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The reinvention chronicles

As the economy forces all of us to rethink our careers—hell, the whole arc of our lives—a vanguard of the adventurous and the desperate is navigating an unrecognizable landscape that has little to do with résumés and contacts. Reinvention may be the Bay Area’s global brand, but as tens of thousands of us are discovering, the Great Recession has changed all the rules.

Over the past few months, I’ve spent a lot of time at Starbucks and Peet’s, talking with men and women who used to have stable careers but now have migraines, insomnia, depression, and the gnawingrealization that most of what they know about earning a healthy living is, or will soon be, obsolete. Often, during a pause in the conversation—maybe we’re talking about how companies in Chapter 7 bankruptcy don’t have to offer COBRA, orwhat it’s like for someone with 10 or 20 years of experience in user interfaces or mortgage banking, earning a great deal of money, to start from scratch, competing with kids who will work for peanuts—I look around and notice that the place is full of other people talking about the same things, in the same stunned way, trying to pretend they’re fine when in reality, they are scared to death.

[Click photos for stories from our reinventors.]

I try not to eavesdrop, less out of politeness than because such conversations can be painful. Many of these people are either already unemployed or clinging to jobs that could evaporate tomorrow. This is plan B time, and it’s daunting to realize how many people—especially the ones old enough to have known better—have been caught without one.

In Northern California, of all places, it seems odd to think about personal and career reinvention as something that can make yourskin crawl and your stomach turn. For the past five decades, reinventing everything, all the time, has been the Bay Area’s global brand. The results have sometimes been paradigm shifting (see: free speech movement, venture capital, gay culture, Google, YouTube, iPod, iPad), sometimes just gratifying and cool. People who don’t fit in elsewhere have always flocked here, hoping for a redo. But the flip side of this penchant for fresh starts and rad­ical remixes has been a certain delusion about what reinvention actually involves: the twists and turns, the sacrifices, the uncertainty, the ulcers. “There’re always so many people doing it here, you can get this unrealistic notion that it’s supposed to be really easy,” sighs a friend of mine in San Francisco, jobless for going on two years.

“It isn’t like the fantasy,” a mid-50ish former tech worker, laid off in 2007, says wearily. “It’s more like, ‘Oh shit, what am I going to do?’ ”

I. THE PREDICAMENT
 “There are no jobs.” —Shakirah Simley, reinventor

Indeed, what are we going to do? This uncertainty goes way beyond the Bay Area, of course. The entire economy is in transition, with many sectors imploding or restructuring in ways that might not shake out for years, and the country’s return to boominggrowth is not at all guaranteed, despite recent signs of improvement. The changes in how people work are just as fundamental: gigs rather than jobs, a portfolio of careers rather than a single employer, multiple revenue streams instead of a bimonthly paycheck. A new crop of books sums up the emotional and intel­lectual traits required now: Drive, Pull, Nudge, Shift, Mindset. People whose job it is to help other people reinvent reach for sweeping analogies to explain the scale of the current undertaking: The global economic collapse is like the fall of the Roman Empire; workers trying to figure out their new path are like Moses and the Jews wandering in the desert for 40 years; those who refuse to retool for this new Industrial Revolution will be flattened by it. Mark Guterman, a principal at MeaningfulCareers.com, a career-consulting firm in San Francisco and Boston, brings the history lesson forward when he tells me, “Reinvention has become the modern American hero’s journey.”

For people under 40, who grew up during the web revolution and so are used to perpetual upheaval, this is still a great place to be a hero—and as good a time as any to do it. Neither the rhetoric nor the reality of earth-shattering transition paralyzes someone who can text, tweet, and Yelp as fast as he can talk. “No one’s going to hand us the perfect opportunity,” says 25-year-old Shakirah Simley, the community-food activist behind Slow Jams, a Mission-based startup. “We don’t want to become victims of this recession. In a way, it’s been a blessing in disguise. There are no jobs, so it becomes, ‘How do we create our own paths?’ "

To a Bay Area boomer, though, plan B feels more like plan Z—your last chance, and it had better be brilliant, or you’ll be exiled to Nevada, where you’ll die bored, resentful, and broke. 

