Getting Sticky With: Yolanda Edwards

We are pretty firmly in the anti-advice camp for most things, though we can all collectively agree that when it comes to travel, Yolanda Edwards is probably the best person to talk to.

This expertise comes from an impressive résumé that touches so many facets of the legacy media world. The abbreviated version of her professional life goes as follows: a year at Elle, a stint at W—one that shaped her philosophy on flexible work environments—followed by roles at Condé Nast Traveler, the Condé-backed, parent-focused Cookie, and Martha Stewart.

Now, Yolanda has her hands full with YOLO Journal, a travel publication and little black book of all the wonderful things to do in a new city, that includes an owned site and companion Substack called Club YOLO, where readers and travelers can tips in a true peer-to-peer way (“I call it the café next to the library.”). 

In a full-circle moment, her daughter Clara, a recent college graduate, is now lending a hand to the media nest she and her husband Matt have built.

In our conversation with Yolanda, we asked her about traveling with a young daughter, how she still questions if she should have sleep trained 22 years later, road trips with a child perfectly content in a car seat, and her most practical advice for traveling with kids: always pack a spare set of clothes. Life is so much better when you’re not sitting in puke-covered jeans. Consider that your essential travel rule. Everything else is optional.

“Travel always felt like a ‘someday’ thing” 

I got a position as a maternity-leave fill-in at Condé Nast Traveler on their photo team. With that job, I realized I’d always loved travel—not because I grew up traveling, but because we never did. I was always trying to escape what felt like a boring upbringing, so I glommed onto anyone whose parents were into food, flea marketing, travel, clothes. I lapped it all up like a sponge. Travel always felt like a “someday” thing. I would take any travel articles I found, make files, and had folders for places like New York and Greece.

I never knew it could be part of a job until I ended up at Traveler. Even though I was the youngest and lowest person on the totem pole, I could feel I had something the other editors didn’t: I loved hearing from regular people who traveled, not just people who were qualified as “travel writers.”

One day, a friend from college walked into my office. She was there to develop a new magazine Condé Nast was considering called Cookie, a parenting magazine. Cookie was great. I was covering all travel, and my daughter Clara was about a year and a half, two years old at the time. 

At Traveler, our motto was “Truth in Travel,” because the magazine had been started by British editors who’d worked in the ’70s and ’80s when everything was press junkets and freebies. There was nothing that felt authentic, so they came up with that tagline. When I got to Cookie, I thought our version of “truth in travel” should simply be that I’m traveling with my kid. That was the truth. I wasn’t pretending to have a child with me; I only traveled with her. And the whole idea behind the magazine was that you’re still you. You’re not suddenly going to Disneyland just because you have a kid. 

Then in 2009, the company started losing so many assets—Gourmet, Cookie, Domino, Elegant Bride. They were hemorrhaging money. When Cookie closed, Pilar Guzman, who was editor-in-chief, and I were like: What are we going to do? There are no jobs. So we started something called Momfilter. Momflter was very much about the mother. It took us a long time; this was before those easy website builders like Squarespace or Wix. We spent a lot of money building it, and then the day after it launched, we were offered jobs at Martha Stewart.

Supporting moms = supporting flexible work environments 

We had friends with a son who was four years older, and when I got pregnant, they said, Your lives are going to change a lot. And I remember thinking, really? No. Absolutely not. It brought out this rebellious side of me. I was determined to prove them wrong. We were not going to stop traveling. So I brought her everywhere.

Matt was a photographer full-time then, and he was shooting in San Francisco constantly. He’d be there for two to four weeks at a time. I had a boss at W who gave me so much flexibility. I told him, I have a baby. I’m happy to keep working here, but I need limited hours. I needed to come in at 10, go home at lunch. I was in the Fairchild Building on 34th between Fifth and Sixth, and I lived on West Fourth, which was one express stop away. I’d go home, nurse Clara, come back, and leave every day at 4:30. I worked like that three days a week. And when I wanted to go to San Francisco, he didn’t care, as long as the work got done.

One of the things we try to do now at YOLO is: if you’re having fun and the work is getting done, it doesn’t need to be in an office. I’d rather have joy and work than just work. Face time is good, but not if you’re unhappy while you’re doing it. I feel like the whole system needs to be overhauled. Even before you’re a mom, it’s bad. It’s like: come to prison every day, get it done, then go back to your life. It’s not good.

Whenever I run into Dennis now, my former boss at W, I tell him that job allowed me to set the course for how I wanted to parent. I never had to be in a resentful place—resenting work, resenting home—because I couldn’t be present anywhere.

The trend du jour? Clothes not covered in vomit 

I wasn’t someone who was into sleep training. I always felt guilty because, working at a parenting magazine, there were all these things being pushed at you about the “responsible” way to raise a healthy individual. We didn’t do any of that. But it meant Clara could roll with us. We’d show up in San Francisco at midnight our time and go out to dinner. If she fell asleep on my lap, that was fine. We were very easy-breezy about it. You either get beaten down by it and run back to structure, or you go with it and accept that sometimes it’s going to suck.

I was often traveling to San Francisco by myself because Matt was already out there, and I experienced everything from her throwing up on me to having diarrhea before the flight even took off for a six-hour cross-country trip. And when that happens and you’re still fine, you learn how to deal with it. It’s not that bad. You don’t just pack extra clothes for your baby and you learn that you need to pack extra clothes for yourself, too. 

I always tell moms: even if it’s the thinnest T-shirt you’d never actually wear in public, or a thin pair of leggings, just shove it into your diaper bag. At least you’re not sitting in crapped-on jeans and a puked-on shirt. Presentable enough that you’re not naked, even if it’s not something you’d actually wear out to lunch. Dark colors help… or don’t; vomit shows on everything. But everything is better when you have something to change into.

