How Millennials and Entrepreneurs Can Grow Their Value from the Ground Up
Millennials and entrepreneurs. They’re both upstarts and outliers. Both famously work “for themselves,” driven by a strong set of personal values born of an internal ethos and a passion to be in charge of their destinies. Although published reports say that neither is winning awards for intrapersonal likability, both apparently have a high tolerance for change, an appetite to accrue a variety of useful skills, and an impulse to take promising risks. But there’s a proving ground. These two types of workers must learn tough lessons in the marketplace to succeed—and even so, the decks seemed stacked against them.
Millennials are the best-educated generation in American history, but they also have the highest jobless rate in recent history. Entrepreneurs have an eight-in-ten failure rate on the market. To be successful, both have to push against discouraging statistics like this, figuring out how to work to market themselves in a way that impresses the people who pay them, meets their own professional and personal goals, and locks down vital contacts at every stage that will help them in the short and long term. Of any two sets of women, knowing and growing their inner value and professional value—and braiding the two together—is essential to their mission in life, personally and at work.
Millennial women and female entrepreneurs are much discussed in the news these days. Ladies, if you fit into either group—or both—you know what I’m talking about. You’re both navigating uncharted territory by virtue of your age, your pioneering disposition, and this period of America’s socioeconomic history. If both news and academic reports are correct, you are characterized by your drive as independent operators dedicated to living life and to working on your own terms. And although, in general, you are in command of strong traits that people admire and look to as harbingers of the “new” way of working, you are also sitting ducks when it comes to being the target of blame and criticism. Employers and people in the judgment seat love to talk about how entitled, self-absorbed, and lazy you are. Entrepreneurs’ failure rate is attributed to impulsivity and a lack of foresight and for not being realistic, prepared, or disciplined enough to handle the prolonged uphill battle.
To the Millennials and entrepreneurs reading this, I say: let’s give them nothing to talk about—other than how impressive you are. Other than how handily you turn those stereotypes on their heads. In this chapter women who have done just that are going to tell you how.
MAKE A GREAT FIRST IMPRESSION
My advice to Millennials? Know your audience and be savvy when you interact with these important people. Whether you’re a Millennial trying to advance in her career or an entrepreneur trying to drum up investors, these are the people who are going to make it happen for you. Even if you were brought up to appreciate your own inner gifts above all else, you need to learn how to play well with others now.
The truth is that an undue proportion of young women who have crossed my threshold looking for a job—or who have crossed those of my friends’ and colleagues’—have not made a great first impression. And I am going to explain why.
I know this sounds harsh, but you need to hear me out on this. You may think you’re putting your best foot forward by presenting yourself in your most fabulous attire, but you risk rubbing your potential employer the wrong way. You don’t want to make a statement with your outfit when applying for your first or second job. You don’t want to be overdressed and appear as if you don’t need the job. You don’t want to be underdressed either. It’s a fine balance. But here is the key—anyone can afford the perfect outfit, because it should be simple and clean.
Besides, the outfit should not detract from the person. I don’t want to be distracted by clothes and accessories rather than paying attention to your credentials. Most employers want what I want: someone scrappy, someone who isn’t too proud to do whatever it takes from the get-go to make what we do as successful as possible. The passion to work should be your professional value at the beginning.
A NICE, STRONG LINE
If anyone knows about the subtleties and importance of that sentiment, it’s Andre Leon Talley, longtime Vogue editor and fashion impresario. From his early days as Andy Warhol’s assistant in the mid-1970s to his work with Diana Vreeland and Anna Wintour, Andre has held court at the front row of designers’ runways and fashion’s inner sanctum. He knows that clothes have the power to say a great deal about a person—and not all of it is positive, particularly when your career is at question. When I talked to him about his experiences as employee and employer over the years and about how clothes make an impact on your professional impression—indeed, on how it is the package in which your professional value is delivered—he had amazing stories and extremely valuable advice to relate. His first piece of advice: dress according to your work culture.
“When I was with Andy [Warhol] I wore a certain kind of look that was very cool and kind of casual. They were wearing blue jeans with those custom made jackets. All the big bosses,” he said. “Then when [I went] to Women’s Wear Daily [I had] another look. . . . I went to my interview at Women’s Wear Daily in the green shirt that Karl Lagerfeld tossed to me in May of 1975. In August I got an interview for Women’s Wear Daily, and I wore the green shirt with a matching muffler because it was fashion, and this was Women’s Wear Daily,” he said. But how did he know when he was putting it on for the interview that the shirt ensemble was going to work for that specific job instead of a position assisting a major artist? “Through my instinct and intuition, through reading and a knowledge of what fashion was. I can’t stress [this enough]: Prepare for your interview. Prepare for your subject. You have to be prepared. You may say the wrong thing, but someone will know that what you say comes from somewhere deeply prepared, deep within you. It’s entrenched in your own passion.”
