#50 On being a messy traveler

and self-improvement as "a subtle form of aggression against who we really are"

Greetings from Hove, England, a place I didn’t know existed until a few days ago and where I’m a week into a three-week long trip, currently staying with a friend who reminded me yesterday that next week marks ten years since I quit drinking. On April 14th my sobriety will become a fifth-grader, and by some kind of miracle I will be in my favorite place in the world which is Sicily.

Every year since I stopped imbibing ethanol I’ve written a thing about it on the anniversary (like “Nine years of not drinking” or “103 ways my life improved in 3 years without alcohol”—all of them are in the archive if you’re extremely bored), and yesterday I told Cath (the friend I’m staying with, who is also sober) that I might not mark the anniversary this way for once, that because I feel differently about so much it might not make sense to continue to the tradition. But then I started thinking perhaps that’s the very reason to write about it, because it feels so different ten years in, so maybe next week (which is now this week), a post on not drinking for a decade.

This week I’m writing about making peace with the fact that I’m a mess when I travel, and how the idea of improving ourselves is a kind of self-aggression¹.

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The first time I ever traveled by myself internationally I went to Costa Rica. It was 2010 and I’d just broken up with a man who, every time he got remotely tipsy, would tell me that he was upset I hadn’t ‘seen the world’ or ‘traveled widely’ or whatever euphemisms a certain class of person uses to tell you that you’re an embarrassment. I booked that trip as some kind of revenge, and also as a way to impress him.

That June on a Sunday at work I spent a few hours Googling “good places women traveling alone safe” and Puerto Viejo was mentioned in the first article I clicked, and that was the extent of my research. I rented a small hut from a travel website and I bought a plane ticket from San Francisco to San Jose and a bus ticket from San Jose to Puerto Viejo, and then I just went. I landed in San Jose in July, mid-afternoon, wearing a ridiculous outfit and a fedora and towing a huge black suitcase. The most conspicuous, clunky, terrified thing pretending not to be, pretending to be so brave and so casual and appear like I’d done this all before.

By some miracle I found the bus, then I got on the bus, and then I realized that no one around me spoke English and I didn’t speak Spanish, and the bus was a four-hour standing-room-only kind of deal that kept stopping at deserted roadsides in the middle of nowhere to drop people off. It became apparent I was going to arrive in Puerto Viejo late at night at one of those abandoned, dim-lit stops in that poorly-chosen outfit and that stupid hat with that massive suitcase, and be just totally fucked.

But then a group of guys on that bus standing across from me kept looking toward me, and one of them finally asked me if I was traveling alone, if I spoke Spanish, if I knew where I was going or if I had any clue at all, and when I answered in the negative to everything he asked, he said Okay on an exhale like he’d been briefed on how bad it was and he was up to the task. The bus stopped at the exact situation I was expecting (deserted roadside, single flickering light, late at night), and Tavo—that was his name—took my suitcase, found out where my room was by asking around, and walked me there.

Later that night he and his friends came back to pick me up and take me out, and they came the next morning to help me rent a bike, and for the rest of the week they folded me into their group, arriving every day on their bikes to get me like we were in The Sandlot or something. I couldn’t have been more negligent or planned it any worse than I did and it couldn’t have been any better than it was. One of the best weeks of my life and one of the reasons I travel so much.

Because it was such a mess it became such magic.

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I’m in Europe for the month, my twentieth-ish solo trip to some other country since that first time thirteen years ago, and I tell that story because even though now I have a passport full of stamps and so much experience and far more resources than I had back then and I’m not in active addiction and drinking my way through airports and am actually a moderately organized and responsible human that identifies as ‘having her shit together’—and a hundred other reasons for why I might not show up now, at this point in my life, to a foreign country entirely unprepared—I still travel like I did back then. Which is kind of like a jackass.

This time I brought a too-big suitcase that exceeded the weight requirements, which I had to unpack and divide at the counter in Gatwick into additional bags to fit onto the plane. I brought too many clothes, all wrong, intended for the spring of Southern California and not the spring of the Netherlands or England or even Sicily, which is still basically winter. I brought three pairs of sandals and four cotton dresses and a tiny linen negligee to sleep in that I don’t even use at home in the summer. Four yoga outfits. Two bathing suits. Three types of hair conditioner. Twenty pairs of mostly thin socks. A lint roller. Only two sweaters, total. No heavy jackets or scarves or mittens or hats.

I went first to Amsterdam because I used to want to see Amsterdam but forgot to remember the reason I used to want to see Amsterdam is because I also used to be a stoner. I did not consider that part until I was in the cab and my driver warned me that coffeeshops were not coffeeshops but drug dens. I booked a bike tour for the first morning there, the only activity I bothered to make and pay for in advance, which was a mistake because I was jetlagged and overslept and missed it and had the wrong clothes for it, anyway.