Based on my own unscientific survey at job fairs and networking groups from Cupertino to San Rafael, the chorus of oh-shits is unrelenting among this demographic—ironic, given that the same generation pretty much created the concept of personal reinvention (and that its entrepreneurial drive made this region what it is today). For those burdened with 20th-century educations and expectations, as well as San Anselmo–size mortgages, child support payments, and their parents’ nursing-home bills, the hurdles to reinvention start with the Bay Area’s cost of living, the third or fourth highest in the U.S. “The financial side is seriously difficult,” says 55-year-old math-teacher-in-training Penny Mudd, a refugee from a health-industry startup in Silicon Valley. “I’ve gone through severance and savings, said ‘I’m not going to touch this or that money,’ and burned through that, too.” Meanwhile, California’s bud­get crisis has forced savage cuts in higher edu­cation just as enrollments are swelling. Colleges and government programs are geared toward the young, as are career pathways such as fellowships, internships, and apprenticeships. For people at midlife, reinvention “is a do-it-yourself proposition,” says Marc Freedman, founder and CEO of San Francisco–based Civic Ventures, a think tank on boomer social-policy issues. “They’re being forced to make it up as they go.”

Then there are the mental blocks: the fear of failing or flailing around, which can be a side effect of early success and the belief in one’s superior intelligence; the pop-culture examples of reinvention, which can intimidate and inhibit more than they inspire. “Thestories that have become part of the myth of Silicon Valley may be setting the bar too high,” concedes Chip Heath, a Stanford Graduate School of Business professor and the coauthor (with his brother Dan) of this spring’s Switch: How to Change Things When Change Is Hard. Other experts I talked to highlighted a generational divide created by the speed of technological change here—a sense, even among those who spent a decade in the software industry, that “they aren’t just falling farther behind; they’re falling farther behind faster,” as Guterman puts it. After working 70-hour weeks for much of their careers, these reluctant reinventors find that push­ing the reset button holds little appeal.

Women, many of whom have cycled in and out of full-time work, are more experienced at this ad hoc process. “The idea of being more than one person in your lifetime—women have always had to do this,” says Bay Area demographer Maddy Dychtwald, author of the new and very good Influence: How Women’s Soaring Economic Power Will Transform Our World for the Better. But this prospect freezes those boomer men who have long defined reinvention as yet another, better-paying job. With that prize now as rare as a pension plan, they have been left feeling crushed by the sky-high expectations of what constitutes the comfortable Northern California lifestyle that they still feel obligated to provide. “Men around here often can’t describe what feeds the fire in their belly or even what they liked about their last job,” says Bart Penfold, executive vice president and managing director in San Francisco for the executive search firm DHR International, who has done hundreds of interviews with high-achieving men. “They will just spend 45 minutes explaining why they lost it.”

Men and women, excited and freaked out—I’ve talked to dozens of people in various stages of reinvention, voluntary and not, from kids in their 20s to boomers old enough to be grandparents. My goal was to tease out what it takes to rethink your future in a Bay Area that no one pretends is predictable. Given that everyone and her mother now has to deal with reinvention, not as a fantasy or luxury but as an inevitability, it wasn’t hard to find smart people with up-to-the-minute lessons to impart. I met a reassuring number who have already managed to acquire or invent satisfying new jobs. But I met many others who are struggling: a few who thought they had found new careers that would sustain them, only to discover that the fit wasn’t right; others who still don’t have a clue what they can or want to do. Pretty much everyone complained of feeling invisible and powerless at some point, cast adrift in a world whose rapid changes they were too busy or too comfortable (or too in denial) to grasp. Surprisingly, the sanest people weren’t necessarily the ones who have figured out their path but those who forged ahead nonetheless, with no career experts or how-to books (most of which are sadly outdated, anyway) to guide them.

The biggest takeaway: In the Bay Area, rein­vention is no longer a transition between “before” and “happily ever after.” How could it be, with the economy in metamorphosis and no secure, old-fashioned “after” on the horizon? No, reinvention has become a long-term condition—and, once you get used to it, it’s not a bad way to live. 