I asked: Is part of preparing planning on what you are wearing? “Planning what you are wearing, but preparing it appropriately,” he said. “Now, I’ll tell you another story. I was looking for an assistant [at Vogue] and I was interviewing men, girls—girls from different walks of life. The girls were coming in wearing what they thought that I would like: the Calvin Klein with the Gucci bracelets. The right shoe . . . I sit and talk to the girl, and I think, ‘She spent more time preparing the right brand, or what she thinks I would like, because it’s Vogue, than the substance when I am asking her questions!’”
I think the message is not necessarily that it doesn’t matter what you wear, but that you shouldn’t be so focused on your outfit that it is clear you spent hours fussing with it. Andre agreed. “You are not going to walk in and get a job because you have on the right shoe or the right bag,” he said. “Dress with confidence. You could have a sweater and a skirt or a white shirt or a simple black skirt—I don’t suggest you have a sausage-casing skirt, pencil thin. . . . Just sit down, and you will just talk with confidence, and you will look the person directly in the eye.”
To me the hair and the clothes should not detract from eye contact. He agreed. “You go in there, and no matter how much you are trembling, you compose yourself, shake that person’s hand, and you just sit down and look that person in the eye. And you have to be very, very focused on what you are doing. . . . Don’t say anything false,” he continued. “Dangling earrings are strictly forbidden. Dangly, flashing, clanking jewelry. Have a handbag you can put neatly on the floor, not a status handbag that has a big label. You could have a little clutch with just a cell phone. . . . You want to see someone looking neat. Neatness. Grooming. Fresh. You might not even want to have makeup if that’s who you are. [You don’t] have to have a makeover. You just have to find your style and be confident that you are doing the right thing.”
Other fantastic advice came from my friend and the fashion entrepreneur Michelle Smith, founder of Milly. Her clothing line is one of my favorite labels for projecting my professional and inner value because its color palettes and lines are fresh and classic at the same time. Michelle’s advice is great for Millenials and for entrepreneurs going after funding at big investor meetings—anyone wanting to make a good first impression on her employer. “You want a potential employer to see you as a good investment,” Michelle wrote to me in a note. “Keep your look simple and smart, subtly attractive.” Here are some breakout tips Michelle offered up:
• Hair: Your hair should be neat, tidy, unfussy. If your hair is more than three inches past the top of your shoulders, pull it back into a sleek ponytail. Long, untidy hair can look overwhelming and unprofessional.
• Makeup: You want to look natural and fresh-faced. This means minimal but well-done makeup. Healthy, moisturized skin; a little mascara; a tiny touch of eyeliner; natural lip color. You don’t want your makeup to be noticed. Practice a few different options with a professional at a makeup counter until you get it right.
• Dress: Invest in a slim, well-cut sheath dress. Do a solid color, not a print. Black or navy is least risky, the best option, but a solid color like dark red is tasteful and could also set you apart from the pack. Length of dress should not be shorter than mid-kneecap. Depending on how formal your chosen field is (legal, banking), a well-cut suit jacket may also be needed. Single-breasted, one to two buttons. A suit jacket is better than a cardigan. Cardigans can read as soft, weak. Jackets give the shoulder a nice, strong line and look more powerful.
• Shoes: Always a closed toe. Three- to three-and-a-half-inch heel. Never show your toes. I like the Manolo Blahnik “bb” pointy-toe pump. A great investment shoe as it is classic, never goes out of style. There are some really good, inexpensive copies out there for those on a tighter budget. (Note: Although Michelle and I are tight, here is where we diverge. I would never spend this much money on a pair of shoes; the ones I have were a gift. Just make sure you look for classic and well-made shoes that you can move in with grace.)
• Jewelry: Keep it minimal. A tasteful watch, maybe stud earrings. Don’t overaccessorize.
THERE’S NO LID ON THE SOUP
Joanna Coles, editor-in-chief of Cosmopolitan, had this illuminating piece of advice. “What do Millenials do wrong when they’re talking about career? I think they often want a progress report, and they want to talk about their career all the time with their boss, and actually their boss just wants them to do the job,” she said to me in her fabulous British accent one morning while we were having a conversation for this book. “So, for example, I have someone who, after two months of working here and doing a perfectly fine job, came to say, could she get on my calendar to talk about her career. . . . So I made time for her, she came in, and she sat down and said, ‘I would like to talk about my career,’ and I said to her, ‘The good news is you still have a job here.’ And then I got up and I said, ‘Come back in six months’ time when you have something meaningful to say.’”
