How to Ditch the Endless Quest for Perfect and Find the Career -- and Life --That's Right for You


By Barbara Kelley

By Shannon Kelley

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In a world of unprecedented opportunity—and pressure—women are struggling more than ever to make career decisions and move forward without second-guessing themselves. Young women graduate from college and believe they have to find the perfect path and then can’t decide which way to go. 

Undecided is an invaluable guide to this cultural phenomenon of "analysis paralysis.” Looking at both what the media and academic studies have reported on women, careers, and particularly the undecided phenomenon—as well as personal accounts from numerous women—mother and daughter Barbara and Shannon Kelley discuss how we got to this frustrating place, why it affects women in particular, and how today’s culture fuels our fears and distractions. 

The Kelleys cast a critical eye upon the psychology behind the pressure to choose, and they argue that if women are going to succeed in rising above the often-crippling demands of the modern world they need to take action . . . starting with a serious shift in perspective.


We dedicate this book to anyone
who's ever made a decision for us.

The events, facts, and conversations presented in this book are true and based upon our own reporting and personal experiences. To protect the privacy of all the undecided women who so freely shared their stories with us, we have referred to them by fictional first names. In rare cases, we've also altered minor details.
References to "Shannon" and "Barbara" refer to the authors of this book.

'Would you tell me, please, which way I ought to go from here?' asked Alice. 'That depends a good deal on where you want to get to,' said the Cat.
—from Alice in Wonderland
AS GOOD IDEAS OFTEN ARE, this one was born of sweat and booze.
We began this trek on the Dipsea Trail, a notorious Northern California hike that starts in Mill Valley, a small town just past the Golden Gate Bridge. The trail begins with a wicked climb up 650 steps carved into a hillside and ends a brutal (and lovely) seven miles later (and after a 2,200-foot climb and descent) on the other side of Mount Tamalpais, at the tiny town of Stinson Beach on the coast of the Pacific Ocean.
We'd begun the day talking about a phenomenon we'd noticed again and again in women of the postfeminist generation—a general malaise with symptoms that are a combination of "analysis paralysis," "grass is greener" syndrome, and a sense that there are far too many choices to deal with. It was a mystery, yet it seemed an indisputable touchstone of the zeitgeist: women who, despite apparently having it all (good education, great job, cool place to live), are miserable. And for a reason they seem unable to quite put their finger on.
Sure, it could be easy to dismiss these ladies as spoiled. Here they have everything their mothers had ever dreamed of. And yet, the angst is real. And universal. These are women who were bred for success. And seem to be miserable because of it.
By the time we'd come down the mountain and crawled to the nearest bar to grab a beer (it was a sunny day in September, after all; it practically demanded an ice-cold Hefeweizen with a slice of lemon), we knew we wanted to explore this phenomenon. And later that night—as often happens when you combine an exhausting hike, iced knees, and a glass or two (okay, maybe three) of pinot noir—an idea took shape.
This mystery, let's investigate it. Talk to these women. Find the research. What are the causes? Is there a fix? We wanted to connect the dots. Get to the bottom of what seemed to be a generational epidemic of chronic indecision. And invite the reader along for the ride.
As backstory, Barbara had written a short op-ed on "choice overload" for the Christian Science Monitor a few months before, noting what she'd noticed in her students, her kids, their friends, and her friends' kids. The op-ed was picked up by her university's alumni magazine, and the response was overwhelming: "That's me!" "That's my daughter!"
But, Shannon insisted during that hike, just documenting the malaise in an eight-hundred-word editorial piece couldn't even scratch the surface. It's so juicy, she said. Let's dig deeper, lots deeper. Let's get to the bottom of it. And thus, Undecided was born.
