I Like to Be Prepared, but My Travel Partner Just Trusts That Things Will Work Out

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.

My sister is my travel partner. We’re both in our thirties, and have been traveling together our whole lives. She’s someone who everyone knows as a cheerful person, which is something I usually appreciate about her. 

However, there are times when her optimism drives me crazy. For instance, she doesn’t feel the need to reserve camping spaces in advance because she “knows that things will work out the way they’re meant to.” More recently, we are planning a trip with our mom, who’s getting older, and I said we should make sure we’re near a hospital just in case, because she has some health problems. My sister accused me of being negative. I’m sure that if she were writing this letter, she’d say that her sister is pessimistic and always puts a damper on trips by anticipating the worst, or only seeing the bad side of things. But it’s getting to the point where we’re both touchy when we plan things because we anticipate the other person will have the opposite perspective. Surely there’s some middle ground?

A few years ago, I went on a long winter backcountry trip, and it rained. Instead of the sub-zero weather that we all expected, temps soared into the high thirties and low forties, and all of our gear, clothing, and shelter got soaked through. Naturally, gear that’s designed for sub-zero temps isn’t usually waterproof, so people were drenched to the bone for days. Nothing was going as planned. And yet everyone kept up a cheery facade, even when their cheeriness was patently absurd. “It’s so beautiful here,” they’d say, their eyes twitching. “We’re lucky to be here”—with teeth chattering, as frigid water streamed down their face. I mean, it was beautiful, sure, because it was wilderness and all that, but it was also totally miserable. Finally someone started laughing hysterically. “I’m sorry,” they said, “but this weather sucks. Tell me nature isn’t playing a prank on us.” Then it was like the floodgates opened; suddenly everyone else started laughing, too. The person who complained about the rain wasn’t being pessimistic, but realistic, and ironically it made everybody much happier; we got to laugh at the absurdity together. We could acknowledge it, roll our eyes a little, and move on.

Of course, it’s easy to overdo it on complaining. If it’s pouring rain and someone goes around every five minutes saying, “This rain sucks,” it’ll only make everyone miserable. Weather happens; it won’t always be ideal. If someone whined about it constantly, I wouldn’t go camping with them anymore. And overall, I’d probably pick a companion who’s more positive than negative.

But depending on the circumstances, false positivity, or positivity that’s knowingly out of touch, can make people feel like they’re in a fever dream. It can be disorienting or invalidating. Not all things are equally good, and it’s OK—in fact, it’s responsible—to acknowledge that. One not-good thing is that your mom’s having health issues. That must be scary for everyone. Maybe your sister’s afraid that by acknowledging your mom’s health problems, or planning for them, she’s allowing them to be real.

Based on your examples, it seems like your sister’s positivity is less about how she views things in the moment (although maybe that’s part of it), and more about how she chooses to plan for the future. Obviously, when she’s deciding whether to pick a campsite, the stakes aren’t super high; if you get to the campground and nothing’s available, you’ll just have to sleep in your car, drive elsewhere, or have a vaguely unpleasant night. But your mom’s health is much more important. You shouldn’t be compromising at all on that one; you should evaluate the situation as objectively as possible, together with your mom, then get your sister to agree. There’s more than a trip on the line.

Unless you and your sister have other conflicts, I wonder if this is something you can talk about really explicitly with her. Like: “I know we have different viewpoints on things, and I love your positivity. I know I probably seem negative to you sometimes. But I’m not going to be able to enjoy the trip if I’m worried about Mom the whole time, and I don’t think she will, either. This is just something I can’t be flexible on.”

Obviously, your mom’s opinion matters most here. What are the odds that she might need medical care? What does her doctor advise? What does she want to experience? You shouldn’t just be thinking about keeping your mom safe in the worst-case scenario, but also about making sure she’s having fun in the best possible scenario. What’s comfortable for her right now, physically and mentally? What does she enjoy? If she’s the one with the most limitations, make sure that the trip is comfortably within her bounds, so that she’ll be able to participate fully without worrying or straining herself. And keep in mind that her needs for comfort might be very different from yours and your sister’s. Even if it’s not a matter of safety, she’d probably be much happier in a soft bed than, say, on the floor of a tent.

There’s a reason that people say to hope for the best, but prepare for the worst. In some ways, your different perspectives have probably made you and your sister good travel partners—because she’s thinking of the serendipitous things that might happen, and leaving space for them, and you’re preparing just in case things go wrong. That’s a nice balance to have represented on a trip: your sister’s helping you be a little more spontaneous, and you’re there to catch her if she falls. When it comes to your mom’s safety, there’s no compromise to be made, and I hope that your sister will have the sense to respect that. But for your other trips, well—stick some extra raincoats in the trunk, then let go and enjoy yourself. They’ll be there if you need them.