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(Photo: Nosyrevy, Getty)
Tough Love

My Friends and I Vowed to Never Settle Down. Now I’m the Only One Left.

We worked seasonal jobs to make enough money to spend the rest of our time traveling and feared a white-picket-fence life. But now they've all put down roots, and I still have the same lifestyle.

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Welcome to Tough Love. We’re answering your questions about dating, breakups, and everything in between. Our advice giver is Blair Braverman, dogsled racer and author of Welcome to the Goddamn Ice Cube. Have a question of your own? Write to us at toughlove@outsideinc.com.


Throughout my twenties I had a close group of friends who traveled together, working seasonal jobs and traveling in between with the money we had left over. Over a few years, we worked in more than ten different places. Sometimes someone new joined the group, or someone left for a while, but then we came back together. We were always having adventures when we weren’t working, and the jobs weren’t bad. We were all incredibly happy. I knew some things would change, of course, but I thought that most of us would live like that indefinitely. Everyone said they were afraid of the white picket fence life.

I’m in my thirties now and maybe you can guess what happened, but the group fell apart. People settled down, some of them had kids, and they ended up staying behind when the rest of us moved. I’m back at a job we had five years ago, but most of the staff is younger than me now, and I don’t relate to them as much. Most of all, I feel abandoned. We used to talk about growing old together and how we’d never live boring lives, but now it seems like they were just saying those things and didn’t mean them. If they hadn’t said those things, maybe I would have focused on finding a different life too. I feel foolish for taking them at their word. How do I move on?

I suspect that when your friends said they’d live on the road forever, they did believe it. Just like we can’t always predict how our lives will change, we can’t predict how the things we want will change, either. “I want to live like this forever” isn’t a lie if someone’s telling the truth about how they feel at the time; otherwise, it would mean that every marriage that ends in divorce was based on a lie. Some of them are, sure. But often, people just change in different directions. They grow and grow apart.

And if your friends weren’t lying to you, then you weren’t foolish to take them at their word. A little naive, maybe; a little extra hopeful. But you shouldn’t feel like a fool for trusting the people you love.

Still, this really sucks, and I’m sorry you’re going through it. It sucks when friends split up. It sucks when the things we thought would last don’t. It sucks that you thought you had your life planned forever and you’d figured out something that made you happy, and you had community, and now that community’s fallen away. It sucks that things you love have come, in part, to an end: swimming after work, jam sessions on bad-weather days, dance parties, beach nights, whatever those moments were that made you think: This is it. This is what I want forever. And then, of course, there’s that terrible whiplash of feeling like you had exactly the life you wanted, that thing so many people dream of, and then watching it drain away.

It is—I hate to say it—pretty normal that a lot of people settle out of seasonal work as they get older. It’s also normal for people to stop hanging out with friends in the way they used to once they have partners and kids. Not inevitable, of course—but normal. And it’s normal that happy times change, just as it’s normal for sad times to do the same.

But normal doesn’t mean easy. After all, few things in life are particularly easy. Although maybe the life you had, the good life with friends on the road, felt easy—and that, too, is part of the loss.

And now, here you are, with your life wide open again. I think it’s worth sitting with your feelings and figuring out which one you’re more upset by: that your friends aren’t like you anymore, or that you’re not more like them. It sounds like you wish you could have lived a seasonal and adventurous life forever—but it also sounds like, on some level, you wish you could be where your friends are now. Or maybe you want both at once, which is totally valid. If life stopped every time we wanted multiple conflicting things at once, we’d all explode.

What does your dream life look like now? Is it the same life you dreamed of ten years ago, or has that dream shifted? You should know that there are lots of people in their thirties who wish they had the chance to redesign things, or are simply too frightened to take the leap—and here you are, pushed to the edge, looking out at the possibilities. Do you want to settle down? Live on the road for a couple more years? Find a partner who wants to travel with you? Keep in mind that stability and excitement aren’t opposites; you might stay in one place forever and live endless adventures right there. You also don’t have to plan the next 50 years right now; coming up with a plan for the next three years, or year, or six months, is still a big step forward if you’re intentional about it.

Whatever you decide to pursue, you’ll need community. We all do. If you stay on the road, it’s worth seeking out and nurturing new friendships, as daunting as that can feel. Some of those should be with the younger staff, but try to seek out older folks, too; they’re more likely to be in a similar boat as you are, and they’ll have passed that late-twenties/early-thirties transition stage that has so many people shifting their priorities.

I’d also encourage you to connect with your old friends about all this. Even if they were the ones who dropped out of dirtbag life, so to speak, they might still miss it—and you—terribly. And those relationships haven’t ended, even if the proximity is a little different. Who knows, maybe you’ll end up in the same place as them again, even if it’s years down the road. Your adventures may look a little different at that point, but I promise they’ll be no less wonderful.

Lead Photo: Nosyrevy, Getty

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