Earlier this year, I traveled alone across Europe. In some cities I knew a friend from college, in others perhaps a friend of a friend, but for all intents and purposes I wandered around by myself with no plan for about a month. Even for someone a close friend recently referred to as “the most extroverted person I know,” it was one of the best months of my life.

Both at home and abroad, though, the idea of extended, solo travel seems oddly foreign. Common reactions to my travel plans included:

“Wow! Good for you to be able to do that!”

“Don’t you get lonely?”

“You mean, you’re going do all these things…by yourself?”

Yes. Traveling by myself was the most thought-provoking, battery-resetting thing I’ve ever done. Here’s how to do it right, and why it’s so much more impactful than traveling with other people (even people you like).

I might as well have titled my photo album “Schiff’s European selfie tour”.

Whatever The Fuck Time

It is only through solo travel that you can truly experience something I call “whatever the fuck” (WTF) time.

Be it school, work, family, or something else, we all have obligations — things we need to do to avoid bad things from happening. It doesn’t mean we don’t enjoy those things, and it doesn’t mean we’re “trapped” in some unfulfilling nightmare. It just means our lives are intertwined with other people, and our actions have consequences. Obviously, getting away from these obligations is good for the soul, and pretty much everyone recognizes time off is a basic human necessity from time to time.

But as much as we may enjoy spending time with friends and family, traveling with other people adds a layer of complication and compromise to everything. Not only do you have obvious stressors like competing preferences, travel styles, etc., but at every turn there’s a hidden pressure to coordinate your plans — or at least tell people where you are. Without even realizing it, you often make subtle but very real sacrifices to keep a similar schedule and stay together.

It’s not that this is the wrong way to travel — some of my fondest memories are road trips with friends and vacations with family — you’re just not doing whatever the fuck you want. To give an operational definition:

WTF time (a.k.a., “whatever the fuck time): a prolonged period of time in which you have have absolutely no other concern besides your own personal, present happiness.

It means you sleep when you’re tired and eat when you’re hungry. It means you don’t care about drinking too much because you don’t have any plans it will destroy tomorrow. It means you spend all day in museums, taking your time to read the signs that interest you, if that’s what you want to do. It means you wander for hours just because a building off in the distance looks interesting. It means you go to a new city in a different country just because the forecast is sunny. It means you can say yes to literally anything and everything that strikes your fancy without feeling like you’re “splitting off” from the group. You can do it in your style, on your schedule, and, most importantly, without having to “check” with anyone else.

It means you can be existentially care-free in a way that simply isn’t possible when traveling with others. WTF for too long and you’ll get lonely and become starved for meaning, but the right amount resets your batteries in a way you won’t have believed was possible.

And it means you don’t have to shave.

A hairy face is a free face.

Disclaimer: The “right dose” of WTF varies from person to person and how stressed out you’ve been. I ran my own startup for the past 4 years, so I needed a long time to fully reset.

Say Yes To Serendipity, and to Strangers

Somewhat related to WTF time is the role of serendipity. When you travel by yourself, random, amazing opportunities present themselves much more often. While this is partially due to the fact that you have no one to coordinate with (i.e., you’re in WTF mode), it’s also a function of basic probability.

When I was in London, I wandered into an African restaurant called Souk. The waitress put down a basket of bread on my table, so, thinking it was mine, I started eating it. Turns out, it was for the couple next to me — a fact I realized when we made awkward eye contact with a piece of their bread in my mouth. Day 2 in Europe and I was already “that American asshole.”

About 8 hours later, I was in a VIP suite watching alt-J with my newly adopted European parents, Andy and Anita.

alt-J in London

What happened? Funny enough, stealing their bread was a great conversation starter. After trading life stories for the duration of the meal, they asked if I was busy that night. It turns out they had an extra ticket to go see alt-J, whose London show I was dying to go to but ended up missing the sale period. I exclaimed, “You’re joking.” To which they responded, “Feel free to take it, even if you can’t come. It’s a VIP suite though — hope that’s okay.”

This kind of thing doesn’t really happen when you’re traveling with others. First, the likelihood of you spending the entire meal talking to strangers rather than each other is tiny, because you’re not as desperate for human attention. Second, the likelihood that a stranger you chat up has an extra ticket to a concert you’ve been dying to attend is already minuscule — the likelihood that they have two (or more) might as well be zero.

It’s not that you’re luckier when you travel by yourself. It’s simply that the probability of a lucky event intersecting with your path in a way that you can actually take advantage of it is much higher. Moreover, because you have no “fallback” for human contact, you start and continue more conversation with strangers (the harbingers of serendipity).

Whether you’re at home or abroad, talk to the people around you — you never know where a conversation might lead.

Thinking Time

At least in American culture, shared silence is typically frowned upon as awkward. We’re perfectly content co-habitating a subway car in total silence with strangers, yet prolonged silence with people we know somehow makes us uncomfortable.