Instead of any of the things I might have done had I thought about it at all, I spent my first morning waiting a very long time for a crepe that was just really a large thin and bad American pancake in a restaurant I didn’t research that was overpriced because of its location. I spent hours walking in and out of stores until I found a coat I probably won’t wear in America and a beanie I already hate, and then I walked across town to a museum I couldn’t get into because you have to buy tickets a week in advance.

I stopped to hear an accordionist play a song that made me cry in an irrational way. I sat at a water feature behind the museum I couldn’t get into for some extended duration and watched people get wet and laugh at each other about it. I bought a postcard and mailed it in the same transaction. I sat in a dog park leaning back against a tree, in muddy grass that wet through my pants and made me still colder in my illogical clothes, watching Dutch dogs play like American ones do. I bought a wedge of Amsterdam Cheese that I asked the clerk to cut up, which he did into sample-sized chunks, and then I went back to my hotel freezing but also sunburnt because I forgot to put on sunscreen, where I sat in bed and ate a pound of tiny cheese squares with a toothpick for dinner and drank an overpriced bottle of fizzy water and watched TV on my phone.

I did absolutely nothing remarkable or recommended by Trip Advisor, and rationally it felt like a failure but spiritually it felt like a win.

working on my night cheese

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I’ve spent on average two months of each year since 2014 living out of suitcases, living in different places. Traveling.

I never plan ahead or if I do I never end up doing the things I plan ahead for because I feel different when I get there or I just get all lazy about it. Half the places I stay in I hate because I didn’t plan in advance or read the reviews or because I’m cheap. I always bring too much stuff and always the wrong things and then always end up buying overpriced items to correct for that and those things are never practical things I will wear in my regular American life—they are kaftans, they are combat boots, they are mistakes. My hair is always frizzy. My clothes are always wrinkled. I never, ever do the Things You Are Supposed To Do. I’ve been to Paris but not up to the Eiffel Tower. It took me five trips to Rome to see the Sistine Chapel. I’ve never ziplined or scuba-dived or chartered a boat or gotten in a gondola or hired the guide. I never see the one painting you are supposed to see and I never eat the one food you are supposed to eat.

Mostly, I sleep through my alarm, put on ill-fitting and inappropriate clothes, take too long to get out the door, meander and procrastinate and worry about how to ask for something in the local language, intend to go to this one museum or to see this one landmark and don’t, end up at the wrong restaurant and eat the wrong food, and waste every opportunity afforded me.

And always with this thought running in the background while I’m there: I am doing it all wrong, I am such a bad traveler, such a mess, I will one day grow out of this and become something else.

And then later, back home, always with this realization: If I could do it all over, I wouldn’t change a thing. It was perfect.

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I realized this trip that I have a picture in my head of the kind of lady I should be when I travel, and it’s not just an idea but a whole vision of an entirely different person, the kind who uses a small suitcase and plans all her outfits and wears mostly leggings and Gortex and an Apple watch. She’s got different hair that sweeps easily into a chignon and different disciplines that fold her exactly into every carefully planned event from her carefully constructed itinerary, which is also color-coded and allows ample time for unforeseen delays. She’s not jetlagged because she sleep-trained and she’s not carrying an exploding 500-pound suitcase because she planned all her outfits, which fit neatly into packing cubes, which fit neatly into her stainless steel carry-on, which meets international luggage dimension standards. I could go on but the point is she is a fiction of exactly everything I am not, and she’s tagged along on every trip I’ve taken since 2010.

I’ve also realized this trip that the best times of my life are when I travel, and the best version of me is the me I find in other countries, and that both these things are true not despite being such a fucking mess (according to me) or being so absolutely bad at travel (according to me), but because of them. That the very things that drive this sense of doing it wrong are the things that allow me to explore in a way that is freeing and gorgeous, even if it’s in the wrong clothes or carrying a hundred-pound suitcase up six flights of marble stairs, in clogs.

Without being exactly who I am, I would have never had such profound and glorious memories, which were all made possible by my mess and incompetence as much as any ‘good’ quality I possess. I would have never been changed in the way I’ve been changed.

So why have I kept insisting to myself there’s something wrong here—something that needs to be apologized for, improved upon, fixed?

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The vision of the traveler I imagine myself to be, or that I chastise myself for not being, or imagine I might one day become if I try hard enough, probably isn’t even a person I’d be friends with, let alone travel with². The lady I actually, realistically am: She’s typing this too-long essay on a smudged, battery-drained laptop from a cafe, drinking her third oat milk latte when she should have switched to water, on a Sunday at noon when she meant to finish this on a Wednesday at 6, rewriting the ending yet again instead of walking along the water, wearing these absolutely stupid white boots she bought in England that she’ll never wear in New York, wrapped in a jacket she probably won’t either. She’s about to cancel plans she made for lunch and skip a date she made later, too. She’s about to try this disgusting ‘toastie’ she saw at a restaurant around the corner called a 'Hide and Squeak', and then probably go meditate and write some more. She, more than anyone else, seems like my kind of person. Like someone I might really get on with, want to travel with.

