Courtesy of Katy McColl
You spent your 20s working toward building your dream career, but now that you’re in your 30s, what do you do when you’ve, well, changed your mind? Or maybe you never quite figured it out, and you’re now ready to commit to something you’re passionate about, whether it’s a job, a city, or just a new way of life. To celebrate the career changes that can come at any age, we’re debuting a new series called Second Life. Each week, we’ll hear from women who got over their doubts and fears and made the biggest changes of their lives.
When Katy McColl graduated from Smith College, she fast-tracked to success, landing her dream job writing and editing for a popular women’s magazine based in New York City within 15 months. She kept climbing the ladder and, over a decade later, had a thriving career, garnering top editing positions at some of the industry’s biggest publications.
At her peak, she received a call from an old friend, asking if she’d be interested in joining his new app venture. App startups are a dime a dozen, and she finally had climbed her way to the top in a cushy gig. But without hesitating, she took the risk, jumping headfirst from NYC’s publishing industry into the world of digital startups at 38 years old. In just a matter of months, she helped launch HeyRide, a transportation platform where restaurants pay for your taxi trip. Though the transition required her to learn an entirely new vocabulary, not to mention skill set, she has no regrets. Here’s how she did it.
MyDomaine: Tell us about your first career and how you evolved from a staff writer and editor at national magazines to a freelancer.
Katy McColl: I had my dream job in my 20s writing and editing at a women’s magazine called Jane. When it folded, I didn’t renew the lease on the $2000 a month Manhattan studio apartment my husband and I moved into after we got married.
The moment I moved out of New York, my whole life got better and cheaper. I discovered that I could support myself freelancing, and that gave me the confidence to try things. I wanted to learn how to decorate, so I worked for InStyle Home, O at Home, and Country Living, for example. In Northampton, Massachusetts, my husband and I had a $1,000 a month loft within a block of three amazing coffee shops. After work, we took an hour-long walk along the Mill River, and on weekends we took back roads to lakes with sand “beaches” and no crowds.
MD: How did you get involved as a partner with HeyRide?
KM: My business partner Anthony is someone I met 20 years ago volunteering on a political campaign. We respect each other, and we share a strong moral code. An attorney once told me that there’s no contract ironclad enough to protect you from a bad character and that struck me as very true. Anthony called me and told me his idea for the HeyRide app. What I liked was the hugeness of the vision, that everywhere you want to go, as a consumer, should be free. Hungry? Let the restaurant send a car to pick you up. Fifteen years ago, you didn’t expect free shipping, but Amazon changed all that. Today, you don’t expect a free ride to restaurants, spas, sporting events, or theaters, but we’re changing that, too.
MD: When did you know you had made the right decision to join HeyRide?
KM: I was in my hotel room in Berlin [where HeyRide is based] on a Saturday night working on the wireframes—specifically, how to get a user to stick with it long enough to confirm their phone number and link their PayPal account. And I realized, scrappy problem-solving is what makes me feel alive.
MD: Did you ever second-guess taking on your new role with the startup?
KM: It’s opened up a whole new world to me, from building wireframes to working with developers to listening to consumers to studying Google Analytics. And it’s using a lot of the same skills I developed as an editor—anticipating all the questions a person may have and asking, Does this make sense?
MD: Why is your current job suitable for your personality?
KM: I’m a really good advocate for consumers because I’m a really demanding customer. So, for me, every tweet, every question—hell, even a mean tweet—is an opportunity to win someone over. I also love crafting a winning email, and I do that a lot. The other big thing is that I believe in what we’re doing, so there’s an authenticity to everything I do at HeyRide.
MD: What are the most important things you have learned in your career life?
KM: Everyone has a different idea of what success is. And it changes! You don’t get into editorial for the money. You do it because you have a sense of mission. And that mission, for me, is improving people’s everyday lives. I like to work with smart people who share that mission.
MD: What’s your best advice for someone who wants to start over or make a big jump in their career?
KM: Do it now. My mom died when she was 63. That’s really young for a lifetime. She taught us to delight in the little things: going out for coffee, reading the newspaper in the sun, growing tomatoes, attending rowdy book-club meetings, scouring the “free” section of Craigslist, nuzzling babies fresh out of the bath. There were no “golden years” for her, just the in-the-trenches ones.
So, to me, days are precious. Why not spend them going for it? My startup philosophy is that the journey itself has to be rewarding—you can’t just be working for some big payday. So, the little things. And if it doesn’t work out, try something else. Or, as my sister (who left her job as an editor in chief at Yahoo to go to graduate school) says, “What if it all works out?”
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