Joanna is hilariously direct, but she is also dead-on. She attributed some of this need to constantly reflect upon and share about one’s life and career to a side effect of social media. “I think that they are used to constant affirmation, partly because of the endless ‘liking’ and ‘favorite-ing’ on social media—and in real life that doesn’t happen. In real life you’ve got to do a job, and you can’t have endless ADD doing your job. Some bits of a job actually require focus and concentration to do well,” she added. “I think it’s extremely difficult for people to draw boundaries with social media and to come in and to switch it off. And you see everybody working with their phones right next to their desk, and the constant traffic from friends interrupts a more professional relationship that they have at work. It drives me crazy when people e-mail or answer texts in meetings, although I’ve now noticed I also do it. So I’m as guilty in some ways as other people,” she continued. “I think it’s hard for people to create boundaries because the phone is with you all the time and you’re always on call. I think that’s a shame for people because it’s good to have boundaries. It’s good to know this is your work life and that it gives you space from your parents or from your friends, where you can do something that’s about you. And it’s good to have a personal life so that you can go home and forget about work if it’s not gone particularly well. And, you know, it’s almost like a psychological break. I think this relentless 24/7—where we’re all connected all the time with each other, and your boss is e-mailing you on a Saturday, and that the boss’s e-mail comes in juxtaposed between a Snapchat from a friend and a text from a friend—is a problem.”
When we talked about the issue, BBC World News America anchor Katty Kay and coauthor of The Confidence Code: The Science and Art of Self-Assurance—What Women Should Know went a step further. She said that, according to her research, she believes social media is creating a generation of young women who feel that they have to be perfect on the surface but who lack inner confidence and drive. “I think this thing of ‘the picture’ [that one uses in social media] having to be perfect is a big part of [insecurity], and I think social media plays into that. All of these images of women looking perfect. Sending out a Facebook image of yourself in a bikini to see how many likes you get and that instant gratification that comes from social media—which is basically just flattery—doesn’t actually build confidence. Confidence comes from things you earn yourself, from overcoming hurdles and working on something. It doesn’t come from pressing a ‘Like’ button on a picture of you in a bikini,” she told me as we spoke on the phone about Millennials’ need for outside affirmation. (She had just stepped into a cab in Toronto en route to a girls’ school to speak about developing confidence!)
“One thing that I say to young women is that if you want to be perfect, you are never going to get there. It’s an impossible standard to meet, so stop trying because it is not possible, and it will only eat away at your confidence. If you want to be perfect at everything, then not being perfect is going to cause you such psychic damage that you won’t take risks, and you won’t be prepared to fail. And you know what? Robots are ‘perfect’; people aren’t.”
Katty went on to describe how dangerously pervasive she believes young women’s craving for approval is—and how social media doubles down on the problem. “It makes them dependent on other people’s perceptions of themselves. It makes them dependent on ‘Likes’ and comments and other people following them; how many [Facebook] ‘Friends’ they have and how many followers they have on Instagram. That is not a solid form of confidence; it is a very fragile form of confidence,” Katty continued. “Psychologists are very worried that we have brought up a generation of kids with very fragile confidence. They seem very cocky, and you hear employers talking about this all the time. They seem very cocky; they know everything. They [think they] don’t have to put the time in and should go straight to the top. But they haven’t really been challenged very much. They haven’t been allowed to fail and beat hurdles. And when you push them, that cockiness crumbles.”
This is extremely troubling to me. What’s also concerning, I think, is that I believe that when Millennials look on Facebook, on any social media platform, they see that there are people their age who are changing the world by creating these very social media companies, making ridiculous amounts of money and having Wall Street at their beck and call. But what they don’t seem to understand is that entrepreneurs like Mark Zuckerberg and the Twitter guys are wildly successful outliers. They’re not truly representative of the generation. For every Instagram there are thousands of startups that crash and burn before you blink. Not everyone can or even should be wearing a hoodie and launching an IPO.
DON’T TRY TO BEFRIEND YOUR BOSS
Which brings me to another important point for Millennials: do not try to be your boss’s friend. Your boss doesn’t want to be friends with you. Your boss wants to keep the boundaries intact. And actually those boundaries make your life easier and make your boss feel comfortable with you. When I spoke to Joanna Coles about this, she agreed. “I’ve become friends with bosses, but I think you always have to respect the line, and I think it’s hard for people to do that now,” she said. “To me, it’s fine to develop friendships and connections. But when you’re starting out in your twenties, I think it’s important to show that you are focused and that you don’t bring everything in your personal life to work with you and let it all hang out.” Joanna drove the point home even harder by bringing up another example of yet another Millennial employee who felt that she was overqualified for her job as an assistant—and ended up losing the job because of her attitude.
