Bossed Up

Introduction

Confessions of a Recovering Hot Mess

Confession: I’m a recovering hot mess.

It really began in college, where I operated more like a hurricane than a human being—I tore through my academic career with a voracious appetite for achievement, unbridled ambition, and a complete disdain for rest. When I wasn’t in class or writing papers, I was at volleyball practice, working on the student newspaper, or volunteering for political campaigns. Hurricane Emilie, coming through. It wasn’t uncommon for me to actually say, “I’ll sleep when I’m dead,” about my frequent all-nighters, whether they were for work or fun.

This, I was sure, was what success felt like.

And my report card confirmed it. Like so many young women, I had become quite adept at figuring out what my professors were looking for, putting my nose to the grindstone, and delivering it.

Perfecting, performing, pleasing. These are the skills I refined in school, and these were the skills for which I was rewarded. From gold stars in kindergarten to my grade point average in college, I graduated feeling like I had it all figured out. Give me a syllabus for life, and I was certain I could succeed.

Unfortunately, that’s not how life after college works. Imagine my surprise when “real” life actually began.

Like so many millennials, I had the audacity to graduate right into the Great Recession. As anyone whose early career included navigating a recession-riddled job market knows, I was told I’d be lucky to find any work at all.

So you can imagine how fortunate I felt after a few months of boredom at a lackluster (but paid!) political internship in Washington, DC, when I was given the opportunity to take a leadership position as one of fifty state directors of Organizing for America, formed by then–newly elected President Barack Obama. OFA was the first-of-its-kind continuation of a presidential campaign that would serve as a grassroots arm of the administration and work to help pass a variety of policy reforms during the president’s tenure.

All that hustle had paid off, I thought.

I hit the ground running and built an organization from the ground up, eventually recruiting, training, and managing more than two hundred volunteers across the state of Rhode Island, who took charge of organizing their communities, hosting phone banks and voter drives, and pushing elected officials to pass the president’s policy initiatives, including the health-care reform legislation that would later afford me the freedom to start my own business.

Fast-forward a few years. The way I was working, well… it wasn’t working.

Being busy had long been a badge of honor I was proud to wear, but I’d finally arrived at the point of diminishing returns. I was reminded of that old economic principle when I finally realized that no matter how hard I worked or how many hours I put in, my to-do list was ever expanding. Chronic overwork left me depleted, exhausted, cynical, and on the brink of burning out.

I was in the office until 9 p.m. or later most nights and habitually worked right through my lunch breaks. I started my days by bolting upright in bed in a panic, my work phone and personal phone in hand before my feet hit the floor, and ended them at political events or networking happy hours (more often they were one and the same). I was in a frazzled frenzy of trying to prove myself worthy of the opportunity I’d been given.

Ironically, I was working myself to the bone even without the direct, in-person supervision of any fellow staff in the state. As a single-staff state director, I had a level of autonomy enviable for many of my fellow recent grads, which was great, except I didn’t use that power to set myself up for long-term success. Instead, I ran myself ragged, while joking that I was fortunate to be my own boss at such a young age but that “I was a bitch to work for.” Oof.

Contributing to my misery was the fact that I’d gone from being a college athlete to having no real fitness in my life at all—for nearly three years. I bristled at my annual checkup when my doctor asked what I was doing in terms of exercise and my answer was walking my dog sometimes.

Worse yet, I used to tell myself—at least during the most intense months of campaign season—I was “skinny” because I couldn’t find time for lunch. I remember, sitting around a health-care policy-makers’ table in 2012 joking with two lobbyists that, hey, at least we got some protein in our breakfast from the soy milk in our coffee. Hilarious.

During this time, my once-close friendships took a hit, too. I rarely put in the effort necessary to keep key friendships with my college besties and childhood friends alive. I genuinely didn’t think it was a big deal that I felt isolated and alone most days, and told myself that I was making sacrifices for a job I loved.

All this was complicated by the fact that I felt stuck in a completely toxic relationship. When I stepped up into the state director role with OFA, I’d just moved in with my boyfriend of a year, a fellow politico ten years my senior, who I’d met on the campaign trail in college. He was elected to local office, a passionate advocate for working people working on behalf of many social justice issues I believed in. He was smart and hardworking, and he also happened to be an alcoholic. The former impressed me instantly. The latter took me quite a bit longer to pick up on, and, once I did, I had no idea how to handle it (somehow addiction wasn’t a topic covered in all my years of formal education).

Everyone has their breaking point. Mine happened one day as I was driving through my alma mater’s campus in the fall of 2012. My organizing work often brought me back to the charming East Side of Providence, at Brown, where I’d just spent four years studying political science, getting my education. I was stopped at a red light while racing between events, bone tired and slumped over my steering wheel. It had been a particularly crazy day, and I found myself wondering how the hell I’d gotten here. Just a few years ago I was one of those students on the other side of my windshield. I was someone who used to feel in control of life. This was decidedly not the life I’d imagined for myself, and, though I was proud of the work I was doing, I felt misaligned and out of sync.

