First of all, what a damn privileged thing to even write or think about!
The more I think about it, the sillier it sounds. “The stresses of planning a trip.” Ha. Sometime last year, my family talked about how we plan trips and vacations. I’ve seen a lot (read: a lot) of the Midwestern United States—you name a city or a suburb or even a town, and I’ve probably been there. We weren’t the kind of family that went to Europe for summer vacation or Mexico for winter break, but we were the kind of family that went to Munising, Michigan for spring break (and that’s upper Michigan for you). But the destination isn’t really the point.
Of all the family trips that we’ve taken, most of them small or oddly niche, I have never seen my mother plan a trip. Like my memory goes back about 20 years and not a single time has she planned something. The thing is, I didn’t even realize this until I started going on trips without my folks as a young adult. I suppose it was a trade off for my parents. My mother dealt with and planned everything at home, from nightly dinners to church events, and my father dealt with the external things that either involved bills or reservations. Because they had kids, my father’s trip planning involved youth-friendly activities, educational items like museums, and food he knew all of us would eat without complaining. But it was all very fluid, because who knew when one kid would throw a tantrum or another kid would throw up or everyone would just ask to go home?
So honestly, I don’t know why I ended up a freak about planning things. (Ironically, my brother doesn’t plan anything besides the flight or drive and decides what he’ll do the next day the night before.)
I’m the kind of person who plans meals and activities down to the hour for trips (with time built in for coffee breaks and subway delays, of course). I tell myself it’s not that weird because I don’t plan down to the minute, but is there really much of a difference? I start the planning process maybe three to four months out. By two weeks before departure, all tickets to attractions have been purchased, all reservations to special meals have been booked, and the itinerary has been double checked to make sure everything makes sense. And what does “makes sense” mean you ask? It means that I’ve written out which train or bus to take, linked websites or Instagram profiles to the itinerary, and confirmed opening and closing times for each location. It’s overkill for sure, and I go back and forth between telling myself to chill out and telling myself it’s OK to just accept this is who I am.
I’d say half of the trip planning process is fun. I get to look through dozens of reviews and articles about the destination or sift through the posts I’ve saved on Instagram over the years that I might finally make use of. I get to dream about what it will be like once I arrive and see the sights or eat that bowl of noodles that I’ve been looking forward to. I get to think about what moments I can share with the person I’m traveling with and where we can take a cute photo or two. Besides, future trips are one of my favorite things to think about in general.
The other half of planning is just pure stress. Searching for restaurants and things to see, then narrowing down the list can feel overwhelming. Working around opening hours for businesses and museums, figuring out what places are near each other, and considering the money I can spend can all be draining. Still, I know that the more planned I am, the better the vacation I will have—this may not be true for everyone, but this has been my own experience. Upon planning for a trip to Korea that I have upcoming, I asked myself again: why do I find it stressful? I’ve ignored that question a few times in the past, however this time I identified a few reasons.
Reason One: I feel the need to make my time and money count.
This is the biggest reason and definitely what came to mind first. If I’m spending my hard-earned money and my precious PTO, I better make it count. I want to enjoy every museum I go to, every meal I eat, every coffee I buy, and every landmark I visit. I know very well that this is not possible because some things just aren’t going to be my cup of tea, and I won’t know this until I go.
Take the Museum of Natural History in London for example. It’s one of London’s most famous and popular museums, and while the architecture of the museum is super cool, I just didn’t think most of the exhibits were exciting. Yeah, I’m kind of bummed I spent two hours there, but I also just had to learn what the place was like. On the flip side, I wasn’t sure I wanted to eat at Masala y Maíz (which a friend recommended) because there were so many other spots I wanted to try in Mexico City, yet it turned out to be one of my favorite meals in the city.
Reason Two: I want both myself and those I’m traveling with to be impressed and satisfied.
One disappointed person is bad, but multiple disappointed people is just awful. I want everyone, including myself, to be happy with the trip! This goes back to the first reason: we all want to feel like we spent our time and money wisely. I usually travel with my partner and add things he wants, but I don’t want the things I pick to be a letdown for him.
Reason Three: I don’t want other people to think what I did is lame.
This is so, so, so stupid. I know it is, and I think part of it is just due to living in the age of social media. Did you even go if you didn’t post? Did you even have a good time if you didn’t do that super trendy thing in that city? Saying this line of thought is dumb is an understatement, but I still have these types of thoughts come and go.
A non-internet example of this is why my father said “you went all the way to Iceland to go on a bus tour?” I’d be lying if I said I didn’t feel self conscious, though that thought disappeared pretty quickly because I wouldn’t have seen the Golden Circle on my budget otherwise.
Reason Four: I want to enjoy my time when I’m there rather than think about details as I go.
This is another big one. If everything is planned, 90% of the trip goes smoothly (and the other 10% like traffic issues or sudden closures are out of my control). Sure, there are spots in my itinerary where there’s time to roam around or get a cup of coffee at a place I didn’t know about, and sometimes that ends up being the best part! However, I’d be seriously bummed out if a gallery or restaurant I’d been dying to go to didn’t have last-minute tickets or walk-ins. There are also time-dependent things I like doing, like catching a view right at sunset, that I wouldn’t want to miss out on.
So what am I going to do with this information? I’m not going to stop planning my trips because it causes me stress, but I’m going to try to lean into the fun parts of the process more. If things get stressful while planning, I’ll pause for the day and start again later. Given that I understand that wanting to plan is part of who I am, I’m going to be focusing on how to make the process more enjoyable and relaxed instead of just letting all of it loose and figuring out all of it as I go.