And soon, it took on a life of its own.
And once it began taking shape, Shannon too found the response to be torrential. Her friends, their friends, near-strangers she'd meet at a party, would all pull her aside to confess: This thing you're talking about, this book you're writing. That's me!
We'd tapped a universal issue and we knew it. A few months later, we started our blog on the subject, and from day one were rewarded with comments—some funny, some heartfelt, all breathtakingly honest—from women throughout the country, weighing in on the ways in which they felt sabotaged, by everything from the opportunities (and mirages) of a postfeminist society to their own expectations.
Once we started our trip, our investigation took several routes. The first was shared experience: We talked to hundreds of women—Millennials, Gen-Xers, Baby Boomers—across the country and listened to their stories. We dug into the research to understand what goes on in our brains when we try to choose between Door No. 1 and Door No. 2—and why no matter what we choose, we're often dissatisfied. We explored the very nature of happiness, and why it can be so elusive. We explored why it is we sometimes find ourselves caught up in the chase for the symbols of someone else's definition of success. We talked to the experts, both the folks in the trenches and academics, too: men and women who could explain some of the issues—societal and otherwise—that underlie our dissatisfaction, and who could offer insight, perspective, even solutions.
We thought deeply (okay, and argued, too) about the weight of great expectations, the insidious lie of "having it all," and the illusion of unlimited options on women who had not yet learned to deal with them.
What we found were growing pains: It may be great to have options, but until we learn how to deal with them, life can be a bitch.
We also found prescriptives, including the route to the simplest and yet most profound remedy of them all: Know yourself.
Along the way, we came across a couple of media firestorms—an idea that if women were unhappy, well, feminism was to blame. What we found was that if anything, feminism hasn't gone far enough: We're living in an unchanged world whose reality turns out to be a far cry from the messaging we're fed. (We'll go there.)
New research also surfaced, implying that twentysomethings are in the throes of a new stage of development. Dubbed "emerging adulthood," it's marked by a reluctance to commit. While there is some credence to that (we'll go there too), we think the root of all this angst goes way deeper.
We also were asked, more times than we can count, why this dissatisfaction, this indecision, was a woman's issue. Weren't young men equally undecided, dissatisfied? Equally stressed out? Why women? To which we answered: It's generational. Men have been raised for generations to go, seek and conquer; to succeed in a workplace designed expressly by and for them. For women, there's a layer of newness to it all: We're going forth without either a net or enough role models to pave the way. Sure, men can be equally angsty in the face of choices, and we appreciate that, but for women, this angst, this indecision, this trial and error is a product of less than fifty years of progress. It's uncharted territory. (Don't believe us? Ask your mother. Or your grandmother.) We're hacking our way through a landscape that proves, time and again, that the reality doesn't quite measure up to the rose-colored image we expect.
In fact, because this is a generational issue, we think that our collaboration on this book (with all the discussions, arguments, and attempts to see things through each other's eyes) results in a more complete picture. You, dear reader, are not getting one perspective or the other, but rather a shared perspective that offers a deeper, richer, and more textured analysis than either one of us could have offered on our own.
Which brings us to some questions we've been asked, over and over: "What's it like for a mother and daughter to work together? And who's the boss?"
To which we would have to say, you know, we're undecided.

