How To Travel — Some Contrarian Advice

November 21, 2013 — 16 Comments

Why are you traveling?

Because, you know, you don’t magically get a prize at the end of your life for having been to the most places. There is nothing inherently valuable in travel, no matter how hard the true believers try to convince us.

Seneca, the stoic philosopher, has a great line about the restlessness of those who seem compelled to travel. They go from resort to resort and climate to climate, he says. “They make one journey after another and change spectacle for spectacle. As Lucretius says, “Thus each man flees himself. But to what end if he does not escape himself? He pursues and dogs himself as his own most tedious companion. And so we must realize that our difficulty is not the fault of the places but of ourselves.”

It’s hard for me to see anything to envy in most people who travel. Because deep down that is what they are doing. Fleeing themselves and the lives they’ve created. Or worse, they’re telling themselves that they’re after self-discovery, exploration or perspective when really they are running towards distraction and self-indulgence.

Is that why you’re packing up your things and hitting the road?

Are you, as Emerson once put it, “bringing ruins to the ruins?”

The purpose of travel, like all important experiences, is to improve yourself and your life. It’s just as likely — in some cases more likely — that you will do that closer to home and not further.

So what I think about when I travel is that “why.” (Some example “whys” for me: research, to unplug, to go straight to the source of something that is important to me or I need to see in person, a job or a paying gig, to show something that’s important to me to someone who is important to me, etc etc) I don’t take it as self-evident that going to this place or that place is some accomplishment. There are just as many idiots living in Rome as there are at home.

And when you make this distinction most of the other travel advice falls away. The penny pinching and the optimization, the trying to squeeze as many landmarks into a single day, all that becomes pointless and you focus on what matters.

So what I am saying is that saving your money, plotting your time off work or school, diligently tracking your frequent flyer miles and taking a hostel tour of Europe or Asia on budget is the wrong way to think about it.

In the vein of my somewhat controversial advice for young people, I thought I’d give some of my thoughts not just on traveling but on how to do it right.

My Travel Rules and Criteria

[*] Instead of doing a TON of stuff. Pick one or two things, read all about those things and then actually spend time doing them. Research shows that you’ll enjoy an experience more if you’ve put effort and time into bringing it about. So I’d rather visit two or three sights that I’ve done my reading on and truly comprehend than I would seeing a ton of stuff that goes right in and out of my brain. (And never feel “obligated” to see the things everyone says you have to).

[*] Take long walks.

[*] What are you taking all these pictures for? Oh for the memories? So just look at it and remember it. Experience the present moment.

[*] Read books, lots of books. You’re finally in a place where no one can interrupt you or call you into meetings and since half the television stations will be in another language…use it as a chance to do a lot of reading.

[*] Eat healthy. Enjoy the cuisine for sure, but you’ll enjoy the place less if you feel like a fucking slob the whole time. (To put it another way, why are you eating pretzels on the airplane?)

[*] Try to avoid guidebooks, which are superficial at best and completely wrong at worst. I’ve had a lot more luck pulling up Wikipedia, and looking at the list of National (or World) Historical Register list for that city and swinging by a few of them. Better yet, I’ve found a lot cooler stuff in non-fiction books and literature that mentioned the cool stuff in passing. Then you google it and find out where it is.

[*] I like to go and stand on hallowed ground. It’s humbling and makes you a better person. Try it.

[*] Come up with a schedule that works for you. Me, I get up in the morning early and run. Then I work for a few hours. Then I roll lunch and activities into a 3-4 hour block where I am away from work and exploring the city I’m staying in. Then I come back, work, get caught up, relax and then eventually head out for a late dinner. In almost every time zone I’ve been in, this seems to be the ideal schedule to A) enjoy my life B) Not actually count as “taking time off.” No one notices I am missing. And it lets me extend trips without feeling stressed or needing to rush home.

[*] Don’t check luggage. If you’re bringing that much stuff with you, you’re doing something wrong.

[*] When you’re traveling to a new city, the first thing you should do when you get to the hotel is change into your workout clothes and go for a long run. You get to see the sights, get a sense of the layout and then you won’t waste an hour of your life in a lame hotel gym either.

[*] Never recline your seat on an airplane. Yes, it gives you more room — but ultimately at the expense of someone else. In economics, they call this an externality. It’s bad. Don’t do it.

[*] Stay in weird ass hotels. Sometimes they can suck but the story is usually worth it. A few favorites: A hotel that was actually a early 20th-century luxury train car, a castle in Germany, the room where Gram Parsons died in Palm Desert, a hotel in Arizona where John Dillinger was arrested, a hotel built by Wild Bill Hickok, etc etc.

[*] Add some work component to your travel if you can. Then you can write it all off on your taxes.

[*] Don’t waste time and space packing things you MIGHT need but could conceivably buy there. Remember, it costs money (time, energy, patience) to carry pointless things around. (Also, most hotels will give you razors, toothbrushes, toothpaste and other toiletries).

[*] Go see weird shit.

