on a trajectory that would help him realize either one.

Still, he had a hard time figuring out what to do. Over the years, his coworkers had come to seem like family, and he felt especially indebted to the man who’d hired him. The economy presented another stumbling block, he says. “I had a better paying job than most, with lots of potential growth. Why would I give up a steady paycheck and a comfortable life to gallivant around Asia when I had no idea what that would bring?”

But in the end, that’s exactly what he did. After he was asked to suggest some money-saving ideas for the company, Ogle proposed that he work remotely for a pay cut—which his boss unexpectedly interpreted as his resignation. Rather than focus on finding another traditional job, Ogle embraced the chance to pursue Plan B: a career centered around his passions. Months before, he had reached out to blogger Chris Guillebeau, who, through his website, The Art of Non-Conformity, encourages others to make a living doing what they love. With his guidance, Ogle sold his car, landed a half-year, Internet-based gig he could do remotely while starting his own blogging business—and transplanted himself to Thailand.

Follow the money. Follow your heart. For many, these messages resonate—and sometimes compete—as never before. In the wake of the Great Recession, the pressure to think practically about jobs has never been greater. There might be college loans looming or a mortgage to pay, and in a rocky financial climate we’re constantly reminded that a stable job with benefits is something to feel grateful for. Yet that hasn’t prevented many nine-to-fivers (or increasingly, eight-to-sixers) from fantasizing about more autonomy and authenticity in their careers. As Web-savvy entrepreneurial types claim center stage in the new globalized economy and the marketplace of ideas, the call to take risks and build a brand around one’s passions has never been louder—especially on the Internet. In fact, in the blogosphere, a growing number who’ve taken the plunge now claim that in volatile times, following your dreams may very well be the safest bet. No wonder we’re more conflicted about what work means and what it should be than ever before.

Of course, for millions of Americans struggling to make ends meet, the push-pull between work that fuels the spirit and work that fuels the bank account isn’t even on the radar. It’s white-collar workers who tend to grapple most with their expectations: the desire to be fiscally responsible competes with a nagging anxiety that as accountants or marketing executives they’re not fulfilling their promise, that they might be happier opening a brewery or making films.

Personality also plays a role. Anyone open to different types of experience is inclined to see the appeal of forging a new path, says Ronald Riggio, an organizational psychologist at Claremont McKenna College. “Those who tend to be creative or independent are likely to fit this pattern; they want careers that allow them to express who they are,” adds Katharine Brooks, author of You Majored in What? Mapping Your Path from Chaos to Career.

Concerns about career identity are particularly acute among Millennials, who came of age with extraordinary expectations for themselves, boosted by Boomer parents who encouraged them to dream big. “They see themselves as having many career options. They’re interested in doing what they want, rather than acquiescing to norms,” says psychiatrist Gabriela Cora, a corporate consultant at the Executive Health & Wealth Institute in Miami.

Having grown up in a time of prosperity, many members of Gen Y have trouble reconciling the belief that they should be creating their bliss with the reality that it can be financially risky—and likely won’t allow them to live at the level they did with their parents, Cora notes. “It seems clear that there’s a growing gap between expectations and reality,” confirms San Diego State University psychologist Jean M. Twenge, author of Generation Me: Why Today’s Young Americans Are More Confident, Assertive, Entitled—and More Miserable Than Ever Before.

Yet it’s not just Millennials who desire careers that align with their passions; a generational study of high school seniors led by Twenge suggests that Boomers, Gen Xers, and Millennials all place an extremely high value on jobs being interesting. Underscoring the widespread nature of the strife over what matters most in a career is a study by Encore.org, a think tank focusing on Boomers, work, and social purpose. Among its findings: Financial concerns are holding back millions of Americans between the ages 44 and 70 who would like to move into “encore careers” that place their talents in service to the greater good. “The urge to create something new seems very invigorating to people,” says Encore.org Vice President Marci Alboher. “What I hear a lot is, ‘If not now, when?’ ”

A TIME OF CONFUSION

Through much of the last century, work trajectories seemed relatively clear. “Thirty years ago, people started a career believing they would do well and then grow old in that same job. People valued stability,” Cora says. Ideals have since shifted: “Now, people want a calling.” At the same time, traditional work is getting worse—jobs have become more demanding even as they offer fewer rewards, she asserts. Workers frequently find themselves with less autonomy and more tedious dead-end projects. Many of the old security guarantees are gone—without a compensating upside. “When our fathers took jobs, they at least knew they could buy a house and raise a family,” says one financially strapped freelance writer, weighing the pros and cons of seeking full-time employment.