II. THE PRECONCEPTIONS
"Faced with stories of doctors who become chefs, real-life human beings are bound to feel inadequate."
—Carlo Strenger, psychologist

Here’s the first lesson I learned: Success today comes to those who think small. It doesn’t sound all that radical, until youconsider that the Bay Area’s makeover fantasies tend toward extremes—the Montessori teacher who starts a culinary revolution, the Silicon Valley superstar who takes on Sacramento. We think reinvention should be fueled by passion (“Do what you love, and the money will follow”), and we award extra points if it happens quickly, especially in midlife, because by the time someone’s that old, she should know what she wants.

Not only does reinvention rarely work that way in real life, but the fantasy itself can hold people back. “When people get caught up in the bigness of all those changes, they become paralyzed. It can fry your brain,” says career consultant Guterman. Or, as Israeli psychologist and philosopher Carlo Strenger wrote in the Harvard Business Review in 2007: “Faced with stories of doctors who get up one morning knowing that they want to become chefs [and] housewives who have a sudden vision of the empires they are about to build…real-life human beings are bound to feel inadequate. They have fears, doubts, and vague ideas at best, so they’d better stick to their knitting.” Civic Ventures’ Freedman doesn’t even like to call the process reinvention; he prefers the less intimidating redirection. “You’re still the same person,” he says. “This is just another chapter.”

In many ways, my friend Laura Griffith is a poster child for the next-chapter approach, though she came by this realization the hard way. When she lost her fashion-exec job after Oakland-based Mervyns went bankrupt in 2008, she decided to make a 180-degree turn into the field of cardiovascular technology. She had good reasons, including a deep personal stake in the technology (it saved both of her parents from potential heart attacks) and decent job prospects in the Bay Area. But she soon discovered that aradical reinvention has some major downsides.

With all the community-college cutbacks, waiting lists, and prerequisites, the two-year training program she found would take her closer to five years, and when she graduated, she’d be lucky to earn 50 percent of her former salary. And the job itself would involve “being in a dark room all day long running a sonogram machine, not really engaging with people,” she says—not a great fit for a woman who’s hiked Patagonia, kayaked the Inner Passage, and can’t stand to be cooped up and bored. Most important, it felt wrong to throw out so many years of being good at what she did. So, a few months into her reinvention, she went back to the drawing board and decided to build on her existing skill set, combining her love of fashion and the outdoors by becoming a designer of active- and outerwear. Even this less dramatic shift has required enormous determination—“I had to teach myself six new computer programs in the last year,” she tells me—but she’s certain it’s more sustainable.

The more I look around, the more I realize that radical midcareer reinvention is so rare as to almost be an urban myth. The Bay Area is too competitive and expensive a place to pull it off (unless you have Meg Whitman’s hundreds of millions, and even then, it’s no sure thing). The same holds true for younger people: A reinvention that at first glance seems sudden and extreme usually turnsout to be incremental or a return to roots.

Passion is another false siren in the reinvention fantasy, despite its enduring allure. Not only can it burn out, but it burns people out, too. Given the high degree of difficulty here (and all the churning emotions), reinventors need something more steady to power them over the long haul. In Guterman’s view, purpose is much more fundamental: “It helps you answer the question, ‘What am I here to achieve?’; it gives you the basis to build a plan; and it gets you past the rocky parts.”

In Silicon Valley, “passion was for crazy artists,” Penny Mudd says. “Someone would say they had a passion for accounting, and we would roll our eyes.” When it comes to teaching, “I don’t really feel all this highfalutin passion stuff. It’s more a question of ‘where do I fit into the world? Where can I do good?’ ” Bestselling author Daniel Pink describes purpose as one of the main components of Motivation 3.0, aka Drive: the intrinsic urge among employees that is replacing the carrot-and-stick approach top-down employers used to invoke to spur innovation. “The most deeply motivated people—not to mention those who are most productive and satisfied—hitch their desires to a cause larger than themselves,” he writes.

