“My Family Disapproves of My Nomadic Dreams!”

Welcome to Tough Love. Every other week, 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@outsidemag.com.

I am fortunate enough to have a stable job that pays pretty well in an industry not known for its stability or pay, but I am pretty unhappy in it and somewhat disenchanted with my field of work as a whole. When my apartment lease is up, I’d like to quit this job and travel for a bit. I never really got to do that post-college, because I was always going from one thing right into another. I’m thinking of doing a thru-hike or pursuing some other extended outdoor adventure for a few months—something physically and mentally challenging—then figuring out career next steps.

Here’s the problem: My family really values stability and consistency. They don’t take risks, financially or physically or life plan–wise. I’m worried about how they’ll react to these plans—not the “woman adventuring alone” part so much as the “throwing stability and certainty to the wind and taking a big plunge into unknown adventure with an unforeseen destination.” I’ve thought a lot about how this’ll work financially, and I’m pretty confident that I’ll be able to find freelance work in my field to make ends meet post-adventure until I find a full-time job again. But still, I suspect my parents will frame this announcement as “she’s running away from her problems” or “she doesn't know how good she has it.” Meanwhile, I’m framing it as “I feel stuck in one area of my life, I’ve worked on improving it, and it hasn’t really changed, so now I’m going to focus on a totally different goal for a while.” How do I have this conversation with them?

It sounds like your family did a great job of instilling their values in you, because you’re being super-responsible in your adventure planning in both the medium term (how to afford your adventure) and the long term (how to have a sustainable career after you’re done). You’ve made the thoughtful, courageous decision to leave a field that makes you unhappy, and you’re taking the chance to build yourself up along the way. You may or may not hear this from your family, so let me tell you now: You’re doing an incredible thing and should be proud of everything you’ve done to get here. I’m excited for you!

On the day you tell your family the news, let a friend know what you’ll be doing, then ask to meet your parents at a restaurant or other neutral space. That’s not because you’re likely to fight, but because there’s nothing like sitting between your parents on your childhood couch to make you feel like you’re 12 years old again—and in this case, you’ll want to remember that you’re an adult informing other adults of your life decision. Know that you’re not asking their permission, nor are you apologizing. In fact, you’re doing something far better: You’re sharing good news.

Expect them to balk; even the most open-minded parents do. Take time to answer their questions, outlining the steps you’ve taken to plan the trip responsibly. Let them know that you do take your career seriously, and that this decision is another way of prioritizing your life goals. You can suggest plans to take a hike or watch a thru-hiking documentary together so they have the chance to conceive of the trip from a different angle. (It might help them to hear about it from someone other than you; some parents will always treat ideas from their child as ideas from, well, a child.) Tell them you feel happy about your decision and that it would mean a lot to have their enthusiasm and support. Then give them a hug, tell them you love them, and leave.

Now call your friend, meet up for beer or cheese fries, and either celebrate or vent about the evening’s conversation. You did a tough thing and deserve to decompress with someone supportive.

Maybe, once they’ve slept on the idea, your parents will come around. In that case, great! But you should be emotionally prepared for the possibility of embarking on this journey without their blessing. It doesn’t mean they’re not proud of you or that you’re running away from your problems (well, except for this particular one). It just means you’ll have to move forward on your own. Nobody’s family agrees with their decisions 100 percent of the time, and if you’ve done the work to take care of yourself and break the news to them with compassion, you’ve done your part well. If, during your travels, you still feel the burden of your parents’ judgment, send them postcards rather than making phone calls. They’ll still hear from you, but you’ll be protecting yourself from the weight of their disapproval.

In the long term, it could be that the only way to reassure them is to do the trip and be okay. People’s narratives change. Once you get home and your life is stable again—at least by their definition—you might hear them talking about your adventure as if they approved from the beginning or even came up with the idea in the first place. If that happens, just smile and embrace it. It may be annoying, but it means they’re coming around. They taught you how to live, and you’re teaching them, too.