For those who are feeling less than satisfied with the corporate grind, the idea of a Plan B can be undeniably alluring—and all the more so as self-starters who’ve made the transition have been lionized in the media in recent years. It’s also increasingly billed as practical by those who’ve succeeded at it, like Harvard Law School grad turned career coach Tama Kieves. “You probably have a voice of fear telling you to play it safe, heed convention. I want to represent your other voice, the one that tells you to really play it safe, by following your desire,” she writes in her new book Inspired and Unstoppable: Wildly Succeeding in Your Life’s Work!

The clamor over the benefits of taking a risk is especially conspicuous on the Web. One voice among many in the digital chorus: Ogle’s. Today he’s a visible exponent of one particular brand of the pursue-your-passion message; he promotes a “location independent” lifestyle through his blogs Location 180 and Location Rebel, while also traveling the world. (To make ends meet, he juggles other projects, including part-time work for his mentor, Guillebeau.)

“The more time you spend on the Internet, the more you get a sense that following your dreams and starting your own business is the norm,” says Judith Donath, a faculty fellow at Harvard’s Berkman Center for Internet & Society. While experts agree that entrepreneurship has become more common in the past decade, “the startup community is disproportionately represented online,” she explains. “Someone may say, ‘I quit my job, so I’m going to start a blog about my new wine business.’ But there aren’t many who will say, ‘I’m going to start a blog about my day as a middle manager at Staples.’ ” All the bandwidth devoted to entrepreneurship may make it seem less of a gamble—but while that likely helps boost the appeal, it doesn’t mean such ventures readily succeed.

FINDING THE WAY

For some, it might be relatively obvious which road makes the most sense. “A lot depends on whether you have kids,” notes University of Texas, Austin, psychologist Kristin Neff, author of Self-Compassion: Stop Beating Yourself Up and Leave Insecurity Behind. Among other things, how comfortable you are with ambiguity may also play a role in whether or not you take a leap of faith. “Folks who have a high tolerance for it are better able to deal with the uncertainty that comes with following your heart, while having a low tolerance often leads to sticking with a ‘safe’ path,” Claremont McKenna’s Riggio says.

Still, knowing what’s right doesn’t mean that letting go of a dream and making peace with a workaday job is easy. “Concentrating on the good aspects of your current job—the reasons you chose it in the first place—can help you go from feeling like a victim to someone who’s actually in control of the situation,” Cora advises. In addition, she recommends thinking of ways you can bring what interests you about a Plan B career into your current position: “If you’ve always wanted to start something from scratch, look for ways that you can head up a new project within your company.”

It may also be helpful to know research suggests career satisfaction is linked to obtaining work that offers scope for autonomy, a sense of impact and mastery, and creativity. “When you recognize that these conditions have little to do with following a pre-existing passion, you can abandon the myth that there’s one perfect job for you,” says Georgetown professor Cal Newport, author of So Good They Can’t Ignore You: Why Skills Trump Passion in the Quest for Work You Love.

Meanwhile, for those still awash in confusion, Harvard Graduate School of Education’s Robert Kegan, author of In Over Our Heads: The Mental Demands of Modern Life, counsels finding ways to tease out and reflect upon the various competing voices. One strategy he suggests is creating a four-column document identifying, in turn: a goal (“I want to better follow my own heart”), behaviors that run counter to this goal (“I accept jobs that aren’t meaningful to me”), competing commitments (“I can’t let down my family”), and last, assumptions that keep the third column responsibilities feeling necessary (“If my career change disappoints my family, they will stay unhappy with me”). Simply getting these ideas out of your head and onto paper will often lead to a profound shift in perspective, Kegan says.

If that ultimately convinces you that it’s time to give Plan B a chance, Cora stresses the importance of pragmatism and careful planning. Rather than just quitting your job and diving right in, “work part time on your own—begin testing the water, making it an opportunity,” she says. Not only will this help you determine how viable your plan is financially, you’ll get the chance to find out if you actually like the work involved.

Another critical step in any successful transition: getting support. Having voices of encouragement is key to handling the stress of making a career jump, Neff points out. Fortunately, it’s possible to get support 24 hours a day via the Internet—through Facebook, Twitter, and an array of niche online communities. Moreover, “the access to information and the ability to find collaborators and people who can offer advice actually reduces the real risk of starting something new by giving you practical resources for doing it,” says Harvard’s Donath.

No one knows this better than Ogle. “From a business standpoint and an emotional standpoint, none of this would be possible without the Internet,” he says, reflecting on the road he’s traveled in the past few years. “As I built my sites, I developed a support system. I had people to turn to if things didn’t work out. If you sit down at a bar, what are the odds that someone next to you will share your goals and interests? Through the Internet you can find people who want the same things you do.”