Simplicity is making the journey of this life with just enough baggage.
—Charles Dudley Warner

You take your life in your own hands, and what happens?
A terrible thing: No one to blame.
—Erica Jong
WHEN WE FIRST CATCH UP WITH thirty-year-old Hannah—a pint-sized blond with intense eyes and a wide smile—she's at home in her New York City apartment, studying for the GRE, the generic entrance exam for graduate school. This would be unremarkable except for the fact that until a week and a half ago, she was studying for the GMAT, the specific entrance exam for business school. In fact, she went through the entire Kaplan GMAT prep course—which she decided to do after initially signing up for the Kaplan GRE prep course in the hopes of earning a Master of Public Administration (MPA) degree ... and then, two classes into it, changing her mind.
Confused? So is she.
After this last and hopefully final change of heart, she is now planning, once again, to earn an MPA, and to then parlay that degree into a job in ecotourism, voluntourism, or a cultural exchange program like Unesco because, she says, travel is all she's ever wanted to do—especially after spending her entire junior year of college abroad. But back then, she says, "I didn't think there was any possible way that it could be a career, that I could travel for my whole life. My parents are conservative; me and my sister were raised, like, you find a good job—you have one job after college, and that's all you do."
So, convinced that a career in travel was too pie-in-the-sky, she pursued a career in fashion (itself pretty lofty) with single-minded focus: while still an undergrad at UCLA, she cold-called Hollywood stylists and other industry players and eventually scored internships at Hugo Boss and Saks Fifth Avenue, as well as a job with a stylist for the MTV Movie Awards. After college, she moved to New York; a few years later, she was an assistant market editor at Vogue.
She was no doubt living out the very fantasy that countless other girls had deemed too pie-in-the-sky—and the sort of American Dream her parents may have been chasing when they immigrated to the United States from Slovakia when she was six. Yet before long, she found herself a little antsy, a little bored, a little distracted by what she wasn't doing. So she took a different position—as associate fashion editor—where she was fulfilled both in terms of creative expression and in terms of travel, producing six-figure photo shoots in far-flung destinations, dressing the likes of George Clooney, Jennifer Aniston, and Kate Hudson. She also found fulfillment in getting her fashion fix—she was granted access to the iconic "clothes closet," where designer duds were hers for the borrowing. (Swoon.) Even her anal-retentive side was fulfilled by the huge amount of organization required to pull off such large-scale spectacles.
It was almost perfect.
So she quit.
Thinking she should maybe explore the business side of the industry, she took a job as a buyer at Bergdorf Goodman. Hated it.
"I lasted six weeks before I quit," she says with a rueful laugh.
But Elle was hiring and offered her a market editor position. "So I went back to editorial work, thinking I would like it more because it was a different position than I had at Vogue. I thought I would like it, and I kind of did, but the work environment was awful ... the infrastructure wasn't what I was used to after being at Vogue."
Unfortunately—or, to hear her tell it today, fortunately—she became a casualty of a restructuring not long after taking the job.
"I was laid off and I didn't care," she says. "I packed my bags and left for Asia for four months.... When I left, I was like, I don't want to go back into fashion, I don't like the industry, I don't like the players, it's not fulfilling enough. I was very much wondering, what's on the other side of the fence? So when I went to Asia, I didn't even think about it. I just knew that I loved traveling more than anything on the planet."
Case closed, right? Hardly.
Immediately upon her return, she started to panic about being unemployed, so she put out her feelers. Not surprisingly, after having spent her entire career in the fashion industry, those feelers snagged her yet another job in the world of high fashion, this time at the label Theory—where she was again laid off, five days shy of her thirtieth birthday.
And that brings us to her plans to take the GRE, apply to grad school, earn an MPA, and, at long last, find a way to make travel a part—a big part—of her career.
Yet despite the fact that travel is her passion and she's come up with a coherent vision for a career in the travel industry, she continues to second-guess herself. "I was back and forth between an MPA and an MBA for weeks," Hannah moans.
She started out on the path to the MPA and the life she'd always dreamed about, signing up for Kaplan's GRE prep course. She stuck with it for two classes. And then she panicked.
"I got nervous that I made the wrong decision," she says. "So I emailed a girlfriend of mine who worked in finance and said to her, 'Oh my god, I don't know what to do, MBA or MPA.' And she said MBA. Why I listened to her I have no idea. She's not me; I don't want to be in that world; it's just not my environment. But I went to Kaplan and changed to the GMAT prep course. And then I went all the way through the class and went so far as to sign up for the GMAT. And then, about a week and a half ago, I changed my mind. I thought, what am I doing? I don't want to be doing this. And now I'm taking the GRE; I'm studying for it now."
Hannah talks as quickly as she changes direction. She's clearly smart, motivated, and successful. She's also thoughtful, reflective, and completely convinced that there's something seriously wrong with her. She peppers her story with self-lamentations and analyses: "Why am I like this?" "I don't know what my problem is." "I have a tendency to leap before I look." "I am a walking contradiction."
"The grass is always greener," she says. "Like, do I want to move to San Francisco? Colorado? South America? Will life be any better in any of those places? Probably not. But it might be, so there's that risk that I'm taking by not moving." And something in her tone suggests that she's not simply throwing out random examples. In fact, it sounds as though, just by putting voice to the options, she might be convincing herself that these are other avenues that she needs to explore. Like, right now.
