The Front Room. Portland, Maine.

Janna and I met during the coldest summer that California had seen in decades, in 2010. She had perma-tanned skin despite the near-constant cloud cover, and an entirely disarming smile, even though she was an editor at SURFER magazine while I was an intern there. Even though she was a former competitive surfer from Kauai. Even though, yes, she is one of those Ironses. She was also the only woman on SURFER’s editorial staff. Eventually, she became managing editor of SURFER and Editor-in-Chief of the women’s surfing magazine, SALTED, before moving into creative strategy. She and her fiancé John Stifter, former Editor-in-Chief of Powder magazine, both recently quit their jobs in pursuit of life on the road. They have been chronicling their traverse of the U.S. and Canada in their Sprinter van, Shaquille, on their site Van Ventures. (And Instagram, of course.) I was fortunate enough to intercept Janna during their layover in Maine. After almost six years, Janna and I talked nomadic tendencies, paranoia, and politics as aphrodisiac over breakfast at The Front Room in Portland.

You were at SURFER for a while after I was there, and then you did SALTED, right?

Yeah, so I did the first issue of SALTED when I was still on staff, and it was kind of like, “Let’s try this and see if it works.” And it was very –

Server: I don’t want to rush you, but do you have any questions or anything?

Maybe we’ll look for a minute.

Yeah, thanks.

This is the one pitfall of doing interviews over breakfast (being slow to order). Do you have a breakfast go-to?

I love anything with sweet potatoes in it! That sweet potato hash is right up my alley. I will probably get that.

[Long, contemplative silence.]

Pick something?

I think I’m going to do the omelette.

Yumm. So yeah, Brendon Thomas, who was editor [of SURFER] at the time, was all for it, which is why I think it happened. But I was the managing editor [of SURFER] and also doing this on the side, so it was a lot of work. By the third issue, I had left SURFER and I got a job at a creative agency in Encinitas, which was really awesome. I was actually hired as a project manager at first, and I was just thinking, “Yeah, I managed a lot of projects at SURFER,” but I didn’t realize that in an agency setting, they’re not part of the creative process; they’re just managing it. So, within the first few months, my job was changed to creative strategist. They took a chance on me. I’d never done that before, and they just let me learn and dive in and do it. The people who own that agency are just amazing people. I learned so much. And I realized that all of the skills I learned at SURFER are all directly applicable to what I was doing. John’s been in the ski world since he was in college and he’s been [wondering], “Do I know how to do anything else?” And I’m like, “You do.” You just don’t realize that everything you do is bigger than [it seems].

I have also had to figure that out. Actually, the last job I had was a development job and [I had never done that before]. When I was applying, I was like, “Look at all of these skills that I have from journalism and freelancing that I can apply to your organization,” and now I can take what I learned there and hopefully put it into something else. But sometimes, it’s hard to see that. Has he been in editorial his whole life?

Yeah.

So does he want to go into more marketing stuff or…?

He doesn’t really know. He’s very interested in doing something where he’s giving back, like working for a non-profit. I would love for him to find something in that field because he would be so good at it. We’re trying to figure out what that could look like. I think that was another purpose of this trip for us. Both of us had a really amazing time in Southern California over the last eight years, but we were like, “Okay, I’m ready for whatever the next chapter is. Let’s go on this trip and figure out what’s important to us and what we really want, and go from there.”

You’re from Kauai, right?

Yeah.

Where is John from?

He’s from Spokane, Washington.

So yeah, [both of those places are pretty different than] Southern California, which is great, but I could see how if you’re there for almost a decade, you might want a change.

Totally. And we love Encinitas. If Encinitas were surrounded by forest, we would never leave. But to get to quiet, empty nature with green trees takes like three hours, and that was hard for me. I went to college in Santa Barbara and you can go 10 minutes from downtown and go on a hike, and be alone in nature, and that, to me, is so important. You cannot do that [in Southern California]. You can take a walk on the beach, but there are like a hundred people there and it’s not the same. So, I think both of us really crave that.

I wanted to move back out there after grad school, and then I went to Australia instead, and came up here [to Maine]. [Now,] I feel like I’m so used to not being around quite so many people. And I really like being in a quiet area, surrounded by nature. I do miss the ocean, though. I mean, there’s an ocean here, but –

It’s a little different! [Laughs.]

Yeah. Have you been surfing?

We haven’t surfed since we were on the West Coast. But I have my 5/4 with a hood – I don’t even know if that’s warm enough for here!

Yeah, I think it should be. I have surfed here in a 5/4 with a hood and mittens and booties. It works. I mean, your face is cold, but… I haven’t been in a while, but I’ve heard the water is pretty warm for Maine in the winter.

Yeah, I want to go surf in York. That’s been my mission.

York is really fun. And I feel like as a longboarder, you’ll totally appreciate the wave.