“There are downsides” 

When Clara started preschool, she went to this really unusual place in New York called Blue School. It was filled with creatives and started by the Blue Man Group. It was okay if you were traveling. There was a lot of support for that. But then we moved her to the local public school, and they were really weird about travel. It became clear you’re not going to be able to be a free-range parent in that environment. So we just got smarter about it. 

For Thanksgiving, for example, they’d get two days off anyway, and Wednesday might be a half day. So we’d take the Monday, Tuesday, and that half-day Wednesday, leave on a Friday night the week before, and come home on Sunday. That gave us a good 10-day trip in the fall. Then we’d travel over the holidays, and always over winter break and spring break. 

And then when I went to Martha and then Traveler, those weren’t jobs where I could be on the road all the time. They were more management/face time jobs. It worked well because Clara didn’t want to be on the road all the time, either. By then, she was a teenager and wanted to be with her friends, not gallivanting. We still traveled a lot, just not as much as before, or as much as we do now.

I was talking to a travel planner who works with clients, almost like a financial planner. They talk about their intentions for the rest of their life—what are the big trips they’d be unhappy not to do before they die or can’t really move around anymore—and then they map it out. Because it’s not going to happen if you don’t map it out. All of a sudden you’re 56 and you’re like, Okay, in 25 years I might be less mobile. You have to think about that. Twenty-five summers, or 25 years, isn’t that much.

You also don’t want to be on the road nonstop. There are downsides: people assume you’re never around, so they stop inviting you to things. You lose that close, everyday contact you get when you’re taking your kid to school, seeing the same moms, having coffee. All those routines disappear when you’re constantly traveling.

So I think you have to do what makes you feel comfortable, but if part of your comfort is, I really want to go to X, Y, and Z at some point, just hold that in your mind. Maybe you want to do that trip when your kid is 20, maybe you want to do it without them. And you don’t know who your kid will be—they might hate travel, or they might love it.

The most under-appreciated form of travel with small children is…

When Clara was little, I loved road trips. They felt so much easier. We did a lot in the Northeast—Vermont, Maine—and tons of road trips in California. It was incredible. 

I wish we had done more of those. Maybe the Southwest, more across the top of the country, or Canada. Depending on the season, there are places no one thinks of. From New York, we went to this place called Château Montebello near Ontario, which is the largest log-cabin hotel in the world. There are all these hotels that were built by the railroads across Canada, and this one is part of that group. 

Road trips feel like your own universe. You’ve got the soundtrack going, you can change a diaper whenever you want, you can bring all the food you need. That would be my big suggestion: all those road trips you’ve ever wanted to do, do them while you have a kid who’s happy in a car seat.

And now, with Google Maps, it’s so much easier (antique store near me, or maybe pharmacy near me is more like it!). And HotelTonight is like the greatest invention. When you’re on the road, you just want a clean place to lay your head, and sometimes there are places on it that are better than you’d expect.  

One caveat is that we were considerate about where we went when Clara was younger. We weren’t doing any really long-haul travel further than Europe, for example. For the time we had, and how disruptive it would be, it didn’t feel right.

“I’ve always struggled with the very achievement-oriented parenting style” 

What motherhood means to me—especially now that my daughter’s older—is that you really are their guide. When I look at the parents I admire, they’re the ones who deeply understand who their kid is and allow them to be themselves, but also give them a couple of guardrails. You allow enough room for mistakes, because that’s where they learn. 

Having fun, being funny, and finding joy and laughter in simple things; that’s so important. We try not to argue in front of Clara, but when it happens, explaining it matters: This is normal. We’ve made up. You’re safe. I’ve always struggled with the very achievement-oriented parenting style—great grades, tons of activities, finding “the thing.” We weren’t those people.

Should you sleep-train? We don’t know! 

My friend Pilar used to tell me I was too free-range and that Clara should’ve been sleep-trained. A couple of months ago, I told her that Clara had this moment where she couldn’t find me. I’d left my phone at home, and when I got back I had all these missed calls and texts—she thought something terrible had happened. I called her and she was just in so much distress. I told her, You need to learn how to self-soothe. This is why I got you a meditation app. I told Pilar that the whole time I was thinking, Maybe I should have sleep-trainer her. And Pilar responded by saying that everything she’s been reading lately makes her think maybe they messed up by sleep training. 

It was such a relief. Two mothers, our kids grown, still asking ourselves if we should’ve done something differently 22 years ago. And in the end, we came back to the same thing: whatever feels right to you. If you have conviction, you do it. Even if five years later you think, That was kind of a mess. It’s okay.

When they’re small and you’re a young parent without experience, everything feels huge. The things people say to you matter more because you need the choir; you need to hear what resonates with you and what doesn’t. If a phrase doesn’t resonate for me, but if it resonates for someone else, then that’s their truth.

As they get older, the worries change. When they’re little, everything is more formulaic—you feed them, change the diaper, keep them safe. Once they’re 16, the whole world is out there and you can’t protect them from it. But I don’t feel like the problems are “bigger,” just different.

Parenting makes you feel like you need to think everything through so intensely, and it’s like—don’t lose your gut instinct. Keep that. Don’t listen to people like me giving advice.

The biggest thing is: it’s going to be fine. You can’t sit there worrying about every little thing because you’ll never enjoy your life. And this narrative we grew up with, that your life ends for 18 years, is just not healthy. It’s not healthy for you, and it’s not healthy for your child. Your child needs experiences, and they need to understand that you are a whole human being with interests and hobbies and a life outside of them.