“The first two or three jobs that you do may not be the most fun you’re ever going to have in your life. There will be lots of boring things in them. There will be lots of stuff that you feel is below you—that you still need to do and, annoyingly, you still need to do it well. And that irritates people!” she said. “I remember we had someone who had come in as an assistant. She had very little experience; she was a very bright girl who wanted to be a writer, and we’d said to her, ‘You must write as much as you can, but you have to be able to do this administrative work too, and that’s how you get your foot in the door. Maybe your next job will be an assistant editor. But for now, for the next eighteen months, we need you to do this administrative work.’ And her excuses for not coming in to work became greater and greater until one day she called up and said, ‘My dog ate a pair of my knickers, and I have to take it to the vet.’ And I was like, ‘And why are we paying you again? I’m sorry: you have to do administrative work. Someone needs to do it. This can’t be done by a machine. It needs to be done by a human being. And right now you don’t have a big enough skill set for us to put you straight in as an editor. But if you do this and spend 40 percent of your time on the editing work, you’ll get there.’ But she just couldn’t do it.”
Joanna agreed with me that this means getting every aspect of the job done right, no matter how menial. (Note to Millennials: getting the coffee is far, far more important in launching your career than you could ever have imagined!) “You have to be able to complete a task, and I think you have to be able to do it with grace. I mean, if someone asks you to go get the coffee, come back with the coffee—with the right coffee! I once asked my assistant why he never delegated getting my lunch, and I said, ‘For God’s sake, have an intern go get my lunch, so you don’t have to do it every day.’ And he said, ‘You don’t understand. They can’t even go and get your lunch,’” Joanna said. “So to challenge him, I said, ‘Right. Let’s find an assistant, go, and task them to get me lunch.’ And the lunch was soup and a sandwich. When he came back to me, the girl handed me a brown paper bag with some tomato soup and a ham sandwich in it. And the bag fell apart because she hadn’t put a lid on it, so the soup had spilled inside the bag. And when we said to her, ‘Oh, that’s odd, there’s no lid on the soup,’ she literally turned to [my assistant] and said, ‘You didn’t tell me to put a lid on the soup.’ I mean, it was just ridiculous!”
BLACK EYE MISTO, EXTRA HOT, EXTRA FOAM!
Again, it all comes back to the coffee. That’s why I actually say to entry-level women (or entry-level men, for that matter): “Take even getting coffee, getting lunch, running an errand as seriously as if you were dealing with the White House social secretary. These are your tests—these are your chances to prove yourself.” I’m glad to know that many of my assistants and the other Millennials I’ve worked with have taken this to heart. One of them, Daniela Pierre Bravo, had a lot to say about it. I think it’s worth sharing here.
“Even before I started at Morning Joe I was a huge fan of the show and was excited to meet everyone who sat around the table, especially Mika. Before making my way into television through the NBC Page Program, I had just finished college by way of being a DREAM Act student [which is for those who have grown up undocumented by no fault of their own and have been granted access to higher education through stipulations under Executive Action, thus enabling them apply to obtain work permits]. As such, I gained a certain sense of resilience from facing day-to-day obstacles. I was used to doing the tough job, working around the clock. . . . My thought was that working in television wouldn’t compare with the type of challenges I [already] had to struggle to conquer,” she wrote.
“Regardless, I was elated at my chance to contribute to Morning Joe back then as an NBC Page. One of the most important lessons I learned from Mika came from the first time I met her. I was introduced to her in the midst of getting ready for the show in her dressing room. After telling me she was happy to have me on, she intently asked if I would be the one getting her coffee in the mornings and then followed up with a, ‘You better not f—it up!!’ This was followed up by laughter around the room. Although partly joking, I was shaken up in a way that allowed me to understand the importance of the tasks ahead with clarity. I understood this wasn’t just about coffee. Instead of being intimidated, I saw that as an opportunity to do well and gain Mika’s trust. I had to learn and shift my mindset—that although I thought my hardships in the past had prepared me for more than just getting coffee, this simple task wasn’t a step back.
“From then on, at the beginning, when one of my tasks of the morning was to get her coffee, I would run to and from Starbucks, understanding her timeframe and the necessity to get it in the earliest window of time possible before the show. The words, ‘Black Eye Misto, Extra Hot, Extra Foam!’ rang in my head incessantly. When it was still my job to get her coffee, I would check once, check twice, and even a third time with the person behind the counter to make sure it was done right. Even to this day, managing a group of interns who now have that task, I make sure that tune rings the same in their heads every morning: ‘Black Eye Misto, Extra Hot, Extra Foam!’ I still drill the idea that it is one of the most important tasks of the morning to get done quickly and correctly,” she emphasized. “Sure, it’s only coffee, but in the end I understood it was more than that. Getting Mika’s coffee order right, along with other [seemingly] random demands she requested, had more value than just doing a good job. It allowed me to understand the importance of attention to detail.