This was meant to be one or two paragraphs about being a messy traveler, a thing I wrote in my head last Monday while I was sitting in that dog park instead of looking at Vermeer, that I ‘should have’ banged out in an hour and sent to you the next day. But writer me, like traveler me, is not so simple, so I ended up working on this essay for the whole week.

Because writing is how I make sense of the world, what I mean to say is that this week I tried to get to the bottom of why I’m so hard on myself about the person I actually am by writing about it, and then going out and living it, and then writing about it some more. Throughout, I kept coming back to these two ideas from The Wisdom of No Escape: (1) That trying to improve ourselves or change ourselves is a form of aggression against who we are, against our nature and all the things that make us so uniquely us³, and (2) that when we become good friends with our situations and ourselves, our situation will improve.

This is about being a messy traveler. It is also not.

Eleven Things Right Now

A book I want everyone to read so we can talk about it, how useless we are at predicting the future, how bad we are at judging our age, social media as attention alcohol, Mussolini’s granddaughter, a podcast on not using your camera all the time and another one on not using TikTok, a good album, some good books, etc.

1. “A book I keep telling my friends to read”: I found Meganets probably from this article and I couldn’t put it down. It’s given me a different appreciation of how influenced we are not by some advanced, not-yet feasible technology, but by the combination of systems and humans that already exist, and how no one is actually in control in the way we think they are, and how (deep breath) basically, we are simplifying our desires and choices to be more easily organized and influenced by systems—like we’re dumbing ourselves down so the machines can sort us kind of thing. The author of the NYT article said the book made her feel “deeply queasy about the amount of time I spend on Instagram, Reddit, TikTok and Twitter” and “please take my WiFi” and same here! But it also gave me a lot more context than the normal books on why social media is a hellscape, etc. It’s dense and reads like a dissertation instead of a popular non-fiction book, but I think it’s worth the time, if you’re into this kind of thing.

2. Related: There’s been a lot of press and media about AI, and I’ve listened to a lot of it, and I’m compiling a list of good things I might not share because I don’t think you need any more people talking about AI or Ozempic? That being said, this article on how bad we are at predicting the future was so, so good. We don’t know what’s going to happen!

3. Related: Social Media is Attention Alcohol

4. “I want to be great over time; I don’t want to be the best for a minute”. This podcast with Alison Roman, which I appreciated because so much of what she expressed are things I’ve been considering but haven’t felt confident claiming. She’s not going to ever learn TikTok. She’s fine with the fact that she’s aged-out of certain technology and fads. She thinks Instagram is for furniture shopping! She believes in creative inspiration and quality over quantity which is why she won’t publish something for a few weeks or a month. She’s honest about money and how little she made until recently. She’s not afraid to start over from scratch! It was refreshing and surprising and permission-giving. I’m working on the third installment of that series on Transitions, which is about finding creativity after losing what you thought was your purpose, and many of her conclusions felt familiar and relieving

5. This podcast on Susan Sontag which has encouraged me to not take pictures of everything all the time (especially while traveling), and not document my life as much but live it. So far on this trip, I’ve taken about twenty photos which feels really sane making

6. The best advice I’ve read on how to be human right now

7. Mussolini’s granddaughter chugging wine out of a bottle at 11am in order to protest health warning labels on alcohol tells me warning labels on alcohol are probably even better than I imagined

8. The Atlantic on why I think I’m still closer to my college years than my retirement years, and Cheryl Strayed on feeling her age

9. Easier is better (this was in last week’s newsletter but hardly anyone clicked on it; I love Kate Manne’s writing)

10. This album on repeat, two years after I ruined it by listening to it on repeat

11. Other books I’m reading: Poverty, by America; Sand Talk (recommended by Chris La Tray); Wuthering Heights, which I’m reading because of the movie Emily—I am finding it so difficult and awful but I keep reading it anyway mostly because I want to be a person who can say I read Wuthering Heights

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1. From Pema Chödrön, The Wisdom of No Escape: “When people start to meditate or to work with any kind of spiritual discipline, they often think that somehow they’re going to improve, which is a sort of subtle aggression against who they really are. It’s a bit like saying, ‘If I jog, I’ll be a much better person.’

2. But I would absolutely date this person and should probably assert I have dated this person, and they were great because they did all the things I hate.

3. From Pema Chödrön, The Wisdom of No Escape: “Our brilliance, our juiciness, our spiciness, is all mixed up with our craziness and our confusion, and therefore it doesn’t do any good to try to get rid of our so-called negative aspects, because in that process we also get rid of our basic wonderfulness.”