I know, I’ve seen pictures that [Nick LaVecchia] has posted of Mikey DeTemple and I’m like, “I want to surf there!” We stayed a night there on our way up from New York. We got in really late and pulled onto a random street and slept, and then got up in the morning and drove around, and it’s so cute there.

That’s another place that felt like it could be home for me. It’s tough trying to pick where you want to be!

I know. Have you ever thought of living here in Portland?

That’s kind of where I’m at right now. Do I want to move to Portland or move far, far away?

If I were going to move back to California, I’d probably move to Santa Cruz. It’s like an hour from San Francisco, closer to the mountains, the surf there is so fun, and it’s such a fun community of great people who are down-to-earth.

It is a cool town. I’ve got to make some kind of moves, because I’m like having visions of myself being a 40-year-old cat lady living in my parents’ house in the woods.

[Laughs.] Yeah, I hear you.

How long have you been vanventuring?

We started at the end of July, so just about six months. We left from San Diego, drove up the West Coast, and skipped Big Sur because we’ve done it a bunch. We timed it poorly because we had a wedding in San Diego and then my family reunion in Hawaii like 10 days later. Our plan was to fly out of Seattle, so we only had 10 days to get up the coast. That was another reason we skipped Big Sur. Anyway, we spent a lot of time on the Oregon coast, which was amazing. It’s so beautiful. And then John proposed there…

Yeah! Congratulations!

Thank you! It’s really exciting. After that, we went up into Vancouver Island, and then my back went out. I don’t know why or what happened. Our plan was to go all the way up to Tofino and surf up there, then go to Whistler and mountain bike or whatever, but we had to cut that short because I couldn’t do anything. I went to chiropractors, a naturopath, and a masseuse, and couldn’t figure it out, so we went to [his cabin in Washington] for like a week to rest. After that, Tofino was so far out of the way, so we went to Banff and Jasper.

I’ve heard that Banff is amazing, I’ve been wanting to go for years.

Oh my god. Go there. Immediately. Or, actually, go there in the fall. September was amazing because the trees were all bright-colored and there were glaciers behind them. It was like the most stunning thing you’ve ever seen. When we were there, I was like, “Man, I wish I would have come here when I was in my early twenties and just lived [here],” because there are so many young people and everyone’s just working at the yoga studios and at the mountain, and just doing their thing. And there are really good restaurants. It’s a fun vibe.

After that, we had a wedding in Montana, then we went to Missoula, Bozeman, and Sun Valley, Idaho, which was really cool. We went back into Yellowstone for a couple of days and then to Jackson Hole and spent a week there.

So was all of this in the summer and fall?

Yeah, September and into October.

Was it killing John to not be able to ski?

Yeah, I know! It was. But it was so beautiful and they have the best camping [in Jackson] that’s just public land that you can go park on. [It’s] free and there’s no one around, and you’re waking up to these crazy views of the Tetons like, “Is this for real?” The best camping of our trip, by far.

That’s cool. When I was out there, we just stayed in the National Park campgrounds and they were great, too, but I did not know that it was an option to camp on public land.

We had friends there, luckily. Otherwise, we wouldn’t have known, either. We’re going to try to be better about doing our research and finding places like that.

[When people hear what you’re doing] I imagine that you must get a lot of, “That’s amazing and so inspiring!” Because what you’re doing totally is, but I was wondering if you had any naysayers when you first said, “So, we’re going to quit our jobs and live in a van.”

No, I don’t think we really did. I think that most of the people who are in our lives are similar and wish they could do it, too. [Laughs.] And our parents – my dad, especially, was like, “Finally! You’re living your life and not just working!” Because my dad moved to Hawaii from California when he was like 20, and has been an artist/musician/caretaker of this beach house for almost 40 years, and has always been like, “You work too hard! What are you doing? Live!” [Laughs.] And even my bosses – the first thing they said when I told them was, “Can we come?”

That’s awesome. Since you’ve been on this trip, have you surprised yourself at all?

Yeah, I’ve always thought myself really carefree and spontaneous, and finding myself in places that are outside of my comfort zone leads me to wanting to plan out where we’re going to sleep, and feeling like this uptight planner person, which I never thought I was. And, realizing how much of a scaredy-cat I am. [Laughs.] And how much I’ve lived in a bubble my whole life.

Yeah, I can relate to that. I think I’m brave, and then I’m in a tent in the middle of the woods and I’m like, “I’m so scared right now. Why?” But I feel like that’s so valuable. Do you feel like you’re getting past it?

I think we’re on our way to getting past it. I think it’s going to take some more doing it. For me, little things [are helping]: Hearing every noise, your brain just takes off, and then you can’t sleep, [so] I downloaded an app that creates white noise, which has [helped].

How long have you and John been together and how did you get together?

He has been at Powder the whole time I was at SURFER. I had met him at the office, we said hello in the halls, but we had never had a conversation before. Like for five years. And then I don’t know what changed. I think I changed and got out of my shallow, I-want-to-date-a-surfer thing. I started going over to their side [of the building] and talking to people there. And then he invited me to come over and watch the – this is so dorky – The State of the Union Address.