“[Carrying out] Mika’s demands (which often come with short notice, with a small window of time to get finished, many times during the live show) allowed me to do a better job in my overall role of managing the studio and guests. It allowed me to understand the overall needs of the show better because I gained an acute ear to needs around me. I learned to anticipate those needs, and this helped me to be one step ahead of what was asked of me. This was especially helpful when dealing with four or five requests at the same time while managing the studio during the live show. It stopped being about coffee and quickly became about gaining a greater understanding of attention to detail with the overall production. It became relevant to everything I did, from prepping guests before their appearances to my job with booking and logistics in the afternoon.”
Daniela really grasped, in an impressively deep and nuanced way, how important every single component piece is to the whole—making her a tremendous asset now and wherever she will go in her career. “In stressful work environments it’s easy to get caught up with finishing bigger-picture matters, but what I’ve learned is that if you pay attention to the small needs and details early on, you are able to do a better job with the bigger tasks at hand. I have learned to master attention to detail because of Mika, which allowed me to do all my other tasks more effectively and efficiently. It also grounded me and allowed my attitude toward small tasks to rebuke the entitlement stigma most of us Millennials face,” she wrote with remarkable insight.
“By working with Mika, especially with the initial interactions I had with her, I have also understood the importance to take cues from those around you, especially your higher-ups. Whatever industry you enter, your first few roles will be to support others. In order to do that, it is imperative to take cues about the needs and preferences of others, because at the end of the day, if you are there in an entry level position, whatever the industry is, you are there to make the jobs of those above you easier. That is what gives you added value and helps you excel at your role. What was supposed to be a three-month assignment as an NBC Page eventually led me into a full-time coordinating position for the show—a month and a half into that rotation.”
Daniela’s message is universal—and she is flourishing as a coordinating producer on the show. She has been given responsibilities that are far beyond her age, and I can honestly say that this is because she took that coffee order as seriously as if her life depended on it.
Another fantastic example is Maria Gronda, Morning Joe’s special projects coordinator. Here is her experience in her own words, and then I will add context and advice. “Although it has been over a year since I began my career at NBC, I have never let my guard down. I think it was Mika’s celebrity that created an internal triple-check when I would do even the most mundane of tasks, but I will carry that apprehension into every job that I have (whether my future boss has Mika Brzezinski status or not!). If your boss is a celebrity, you can’t help but feel replaceable. Through Mika I have recognized the importance of never allowing myself to get comfortable, because comfort can be equated to a lack of drive and respect,” she wrote.
“There certainly isn’t a blanket rule directing Millennials on how to be the right amount of ‘go-getter.’ I myself am still trying to figure it all out. The best I can say is: Don’t get comfortable, treat your boss like a celebrity, find a way to show your authenticity.”
NO TRADE-OFF
I love Maria’s message, and I own up to everything in her disclosure. Having said that, I also believe that there is a mixed message that twenty-somethings feel about this kind of advice. After all, I teach women to know their value and to communicate it effectively. So when I tell twenty-somethings to do the grunt work, I know they’re thinking, “Well, wait a minute—I thought I was supposed to know my value!” So how do you know when to make that transition from doing all of the irritating work, and doing it really well, to then saying, “Hey, I am more, and I want more”?
As I mentioned earlier in this book, your boss probably doesn’t remember everything you’ve done, and he or she probably isn’t going to come to you. You do need to raise your hand. But how and when should you do that? My opinion is that if you prove yourself the way Daniela or Maria have, you will feel comfortable asking for more. They both did, and they both got more responsibility right away. Again, when I asked Joanna Coles what she thought, she had a very savvy piece of counsel to offer on the topic.
“It’s partly about really doing some research into the environment in which you’re working and paying attention to what’s going on with other people in the working environment. Look at people who are doing well. What are they doing? Are they doing things you’re not doing? If you’re ready to have that conversation, and you’ve got a list of things that you’ve accomplished—and it might be perfect coffee collection for the last nine months, and you simply can’t collect another cup of coffee, then that’s fine,” she said, wisely.
“But you need to have a list of your achievements, and you need to approach it with real intelligence. Are you being unreasonable? Are you being fair? And if you’re being fair, and you feel the environment around you is not rewarding you, then it might be time to move. But I think you have to research. How long do people usually stay in this job? Approximately how much do they get paid? If you were working at a different similar place, is it in the same ballpark? You have to find two or three people who are a bit further beyond you, who are a little older, and ask for their advice before you march in [to your boss] and say you need this, this, and this.”
As a last bit of counsel, Joanna shared with me—and you—about how important it is for young people just starting out to know how to make and keep contacts—and to have a sense of timing. Part of being able to build and maintain a good professional network is not alienating your superiors or your peers. That is, your sense of self-importance, entitlement, and whatever comes across as arrogance can negatively influence your future for years to come.
