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 Small Game and Welcome to the Goddamn Ice Cube. Have a question of your own? Write to us at toughlove@outsideinc.com.

　　I grew up at my family’s kayak company, and have been helping to guide trips ever since I could hold a paddle. As I got older, I started bringing my friends along. Two of them got really involved with the company, and this summer, they’re both working as guides. Now, it seems like they think they own the place, and it feels disrespectful. Do you have any advice for handling one’s own friends in a workplace?

　　Here’s the thing: your friends are insiders at your family’s company. They’re not as close as you, of course. No one will ever be. But they work there. They’re on the inside track.

　　That changes your relationship with them—and your sense of authority—and it’s gotta feel weird and unfamiliar.

　　For years, you’ve been the one in charge. You’ve welcomed your friends on adventures that they couldn’t access any other way. You’ve granted coveted invitations. You’ve shared your family’s gear, and more than that, you’ve shared your world. And what a world it is! The only thing cooler than having a friend with a family kayak company is being the friend with a family kayak company.

　　Trust me, I know. I grew up with a pal whose dad was a rafting guide (as it turned out, he had guided my parents on their honeymoon) and she invited a small group of us on a multi-day float trip each year. It was incredible. We left school early on Friday. Slept on the shore. Spent hours twirling in the current, cracking open cans of root beer, and leaning back to dip our hair in the water. I remember floating on my back in the brown river, watching my toes breach the surface, and thinking that there was absolutely, definitely, nothing better in the world than this.

　　My friend, the guide’s daughter, captained the kids’ boat. She knew how to navigate rapids, identify birds and turtles, and set up camp in the evenings. She did this kind of thing all the time. 

　　She was our queen.

　　Until now, that monarch has been you.

　　But now your friends are guides, too, and that’s destabilizing. You were the cool one because you got them access to kayaks. Now they don’t need you for that, and it makes your role seem superfluous. Where does that leave you? What do you have to offer? I want to assure you that kayaks are cool, and you’re cool, but not just because you’re doling out kayaks. And the fact that your friends are moving up in the kayaking world doesn’t mean that you’re moving down. 

　　You’re always going to be more of an insider than they are, because this is your family’s company. Even if your friends start their own kayak companies, you’ll have something they don’t, which is the experience of growing up with this. Seriously! You can be 50 years old and mention that you grew up at a kayak tour company, and people will be impressed and want to hear about it. I know I do.

　　The fact that your friends are moving up in the kayaking world doesn’t mean that you’re moving down.

　　Although by then, I hope you’ll feel confident enough in your own worth that you won’t feel the need to measure yourself against the people you care about. I don’t say this with judgment, truly. It sounds like you’re young, which means you’re still negotiating all that you are, and all that you have to offer. That’s a big journey. It’s destabilizing by necessity. Your identity, your authority, your passions—all of those things will evolve, and the feelings and insecurities you struggle with now will work themselves out with time.

　　Which is all to say that if your friends’ new roles make you uncomfortable, that’s not necessarily a bad discomfort, but an important one. If it helps, try to find another friend (someone you don’t work with) who will help you process all the worry and annoyance this brings up. Ideally, this should be someone who’s not prone to drama, and who can empathize with the ways you’re feeling challenged without assuming that someone must be at fault.

　　If the problems with your newly-employed friends shift from the emotional to the practical—if, for instance, they’re going places they’re not supposed to, using equipment that’s not permitted, and so on—then that’s a different kind of challenge, one that puts you in a tough spot. Your best bet for managing their behavior (while maintaining your bond) isn’t to issue demands, but to appeal to their friendship: “Hey guys, this is against the rules, so it puts me in a weird position. Can you not?” Good friends will stop. They’ll value your friendship more than their personal goal of a moonlit naked kayak trek or whatever. And if they don’t, then maybe their friendship wasn’t that real to begin with.

　　But it doesn’t sound like things have come to that, and I doubt that they will. The season is just starting. Pretty soon, you’ll be less startled when your friends bust through STAFF ONLY doors. And by then, I wouldn’t be surprised if you’re well on your way to embracing your best summer ever.