When you travel with others, you obviously tend to talk with them quite a bit. This isn’t a bad thing — communication strengthens bonds, and everyone brings a unique perspective to the conversation. However, in the pressure to externalize your thoughts, you don’t really get a chance to reflect internally. But if there’s any time when you should be thinking, it’s when you’re experiencing new places, cultures, and history for the first time.

Traveling alone for an extended period means you spend a lot of time inside your own head. As you float around cities and countries, your mind also wanders — thinking, reflecting, analyzing, observing, and drawing comparisons about whatever happens to be interesting at that moment. It’s not that we don’t spend time thinking when we’re with other people, it’s that our thinking is guided by the conversation. Alone, bombarded with new stimuli at every turn, your mind can truly appreciate the juxtaposition of people, places, and things.

One day, while walking by French parents dropping off young children at school, I noticed that they watch their children run away from their arms with the same combination of pride and sadness in their eyes as mine probably did — shouting, “Behave for your teachers!” and “Have a good day!” (in French, obviously). The next, I was reading the tombstones of Egyptian pharaohs in the Louvre, boasting of conquests of people I’ve never heard of all in an attempt to convince their gods they’re worthy of entering the afterlife.

Another day, I saw a guy and a girl on a blind first date hit it off, hang around for 3 rounds, and walk out of a South London pub arm in arm. Later that week, I found myself wandering around the steps of the Colosseum, where thousands of people watched men kill each other for sport.

On Tuesday, I wandered through the caves of Europe’s most active volcano (Mount Etna). By Friday, I was listening to a Slovenian jazz group perform in Vienna.

Yet another day, I was hugging jumping up and down with strangers at a rugby match, with old Irish guys shouting, “DESTROY HIS FUCKING LINEAGE!” behind me.

Rugby Six Nations Ireland vs. France in Dublin

The week prior, I felt my stomach sink instantly upon walking into an old building in Poland.

These two furnaces incinerated the bodies of hundreds of thousands of people, where an incomprehensible number of lineages were literally severed at Auschwitz.

A few days later, I sat for about 30 minutes staring at two walls stacked on top of each other. On the bottom was the remaining foundation of the SS building, where these atrocities were planned in the 1930's. At street level was a segment of the Berlin Wall, one of the 20th century’s most iconic examples of segregation, erected just 30 years later.

Spending that much time reflecting on the human condition isn’t for the faint of heart, but it’s good for you. You’re going to think about death. You’re going to think about your own insignificance. You’re going to think about how silly violence is. You’re going to think about how literally nothing good has ever come from walling people off from each other. Yes, you’ll think about how different certain parts of the world are, but more often you’ll find yourself marveling at how everyone is worried about the same mundane bullshit. You’re going to think about how incomprehensible and beautiful it is that the sum of everything humanity has ever created— all the buildings, people, languages, music, and politics — is because random organic compounds somehow combined into a prokaryote billions of years ago.

Most importantly, you’re going to think deeply about whether or not you’re living your life meaningfully. That’s just where the mind tends to go when left to its own devices.

Other Tips For Solo Travel

Convinced you should give solo wandering a try? Awesome. Here are some tips for how to take advantage of it:

1) Stay at hostels with bars. They usually have the cheapest drinks in the city, and it’s way easier to meet people at hostels that have a bar where people hang out at night. You’ll meet really interesting people from all over the world. Especially Brazilians. Brazilians, you people are everywhere.

“But aren’t hostels dangerous?!” you protest. “It’s a room full of strangers! And what about bed bugs?”

Incidents happen, certainly, but just read the reviews on Hostelworld and you can avoid most sketchy places. Yes, you’ll stay in places that have bad electricity, or have weird characters, but I never felt unsafe. If that’s going to be an issue for you, you’re probably not going to feel comfortable traveling alone in the first place.

2) Hostelworld is the best way to book hostels. In big cities, TripAdvisor is the best way to find activities/attractions, but use Yelp to find food. When visiting small cities (like Catania), don’t trust Yelp (not enough ratings to be valid). Just Google “best restaurants in <city>”.

3) If you don’t have indefinite time, stay ~3 nights per city. This might just be my style, but two full days is enough to get a feel and do most of the touristy things you want to do.

4) Don’t be stupid. Some places in the world are definitely not safe to travel alone, especially for women.

5) Have a general idea of where you want to go, but don’t plan out more than a few days in advance. That way, you avoid being stuck somewhere, but you leave yourself plenty of optionality in case something sounds cool along the way.

6) While you’re eating meals, try to read the news of that country. If you speak the language at all, try to read a print copy (I did this with Le Monde in Paris). If you don’t, load up a few articles from an English language version of the news on your phone when you’re somewhere that has wi-fi. It gives you a better perspective on what people are thinking about where you are.

7) If possible, schedule stops where you have a friend or two you can hang with — even if you haven’t seen them in decades. Unless they actively dislike you, people are usually thrilled to meet up with international travelers.

8) Splurge on food in Italy. Jesus Christ.

From Osteria Del Cavaliere in Rome. I nearly proposed to my waitress.

Need more recommendations? Hit me up any time!