[*] Ignore the temptation to a) talk and tell everyone about your upcoming trip b) spend months and months planning. Just go. Get comfortable with travel being an ordinary experience in your life and you’ll do it more. Make it some enormous event and you’re liable to confuse getting on a plane as an accomplishment by itself.

[*] In terms of museums — I like Tyler Cowen’s trick about pretending you’re a thief who is casing the joint. It changes how you perceive and remember the art. Try it.

[*] Don’t upgrade your phone plan to international when you leave the country. Not because it saves money but because it’s a really good excuse to not use your cellphone for a while. (And if you need to call someone, try Google Voice. It’s free).

[*] You know there are lots of cool places inside the United States. The South is beautiful and chances are you haven’t seen most of it. There’s all sorts of weird history and ridiculous things that your teachers never told you about. Check it out, a lot of it is within a day or two drive.

In other words…

Travel should not be an escape. It should be part of your life, no better or no worse than the rest of your life. If you are so dissatisfied with what you do or where you live that you look forward to NOT being and spend weeks and months figuring out how to get a few days off from it, that should be a wake up call. There’s a big difference between wanting a change in scenery and some new experiences vs. needing to run away from a prison of your own making.

There is to me, a lot more to admire in someone who stayed put and challenged their perspectives and habits and lifestyle choices at home than there is to some first world Instagram addict who conflates meaning with checking off boxes on a bucket list.

So ask: Do you deserve this trip? Ask yourself that honestly. Am I actually in a place to get something out of this?

Over the years, I feel like I have mastered the art of something I wouldn’t call travel. I’d call it living my life in interesting places. When I can help it, I try to get paid to go to the places I go. What I don’t do is pine for the “opportunity” to go somewhere — because if I want it, I will make it happen.

These rules and tricks have helped make that possible. Maybe they’ll work for you too.

This post originally ran on Comments can be seen there. A different, expanded version, also ran on

Ryan Holiday

I'm a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

16 responses to How To Travel — Some Contrarian Advice

  1. This was so encouraging! I love traveling but I want to be a master of “living my life in interesting places.” I was getting pretty good at it but then I let dissatisfaction creep in…you just helped me slam the door on it again. Hooray!!

  2. Hey Ryan-

    Great post. I’m an avid reader, as are you. How do you deal with the challenge of reading and travelling? I dl tons of things to my ipad/kindle, but I know you (like me) enjoy the tangible object. Ever try out libraries on the road?

  3. I like the info Ryan, thanks for sharing! I’ve been reading Vagabonding by Rolf Potts and feel like I’ve started looking at extended travel as 1.5 years away from now, something in the far future. I forgot that I CAN challenges my situation in life in a meaningful way and don’t need to live in a fast-forward kind of way – thanks for reminding me.

    Vsyevo luchyevo!

  4. Ryan,
    I agree with your advice about not focusing on too many things. We don’t really appreciate things unless we invest in them first.

    I know you’ve read Montaigne. Here’s a nice quote on traveling by him:

    “…Travel is in my opinion a very profitable exercise; the soul is there continually employed in observing new and unknown things, and I do not know, as I have often said a better school wherein to model life than by incessantly exposing to it the diversity of so many other lives, fancies, and usances, and by making it relish a perpetual variety of forms of human nature.”


  5. My sentiments exactly. While getting to know fewer destinations more intimately, some of my best travel memories have come from plugging into unique experiences specific to the region: 3am fish auction in Spain’s seafood capital La Coruna, or learning butchery under a master butcher in Argentina, the land of beef.

  6. Nice article, I agree that many people travel for the wrong reasons. A lot of times it just generates into pointless consumption of “experiences.” Plus, listening to people brag about their travels is awful.

    That’s a cool idea to pretend you’re a robber casing the museum, I’ll have to try that out. Whenever I go to museums I like to pretend I made the stuff on display. It makes looking at old artifacts a lot more fun.

  7. Ryan,

    I totally agree about getting out and making a new destination part of life rather than an escape. Because of business, I fly 2-3 a month to new places around the United States. At first, I was the guy that would grab some beer, order a pizza and watch some movies after work. It got depressing and I, along with some business partners, went out and saw what was around. We walked through the town, talked with the people and now, traveling is actually enjoyable. I have had a bunch of great times on business trips. Great information as always.

  8. Great article Ryan. Going on a run as soon as your are in a new city is such great advice. It always makes me feel refreshed, and I usually see something that I want to revisit or do on the way.

  9. How to get in contact with you?

  10. Ryan, what is your Mail address?

  11. Wow. I wish I read this before I started my world trip. I’m a 27 year old American who left an high paying yet unfulfilling job and life in general. I always wanted to do a Eurotrip, Olympics, run with the bulls etc. I spent most of my savings and did nearly all of my bucket list yet now feel like I cheated myself. I was escaping my life and it was an exercise in self-indulgence. I would brag about all the countries and places I’ve been but I really should’ve spent my money more wisely. Now I’m unemployed living with my parents looking for a job. At least I read your piece on New York and can follow that advice. I hope every traveler reads this gem of a blog.

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