But passion and purpose are not mutually exclusive: “Purpose creates a feeling that people think of as passion,” says Susan Hanshaw, who spent 20 years in direct marketing, then reinvented herself first as a self-help author and motivational speaker, and again as a San Rafael–based social-media consultant. “It’s what we are good at, the skills we have, what we like to do.” Case in point: Shira Tannor, who until recently was the manager of legal resources in San Francisco for legal giant Skadden Arps (she spent 22 years at the firm). Tannor, now 50, started thinking about making a shift several years ago—she liked the people she worked with but not the megacorporations whose bidding they did—and her mind naturally drifted to her first love, theater. (In her twenties, she was as an assistant to Stephen Sondheim and Wendy Wasserstein and earned her MFA in playwriting from NYU.) But, she realized, “what really gets me going is collaboration, planning, synthesizing information, working with creative talents to make things happen. That translates to a lot of industries for which there may be an interest but not a passion.” Tannor had been friendly for years with the folks at Veritable Vegetable, a San Francisco organics pioneer; this month, she starts work there in an as-yet-untitled role. “What I do well is manage people,” she says. “That’s what I’m bringing."

Tannor’s headline-worthy reinvention—legal eagle shakes off golden handcuffs to sell lettuce and peas!—isn’t remotely startling once you dissect her process. She made the switch on her own terms, after much thought and discussion. Neither passion nor disasterplayed a role; that makes her the ideal reinventor for the new era. In good times or bad, she never stopped reflecting about what she should do next. Ideally, in Guterman’s view, reinvention is (and always has been) a perpetual process of self-discovery and preparation, not a jolt out of the blue. “Most people wait for the pain before they go through the change,” he says. “These techniques should go on all the time.”

It’s never too late to begin, though, as I discovered from the great majority of reinventors who were dragged into it screaming and kicking. One of the fringe benefits of purpose is that it can function as an important catalyst for people who have no idea what they ultimately want to do. Last year, Laurie McManus, 58, lost her six-figure job as an executive assistant to a real-estate company’s CEO in San Francisco. “I had decided I wanted  to make a lot of money, so I scratched my way up the food chain, but when I got there I was totally unchallenged and unfulfilled.” She has joined with a group of other unemployed Marinites to organize career education events (under the name Career ReVision) and is ecstatic to be doing something meaningful at last. “I will be eternally grateful for being laid off. I know it sounds cheesy, but I feel like I’ve been born again.”

III. THE PROGRESS
"It’s less important to figure out your ultimate path than to figure out how to get through the process."
—Carlos R. Hernandez, reinventor

It turns out that much of what the Bay Area thinks about how to reinvent is wrong. Let’s start with a basic idea, that there is astraight path from point A to plan B. That’s outdated, many experts and reinventors tell me. Instead, what people face these days is a huge, empty field; the goal shouldn’t be to get across it as quickly as possible, but to plow deeply and to plant as many seeds you can, then wait to see what grows. Guterman explains the new goal in language that will sound familiar to readers of Mindset, by Stanford researcher Carol Dweck, and NurtureShock, by Po Bronson and Ashley Merryman. “For those of us who have done this work for a while, it’s not really about reinvention,” Guterman says. “It’s about how you build a development mindset so that when you need to, you don’t have to go radical, you don’t have to panic—you’re ready.”

In the Bay Area, Dweck’s research on developing a “growth” versus “fixed” mindset is discussed mostly in relation to kids, yet it’s just as much of an issue for adults here, many of whom think of themselves as being more liberal- and growth-minded than they actually are. One of her most fascinating findings is that people who believe they are innately intelligent (that would be large swaths of the Santa Rosa–San Jose corridor), and that intelligence is at the root of their past success (as opposed to hard, hard work), end up avoid-ing risk and challenge because they don’t want to fail—failure being a sign of stupidity or of losing their marbles. Now is not the time to give in to this kind of fear or to be paralyzed by what Strenger calls “the myth of midlife decline.” “People here need to remember that failure doesn’t black-mark your record, especially in Silicon Valley,” says Stanford’s Chip Heath. “To fail here is almost a badge of honor. It means you’ve learned something.”

Serious learning is the point. Reinvention has been miscast in some corners as retooling—brushing up on computer skills, signing up for a program in nursing informatics. Instead, the people I met described how changing their lives has first required them to change their brains, to feel not just stretched but deeply uncomfortable as they wrestle with new ideas, master new skills, and will their neurons to be more agile and adaptable—“plastic,” as the scientists say.