The New Plan B’ers

As attitudes toward lifelong careers have SHIFTED, FOR MANY Plan B has come to represent a work CHANGE born of passion rather than necessity. here’s HOW it paid OFF FOR THREE risk-takers.

A MOVE AT MIDLIFE

In 2009, Kenny Likis was exploring postcollege opportunities for his son when he discovered that Teach for America didn’t have an upper age limit. “I instantly decided to apply,” says Likis, who became fascinated with the program after hearing founder Wendy Kopp speak in 2006.

Having previously spent more than two decades in the Boston-area high-tech world as a technical writer, a manager, and a vice president of engineering, by the mid-aughts, he was ready for something “that had more social impact.” Inspired by his wife, who had moved from the tech world to education, in 2005 he left a job that felt like an increasingly poor fit. But he struggled to find his place, dealing with stretches of being “unemployed and underemployed.”

Finally, Likis made a U-turn back to the tech world, a foray that was cut short by a layoff in the wake of the financial crisis. That, coupled with a life-threatening pulmonary embolism 10 days later, brought new clarity. “It all had me thinking, ‘Do what you want to do,’” he says; when the Teach for America option appeared, he was more than ready.

For Likis, who began his working life as a college English teacher in his native Alabama, the five-week Teach for America summer training was “as invigorating as anything I’ve ever done.” He spent the past two years teaching high school English and Special Education in South Boston. The good: It’s exactly where he wants to be. The bad: The school where he spent the past year has no openings for this one. Despite the uncertainty, Likis has no regrets about his full-circle journey. “Once I started teaching again, I remembered how much I loved it. Finishing my working life in the classroom was a good choice for me.”

ON TO PLAN C

Having completed a B.F.A. in drama, Ned Menoyo, then 22, took a deep breath and assessed his next steps. “I loved acting, but I also lived in perpetual terror when I saw how actors live,” he recalls. Born into a family of lawyers, it wasn’t long before he found himself considering the obvious, time-tested option.

After law school and several years working in Boston, he and his wife moved to Maine, where he shuffled between the private and public sectors before landing a job in government relations. By then, he was divorced—and finally ready to take a risk.

When his best friend announced a move to Los Angeles, Menoyo was inspired to do the same and give acting another shot. As crazy as it might have seemed to others, “the decision was clear for me. Acting felt like unfinished business. I wanted to put that to rest,” he says. In the years that followed, he enjoyed a certain success: a few commercials, student films, a single scene with Tatum O’Neal—capped by being cast as the lead in a (yet-to-be-released) independent action film.

Then life intervened. While Menoyo didn’t find fame out West, he did find a second chance at love and a family, which led him to reimagine his career once again. Now a married father of two, he’s spent the past six years as a staff attorney at a Los Angeles law firm. He’s grateful for the law degree and stable career he once took for granted, even as he continues to pursue his love of acting. “I’ve found a way to do both—for now, that’s good enough for me.”

GALVANIZED BY GLOBAL TRENDS

At 25, Rachel Cook was making more money than she’d expected, but as a futures and equities trader, “I wasn’t creating a product or helping anyone. I especially wanted to help women,” she recalls. It was fun, but unfulfilling.

After happening upon a story in The New York Times about how microlending is transforming life in impoverished communities by providing women with small loans to start businesses, “I decided on the spot to make a global documentary exploring the impact of microfinance.”

With no film industry connections to speak of, Cook’s first stop was Craigslist, where she posted an ad seeking a director of photography. Among the respondents was Steven Hiller, a veteran of dozens of Hollywood studio films, including Terms of Endearment. Once he signed on, others quickly followed. Funding came from Duke University, Royal Roads University, Kickstarter donors, and Cook’s own savings. Shooting began in South America in April 2010; next came stops in India, Bangladesh, Kenya, and even Detroit.

With the film slated to premiere this October at Duke, Cook’s alma mater, she’s also deeply focused on a related for-profit venture: a (patent-pending) social game called Seeds, which combines micro-lending with the lucrative online game world. “I believe what I’m doing can transform the world in positive ways while also generating healthy financial returns,” Cook says, noting that microfinance and social gaming are both multi-billion-dollar industries. “Profitability and social conscience are not mutually exclusive.”

While her days are far longer and her bank account far lighter than in her trading days, “I’ve never been happier,” Cook says. “I care deeply about what I’m doing. I feel I’m making an impact—so I have the energy to do whatever needs to be done.”