Raise your hand if you’ve ever turned to a trusted mentor and asked something along the lines of, “How can I be you by the time I’m 35?” It’s a well-intentioned question, certainly, but it doesn’t really serve our best interests. To ask for someone else’s highly specific blueprint on how they got to where they are is not only limiting, but it may yield such dated advice that it’s actually irrelevant to the current landscape. If your goal is to follow someone else’s playbook, you may miss out on (and close yourself off to) unexpected opportunities.
Alyssa Mastromonaco, who’s lived many illustrious lives over her professional career (so far)—working on two presidential campaigns, serving as the Deputy Chief of Staff to President Obama, and heading up operations at Vice and global communication at A+E—explores just that in her new book,So Here’s The Thing… Notes on Growing Up, Getting Older, and Trusting Your Gut (on sale March 5). Ahead, an excerpt that will make your rethink that most basic of mentorship questions.
What are gut feelings, and how do you use them? We all want to know the secret to success, and we all want the secret to be “It’s really easy, actually.” So when we see someone we consider successful, we immediately think they can tell us the one easy trick to become successful ourselves. But the truth is it’s very hard. Or at least it was for me. Too often, advice is understood to mean “telling other people what to do.” But beyond “life hacks,” good advice is entirely situational. Don’t get me wrong—I love a good hack. (The thing Sophia Amoruso says about wearing a tampon when you go commando—life-changing.) But you can’t hack your way to a fulfilling career.
Nevertheless, as my career has developed and become more “public-facing,” young people approach me asking for advice. The way they phrase it is usually something like: “I want to be you by the time I’m thirty-five.”
I’m sorry—I know it’s well-meaning. But “I want to be by the time I’m thirty-five” is the worst way to approach your life ever. I would not have been me by the time I was thirty-five if I hadn’t been open to random opportunities that presented themselves unexpectedly. I would not have been me by the time I was thirty-five if I had a list of characteristics and accomplishments that I thought defined who “me” was.
The message I wanted to get across in Who Thought This Was a Good Idea? was that there’s no path, and even if there were, you certainly don’t have to follow it. To me, an instinct is a good way to balance what you need to do with what you want to do. You may feel pulled in one direction or another, but deep down you know what’s right. When you have to consider both your dreams and your nightmares, your passion and practicality, practicality usually wins out, until it doesn’t have to anymore.
No one can do what I did by being safe, and you can only take risks if you’re relatively financially independent. Every component of good decision making—risk taking, trusting your gut, setting priorities—is contingent on your ability to take care of yourself. Even if we look at industries we think have clear, step-by-step procedures for reaching a senior position—investment banking, say—women rarely have opportunities to make it that far. Women are 18 percent less likely than men to get a promotion to management level, and from there their numbers in senior positions drop.
This is scary, but it’s also exciting. You can’t figure out how to get where you want to go without first figuring out where that is. “Success” is not a place. “Success” is everywhere and nowhere at once. It means wildly different things to different people.
Here is my trajectory, in more or less chronological order from around age fourteen, for proof: Babysitter; bagger at Kilmer’s IGA; cashier at Del’s Dairy Cream; cleaner at the Beekman Arms hotel; hostess at the Beekman Tavern; babysitter; unpaid intern for Rep. Bernie Sanders; hostess again; audio transcriber for Ed Garvey, a progressive icon who unionized the NFL; babysitter; congressional intern for Rep. Bernie Sanders; babysitter again; real estate paralegal; secretary at Merrill Lynch (for five days); assistant at a very random start-up company; client relations person at Sotheby’s; all-around staff assistant for John Kerry; babysitter; associate at a Republican lobbying firm (I can explain!); press secretary for Democratic congressman Rick Boucher (from Virginia’s Fighting Ninth!); director of scheduling on John Kerry’s presidential campaign; adviser (and then political director) to Senator Barack Obama; lots more with Obama; deputy White House chief of staff for Obama; chief operating officer at Vice Media; New York Times–bestselling author; president of global communications for A+E Network; podcast host; and now . . . TBD.
I don’t think anyone would be able to make the connection between bagger at the grocery store and assistant to the president of the United States. But a lot of the skills and behaviors I developed doing odd jobs and grunt work have been useful. What will probably help regardless of your age and desired career: diligence, humility, and perspective. In every job, I tried to keep my head down, do good work, and own up to mistakes when I made them. I learned that not because someone had to tell me—doesn’t it seem a little obvious to see it written down?—but because all the people I admired worked in the same way. For all his rhetorical genius and charisma, Barack Obama wasn’t showy; he wasn’t constantly calibrating how an action would or would not make him appear. The same was true of all my previous bosses and mentors.
