(Photo credit: Moyan Brenn)

This is a tactical post on travel from Ryan Holiday, who’s written on this blog before about the pragmatism of Stoicism and lessons learned as Director of Marketing for American Apparel.

To his 21 rules, I’ve added a few of my own tricks. Please share your own rules and tips in the comments!

Enter Ryan Holiday

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, and continues:

“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 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 new perspectives when really they are running towards distraction and self-indulgence.

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

Not that I don’t travel myself–I did my fair share this year alone. Both coasts of Australia. I was in Amsterdam for a speaking gig (and I found myself at a tulip farm with Tim where he caught a chicken with his bare hands). I researched for my next book in Rome. I went down to Brazil. I went to Copenhagen. I spent enough time in New York that it felt like I lived there. I road tripped across the United States more times than I can count–New Orleans to New York; New York to Miami; Miami to Austin… The list goes on. If there was a chance to go somewhere I’d never been, I tried to take it, especially if it was historic.

But 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, a job or a paying gig, to show something that’s important to me to someone who is important to me, etc.) I don’t take it as self-evident that going to a given famous place is an accomplishment in and of itself. There are just as many fools 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.

I am saying 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 may be 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 21 Travel Rules and Criteria

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

[TIM: I second this and encourage you to take things to extremes. Here’s exactly how I travel the world with 10 pounds or less.]

2. 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. (Oh, and never feel “obligated” to see the things everyone says you have to)

[TIM: Need some inspiration? Here are my highlight lists for Tokyo and Buenos Aires.]

3. Take long walks.

4. Stop living to relive. What are you taking all these pictures for? Oh, for the memories? Then just look at it and remember it. Experience the present moment. (Not that you can’t take photos but try to counteract the impulse to look at the world through your iPhone screen)

5. 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.

[TIM: I strongly suggest that non-fiction bigots (which I was for 15+ years) read or listen to some fiction to turn off their problem-solving minds. Try The Graveyard Book audiobook or Zorba the Greek.

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

[TIM: If you want to follow The Slow-Carb Diet, my default cuisine choices in airports are Thai and Mexican food. Also, keep a *small* bag of almonds in your bag to avoid digressions in emergencies.]

7. 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.

[TIM: I like to spend an afternoon visiting hostels, even if I’m staying in an apartment or hotel. The hostel staff will know which free and low-cost activities get the best reviews from the non-museum-going crowd.]

8. I like to go and stand on hallowed ground. It’s humbling and makes you a better person. Try it. (My personal favorite is battlefields–nothing is more eery or quiet or peaceful)

9. Come up with a schedule that works for you and get settled into it as soon as possible. You’re going to benefit less from your experiences if you’re scrambled, exhausted and inefficient. 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 it. 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 feels that I am missing. And it lets me extend trips without feeling stressed or needing to rush home.

10. When you’re traveling to a new city, the first thing you should do when you get to the hotel is change into your work out 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.

11. 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.

12. 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, and a hotel built by Wild Bill Hickok.

13. Read the historical markers–*actually* read them, don’t skim. They tend to tell you interesting stuff.

14. Add some work component to your travel if you can. Then you can write it all off on your taxes (or better, be paid for the whole thing).

[TIM: Here’s how an entire family moved to a tropical paradise in Indonesia and continued to earn income.]

15. 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.)

16. Go see weird shit. It makes you think, shake your head, or at least, laugh. (For instance, did you know that there is a camel buried in the soldier’s cemetery at Vicksburg?)

[TIM: If you go to Japan, don’t miss the incredible Ghibli Museum, made by animator Hayao Miyazaki and located in Inokashira Park.]

17. 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 with an accomplishment by itself.

18. Regarding 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.

19. 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)

20. Explore 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 wonderful things that your teachers never told you about. Check it out, a lot of it is within a drive of a day or two.

[TIM: Here are 12+ gems of the Pacific Northwest, encountered on a road trip from San Francisco to Whistler, Canada.]

[TIM: 21. OK, this one’s from me, just because it’s so much fun. Take pictures of yourself jumping in different places! It can turn a boring “adult” afternoon into a giddy kid-like experience. The below is from Burning Man 2010.]

(Photo: Mike Hedge)

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 spend weeks and months figuring out how to get a few days away from either, that should be a wake-up call. There’s a big difference between *wanting* a change in scenery and *needing* to run away from a prison of your own making.

To me, there is more to admire in someone who challenges their perspectives and lifestyle choices at home than in some Instagram addict who conflates meaning with checking off boxes on a bucket list.

[TIM: I’m a fan of bucket lists, but different strokes for different folks…]

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.

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

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What rules and tools have worked for you? Please share in the comments!

(A much shorter version of this piece, without my comments, first appeared in Thought Catalog.)

If you’ve ever fantasized about taking time off to globe-trot, I would highly recommend Rolf Pott’s Vagabonding . It is one of only two books I took with me when I traveled the world for 18 months. Outside Magazine founding editor Tim Cahill calls Vagabonding “the most sensible book of travel related advice ever written.”

I recently partnered with Rolf to release the exclusive audiobook for Vagabonding. For more on this incredible book, click here

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