Elaine Welteroth On How To Land Your Dream Job

Photo: Courtesy of Penguin Random House
A young woman named Sabrina is standing (and visibly shaking) in front of Elaine Welteroth and 150 other people packed into an Indigo bookstore in Toronto. She’s about to ask Welteroth a question, but first she must participate in the exercise the former magazine editor turned Project Runway judge, author and entertainment mogul encourages during all of her book-tour appearances. Anyone who asks a question must state their name and say, “I am claiming space for ____, no matter what ___ says.” It’s a play on the title of Welteroth’s debut book, More Than Enough: Claiming Space For Who You Are (No Matter What They Say). Welteroth, 32, calls the book “part memoir, part manifesto.” It chronicles her life from her working-class childhood in small-town California to landing her first job at Ebony magazine (under her mentor Harriette Cole), all the way to her rise to the top of the publishing industry as the first black editor-in-chief of Teen Vogue. She was the youngest EIC in Condé Nast history and the woman responsible for the magazine’s socially-conscious, politically-minded, “woke” rebrand.
Sixteen-year-old Sabrina trembles as she softly says, I’m claiming space for my voice and my opinions, no matter what my inner doubts may say.” The room erupts into applause and her shoulders relax. Welteroth tells Sabrina she reminds her of herself and calls her a “young Oprah.” Everyone else in the room — I moderated the event — could feel that with those words, Welteroth gave Sabrina a proclamation that she will carry with her for the rest of her life. This exchange is emblematic of Welteroth’s enormous influence on young black girls just like Sabrina who look to her as a walking validation of their dreams.
Earlier in the day, dressed in a white linen suit and perched gracefully on a chair in the lobby of Le Germain hotel in downtown Toronto, Welteroth shared some of the secrets to her barrier-breaking success, and debunked some myths about what working at your dream job is really like.
What’s the biggest myth about the idea of a dream job?
That everyone has one. We need to stop expecting people to come out of the womb with a sense of what they want to be when they grow up. That's the wrong question to ask. It should be, “what makes you feel alive?” Do the odd jobs, do the jobs you hate, make mistakes. Trial and error is super important because the closer you get to failure, the harder you want to run toward success.
One of the things I find so inspiring about your story is how tenacious you were before you started at Ebony in getting a hold of the mag's creative director Harriette Cole. You were a student living in California and offered to fly to New York just to get her coffee! I would never have been able to do that at that age.
I still feel like that. I'm like, “who's that girl?” I really don't know who she was [laughs].
Do you think you need that kind of tenacity to land the job that you want?
There’s a certain amount of luck that's at play that any successful person has to acknowledge, but I think there is a lot you can do to reverse engineer luck. A lot of it is just doing the work, being relentless and being unapologetic about going after what you want. For me, tenacity and relentlessness were the keys to my lucky break which ultimately helped put me on the path to a fulfilling career.
You write about how your dream workplace didn’t exactly meet your expectations. There’s a story in the book about crying on your first day at Ebony. Talk about the expectation versus the reality of a dream job.
All that glitters ain't gold. It's just like your mama told you. I had a rude awakening in my first dream job about the limitations that come along with systemic racism and how it affects some or most black-owned business. [Welteroth writes about feeling like Ebony was at the bottom of the media hierarchy.] It was a blessing and a curse to start my career that way because I learned how to lift up the underdog and be the underdog. Sometimes there is a bay in between what your expectations are and what your realities are, but there's always an opportunity for you to get closer and create the dream. I just took it. Don't wait to be handed an opportunity, Create the opportunity for yourself. I mean, don't go as far as I did and give yourself a promotion. [Welteroth promoted herself to production assistant at Ebony and negotiated a 50% raise.] Who was that girl?
When you are successful as a woman of colour, especially as a black woman, that also comes with breaking through glass ceilings. Talk about the added layer that comes with landing a dream job when people are not only talking about your work, they are also talking about your race.
Yes, and then you become a diversity-and-inclusion expert overnight. You’re thrust into the spotlight of being asked these existential questions about where we are in terms of making progress on the diversity issue in every industry and you’re like ... I just got a promotion and I'm just trying to figure out how to do my job well!
I learned in headlines that I was a “first” [after being promoted to editor-in-chief at Teen Vogue], when I thought I was just a hard-working girl that got a dream job. I think that threw me for a loop. It also came with a unique responsibility because I recognised how many young girls who look like me were now for the first time seeing someone they could relate to in a position of influence. I learned that the more I was able to be exactly who I am and speak for those who had not been spoken for in that space, that was my unique value. I saw myself as serving the reader and not serving the system that hired me. My job at Teen Vogue was to pass the mic, to identify and amplify voices.
Some people may think that in order to land a job, you need to conform to the workplace in the interview process. For your Teen Vogue job interview, you wore your hair in a low bun because you didn’t want your hair to be too big. That’s a really relatable concern for black women. So, let's say you've got a job interview for your dream job and you’re worried about going with your natural hair. What's your advice?
Do it anyway. Now, people in positions of power in every industry are more aware of micro-aggressions and how important one's identity is to their work. If a company is not, then they're not paying attention. If that is the case, is that a culture you want to work in? There are unspoken cues when you are brave enough to go into an interview with unconventional look for that industry. It communicates confidence, individuality, and that you're not going to conform. For the right organisation, that is a strength.
In a dream job, there is this idea that “you should just be happy to be here,” especially when it comes to salary. Talk about advocating for the salary you deserved.
It's the single hardest part for most women when navigating landing their dream job. We have been conditioned to play nice in the sandbox but that only takes you so far. Your most transformative work is on the other side of fear and the scariest thing to do is to advocate for yourself when the stakes are really high. We need to be talking loudly and proudly about the wage gap and not just in statistics, but in real-life anecdotes. That is why I shared some of my career trajectory [in the book] because I didn’t always get it right. What I learned from these hard negotiations is to know your floor and know your ceiling and always come in at your ceiling. Don't apologise for asking for what you deserve.
Finally, is there only one dream job for all of us?
Our lives are a series of dreams realised. You do not have to be defined by one title, one career for your whole life. You get to decide what your purpose is. Your purpose is multi-platform. You can take it and do many different things through the course of your life. And guess what? In this economy, you better plan on it.
This interview has been edited and condensed.

More from Work & Money

R29 Original Series