I watched as college students saddled with heavy backpacks crossed Thayer Street in the crosswalk before me. Sure, they looked pretty beleaguered too, but they were heading home for Thanksgiving break. As they rolled their bags across the street to the airport shuttle, I desperately wished I could trade places with them. I thought, “I’ll gladly tackle your finals if you figure out my life for me.”

In that moment it dawned on me: I was waiting for an end of the semester that would never arrive. I wanted permission to head home for a week and put my feet up on Mom and Dad’s couch. Those same skills that got me so far academically—perfecting, performing, and pleasing—had set me up for a spectacular burnout.

This was depressing, sure, but I also started to feel bad for feeling sad. I felt guilty for wanting more when so many others had less. I thought of all the privilege I had going for me, all the opportunities I’d been given. My problems paled in comparison to those of the people on whose behalf I was fighting each day. So what the hell was my problem?

I just needed to suck it up. Do my job. Push through. Keep my nose to the grindstone, and surely I’d be rewarded, right? That’s what I’d always done before, but, this time, it wasn’t working. I was working hard but didn’t know what I was working toward. I wasn’t sure what I wanted my life to look like, and I sure as hell didn’t know how to go about advocating for it.

As I sat there at the crosswalk, tears of frustration started rolling down my cheeks. I was tired of being tired. I was sick of feeling like I was in the passenger seat of my life, just watching the world pass me by. I was done waiting for permission to start living a life that made me happy. It was time to stop looking for “the right answers” and start figuring out what felt right for me.

As this fire rose up in me, I also realized that if I want to be in this fight for the long haul—if I want a career with real and lasting impact—the way I was working was unsustainable. I felt like I was just barely making it through each week, hardly keeping my head above water. I was going to have to stop sprinting through life and start training for my career like a marathon. And no one else could—or would—steer my life for me.

Sitting there in the driver’s seat, I straightened up. Dried my eyes. The light turned green. I drove off feeling an unfamiliar sense of presence behind the steering wheel. I no longer wanted to be that harried, self-deprecating Hurricane Emilie. A calm confidence started to wash over me, and the cityscape outside seemed to move by my window more slowly.

This was the beginning of a rocky two-year journey full of reading, reflection, research, and experimentation to figure out how to own my power and step up as the boss of my own life—without apology.

My story is hardly unique. Along the way, I learned that so many of us are suffering in silence, feeling like we’re stuck playing a supporting role in our own life story. So many of us feel like life is happening to us instead of the other way around. Many of us feel like we have no choice, no power, and no options when it comes to how we steer our lives forward. Or perhaps we find ourselves achieving hollow success, still unsatisfied when we get what we thought we should want only to find out it’s not all it was cracked up to be.

And when our personal lives get in the way of our professional ambitions, we feel guilty and worry whether the two should intersect at all (spoiler alert: they always do). Exhausted, we might find ourselves asking, When is it time to stop achieving just for the sake of achieving and start designing the life we would love to live for ourselves?

I witnessed so many of my friends struggle through those internal conflicts, but my fellow young women seemed hobbled by hesitation in a way my male peers just… weren’t. As much as we may hate to admit it, there’s a sort of appeal to being a hot mess. I caught myself being especially demure and self-deprecating around prospective romantic partners, downplaying my achievements and ambition and playing up my overwhelm. The flustered young lady is often depicted as cute, loveable, and attractive to a suitor waiting in the wings to play the role of Knight in Shining Armor. This is something that is deeply ingrained in our culture and took me years to unpack (and, yes, we’ll be talking about it much more in the chapters ahead).

But if you’re a flustered young guy? The attitude is, well, you should get your shit together, bro.

This double standard is constricting for all of us. Men should be able to feel lost and unsure without reproach. And women should be able to own our lives with unapologetic swagger without being seen as bossy or braggy.

But here’s the truth: It’s hard to get out of the habit of living the hot mess lifestyle. It’s not easy to assert control in your life, get out of the cycle of burnout, and aim for a more sustainable success instead.

We have to put our own oxygen masks on first so we’re better able to help others—and because we deserve some fucking oxygen, too!

The basic principles behind self-care shouldn’t be radical, but they are—now more than ever. Investing in your personal sustainability is an especially subversive act for women, who have long been lauded as the martyrs of the family.

In a world that’s always placing more demands on our time and attention, the pursuit of sustainable success is the fight to actually use the power previous generations of feminists secured for us. From Rosie the Riveter to those shoulder-pad-wearing glass-ceiling shatterers of the 1980s, our foremothers paved the way to provide our generation with unprecedented choices. But that doesn’t mean choosing how to design our lives is easy. We no longer have to follow the prescriptive path for success so narrowly defined by the man’s world we lived in up until very recently. Now it’s on us to mindfully design the lives and careers we would love—and do the work of advocating on our own behalf to make them a reality.

