Turning Travel Frustration into Mindfulness

In January of 2023, I set out on what was supposed to be the ultimate Tokyo trip. This would be my fourth time in the city—having visited previously with my family, friends, and even for work. I was excited for this one because it would be my first group trip, and I was looking forward to the "hangover style" activities: crazy nights out, but in an organized way with some real planning behind it. The plan was to go with four other guys—co-workers from the restaurant bar I used to work at. We weren’t the closest, but close enough to plan a trip together. At least, that was the idea. Before the trip, we met up to plan everything out and make sure everyone’s needs and desires were accounted for. We figured that with everyone’s input, we could design a trip where each person got something they wanted without stepping on anyone’s toes. It was supposed to be a win-win for all. However, things took an unexpected turn before we even left. One of the guys, who I considered the “glue” of the group, got grounded by his new girlfriend at the time, which meant he couldn’t come. But that wasn’t the worst of it. Another co-worker—someone we weren’t as close with—overheard our conversation about the trip and decided to invite himself into the mix, bringing us back to five people again. So, while we were still a group, the dynamics were already shifting before we even boarded the plane.

When Expectations Don’t Match Reality: The Early Signs

Before the trip, we had a clear vision: a laid-back week of great food, spontaneous drinking nights, and easy laughs across Tokyo. We weren’t expecting perfection, but we did expect fun—and for the most part, we thought we’d planned well enough to keep things smooth. Tokyo, after all, is a city where just walking down the street feels like an adventure. Add ramen, izakayas, and late-night convenience store runs? We were all in.

But almost as soon as we landed, something felt off. Not in a dramatic way—just enough to make me and my closest friend start noticing the shift. There wasn’t tension, but there wasn’t flow either. The vibe we had back home didn't fully translate on the road.

I found myself naturally sticking closer to that one friend—the person I could count on to check in, adjust when needed, and just move through the day without friction.

It wasn’t chaos, but it wasn’t the energy we had hoped for either. Conversations turned into group shrugs, plans turned into random decisions made at intersections, and the group started to split in ways none of us had expected. We were only two days in, and I already knew: this trip wasn’t going to go the way we imagined.

What Not to Do When Traveling with a Group: 4 Things I Learned the Hard Way

Traveling with friends can either make the experience ten times better — or ten times more exhausting. Whether it’s a trip to Tokyo or anywhere else, group travel requires the right mix of personality, communication, and boundaries. If not? It turns chaotic real fast. What started out as a well-planned idea quickly became a game of damage control. Here's what I learned the hard way during one of my most frustrating trips ever.

Don’t Travel Without Clearly Defined Roles

We didn’t really have a “leader” in our group—however, as mentioned, we did have a plan. Did. I usually help kick off the planning since I used to work as a trip planner, but I never try to take full control. I just want everyone to have a say and enjoy the experience. That said, we obviously didn’t stick to the original plan. Most decisions ended up being made on the fly, usually while standing on the side of the street—five guys figuring things out in real time.

The problem was… the “baby brother” had way more needs than anyone else. He was the youngest in the group and often indecisive, mostly because he was getting instructions from his girlfriend via phone the whole time. The other two guys? They treated him like their little brother and just followed whatever he wanted, no matter how random or last-minute it was.

Looking back, I think the friend who could’ve balanced the group dynamic was the one who didn’t come—because his girlfriend told him not to. Without him, everything felt unstable. If I were to do it over again? I’d make sure we had an honest conversation about decision-making roles before the trip even started.

Don’t Let Unaligned People Join Last Minute

This is one of the biggest mistakes we made: letting someone tag along just because they felt emotionally left out. One of our co-workers overheard the trip being discussed and basically guilt-tripped his way into joining, saying stuff like, “You’re not really going without me, right?” No one wanted to deal with the awkwardness, so we let him in.

That one addition changed everything — the plans, the destinations, even the restaurants. He had completely different hobbies and preferences, and the entire group started bending around what he wanted, instead of what we had all originally agreed on.

The truth is, no matter how long you’ve worked with someone or how close you think you are, if their travel style doesn’t align, it’s okay to say no. Don’t feel guilty about it. If you can't avoid it? I’d honestly recommend either rescheduling or splitting into separate itineraries.

Don’t Let Outside Influences Hijack the Trip

Our “baby brother” wasn’t the worst guy. He was actually a decent person — just not a good decision-maker. He would constantly change his mind or freeze up whenever it was time to commit to a plan. And more often than not, it was because he was checking in with his girlfriend.

One moment stands out the most: we waited two hours in line for a sushi restaurant. And we were all confused because that’s not something our group usually does. Turns out, his girlfriend had told him to go try it — and it ended up being one of the worst sushi spots I’ve ever eaten at in Tokyo. The only gimmick was that you could throw your used plates into a slot machine and possibly win some stickers. That was it.

After the trip, we talked to him. He apologized for how things turned out and admitted he was caught in the middle — not just between us and his girlfriend, but also with the extra guy who forced his way into the group. We all agreed it probably would’ve been better if it were just the three of us.

If I could give one piece of advice? Set expectations around personal space and outside communication before the trip. Let people know it’s okay to take solo time — I had to step away a few times just to keep my own sanity. It helped a lot.

Don’t Stay Quiet When Things Go Sideways

We started realizing the trip was going off track by the second day. Me and my closest friend tried to speak up, suggested we go back to the plan, and hit the places we originally wanted to visit. The other guys nodded, seemed to get it… then five minutes later, we were back to winging it.

No one wanted to hurt anyone’s feelings, and I get that. But ignoring the problem didn’t solve anything — it just dragged the frustration out longer. In the end, even trying to speak up didn’t change much, but at least I can say we tried.