“I think what’s really important is that Millennials begin to understand the value of relationships in the workplace both with your peers, who will eventually be your network that help you get other jobs and tell you stuff and are informed about what’s going on in the industry, and also older people,” she said. “Actually leaving a place is very important. One person resigned by coming in and going, ‘Guess who’s the next news editor of People’s Style Watch dot com?’ And we were like, ‘Who?’ And she went, ‘Me!’ And we were just sort of thinking, ‘How—what are you saying?’ It was a terrible way of resigning.”
SEPARATING TWO WORLDS
The relationship point Joanna made was so fascinating and so important. I always tell the Millennials who work for me: “You know what? If you’re here with me for more than two or three years, that’s your problem, not mine. I want you to do a great job for me. I want you to grow and find your dream through me, and find the next thing. Don’t be afraid to tell me about it unless you can create it right here at Morning Joe.”
For example, I had an assistant for about two years, Sarah Tracey. She came to me just absolutely thrilled because she had gotten recruited for a new job. I’d told her, “Come to events with me. Meet people. Put yourself out there.” She did, she impressed everybody, and she got a job at Ralph Lauren. And when she told me, I just said, “That is the best news ever!” And I bet I will see her again; we’re still in touch. She is now working with Habitat for Humanity, and we have discussed collaborations. I think there shouldn’t be this fear to do a really great job and to navigate through it, and then possibly come back again. Your current boss is tomorrow’s contact and potentially your boss in the future—again.
This is what Sarah had to say. “I was working for Mika when she started writing Knowing Your Value, and it was incredible to see how many of these lessons applied to me. I was only twenty-three, just a few years into my career, and I heard the message early, which helped shape all of my decisions moving forward. I felt lucky to have landed my dream job right out of college working for a woman who I admired so much. Mika was the one who explained to me that I hadn’t won the lottery. I was a hard-working, intelligent young woman, and I deserved to be there,” she wrote.
“A few years later, when I had to break the news that I was moving on to a different job, she was the first person to jump up and hug me. Mika was the one who instilled in me the confidence that has been essential to my success. Because of those formative years, I have never had a job I didn’t love, and I’ve never worked for people who didn’t value my contributions. With this confidence I also learned quickly to keep my personal life personal. While I expect collaboration and respect from my employers, I also know not to look to them for sympathy or emotional support. Separating those two worlds has made a huge impact on my career.
“Mika helped me see firsthand that as a working woman with a family, you are pulled in so many different directions, and it’s just not possible to be perfect or to do everything well. Accepting that I am imperfect and will undoubtedly make mistakes has somehow made me less afraid to try the things that scare me. I feel stronger in my career, but also my relationships,” she continued. “It has helped me navigate so many of the difficult situations that young career women find themselves in. I know today that it’s okay to ask my boss for more if I know that I deserve it. I have to be my own advocate in all parts of my life. If I work hard, use my talents, and accept that I am doing my best, then I have no problem communicating to my boss that I am a valuable part of the team who deserves the opportunities I’ve been given.
“Honestly, I was so young when I met Mika and she took me on. I remember exactly where I was when she called and asked if I was up for being her assistant. It led to an experience that completely informed who I am now. Who lets a twenty-one-year-old take control of their schedule, finances, insurance, family stuff? She trusted me completely, and it made me trust myself. There were so many moments where she’d tell me to do something and I’d pause and just stare at her. She was the person who said, ‘Of course you can do this, why not?’ When I left that job, I was launched into the fashion world, and I knew nothing. I walked into my new office every day and reminded myself of what Mika told me. I can do anything as long as I pay attention, work for it, and stay confident. My boss after Mika would constantly ask me where I cut my teeth. She was blown away.”
Having said all this, I also don’t want Millennials—or entrepreneurs—to work so hard that they burn out early on in their careers. And that’s a genuine concern. Arianna Huffington, media magnate, thought leader, and my friend, had some very helpful thoughts on this. “For far too long, too many women have been operating under the collective delusion that burning out is the necessary price for accomplishment and success,” she said. “Recent scientific findings make it clear that this couldn’t be less true. Not only is there no trade-off between living a well-rounded life and high performance; performance is actually improved when our lives include time for renewal, wisdom, wonder, and giving,” she wrote.
“Here’s my advice to young working women: at work and in general, we need to live our lives as women, in our own unique way, not as carbon copies of men. Because our current notion of success, in which we drive ourselves into the ground, if not the grave—in which working to the point of exhaustion and burnout is considered a badge of honor—was put in place by men, in a workplace culture dominated by men. When I was first starting out, I wish I had known that there would be no trade-off between living a well-rounded life and my ability to do good work. I wish I could go back and tell myself, ‘Arianna, your performance will actually improve if you can commit to not only working hard, but also unplugging, recharging and renewing yourself.’ That would have saved me a lot of unnecessary stress, burnout, and exhaustion.”