Of course mentors are wonderful. What I’m saying is that you shouldn’t be emulating them; you should be learning from them, taking what they can teach you, and applying it to your own life. Because not only are people different (duh), but the world changes rapidly, so what worked for me as a twenty-six-year-old in 2002 is not going to work the same for you as a twenty-six-year-old in 2019. For the first many years of my work life—note that this is different from “career”—offices were hierarchies. Lunch was never free, and neither was the coffee.
If you had an office, you were important. If you had a big office, you were even more important. And if you lived in a cubicle, your cube-mates were your only peers. I spoke freely to my cube-family, but in the hallways, when passing partners or other senior-level people, I didn’t strike up a conversation or ask about the weather—I cheerfully said “Hello, Mr./Mrs. Whatever!” Yes—I only called them by their first names once they said it was OK.
In some ways, it was very restrictive. The boss could torture you with whatever he—and it was always a he— wanted. But in other ways at least you knew what the fuck was up—what the power structure was, whom you needed to impress (or at least pretend to be interested in). Back then, the path to promotion was very clear, and while it wasn’t kind to women, you knew what all your bosses had done to get where they were. In a post-corporate era, things can be tricky; when offices are open concept and leadership can be murky, it makes collaboration more fluid and easier, but it’s also hard to figure out what you need to do to get to the next level. Or what you need to do to avoid offending your coworkers. When I worked at Vice— which is famously “non-traditional”—if someone called me Ms. Mastromonaco I would have wondered if they needed to see a doctor. That’s not necessarily fair—there shouldn’t be anything wrong with assuming formality. But in that context—swarms of tattooed millennials in platform shoes talking about sex robots (for work!)—there definitely would be something off about showing up in a suit and addressing everyone like it’s your cotillion.
All this is kind of abstract, I know. That’s both a good and bad thing. This shift has taken place because of the internet, sure, but also because of all sorts of boundaries collapsing and re-forming. But before you get too overwhelmed, luckily there’s still the same, very tangible bottom line for most people: My primary goal with work has always been to make money to pay my bills. It’s awesome to be able to do something you love while earning enough money to avoid Top Ramen. But that’s a privilege, one that has to be earned. Everyone has the right to a roof over their heads, food on the table, health care, and dignity. (Well, in America, they don’t, but what I’m saying is that they should. Which is why I find myself drawn back to politics despite having vowed, when I left the White House, to never think about what tie the candidate should wear in a debate again.) Not everyone has the right to work a glamorous job of their choosing. Especially not right out of college.
When I was about to graduate from the University of Wisconsin, I knew that I wanted to go into politics and government. My internships with Bernie Sanders were some of the most eye-opening and exciting experiences I’d had that didn’t involve some kind of illegal substance or were soundtracked by jam bands. So when the time came to apply for jobs, I sent faxes and letters to more than forty congressional offices, committees, political action committees, re-elects, campaign committees, and state offices.
Not one person responded to me. I didn’t have the luxury of time, so by early August I had to take the plunge into the wild world of headhunters and try to find a place that would pay me to do something and, ideally, provide some health insurance.
Again, rounds of rejection. What was I doing wrong? Well. Despite all of what I just said about there being no right way to have a career, there are, actually, quite a few wrong ways to go about it. Starting with the interviews.
When I was applying for these non-political jobs initially, I have to admit that I wasn’t pumped about it. I was feeling dejected because the positions I wanted—and kind of felt I was destined for—weren’t having it. I can also be a little bit of a brat in general, and this was especially true in my teens and twenties. All this was showing in my interviews. I wasn’t enthusiastic; I didn’t have original answers to questions I could have easily prepared for. (Even if it’s true, the answer to “What most excites you about this position?” should never be “Not having to live at home with my parents.”)
You may not want the job, but you may need the job. It doesn’t have to be your dream, but you can psych yourself up on its possible positive outcomes: paying rent, getting “professional experience,” paying off college loans, putting away some savings (I used my overtime at the job I eventually did get to go to Japan!), learning new software, living in a new city, meeting new people. Try to sell yourself on the upsides, so you can go in with some un-forced positivity. And never act like a position is beneath you, even if it is. The moral of my story is that I wasn’t being particularly enthusiastic in my interviews—I wasn’t acting like real estate paralegaling was my passion, because it wasn’t. Only after a few awkward “We’ll call you”s did I realize that I was interviewing with people who were passionate about it. Well, maybe not about paralegaling, per se, but the career for which being a paralegal is an important first step. It’s pretty easy to offend someone that way. It would be like if someone showed up for an interview to work at a family restaurant and said, “I mean, I don’t really care about food. Or families.”