That’s amazing!

[Laughs.] Oh, so I’d moved from San Diego to San Clemente, and little did I know that a year before, he had moved from basically next door to me in Cardiff to seven houses away from me in San Clemente.

What! That’s so weird.

I know, and we didn’t know at the time. So anyway, I was living by myself and I didn’t have a ton of friends in San Clemente, so I went over. We left at the same time, talked [outside] for a long time, and he was like, “Do you want to go get dinner?” We went to this Mexican place and talked for hours. [We] just started to hang out. Three weeks later, he went on a ski trip and broke his pelvis at a resort outside of Seattle and couldn’t come back for six weeks. Three weeks in, I was like, “I’m coming up there to visit you.” And he was like, “Okay?” I went up there and stayed at his house, with his mom, and after I left, we talked on the phone every day for three more weeks, and by the time he came back, it was like, this is it.

Do you believe in soul mates?

Yeah, I totally do.

And you just know.

Yeah. And if we had gotten together or had a conversation earlier, I wouldn’t have been interested because I had so [limited myself] to one type of person, and I’m so happy that I ended up with someone different than me who has turned me on to this whole world away from the beach. There’s so much more to this world than what’s on the beach. [Laughs.] It’s been amazing.

Were you a skier or mountain person before, or do you ski now?

I had snowboarded like once or twice a year since I was about 17. He’s converted me to a skier – last year, so I’m not good, but I try. And it’s been really fun to learn. I mean, I think he thought he would end up with a girl he could go touring with and do all of this crazy stuff with. Maybe some day.

Yeah. He probably surfed [at least a little] living in Southern California, anyway?

Yeah, but he hadn’t done it until he moved there when he was like 23, so he was new to it, too.

How do you choose your route?

We decided we wanted to spend our winter in the Northeast because John has never skied in the Northeast and he’s skied everywhere –

Awww…

I know, and now we get this winter. [Laughs.] So we’re hoping that if we stay another month, we’ll get some [snow], at some point. We always wanted to go to Maine and Vermont, so it was kind of our mission to get over here while the leaves were still on the trees. We didn’t get up here until the end of December. [Laughs.] We just need to get back out west by the wedding [in September], so we’ll explore the East Coast, probably starting in March, and then do the South in early summer and head back in late summer.

So you have a general idea of where you’re going and then you kind of just wing it?

That’s how we did it for the first part. For the second half, we’re thinking we’re going to pick our key places and not try to see everything, because you just spend so little time everywhere and you’re constantly moving. It’s really exhausting. So, I’m proposing – and I only came up with this a couple of days ago and haven’t talked about it with John yet – to pick the National Parks we want to see, and towns like Charlotte, Savannah, and Austin, and actually spend a week in each of those places. Which I think will make the trip a lot more enjoyable and we’ll get a lot more out of each place. We’ll miss a bunch of stuff, but… maybe we’ll just keep going after our wedding!

You might not miss that much. It could work out that you’re spending a week in Charlotte, but you drive a scenic route to get there. I did one cross-country trip, with my boyfriend at the time, when I was 18.

Oh, wow.

Yeah. [Laughs.] We went like three days after I graduated from high school. We camped and it was really fun, but we had like 40 things on our list and we were determined to see them all. We did see them all, but we were only gone for like five weeks, and it was driving every day, all day, and sleeping one night in each place. It was so exhausting. I didn’t camp again for like another five years.

Were you tent camping?

Yeah.

Setting it up, taking it down, setting it up? Aahh! That would be so exhausting! [Laughs.]

I mean, it was fun and super affordable, and a good adventure, but yeah.

When we were originally trying to figure out which vehicle we wanted to use, we wanted to go the VW route and then said, “We are not mechanically inclined; we’re not going to be able to fix it if it breaks down.” Then we were like, “Well, why don’t we just get a really fuel-efficient car and tent camp?” I’m so glad we didn’t do that. It would be such a different experience. There’s a couple called Fresh Off the Grid on Instagram – who you should follow – they’re driving around the country in like a Geo Metro and it’s awesome. They have a good food blog. But a friend [of ours] got a Sprinter and we started looking at them. They’re so nice. John’s 6’1” and it has a 6’3” clearance and he can stand, which was a big deal, and we finally decided to do that. But yeah, to really see all [of the places] that we went through [on the first half of our trip], you’d need like a year. There’s so much beautiful amazingness in this country. It’s crazy.

We were thinking we were going to settle down after this and move to Portland, Oregon, but just this week, we were like, “Why? If we’re still working remotely, it doesn’t really matter. We don’t need to get a place. Do we?” We’ll see, six months from now, if we’re tired of being so mobile, but right now, we feel like, why would we spend $1,500 a month on rent when we can use that money to travel?

You know, you may not tire of it.

I know.