It's that fear of missing out that's the killer. "My biggest problem is I don't want to not do something.... I need to do everything," she says. "It's just having so many options, and wanting to do all of them. And feeling like I can and I should and I will do everything that has been afforded to me."
It's a sentiment that's easy to relate to. So much so, in fact, that it's easy to forget that this woman was working at Vogue, literally putting clothes on the back of George Clooney. She was living the dream, excelling at the career she'd fought for, the proverbial job a million girls would kill for. Hannah had it all—and it was exactly what she'd always wanted—or what she thought she did. But contentment eluded her. Those doubts, those frustrations—they nagged at her. They still do.
COMMITMENT PHOBIA. ANALYSIS paralysis. Grass-is-greener syndrome. You name it, Hannah's plagued by it. But she's not alone. Far from it. She's a poster girl for the current zeitgeist: Unlike her mother, she was born of a generation blessed with limitless choices—and of a generation that has found that the more choices you have, the harder it is to find happiness. It's a generation that appears to have everything yet can't help feeling that things are just not right.
You might call it an epidemic, a sign of the times for American women. Take Sarah, for example, a twenty-nine-year-old lawyer making well into the six figures only a few years out of law school. She wants only one thing: sweet escape from practicing law. Ask her about it, and she'll claim to have no idea why she ever even applied to law school in the first place—indeed, that she never really wanted to be a lawyer. And yet apply she did, and she found herself at a second-tier law school. She ranked in the top ten of her class, making the law review and ultimately scoring a gig with a big high-end law firm—quite a coup, as very few firms bother recruiting at law schools below the first tier. She's made a huge amount of money from the start but has never liked what she does—has actually pretty thoroughly hated much of the work, spending a significant chunk of her time keeping her fingers crossed that she'll never have to go into court. Raised in California by parents who vacationed at their wine country ranch and vineyard, what Sarah really wants to do is open a wine bar. Her fondest hope is to get laid off—with a severance package, of course.
And then there's Jane, twenty-seven. Worried that only "perfect" will do, she has yet to commit to anything other than a series of uninspiring jobs since graduating from college. This is not for lack of trying, however. Over the years, she's spent lots of time investigating possible careers and grad schools. She took a summer course in the business school at Stanford and conducted countless "informational interviews" with people who seem happy in their careers, gathering information from journalists, lawyers, and entrepreneurs so that she'd be armed to make an informed decision. Perhaps too informed.
As Malcolm Gladwell explained in his book Blink, "too much information" isn't just a clever expression—the best decisions are often the ones made before giving yourself too much time to think.1 And he's not the only one to have found that a clogged mind is a confused mind: The classic 1950s "Magical Number Seven" study showed that the human brain can hold seven bits of information in working memory at any given time.2 Any more, and things can get dicey.
We'll get deeper into the science of decision making in Chapter 5, but here's a taste: In another study, participants were asked to memorize either seven digits or two; then they were offered their choice of a snack—fruit or "gooey chocolate cake." And guess what happened? Those whose brains were maxed out with seven numbers let the emotional side of their brains do the deciding and overwhelmingly chose cake. But the two-digit folks had some room for reason: They chose fruit.3 So basically, when the brain is cluttered with too much information, emotions drive our choices. Ergo, the bigger the cognitive load we're carrying at any given time, the less able we are to think rationally.
As for Jane, she continued to bounce. She applied to business school. She applied to law school. She didn't get in on one count; decided not to go on the other. So overwhelmed by the choices that confronted her, she once confided that she wished she had grown up in a culture where everything, from spouse to career, would be chosen for her.
And then there's Melissa, thirty-eight, who took on whatever was asked of her at a string of jobs, ascending into the upper echelons of project management at large companies ranging from HBO to Microsoft. She recently went back to school to pursue her passion, earning a master's in counseling. She splits her time between several different centers and the local hospital, ferociously logging the hours required for her certificate. But once she gets it, she has no idea what she'll do with it. Private practice? Take it back to corporate America? She doesn't know and often worries that this detour into work she clearly loves is steering her away from work society tells her she is supposed to do, thereby knocking her out of competition for anything but mediocrity. "I just feel like I should be more ... successful," she says. It's as though she fears she can't have both—her passion and success—making the choice to change directions in pursuit of her passion all the more terrifying.
WHAT IS THE matter with these women?
They should be stoked. But instead they're stressed. Restless. Stuck in a cycle where they're constantly second-guessing themselves and looking over their shoulders. And they can't quite figure out why.
Their mothers are left scratching their heads, wondering what's with their daughters, who have more options than they ever dreamed possible. Said Sharon, a sixty-something mother who came of age during the opening strains of the women's movement: "When I was your age, women had three options: teacher, secretary, nurse. You don't know how lucky you are!"