The good news is that you don’t have to try—or fail at—anything life-shaking to feel that progress. I think of Penny Mudd, whose switch from taking wine appreciation to serious math classes when the economy fell apart made all the difference. “It was rigorous, therapeutic, and humbling. I recommend it like a doctor recommends a pow­erful medication,” she says. Or my friend Laura Griffith,whose attendance at a botanical-illustration class offered by the San Francisco Botanical Garden last year restored her confidence and confirmed her gut feeling that drawing—designing—was the right career after all. “We’d walk around every day and look at each other’s work, drawing on each other’s drawings. It was alarming,” she laughs. “But it was unforgettable: about losing control, about the impor­tance of collaboration. I would go home and spend four hours finishing up a drawing, completely absorbed.”

Networking is also key, but not in the way you might think. Mistake one is believing that it’s something you can or should do on the computer. CSIX Connect, the most innovative networking group in Silicon Valley (and the biggest, with more than 5,000 active members and nearly 20,000 over the past nine years), doesn’t even let interested people join online, at csix.org; they have to show up at one of the three or four lunchtime meetings held each week and commit to creating a supportive community in real life. “I wanted to have some reasons to keep them there and talk,” says Hamid Saadat, the nonprofit’s unfailingly cheerful founder. “There’s something about breaking bread together that’s very powerful.” CSIX’s members come from a wide range of professions, as well as from all over the Bay Area, which is a big part of what makes the organization unique.

Saadat is one of my favorite reinvention role models. Over the past 12 years, he’s learned to fly and to drive a tractor-trailer—“I was always fascinated to see how they back up these big trucks to the loading dock”—and now he’s studying Mandarin. Unemployed again, he recently met a woman with an intriguing business idea: making warming socks for dogs with arthritis. It might seem likean off-the-wall direction for a tech guy, but he sees a connection with his oper­ations-management skills. “Networking should be about meeting lots of different kinds of people and seeing new possibilities for yourself,” he says. “The person who is in the right place at the right time have been to many places at many times.” Adds Julie Castro Abrams, CEO of the Women’s Initiative for Self Employment, which helps low-income women start their own businesses, “You need a whole new community to help you become another person. Otherwise you keep getting this rein­forcement pulling you back into those old roles and that old way of being.”

Networking, then, is less about finding specific work than it is about challenging the old ways of being, which means that some of the most effective strategies are the ones that don’t involve actual networking, like taking a class or volunteering. Rebecca Denison, the service learning coordinator at Redwood Day School in Oakland, heard about something called an idea party back when she was still involved with AIDS work and trying to figure out what to do next. Last fall, a friend who was contemplating next steps begged her to throw one of those parties, so Denison (acting as facilitator only—she likes her current job just fine) gathered people from different fields, many of them strangers to each other, who were all in personal or career transition. The price of admission was a potluck dish and the promise to keep everything confidential, including names. “It was extra­ordinary to have strangers support each other in this way,” she says, “and amazing to have people look at your résumé who weren’t your friends.”

Once they do turn on their computers, many people around here make the mistake of thinking that social networks are about networking. Social media has its uses in that area, of course—Facebook to give a shout-out to an ex-colleague’s latest venture, LinkedIn to research the competition. But for reinventors, its most important function is helping to share a new narrative about yourself and what you’ve been, as well as where you hope to go. San Franciscan Megan Bourne, 50, had done everything fromproducing radio programs to directing alumni relations at Tulane University when her computer-consulting gigs dried up in 2008 and her husband lost his job as a healthcare executive. Needing to find work in a hurry, she discovered that she had become, in Internet terms, invisible. “It was like I didn’t exist as a professional person, even though I’d been working for 30 years.” Nor could she make sense of her career in a traditional format: “In the past, I’d always wanted to tell people what I thought they wanted to hear about me. But I’m more than my résumé.”

The LinkedIn tool she found indispensable was the profile section—frequently ignored by job-seekers—which allowed her to construct a mini-autobiography that tied together her disparate career threads into a coherent whole. “It was a really existential process to make sense of all the jobs I’ve had. I often feel like I did not manage my career very well, but as I worked and worked on my profile, I realized it did make sense—it’s not a random, zigzag path. I am the culmination of all my experiences.” Her angst and effort paid off: Last fall, Bourne landed a plum job as executive assistant to the San Francisco Fine Arts Museums’ director and Board of Trustees.