So I did a little research, found some topics that I thought could be interesting to learn about, brought my curiosity to the next interviews, and asked questions. Within about a week I landed my job as a paralegal.
Wanting to change the world as a full-time activist is a wonderful goal, but it doesn’t always pay the bills. It makes sense to have long-term goals—which will inevitably get more specific as you get older—but the route you take there doesn’t have to be a straight line. It probably can’t be. And doing what you need to do to pay the bills doesn’t have to be soul-crushing. It can have unintended positive effects, too.
All this is a lofty preamble for saying that, yes, I did work for Republicans one time. When I came to Washington, DC, in 2001, I had just finished a stint working for John Kerry in Boston. My salary was $20,500, and I augmented it with babysitting for a family named the Nemirovskys. I never could have worked for John Kerry and made what was a huge step in my desired career in politics without them.
Or without my friend Amy Volpe, who let me rent a room in her apartment in Boston with three other women for five hundred dollars a month. That meant I had some money to move with. Even though I knew my salary was going to be low, after living in an apartment with a people-to-room ratio of at least 2:1 for six years, I was anxious to live on my own. Right before my job with Kerry was supposed to start, I went down to DC, found a studio apartment in what was then a dodgy neighborhood, and went back up to Boston to pack my bags.
Four days later was September 11, 2001. My job working on JK’s political/fund-raising committee didn’t exist anymore; it was going to be a long time before people were politicking or fund-raising.
So I had to get a job, and fast, because I had $950 rent to pay. Since I’d just had what I considered a great opportunity evaporate before my eyes, I wasn’t amped about any of the listings I found. Still, I deployed the interview skills I’d learned from becoming a reluctant paralegal. I was maybe too good at feigning enthusiasm, because the best offer I got was for a Republican lobbying firm. It betrayed everything I believed in. In some ways, it was reprehensible. Maybe reading this, you still think it’s reprehensible. But it paid the bills, the people were very nice, and in the end what I was doing was not specifically evil. My job was to attend trade shows and get businesses to join our organization—the American Beverage Institute—lobbying for the rights of beer, wine, and liquor companies.
I wouldn’t and couldn’t have stayed very long—my heart wasn’t in it. But I got a very good bonus, because I was deeply grateful for the job. It paid my bills and allowed me to put some money in savings for the first time ever, which allowed me to eventually apply for another, lower-paying job in politics that I actually wanted to do. Even though it seemed like the totally wrong track, it actually got me back on track. And in the after-hours, I spent a lot of time reading and introducing myself to people who would help me get where I ultimately wanted to go.
Something kind of similar happened when I left the White House. I was so burned out on the fighting and compromising that I thought I never wanted to see or hear about politics ever again. I wanted a fun job with less stress, better pay, and nice benefits.
Everyone said I was crazy. The safest thing to do would have been to go and join a consulting firm and cash in on what I knew best: politics. But the idea made me cringe. My gut said don’t do it. I knew I was young enough to start an entirely new career, that my skills were transferable, and that I had more chapters of life left to live. So after months of languishing on the couch with reality TV, going to meetings that were a little aimless at the beginning, I took the job at Vice.
I won’t lie: It was hard to go from having daily conversations with the president of the United States to laborious debates about getting rid of the cold brew in the office kitchens because it was too expensive. But that’s life! Every job has its challenges. I wanted—and needed—something new. I couldn’t compare the two. And having to ask a twenty-four-year-old how to log into TweetDeck was an eye-opening experience. It gave me perspective.
I’m proud that I lived my dream of having a career in politics, and I’m proud of the work we accomplished with Obama. But I’m almost prouder that at forty, I was able to throw caution to the wind, take a risk to my rock-solid reputation in politics as an overachiever, and move to an industry that was totally alien to me, where I would be the one asking questions, not giving answers. Actually, two industries, because after I left Vice I went to A+E, and the only thing I knew about TV was that I loved to watch it.
Even if I won’t be working in digital media or linear television again—as I write this, it’s a couple of months after I left my job at A+E because I couldn’t sit out of politics anymore—I can now say I’m conversant in both. And who knows what the hell I’ll be able to do with that? (I’m hoping something extremely rad.) So far I’ve been mainly using it to be funny—yes, I am funny—on podcasts and rant about Trump on MSNBC, but this, I’m sure, is just the beginning. Maybe one day I’ll be funny in real life. (Kidding. I’m hilarious.) Would I have ever seen myself as a successful commentator before? No. But the point is that things change, times change, and you will change. A shift in perspective is almost always a good thing.