Senator Claire McCaskill made the point that you’ve also got to help your boss know what you’re capable of. Remember the advice I gave at the beginning of this book, that your boss doesn’t remember all that you’ve done, so raise your hand? Senator McCaskill underlined it. “If more young women would say to their supervisors or their bosses, ‘I am happy to do that for you, but I know if you gave me more responsibility in this area, I can really hang the moon. I can really excel.’ I think there’s a tendency of women to try to do all and be all things so that everything they ever have to do, they think they have to excel at it, rather than taking the liberty of trying to force those people that they work for to know: ‘This is really who I am. If you let me do more in this area, it will pay off for you,’” she said.
“When I was in the courtroom, there weren’t a lot of women who were trying serious felony cases when I was a young assistant prosecutor. And there was a tendency to shuttle the few women that did it into the kind of cases that were called ‘the soft cases.’ Welfare fraud, food stamp fraud—things were not violent crime. Not homicide, not rape and sodomy. It was through a mentor that I pushed and said, ‘No, I want those kinds of cases.’ And rather than say no to one of those files that I was really not prepared to do, I just said, ‘I can do it.’ I just dove in. And it was, in fact, during one of those trials early in my career that I hit my stride. I said, ‘I can do this. I am good at this. There is no reason for me to be worried about the responsibility that I’m going to get. I just need to keep accepting that responsibility and asking for more.’”
But why did Senator McCaskill think young women have such a hard time putting themselves out there—and delivering? “I think there is a dynamic with women, part of this is the nurturing part of us, of security versus power. And when you take risks, one of the things you risk is your security,” she mused. “So if you are in a job and you are making good money and you are comfortable, then why rock the boat? Because you’re secure. You’re bringing home the paycheck. You’ve got your insurance benefits. Why would you rattle any cages? Because ultimately security is power, but seeing that sometimes is harder for us.
“I make the analogy that sometimes it’s like giving money to political candidates. Women will go out and buy a ridiculously expensive purse but will never see themselves writing a check to a candidate because they don’t equate helping a candidate who believes what they believe makes them more powerful. Makes their view of the world more powerful. It’s the same thing in a career, opting for the safe and secure versus taking the risk and pushing through. And just saying, ‘My gosh, I can actually move through this and be in a position where I have power, and I am doing what I love, and I excel.’”
THIS ISN’T KANSAS ANYMORE: EMILY, RASHNA, AND THE WRONG OUTFIT
Emily Cassidy has been my professional manager and executive assistant for over two years now. She works in my home office, which makes her challenges even more precarious because she bridges my life at home, my outside projects like this book, my Know Your Value events, and my job as the cohost of Morning Joe. She balances working from her own apartment, my home office, 30 Rock, and coordinating my every move at events around the country. I love the story she decided to tell when we talked about this chapter.
“Over my two-plus years working for Mika we have established a set of rules (all have primarily come from problems we have had to fix). One thing I like about my job is that when something happens, Mika tells me exactly what needs to be corrected; I always know where I stand. One of my favorites of these rules is to always assume other people are going to f—up. I can’t tell you how many times this one has been instilled in me. Mika has taught me that it is never acceptable for me to come back and say, ‘This didn’t get done because so and so didn’t do X, Y or Z.’ At the end of the day, if she gave me a task, it was on me to get it done, even if someone else dropped the ball,” she wrote.
“This means following up with assistants, getting cell phone numbers, getting tracking numbers, following up with phone calls. . . . Never trusting that a job is complete until you are holding the results in your hands. Mika never lets me off the hook because she wants me to think through every possible situation that can go wrong and get in front of it. Getting in the habit of always thinking ten steps ahead has been a priceless career builder.”
One of the toughest experiences Emily has had was learning how not to give into people-pleasing. “The hardest lesson I’ve learned working for Mika and Morning Joe is that not everyone needs to like me (and I should assume not everyone does). I am from picturesque Lititz, Pennsylvania, where I grew up in a loving, middle-class family where I was always embraced, welcomed, and celebrated,” she wrote. “When I transitioned from my former job as a school teacher in Philadelphia to my current media role in New York City, it was an effort to navigate the many, many changes. I was no longer in the warm embrace of my loving community. I have had to remember that what is most important when I walk into a room representing Mika is that everyone sees me as someone capable and on the clock, working. Whether they like my hair, my dress, or my personality does not matter.”