For Bourne’s friend and sometime collaborator Carlos R. Hernandez, a 53-year-old, Stanford-educated engineer who spent 28 years at a tech giant before he was forced to take a buy­out in 2007, the new story he wanted to tell was that he had not passed his sell-by date. “With older candidates, the one thing HR people worry about is our attitude. Social media breaks down age discrimination. They think, ‘This person might be old, but he is open-minded, he’s resourceful.’ ”

Hernandez has come to see himself that way, too. In the past two years, he has reinvented himself as a consultant spec­i­alizing in “social media for the uncomfortable,” giving 56 speeches last year and working with clients on a sliding scale. This new direction came about soon after he left his old job and started vol­unteering at GraceWorks, a San Francisco career-networking organization. Hernandez was lucky: His buyout package included three months of training and counseling with an outplacement firm. “A lot of the folks I counseled at GraceWorks didn’t have the benefit of professional help—they were just kicked out, gone,” he says. He figured that he could help them the most by teaching them what he had learned in his own outplacement sessions. “I learned along the waythat all I needed to do was be one day smarter than someone else my age.”

Many of the people I talk to have discovered some form of teaching to be a powerful way of networking, learning, and growing. “It’s less important to figure out your ultimate path,” Hernandez adds, “than how to get through the process of figuring out your path.” When I ask him if he finds this uncertainty terrifying, he says: “That’s the cool part. I have no idea where anything’s going to lead—I find that very appealing.” He mentions that he just wrote two chapters of a book after having been asked to contribute by someone he met on Twitter. Never would the old Hernandez have thought he could help write a book. Back then, nobody would have invited him to.

In Susan Hanshaw’s case, she thought she was largely reinvented two years ago, when she published a self-help career guide called Inner Architect and launched a business around it. But as she and her partner, Dean Guadagni, began using social media in their publicity efforts, the possibilities created by the new technology revived her interest in marketing, which she had thought was dead. “I started to want to apply my old skills to this new world,” she says. These days, she and Guadagni still call their business Inner Architect, but you will find no mention of the book on their site. “The process of reinvention needs to start with following your heart, giving credibility to what you find yourself leaning toward, checking that out for a while—but also giving yourself permission to go in a new direction when that seems right. Where you end up is very rich,” Hanshaw says.

Linear-minded Bay Area types may find this lesson about reinvention to be particularly frustrating: It’s a long, twisty, ambiguous process with unexpected breakthroughs that don’t take you where you thought you’d go. Again and again, successful reinventors tell me that there was no plan. They just did things that made them feel better, and then, suddenly, it all made sense. “You have to trust the process,” Guterman says. A lot of people in the Bay Area understand the importance of process, he adds, “but having the trust and faith—that’s another thing.”

IV. THE PAYOFF
"We’ve made huge changes." —Emily Dods, reinventor

Speaking of faith and trust, what are people supposed to do while waiting for seeds to grow into opportunities and income? How are they supposed to support themselves and their families in the meantime?

Some of the answers will be hard for anxious reinventors to stomach. In truth, well-paying jobs that support the full-bore Bay Area lifestyle—restaurant bills, health clubs, summer camps, trips to Hawaii—are in rapid decline. Trying to find one in a new field in this market—the region’s jobless rate is stuck around 12 percent, compared to 9.9 percent for the U.S. as a whole—is like spotting a leopard in the Masai when you’re a tourist. (It can happen, just not to you.) And it likely won’t get easier anytime soon: The 15 career sectors with the greatest predicted growth, according to a report this spring funded by Civic Ventures and the MetLife Foundation, are largely in fields that highly educated professionals around here will find unattractive: home healthcare, childcare, licensed vocational nursing, the clergy. This is not to say that many Bay Area residents won’t resume their career climb. It’s just that their prospects have dropped, as have their potential rewards. So most of the serious reinventors I spoke to have had to pick their poison—some have left town, the rest have scaled back in a big way.