If you’re planning a group trip, please make sure everyone knows what kind of group it is. Are you flexible explorers? Hardcore itinerary followers? Is everyone okay with splitting up sometimes? The composition of the group matters just as much as the destination.

A Walkthrough on Turning Travel Frustration into a Mindful Reset

Now that I’ve covered what not to do when traveling in a group (well, basically... don’t be like me, haha), let me walk you through my thought process and how I managed to work through that frustration and find a little peace of mind. It wasn’t pretty, but in the end, I learned a couple of valuable lessons that really helped me out. Hopefully, they’ll help you too... so please, bear with me.

When the mood turned

After the first night, we already sensed something was off. By the second day, it was obvious. We found ourselves ranting about the guy who had kind of forced his way onto the trip. Apparently, someone in his family had passed recently, and he wasn’t supposed to eat beef. The issue was—he only told the “baby brother,” who, in typiucal fashion, forgot to let the rest of us know.

So we ended up eating at a popular Yakiniku place known for its beef. The guy spent most of dinner guilt-tripping us, saying there wasn’t enough for him to eat. Then he’d head to the convenience store afterward to top up with rice balls AND having to chip in for the dinner when we didn’t ask him to. What frustrated us more wasn’t even that—it was that he didn’t care about the food experience in the first place. He wasn’t there for the food, the fun, or even Japan. He just came to tag along with the baby bro.

Then came the complaints—about how expensive the food stops were, how unnecessary they felt. He started filling up beforehand just to avoid eating too much with the group, so that he wouldn’t have to chip in. It became a cycle that wore us all down. We were constantly planning around someone who didn’t even want to be there in the same way the rest of us did.

It got to a point where my closest friend and I seriously considered splitting off from the group. But they claimed they couldn’t read maps, and we were the only ones navigating. They also didn’t like the idea of separating. The irony? They were totally fine with dragging us through their chaos and canceling the spots we’d actually voted for.

The Reluctant Tour Guide

Because I knew the city best, I ended up leading most of the time. They'd mess around behind me while I navigated through Tokyo. Part of me hated it—being the guide on a trip I didn’t sign up to lead. But honestly? That quiet space in the front gave me a sliver of peace. I got to focus on the details of the streets, the flow of people, the culture. It helped keep me sane.

I reminded myself—I paid for this trip too. I deserve to enjoy it. I wasn’t going to let other people’s energy completely hijack my experience. Self-care isn’t always bubble baths and spa days. Sometimes, it’s mentally drawing a boundary while walking five feet ahead of the chaos behind you.

Finding Tiny Escapes

Any time we ended up in shopping areas or random downtime, I found ways to be alone—or at least pull my closest friend aside. We’d “go check something real quick” just to decompress. Those little vent sessions were gold. Sometimes, just watching local kids run around or students eating snacks after school brought me back to the present moment. That’s the kind of stuff that makes travel feel real again. Even if I couldn’t reset the entire trip, I could still reset myself.

The Silent Protest

By the middle of the trip, I gave up trying to steer the group. I stopped suggesting where to go. I’d simply ask what the next stop was, look up the route, and guide them there. Funny enough, that silence caught their attention. When I stopped engaging, they finally started noticing how much they'd been messing with our plans—and how it was affecting both me and my friend. The baby brother and one of the other guys made a bit more effort to compromise after that. Day 3 and we finally saw a tiny shift. Was it too late? Maybe. But at least it didn’t go completely unnoticed

Finding Peace in Chaos

Looking back, there were a few things I took away from this trip—hard-earned lessons that apply not just to travel, but to life in general.

1. You can’t control people, or everything around you.
   Sometimes, people won’t compromise. Sometimes, they’ll do the exact opposite of what they promised. And it’s not your job to fix everything. You can only decide how you respond.

2. Perfect plans don’t guarantee perfect trips.
   You can plan down to the last detail, and people might still bail when the time comes. Or maybe you’re the spontaneous one, and the group isn’t. That’s okay. Sometimes, with the right travel buddies, even winging it can lead to the most unforgettable adventures. It’s never about the plan—it’s about who you’re with, and how open they are.

3. Do a trial run before committing to big trips.
   Test your travel dynamic with a day trip or a weekend road trip. It might save your friendship. Among me and my friends, we joke that travel is the final test—for both marriage and friendship. (Half-joking… but not really.)

4. In group trips, you are stuck with each other—so carve out your peace.
   You paid for this time too. If it starts to wear you down, ask for a break. Suggest a meet-up time and place, and go find something you actually want to experience. You’re not selfish for needing space—you’re smart for protecting your peace.

To cap off everything, there was one moment that really saved the trip for me. After a particularly terrible sushi dinner where things were just… off, I asked to go off on my own. I made sure the group knew how to get back to the motel, walked them to the station, then peeled off and took a slow walk back toward the neighborhood.

That’s when I stumbled into this tiny little taproom—Okuda Bakushuten, near Asakusa. The place was small, no frills, and had almost no English menus. But I had offline Google Translate, and that’s all I needed. I ended up having a couple of local Japanese craft beers, nibbling on snacks, and just sitting there, quietly watching people laugh and enjoy their night.

That was a golden moment. One where I finally felt like I was on my trip again. No noise, no guilt-trips, no stress—just me, a cold beer, and the hum of Tokyo life around me.

📍 Okuda Bakushuten - 1 Chome-8-4 Asakusa, Taito City, Tokyo 111-0032, Japan

Sometimes, peace doesn’t come from controlling the situation. It comes from stepping out of it, even if just for an hour. And if nothing else, this trip reminded me of that.

P.S. These were just the highlights of the chaos—trust me, there were many little things that piled on. If you're the organized type like me, you'd probably lose your mind too, haha. Curious about the rest of the iceberg? Just let me know.