Kerry Diamond has a piece of paper stuck above her computer that reads: Say No. “It’s my thing for the month,” she tells me, but her partner Claudia Wu looks slightly dubious. Kerry and Claudia have said yes to a lot. They are the cofounders of Cherry Bombe: the radical magazine that celebrates women and food, featuring icons such as Chrissy Teigen, Karlie Kloss, April Bloomfield, Lena Dunham and Jenni Konner. There is also Radio Cherry Bombe (their weekly podcast) and Cherry Bombe Jubilee (their annual event). In addition, Claudia works as a creative consultant, having recently designed the new Kate Spade book, and Kerry is the editor-in-chief at Yahoo Food and co-owner of three Brooklyn restaurants (Nightingale 9, Wilma Jean and Smith Canteen). We meet at the Cherry Bombe office, which is stacked with magazines, books and food, to talk about how life plans are overrated, how they do everything (I still don’t know), and how advice means nothing without a sense of initiative.

Kerry: “I grew up on Staten Island and never felt like I fit in. I went to a Catholic school, wore a uniform for 12 years, and my high school felt like a prison with a lot of narrow-minded people in charge. To give you an example, one of our big projects in religion class was to plan our weddings. It was automatically assumed it was a traditional, heterosexual wedding. Or maybe we were brides of Christ. I can’t remember. But think of the hours wasted that could have been put toward cultivating those young minds! I rebelled against a lot of the things in my childhood, but that’s what made me who I am.”

Claudia: “I grew up in Westchester. There were around 85 kids in my class at school—there were maybe six minority students. Similar to Kerry, being in a small town made me want to be different. We didn’t have the Internet, so music, movies and magazines (I loved Vogue and Sassy) were the only way to get a feel for what was going on in the world. I was also obsessed with Twin Peaks.”

Kerry: “Manhattan was the center of my universe back then and I lucky to live in such close proximity to it. Music and magazines were also my lifelines, and the hunt for them was a big deal. Social media has made things so easy to find, but I don’t know if that’s for better or worse.”

Claudia: “New York City was such a different place when we were growing up. You wouldn’t really go to the Lower East Side, definitely not Tompkins Square Park.”

Kerry: “I worked on St. Mark’s Place for a writer and he wouldn’t let me go down toward Avenue A. It was right before the Tompkins Square riots. Can you imagine that today? I walked down St. Marks the other day and there aren’t even any punks anymore. Now they have macarons. But it’s a friend of ours who is making the macarons so that’s OK.

There’s a lot that influences you before you decide who you are as a person.

If you’re lucky, you’re born to a good family, are surrounded by good people and have access to education. So while I wish my high school hadn’t wasted time on things like wedding planning, I’m lucky with when and where I was born, especially being a woman.”

Claudia: “As opposed to being born in a country where you’re actually getting married at 12, not just planning your fake wedding.”

Kerry: “Exactly.”

Claudia: “I always wanted to work in high school, but my mom said to hold off because I would be working for the rest of my life. Of course, once I got to college, I signed up for three jobs on campus and worked full-time for a year and a half once I left school. Afterwards, I was determined never to work for someone else or have a full-time job again. Toward the end of my 20s I realized my mom was right—all I did was work.”

Kerry: “Now you have three full-time jobs.”

Claudia: “But I’m still somewhat my own boss. I’ve freelanced at a lot of places and I’ve never met anyone who is truly happy with their job. So now I give myself a time limit. Three months and that’s it! Three months before the ugly truth comes out. But my three-month-limit plan is really the only plan I’ve ever had.”

Kerry: “I’ve never had a life plan. I’m amazed when I meet people who do.”

Claudia: “Me too. A friend once told me to create a vision board. I think it’s an Oprah thing? I was like, I don’t even know what I’m doing next week, let alone in five years.”

Kerry: “If you have any plan, you should have a financial plan. I think financial freedom is important to women and I probably should have paid a little more attention to finances early on. But when I started out in journalism I made absolutely nothing salary-wise. I remember going to a job interview and a girlfriend of mine said, ‘If they ask what you make, lie.’ I was like, ‘I can’t lie.’ And she said, ‘They’ll never believe you make as little as you do anyway.’ It’s amazing that you never get any practical financial education in school. I learned about trigonometry, but not about how to get a mortgage or take out a business loan or balance a checkbook. I would love to see stuff like that in schools, not just for young women, but for young men also.”

Claudia: “We might not be planners, but I don’t think we’ve ever waited around for people to say it’s OK to do something. Kerry started her restaurants after dating her boyfriend for three months, and I started Me magazine before Cherry Bombe because I was bored and wanted a creative outlet.

But it’s hard to do something all on your own—you need to find the people who can help you do the things that you can’t.”

Kerry: “I could never have done Cherry Bombe by myself. One of the challenges in being a solo operator, whether you’re an artist, a writer or a businessperson, is knowing whether your idea should be put out into the world or not. I’ve had a number of ideas over the years but not all of them were good enough to become something. Having a partner helps in vetting what may or may not be a crazy idea.”

Claudia: “When we first started the magazine, we were like, who are we going to get to photograph stuff? We had no idea who the food photographers were coming from the fashion/beauty world. It’s hard asking people to do things for you when you don’t have anything to show them yet. But for the most part, everyone trusted us.”

Kerry: “We’re definitely grateful for that. A lot of people said yes without knowing what the heck they were getting themselves into. We knew a lot of people from our previous jobs, which helped.”

Claudia: “One of my philosophies is: be nice to everyone. That will serve you well, for sure.”

Kerry: “As much as it’s been rewarding, it’s been a hard three years too. I don’t think I’ve had balance in my life since my first restaurant opened—a good five and a half years ago—even though I feel like balance is always right around the corner. If you’re not willing to sacrifice some balance, you probably shouldn’t be an entrepreneur. Could we use more frequent vacations? Yes. We’d like to do Cherry Bombe from a beach somewhere, ideally.”

Claudia: “I think balance is a state of mind. I’ve definitely had periods in my life where I’ve been overworked, but I’ve had a goal in mind. Knowing what you’re working toward gives you perspective and can make your current task easier.

People you can guide you, but when it comes down to it, you need to be motivated to get it done yourself.

You run into people who are talking about a thing or a project they’re going to start every time you see them. I don’t like to talk about anything until it’s done.”

Kerry: “The key is having initiative, which so many people don’t. I meet a lot of mind-blowing young women who take initiative, are scrappy, hardworking and resourceful—but you bump into an equal number who aren’t. And you need to be all of those things today because the world’s a harder place than it used to be.”

Claudia: “Being in your 20s is especially hard. I feel a bit more stable in my 30s. I’ve figured out the work thing to a certain extent. I still haven’t figured out my personal life. Who knows, maybe I’ll figure that out in my 40s. I do feel like you relax and get happier as you get older.”

Kerry & Claudia’s #OKREALTALK Tips

  • Hard work beats a 5-year plan.
  • Educate yourself about your finances.
  • Initiative will set you apart.

i. @cherrybombemag
t. @cherrybombemag

Photographed by Amy Woodside

As told to Amy Woodside, November 2015