Sobering? Yes. Depressing? Not really. You might think that reinvention, circa 2010, is just another word for “falling down the ladder,” but here’s the truly startling news: Many people I talked to professed to be happier now, and I believe them. A few seemed almost exhilarated to be forced to make changes they could never have brought themselves to contemplate until now. Even the miserable ones feel grateful to be much better off than they could be. “Not since I was pregnant was I so excited about the possibilities I could create for myself,” says Laurie McManus, referring to getting laid off from her executive assistant job in 2009. “Living in Novato and working in the city, I really didn’t know anyone in my own community. I’ve met more people and had more fun in the past nine months than in the previous nine years. I had the most beautiful garden in the neighborhood. It’s been one of the most wonderful periods of my life.”

It turns out the changes that go along with reinvention often feel less like downsizing than rightsizing. “We were living above our means,” admits Emily Dods, 31, who started Wholesome Hounds, a health-food company for dogs, after being laid off last year as a grant writer for a San Jose nonprofit. “We finally had to say, ‘Why are we doing this?’ ” She adds, “We’ve made huge changes, like moving in with my brother and his wife. It’s really been a way to build our marriage. Every single decision is, ‘Is this a need or a want?’ When it really comes down to it, that rule has given us abundance. Last year, we gave more to charity than we ever had. We’ve paid off every debt except student loans.”

Along with regaining control comes a new toughness. In this economy, people are learning important survival skills, the kind you don’t realize you need when you’re making $200,000 a year and can outsource much of your life. “Never before have we faced such times,” says Deborah Khoshaba, a resilience expert who codirects the Hardiness Institute and teaches at UC Irvine. “Today is calling for a new thing: It’s not quite resilience, it’s not quite optimism. It’s endurance. It’s just getting through this.” According to Khoshaba, self-expression—everything from making art and studying math to running marathons and learning to fly—is an essential element of endurance because it provides relief, something people need if they’re going to make it in the long run. What’s more, growing as people turns us into powerful teachers and role models. I think of the young reinventors who told me how impressed they have been to see their own parents making hard choices. “It’s so important for a child to learn the value of self-expression and how to use their own resources to reach fulfillment,” Khoshaba concurs. “That’s probably the most important step to building resiliency."

Civic Ventures’ Marc Freedman, who specializes in the big picture, sees another angle. He points out that what boomers are going through, often inspired by the entrepreneurial fearlessness of younger generations, is not just a vocational change but “a developmental shift”—a whole new stage of life that will replace retirement and extend for 15 or 20 years. “The arrival of the boomers at this shift gives it a size and scale that would not have happened otherwise, but they’re just the first,” he says. “It’s a permanent change. All other generations are going to have to go through it, too.”

Freedman lays out his own reinvention fantasy in Encore: Finding Work That Matters in the Second Half of Life, in which he calls on hordes of people in their 50s and 60s to reject traditional retirement and redirect their brainpower toward “encore” or “purpose” careers as educators, environmentalists, and social entrepreneurs. “If the same percentage of people who move to Sun City and Leisure World devoted that energy to work instead,” he says, “that would be 40 million people-years of a potential windfall for society.” And he has an idea about where boomers might start—by inventing new social pol­icies and structures to make this life stage easier for them and their children to nav­igate. His wish list includes new kinds of schools and education programs that take into account the special needs of people at midlife; mid­career internships, apprenticeships, and fellowships; something like a GI Bill for older people; and “individual purpose accounts,” instead of individual retirement accounts, that could be used to fund retraining. It’s a safe bet that Bay Area reinventors will be at the forefront of making those changes, social policy being one of our favorite paradigms to shift.

“A lot of these transition issues could be solved if we realized that it’s a social imperative, not an individual problem,” Freedman says. This may be the most important point. In the past, reinvention was personal, something we did more or less on our own. The Great Reinvention is altogether different: more like a social movement that hasn’t been recognized as such. This means that the masses of Bay Area residents who are being forced by circumstance—and potentially by choice—to reinvent have enormous power, if we can only figure out how best to channel all our energy and purpose. 

Here’s another safe guess: Reinventing our careers is just the start. The whole world is in a reinvention moment. With any luck, the lessons we’re learning now can help us make the most of it.

More from our reinventors (click to see profiles):

Gina Cassinelli

Jody Corcoran-Salem

Nina Martin is San Francisco’s articles editor. Additional reporting by Robin Wilkey.