I was so impressed that Emily bravely disclosed her most embarrassing moment to help other Millennials learn from her mistakes. “I learned this lesson on my worst day since starting at Morning Joe,” she wrote. “I had to travel with Mika and staff her at an event. We were very tight on time, and it was my job to be her front person. I will start with my shoes . . . they were the wrong ones. They were a gift from Mika for a party and were really high, too high for me to move quickly in (and probably even gracefully). Even worse, my outfit was very dressy, and my hair was blown out to look as good as possible. But even though this came from wanting to look impressive, I was dressed for a date, not for work—and Mika let me know in the clearest way later! My problem is, I want people to like me and think positively of me. But that day I was trying too hard, and the decisions I made first thing in the morning set off a chain of events that made for a very bad day on the job because I was not physically able to embrace my role. I was too busy trying to keep up with my outfit.”
I did let Emily know that she had botched it later, and truthfully, she has learned much and come far so that she has become a superstar in my life. She puts her heart and soul into everything. Her honesty is so valuable for other Millennials. We had a postmortem about that day, and I was very clear with her about what went wrong and why. I even told her that she had a sense of entitlement, which absolutely shocked her. It was the one thing she pushed back on and took offense over: my calling her “entitled.” But we went deeper, and quite frankly, I spent a lot of time talking about this with Emily because she is worth it, and she is someone I want with me for a long time. If she was someone who I did not think was worth it, I would not have spent the time going through and picking apart every aspect of that day. Emily was smart enough to know that and engaged with me in a very real way about how she does her job.
Remember this: when your boss shuts down on you and stops giving you advice, you know you have stepped over the boundaries, and you will never be able to turn back.
I explained that there are different forms of entitlement that can often afflict today’s Millennial. Many young people in their first or second jobs expect too much too soon and have been given too much too soon. In the age of social media everything moves fast. Millennials are getting constant feedback, so they often expect that to translate into their professional lives. But this is different from what I meant when I called Emily “entitled.” I explained that her loving family and her incredibly supportive friend network was a complete blessing to her growing up as a child, but it actually did not translate well into her professional life. I told her that she had to learn that not everyone in every situation will be as loving and supportive as her family.
And that’s where I felt she was entitled. Trust me, there are worse forms of entitlement, and I revere the closeness of Emily’s family. In the real world, though, especially working in New York City, that can give one false confidence. You cannot walk into every situation, assuming everybody is going to embrace you and want you to be there.
In fact, nobody does. Welcome to New York, baby! You have to take your time before you learn your place, especially when meeting new people—and you should assume that everyone you meet is important.
What she now knows is that she needs to be quick, nimble, and able to run down the hall and grab a last-minute script off the printer. She must be in charge, alert, totally on top of it. At the same time, she needs to blend into the background and let me do my thing—always watching for that moment when she will be called upon. She learned a valuable lesson and applied it after our very honest but difficult talk that day.
But where Emily needed to pull back, Rashna needs to push forward. Rashna Shetty has worked at Morning Joe for several years as a talent producer and stylist: model looks, the perfect outfit always, and pitch-perfect at every task, scheduling disaster, or event staffing that comes her way. I literally cannot think of anything that Rashna has screwed up, ever. If you ask her to do something, you just know it is going to happen. In fact, her reputation is that she is absolutely perfect. What’s wonderful about her is that even when she first came to us in her twenties, she knew exactly how to adapt to any social dynamic at work.
But when it comes to speaking up, I’m the one singing Rashna’s praises because I think she is amazing at what she does. My goal is to help Rashna find her voice, advocate for herself, and, ultimately, get her value. At Morning Joe we hire winners, and every single one of the Millennial women who work for us are top notch. I nudge them all to know their worth, develop their inner value, and have that fulfilling, authentic life that they want. I’m dedicated to helping Rashna get that.
One thing that Millennials do have going for them is the ability to envision themselves as entrepreneurs. Maggie Murphy spent over two decades in magazines, most recently as editor-in-chief of Parade. She spoke about the fact that previous generations of workers didn’t feel they had the fluidity that Millennials have. “Structure is helpful for people of my generation who were raised without the idea of being entrepreneurial. We did incredibly well in corporate structures, as you did in CBS, Mika, and as I did at Time Inc. and then at Parade. We knew how to lead structural organizations. But starting something new is the biggest leap of all.
“I was sitting next to an entrepreneur who is a college student, and I realized that kids this age are hardwired to start something. Our generation is less wired that way, and that’s one of the great challenges in corporate America. For women who have been disrupted in their work lives as I had just been—the organization that you were working for doesn’t necessarily exist anymore, so your choices are to completely stop or to start something new. But that is a big leap. So working for a startup is the right job for me at the exact right moment of my career. And that is what made it so amazing.”
But in a very real way entrepreneurs, Millennials, and all of us reach a certain point in our careers when our lives run up against hard edges that force us to rethink. That’s when we know that our professional value and inner value just aren’t in sync anymore—or that we’ve outgrown one, the other, or both.