When I stopped my car at that crosswalk, my life was at a crossroads, too. I’d been waiting for permission to start reshaping my life and career, and for whatever reason seeing those students solidified my realization that it was time to make some big changes. I began asking for help (starting with my primary-care physician, who gave me tons of insight into what addiction really was and got me into the office of a very capable therapist). I began clarifying my vision for my life—and what aspects of that vision I wasn’t willing to compromise on.

Eventually I summoned the courage to leave that relationship, which had become increasingly abusive. I spent nearly six months couch-surfing with friends while I worked to get out of the lease I had with my ex. In the meantime, I found an incredible new job at a political strategy firm focused on digital media that would take me back to DC, the city I’d always wanted to call home.

I racked up about $6,000 in breakup debt (which is a very real thing we should talk about more), but it was all worth it. I moved into a one-bedroom basement apartment with not much more than my dog, a coffee table, and a mattress on the floor. Despite being in a fragile state, I felt happier than I had in years. The feeling of the blank slate before me was thrilling. I was ready to rebuild my life, on my own terms.

As I started down the road to rebuilding the career and life I wanted, I heard from so many others who were navigating life’s inevitable rocky transitions, too. It felt good to know I wasn’t alone and that, in fact, so many of us women struggle to claim our power to design the life we want for ourselves from the get-go. All the reading, research, talking, and experimentation I did over the course of those tumultuous years led me to start Bossed Up, an organization that helps other women break the cycle of burnout and craft a happy, healthy, and sustainable career path on their own terms.

Now, almost six years later, hundreds of thousands of women across the world have attended our trainings in person, listened to my biweekly podcast, or accessed our free online resources to learn new ways to own their power and step up as the boss of their lives and careers. This book is an extension of that work, and I’m so thrilled to finally share it with you.

This book is for the recovering hot mess who, like me, finally reached a breaking point and is ready to step up as the boss of her life. This is for the wanderer who’s feeling stuck and is looking to clarify her purpose and gain new tools for making it a reality. This is for the burned-out overachiever who’s realized it’s time to stop performing for everyone else and start designing a life that will keep her sustained and satisfied for the long haul. It’s for the boss who’s always one step ahead, looking to gain new strategies for next-level, long-term success. And, yes, this book is for anyone feeling isolated and alone while facing major life changes.

You are not alone. Although I believe in the power of taking personal responsibility for your choices, you don’t get to a life you love any faster by going it alone. We all need a squad of support to get us through life’s tribulations and triumphs without losing our sense of self. And there’s no need to expend energy seeing each other as competition. Bossed up women lift as we climb, bringing those behind us up the ladder of success with us.

Getting bossed up is about owning your power, knowing your worth, and designing your career and life accordingly. In the pages ahead I’ll walk through how to ditch the martyrdom mindset that holds so many women back, and I’ll unpack the steps to cultivate a boss identity and see yourself as the leader you’ve been waiting for. I’ll dive deep into three core skills needed to pursue sustainable success: honing your assertive communication, cultivating resilience, and managing multiple long-term goals. Finally, I’ll get into building a community of courage to turn to when you’re navigating big life transitions.

You’ll hear more about my life and career along the way, too, but that’s certainly not the focus of this story, because the concept of getting bossed up is so much bigger than my company and me. For starters, the term “bossed up” is from hip-hop, an art form I’ve loved since I got my hands on my first Tribe Called Quest CD in high school. As a white girl growing up in suburban Connecticut, I was lucky enough to be raised by a dad who considered it part of his parental duties to give me a musical education that included everything from Beethoven and the Beatles to the Wu Tang Clan and Beastie Boys (thanks, Dad!).

So when I started to take my power into my own hands, it’s no surprise that hip-hop was there to encourage me each and every step of the way. After all, if anyone knows about rising up in the face of injustice and hardship, it’s black America. I think that’s part of the reason why hip-hop culture has gone so mainstream—it’s telling the modern-day version of the American dream.

We all bring different privileges, challenges, and perspectives to the table, and I always strive to bring an intersectional approach to how I think about those differences. In each chapter ahead, you’ll see a few spotlight stories that chronicle the real-life experiences of women in the Bossed Up community. I’ve had the honor of working directly with each of them at our flagship weekend-long training, Bossed Up Bootcamp, and have kept in touch over the years to watch them bounce back from burnout, rise in their careers, and assertively craft fulfilling lives, too.

These women come from all walks of life, different parts of the country, various industries, and diverse backgrounds. It’s my hope that these real-life narratives help illustrate the principles covered in each chapter and inspire you to recognize that no matter where we come from, we all want the same thing: a happy, healthy, and sustainable life.

I hope you’ll add your story to the chorus of women who’ve learned to own their voice and take charge of their lives, too. Join our free online accountability community now at www.bossedup.com and weigh in as you read this book to share what you’re working toward and how you’re stepping up as the boss of your life to make it happen. I can’t wait to hear from you.

Alright, let’s get bossin’!