And now, some unsolicited job advice you should probably take:
On Open Offices:
Today, I know I work well in an open-plan office; I can still focus clearly on what I need to be doing and welcome the occasional interruption from a colleague. Some people are more easily distracted. If you’re that kind of person, or have ADD or ADHD, then a job in an open-plan office may be a real problem for you. Don’t be afraid to consider that if you’re picking among job offers. If you don’t have the luxury of avoiding an open plan, don’t be afraid to ask your boss about ways to limit distraction.
On Moving Up:
Doing your job doesn’t usually qualify you for a raise. Showing initiative and creativity does. So if you’re in a job that doesn’t have a clear path to promotion, make sure to ask when you’re interviewing—or just after you’ve been hired—what that process looks like. The answer will help you understand how you’ll fit in, how you can grow, and if you should take the job at all. If the metrics are clear, great. Sometimes, you need to achieve more than your peers and in some industries that means fierce competition. That is not for me. I know this. I like to collaborate and be a team. If it’s a dog-eat-dog, every-woman-for-herself atmosphere, I can’t work there.
On Interview Outfits:
When you’re getting ready for an interview, think about what you’re wearing. First, you want your outfit to reflect your personality. (It’s actually important! Especially, I hate to say it, if you’re interviewing with a woman. But more and more men care about clothes, too.) Second, you want your outfit to reflect the vibe of the place you’re interviewing at. People who showed up to Vice in suits to interview were immediately deemed suspicious not because we thought they were huge nerds, but because you couldn’t help wondering, Um, did they even google Vice before they replied to the job posting?
For me: Navy pants and a white button-down—even if it’s for Vice, it’s gotta be ironed—is a foolproof, all-occasion outfit.
On The Way You Treat People:
Many years ago, when I was working for John Kerry’s presidential campaign, I was at debate prep camp in Santa Fe—a town I love!—and in charge of a sundry list of tasks, which included things like picking out ties that didn’t “bleed” on TV as well as what you might call more “meaningful” work, like negotiating about format and helping review performance video. I think the bosses let me do some of the more meaningful work so that I wouldn’t feel totally consumed by whether we should do a red or blue tie, but I appreciated it, because not everyone was so nice. One day I walked into the prep just before JK was coming down, and someone quite senior came over to me. He said, without salutation or smile, “Sharpen these,” and thrust about ten pencils into my face. No “please,” no “thank you,” no camaraderie-forming cute joke about how old-school No. 2 pencils are.
My job was to support the team. So I sharpened the pencils. But I never forgot that guy. Fast-forward about eight years, and I found myself working with this person again, only this time I had the power. I’d been promoted before he came into his job there, and although we were mostly peers in the White House, in a few areas I was his designated superior.
How delicious. I’m adept at passive aggression, but this time I just went for it. I knew I’d never get past it and be able to work productively with him if I didn’t say something. “Oh my God, hi!” I said when we sat down for our first 7:30 AM meeting in the chief of staff’s office together. “Remember when you made me sharpen your pencils in Santa Fe?”
No, he didn’t. I assumed he wouldn’t. Because when he made me sharpen his pencils, I wasn’t a person to him. I was a flunky. But he definitely felt embarrassed. Or at least I like to think so.
I’m not telling this story to get revenge—I knew he didn’t mean to be dismissive in Santa Fe. But the lesson I learned from it is really important: Even though we can all be assholes sometimes, you should treat everyone like they could be your boss someday. Even assistants. Even assistants to assistants. Any time I interviewed with an assistant—or even set up an interview with an assistant—in the 1990s and early 2000s, I always sent a nice thank-you note on stationery. Now, I’m very OK with email thank-yous, but regardless: Thank them for their help and time, convey your enthusiasm for the position, and then drop the mic. Assistants are also very busy.
On Believing In Something:
While I can’t tell you how to “be me by the time you’re thirty-five,” if you want to work in politics, I can tell you how I did it. I got to the White House because I only worked for people I truly believed in, except when I had to pay the bills. I got my general assistant job with John Kerry after I saw him give a speech on TV and felt that I really needed to work for him specifically. There are a lot of people who work in government who do it strategically, who latch on to politicians they think have the best shot at winning elections rather than politicians for whom they’d walk through fire. This works sometimes, but I don’t think it would have ever worked for me. And I don’t know how you’d be able to work as hard as you have to work, day in and day out, with no life, if you didn’t really care about the mission.
Excerpted from the bookSo Here’s The Thing… Notes On Growing Up, Getting Older, and Trusting Your Gutby Alyssa Mastromonaco. Copyright © 2019 by Alyssa Mastromonaco. Reprinted with permission of Twelve Books. All rights reserved.