Indeed, for the first time for American women, most all of the doors are open. In fact, the landscape of today would be scarcely recognizable to the feminists of the second wave. In a post-postfeminist, post–Sex & the City, post-Facebook world, recent years have seen us riding an unprecedented economic rollercoaster against the background of some amazing firsts: The first female presidential candidate. The first female speaker of the house. The first female vice-presidential candidate on the Republican ticket. And, whether it's because of the tanking economy (and the fact that more men than women lost their jobs, a phenomenon dubbed the "mancession") or because of life itself, women now make up more than half of the workforce. And yet what we see is that increased options go hand in hand with increased angst.
Take Lauren—a writer, editor, and reader of our blog—who left this comment: "Yes, I swim in a sea of confusion over my options! Being a woman who feels she is unlimited, I've spent too much time debating my opportunities instead of picking one path and sticking with it. I can't complain; life has been good. I do, however, feel concern that I might be overlooking the one thing that is my 'calling.' From orchestra conductor to herpetologist to cartographer to photographer to writer, I've wanted to do it all. I also know that I can; we all can."
Or this one, from Melissa: "My sister used to tease me that I was on the semester system in life because I was always moving and changing jobs. But really I was just worried that I was missing my 'true calling' or not doing enough to fulfill my parents' expectations after all that schooling. (Come to find out later that their only expectation was that I be happy.) Now I'm almost forty and starting yet another new career (this one will be the one ... I hope). Looking back, I can see how the choices and self-inflicted expectations led to a major paralysis in my midtwenties."
It's like the dirty little secret that nobody's talking about, but everybody's keeping. Call it one big growth spurt, with much of this unspoken angst revolving around the pressure to choose, something oldschool feminists might never have predicted.
Slowly, allusions to this syndrome are starting to emerge. There's this commentary on an item from an online installation from the International Museum of Women: "The wide variety of opportunities available to young women today is liberating for some, but for others it can be a source of confusion.... With so many different opportunities and life paths to choose from, how do you know which is right for you?"4 Or this, from a Salon post about Rachel Lehmann-Haupt's book In Her Own Sweet Time: "The downside of having too many choices, it seems to me, is that it can make it hard to know when the time has come to choose just one."5 Or this, from the recent best-selling novel Commencement, in which one character sums it up tidily: "They were the first generation of women whose struggle with choice had nothing to do with getting it and everything to do with having too much of it—there were so many options that it felt impossible and exhausting to pick the right ones."6
And that angst is only magnified because these feelings are so at odds with the conventional wisdom with which today's young women were raised: All these choices—what a blessing! You can be anything you want! You can do anything you want! You don't know how lucky you are to live in an era marked by the number of open doors you have before you!
You. Can. Have. It. All.
But, given that mantra, is it any wonder we can't commit? That, as Chloe, a thirty-one-year-old art director at an alt-newsweekly put it, "For our generation, commitment is like a kind of death"? Could this be why the average tenure of college-educated women between the ages of twenty-five and thirty-four in any one job is only 2.6 years, according to the U.S. Bureau of Labor Statistics?7 Or why a recent Pew Research survey found that 65 percent of women classify themselves as "movers" rather than "stayers," and 45 percent of those who have moved say they will move again?8
We've learned not to settle. After all, thanks to feminism's successes, thanks to the women who gave voice to their dissatisfaction and drove the changes of the first and the second waves, women today are free—no, encouraged—no, expected—to seek out "better." Which is great ... mostly. But the lure of "better," the implicit promise of "better"—well, that's where it gets tricky.
Neither does it help that, while we've been stuck in neutral, stunned in the face of so many options—much like the kid cut loose in the candy store—an idea started to gain traction: A job ceased to be just a job; now it had to have meaning, too.
A ho-hum nine-to-fiver that reliably pays the bills? You can do better than that! Find your true calling—only then will you know bliss! Living your truth will bring you success!
Call it the spiritualization of the career world. And the influences driving this frantic search for meaning are everywhere, from President Obama—who has called on youth to engage with the community—to the growing number of university initiatives that encourage (and in many cases, require) students to participate in community-based learning programs and to consider careers in public service after they graduate in order to foster a spirit of "giving back." The message is that


On Sale
Apr 26, 2011
Page Count
288 pages
Seal Press

Barbara Kelley

About the Author

Barbara Kelley has been a journalist for more than 25 years and a professor of journalism at Santa Clara University since 1997. She earned her master’s degree in print journalism from Stanford. Barbara has written for publications including the Christian Science Monitor, the San Francisco Chronicle, the Los Angeles Times, Parenting, Redbook, Salon, and Bay Area Parent, where she served as features editor and writer and won two national awards. Barbara is married to her college sweetheart and is the mother of two daughters, Colleen and Shannon.

Shannon Kelley is a columnist at the Santa Barbara Independent, a freelance writer and photographer, and a corporate consultant. Her freelance work has appeared in the Christian Science Monitor, Woman’s Day, The Arizona Republic, Relevant Magazine, and Santa Barbara Magazine, and her essay “Something Worth Saving” from the anthology Submerged was nominated for a Pushcart Prize.

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