Is there a right and wrong way to travel?

I recently read an article on Tim Ferriss’ Four Hour Workweek blog that I’m taking some issues with: How to Travel – 21 Contrarian Rules by Ryan Holiday.

He starts of by saying that most people travel because they are “Fleeing themselves and the lives they’ve created.”

Ok, no problem, perhaps this is true. And I don’t have a problem with that. For many people, traveling means 1 vacation a year and taking the kids to Disneyland for a week. Great for them! I’m sure it’s a blast for everyone involved. But the author here seems to take issue with this specific form of travel, insinuating that there is a “right” and “wrong” way to travel.

Who doesn’t like Mickey Mouse pancakes?????

I want to take a look at a few choice quotes and then give my overall take on traveling.

Let’s start here:

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.

The second part of this is very likely to be true. However, if you want to go to Rome and see something completely different than your current surroundings, meet different types of people who have a different language and way of going about life, how is this not an accomplishment in some respect? For me, this would rank highly in the personal growth category.

Pity the fools!

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.

Again, how is this “wrong”? Sure, there are many other ways to go about traveling, but I see no reason to call out a right and wrong here.

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

I’m unclear on why it’s “wrong” to bring luggage! It seems like he’s saying, if you have to go with luggage, don’t go at all. Everyone is different here and there’s no one-size-fits-all when it comes to luggage. I personally like the idea of going as minimalist as possible. But this is different for everyone, and it all depends on the type of trip you are going on.

For example, you may be able to cruise through hot Southeast Asia for a few months with just one backpack (I did it with 2, laptop bag and large pack), but what if you are exploring Eastern Europe in the winter and want to hit a few places? You might be miserable without the right amount of clothes!

There also seems to be a lot of elitism when it comes to suitcases vs backpacks. Many backpackers wouldn’t be caught dead wheeling around a suitcase. But my pack had wheels and guess what happened in SE Asia? I wheeled it more times than carried it on my back. Why? Because it’s easier. Yep, I sacrificed looking cool to make my life easier! (Plus I don’t want to get lumped in with the backpacker crowd!)

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)

This actually works for me for the most part. I like the present moment stuff. I think many people take massive amounts of pictures to impress their Facebook friends. But I wouldn’t say that others should do what I do here.

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.

I disagree. I’m not saying everyone should get Lonely Planet books and follow all of their advice. However, these books can save you a ton of time, give you brief historical facts, and even get you off the beaten path on occasion. For example, when I was in Bali, I was looking for the most authentic restaurant one day, and found a recommendation in my Lonely Planet guide for a lunch spot that was way off the beaten path and it said “You will mostly see local cab drivers in this place” and sure enough, I had my lunch of chicken feet and liver something among Balinese-speaking cabbies and a handful of other locals. No tourists.


Another thing the guide books can do to save you time is to point you in the right direction. Sure you can go compiling all kinds of info online, but who has the time? What has worked for me is to just show up and get a room at one of the hotels the book recommended, then take a walk around town and see what else is around. I’m there, it’s usually not a total nightmare of a place to stay, and I can then decide to move on if there’s a better place out there.

And now for some agreement points.

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.

Agreed. Planning is overrated. However, getting on a plane is an accomplishment by itself for many people, especially Americans! Need some inspiration? Check out my friend Mister J’s blog, Americans Get Out!

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.

So many people forget this! I’m currently in Colorado and had no idea how beautiful this place was until I started exploring here! Assuming that you have to leave the U.S. to see and experience cool stuff is a fallacy. I can’t wait to hit more places I haven’t been around this country.

I’m hiking to this spot on Saturday, King Lake


Let’s wrap up with the author’s conclusion:

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.

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.

I’m glad this works for Ryan. However, this isn’t for everyone. The Instagram addict might be fulfilled in his or her own way. Maybe he likes playing with filters!

And sometimes, I do enjoy checking off boxes on a list. For example, I wanted to visit Singapore for years. I went, and I was there for 4 days.

. That was plenty, I felt very satisfied with my experience and all that I got to see and do there. I would not have wanted to stay there for 3 months. Same thing with Malaysia. Sometimes, quantity of places trumps quantity of time spent in these places.

Another reason I take issue with this is, it’s subjective to say that staying somewhere for 3 months is superior to going somewhere and bouncing around for 3 months. Or just going somewhere for 2 weeks and seeing as many things as possible. For example, let’s say I wanted to see France. Is spending 3 months in Paris “better” than spending a week in 12 different spots throughout the country? Again, this is subjective. What works for one person may be torture for another.

What about you? How do you like to travel and why?






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Kevin Koskella

Kevin is a podcaster and writer on living free, despite the crazy world we live in. Kevin travels full time and explores the world and how to achieve and maximize freedom in life.

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