Alyssa Bailey is currently the senior news and strategy editor for Elle.com. She oversees the news coverage of celebrities and royals. Alyssa previously worked at InStyle and Cosmopolitan Magazine. This beauty and go-getter is a fashionista and loves exploring the great New York City. I had the honor and privilege to interview Alyssa. I was able to get a deeper understanding of her journey in the entertainment industry as an editor for one of the biggest magazine companies in the world. 

How did you get into the entertainment industry as an editor for one of the biggest magazine companies in the world?

I actually didn’t think I would be in celebrity journalism. I saw the movie, Devil Wears Prada and I wanted to work for a fashion magazine so I could write for a living in an exciting, team environment. I went to journalism school, knowing everyone wanted that dream job. I knew I needed to do everything I could—intern, network, write—to make it happen for me. A lot of breaking into the industry is luck, preparation, and good timing. It worked out for me, and I feel like I won the lottery. 

Everyone’s journey in this industry is different. Here’s mine. After graduation, I was a fact checker at InStyle magazine and then worked at Cosmopolitan.com as a freelance editorial assistant. Both InStyle and Cosmo were contractor roles with hour caps, so they weren’t permanent. I wanted to be salaried. Toward the end of my time at Cosmo, the site director then, Amy Odell, connected me to Leah Chernikoff, who ran ELLE.com at the time and hired me. To this day, I think it was one of the nicest things a manager has done. She really looked out for me. I’m so grateful to all of the people who gave me chances. 

I started as an editorial assistant at ELLE.com. I was doing production, expenses, and writing news stories. I decided to focus on doing celebrity news, which our audience was most interested in, to be valuable to the team. I aggressively pitched stories and became very, very good at covering news quickly. I am now the senior news and strategy editor at Elle.com. To me, celebrity news is great escapism. I try to do it in a fun but fact-oriented way. 

I’m one of the company’s top U.S. writers and have, at different points, brought in more traffic than anyone else in the U.S. division. I’m proud of that and my growth. 

I taught myself how to do my job well and made a point to ask smart questions to my managers and mentors. My career didn’t go the way that I thought it would after college, but it’s been better. I’m full of gratitude. I was always an overachiever in school, and I chose to pursue my career above all. I can’t understate this: It was really tough breaking into the industry. It’s even harder now. Something I’m passionate about as a senior editor is doing all I can to create opportunities for young writers to receive mentorship and experience. 

You currently work for Elle.com but you have previously worked for InStyle and Cosmopolitan magazine. How have you been able to navigate the ever evolving changes of the industry? 

Early on in my career when I first started in journalism, I was freshly out of college. Print was more of a thing. I knew early on I wanted to be in digital because that’s where the industry is growing more. Now, e-commerce has become a bigger priority for publications. I’m working to understand more about it, especially because I hope someday to lead a publication as a site director or deputy editor. It’s critical to me to understand where the money is coming from and what the priorities are for brands.

Many people are passionate about feature writing. Fewer are into news, but I really enjoy its fast pace. Many people jump around companies. I’ve been primarily at Hearst. Staying and growing at one publication and one company has been a privilege, and I feel so lucky that after over seven years, I’m still very much growing at ELLE.

What has your career process been like?

In terms of career, I found my passion—news writing—pretty young, but there are a lot of jobs on publications that can have very different day-to-days. My advice is, if you find something you love, get to know all of it. Early on at Elle, I volunteered to help with social—Facebook and Twitter at the time. Even though it’s not my everyday job now, understanding social media has made me so much better at news writing and packaging content. So I would say definitely explore everything, try to understand everyone’s jobs, and choose a path for yourself encompassing what you most enjoy.

I got to do red carpets at InStyle because, while doing an informational interview with a higher-up editor there, I told her I had an interest. I highly recommend, by the way, getting coffee and getting to know each person on the team you work with if you’re at a publication. In my case, that meeting changed my career. I was a fact checker, but I was able to go to red carpets and write stories for the site. Those web clips really helps me ultimately get hired for editorial assistant roles later. So ask for what you want and explore different areas to carve out your career. You have to steer. People will help you go where you want to go, but you have to be your own driver and advocate.

What are some obstacles & challenge you’ve had to endure or overcome?

I think for a lot of young journalists it’s hard to say no, and you take on more than you can handle. Early in my career I said yes to everything. As a manager now, I understand how important work-life balance is to avoid burnout. In news, you’re on call all of the time. I think the challenge has been learning boundaries given that. You want to protect your mental health and have a life outside of work.

…You can’t plan the future and that has helped me find peace. I wish I knew that when I was younger. 

What has currently been your biggest accomplishment?

I think my proudest work has been being able to manage people and help them grow. Some have moved on to different publications, and they’re doing such cool things. Knowing I got to shape their journey, gives me a lot of joy. Also, feeling confident that I can write a news story is really special. There were points where some people doubted me, and that’s where I struggled as a recent college grad. I feel like I’m good at my job. In terms of stories, I helped started ELLE’s K-pop coverage earlier than most U.S. brands. I interviewed BTS in 2017. I remember pitching it to my editor, thinking it might be a hard sell. I told her it made sense strategically given the size of their fan base and all they’ve accomplished. How right I was. It was so cool introducing BTS to our ELLE US audience—and they kicked off what has become our robust K-pop coverage since.

What is your ultimate goal?

 My goal is to be a really great leader. I want to be the boss I wanted to have. I’ve had great bosses and bosses that have been traumatizing. A lot of people don’t have management training. But you have to be empathetic and have people skills while balancing the company’s goals. I want to be kind, inspiring, smart, and just a really good boss and leader, someone who leads with integrity. The stories we publish help shape culture and online discourse. We have a responsibility to do that well and ethically. Journalism is about telling the truth. My hope in journalism is to do that well. It’s not about being a star or media personality. I really want to amplify other stories. I like that my words and work can make someone’s life better. In terms of hard hitting reporting, promoting those stories can change people’s lives. It’s really important, and I hope I can be someone who helps those stories prosper in a healthy way.

What is one piece of advice you would give your 16-year-old self?  

Be nicer to yourself. Be nice. I think I am so intense and such a perfectionist. I loved my 16-year-old self. I was a hustler and a perfectionist and critical. I wish I was more forgiving and recognized I have limits. I felt like I needed to do every AP class and extracurricular activity. I wanted to be in New York and be successful. I would tell my younger self that you can enjoy my life and of course, I’d tell her to always be kind. Kindness is always a good look. And of course, I would tell her she has great style and to never stop playing with fashion.

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