Travel as Pleasure and How To Avoid It

This page may contain affiliate links. Please read our disclosure for more info.

There’s a particular moment in the documentary Comedian when Seinfeld says:

One day I was watching these construction workers go back to work. I was watching them kind of trudging down the street. It was like a revelation to me. I realised these guys don’t want to go back to work after lunch. But they’re going. That’s their job. If they can exhibit that level of dedication for that job I should be able to do the same. Trudge your ass in.1

This is one of the most successful comedians living today challenging himself to improve the thing he loves to do and even he has to tell himself to trudge his ass in.

Travel (as escape) is not the panacea for all of your problems. People who tell you otherwise want your money.

Freedom as a Negative Goal

Lazing around on beaches on occasion isn’t in itself bad—we all need time to recharge now and then—the danger comes when it is the entirety of your purpose.

The hippies had in mind something that they wanted, and were calling it ‘freedom,’ but in the final analysis ‘freedom’ is a purely negative goal. It just says something is bad. Hippies weren’t really offering any alternatives other than colorful short-term ones, and some of these were looking more and more like pure degeneracy. Degeneracy can be fun but it’s hard to keep up as a serious lifetime occupation.2

The final scene of The Graduate offers a painfully visceral example of this idea. Benjamin Braddock and Elaine Robinson escape Elaine’s wedding in an explosive and dramatic scene and then jump on the bus to get out of the growing conformity. As Simon and Garfunkel’s The Sound of Silence plays, their faces begin to betray the looming emptiness of their situation. We’ve escaped, but now what?

Freedom is not a good ambition (not to mention that our present circumstances don’t really allow for it: hegemony is an industrious foe.) People who tell you otherwise want your money.

If you’re bold, lucky and hardworking enough, you can produce the things that you actually want to produce and get paid for it. Doesn’t mean it’s easy, nor does it actually mean you’re free.

What “Lifestyle Designers” and “Digital Nomads” are doing isn’t pursuing actual freedom, they’re simply renegotiating some of the terms of their engagement within the system.
They say, “I can produce value from this hammock.”
The market says, “OK. Make sure you do.”

This is not really ‘freedom’. This is just moving your desk to underneath a palm tree and removing your old boss (oftentimes replacing them with a more sinister and manipulative one: yourself).

However, it turns out this is no bad thing. Despite the appeal and instant gratification of idle pleasure, laziness is not good for us. Be clear: the ability to go out and do something for yourself is liberating (though don’t confuse it with true freedom) but, again, it’s not for everyone. Sometimes liberation means working for someone else more in tune with your core values.

As Viktor Frankl points out in Man’s Search for Meaning:

Life ultimately means taking the responsibility to find the right answer to its problems and to fulfill the tasks which it constantly sets for each individual.3

And it will set you tasks: the greater the risk you take, the harder those tasks will be. Just be true to yourself and don’t allow other people to pigeonhole you.

Thus the hero of the Odyssey is a great fighter, a wily schemer, a ready speaker, a man of stout heard and broad wisdom who knows that he must endure without too much complaining what the gods send; and he can both build and sail a boat, drive a furrow as straight as anyone, beat a young braggart at throwing the discus, challenge the Phaecian youth at boxing, wrestling or running; flay, skin, cut up and cook and ox, and be moved to tears by a song. He is in fact an excellent all-rounder; he has surpassing areté. [Emphasis mine].4

The next person to tell me that I can’t be both a designer and developer gets a lightning bolt to the groin.

You Will Suffer

We need to recognise that we all suffer (even those of us with ‘first world problems’) and that it’s perfectly OK to be unhappy at times.

Once the meaning of suffering had been revealed to us, we refused to minimize or alleviate the camp’s tortures by ignoring them or harboring false illusions and entertaining artificial optimism. [emphasis mine]5

Thankfully, most of you reading this will not have to suffer as much as Frankl did or even, for that matter, as much as the majority of the people living in the world today do.

However, you will have to endure hardships at times even (I would argue especially) in the pursuit of doing what you love.

[Man] will have to acknowledge the fact that even in suffering he is unique and alone in the universe. His unique opportunity lies in the way in which he bears his burden.6

A culture is growing up around us that is confusing this idea of happiness and pleasure. It is a culture that denies the existence of unhappiness with cheap talk of positive thinking and blithely borrowed (and little credited) absolute values from various great thinkers and then (oftentimes ironically) tries its hardest to sell you products that may give you pleasure and/or inspiration in the very short term, but certainly won’t give you any sort of enduring happiness (digital stuff is still stuff and digital junk is still junk).

How To Be Happy (hint: You Don’t Need to Sell Everything You Own and Travel The World)

Happiness is a byproduct of involvement.

For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s personal dedication to a cause greater than oneself.7

So how do you choose the cause?

What moves the Greek warrior to deeds of heroism … [is] duty towards himself. He strives after that which we translate ‘virtue’ but is in Greek areté, ‘excellence’.8

Note that it’s duty towards himself, not others. An interesting twist on the current message.

Often, it doesn’t matter too much what the involvement is—there is the potential for areté in everything we as humans do—the most important thing is that it has to be in tune with who we are as individuals.

If you’re not down with the whole minimalism thing, for example, then that’s fine (it’s practically a cult anyhow). Just understand that materialism (or any -ism, for that matter) is just as bad.

Why? Pigeonholing. You, my cheese-loving friend, are a unique snowflake. Be true to your snowflakeness.

Bad news bear time: This is a lot harder than it seems. Your core values are buried deep under a veritable avalanche of other people telling you what to do (including me right now, though this post isn’t actually for you) and this burial has been going on since you were born.

Sometimes you won’t even recognise them when you find them.

Excellence in Travel

Although travel can be viewed as some as idle and valueless, this is not always the case.

Areté can happen here but only through real, challenging travel: travel that feels, at times, like work (and hard work at that). Suffering through torturous bus rides and dirty, uncomfortable accommodation and difficult people to reach new places or volunteering on backbreaking community development projects will produce feelings of happiness as a byproduct of the endeavor. It is, as always, the journey that counts.

(Just to be clear here: I’m not holding us up as examples of this. We’re really not. Try Kirsty, Dan and Audrey or Gareth.)

Getting drunk with your hostel buddies in a Gringo bar will produce momentary pleasure (not happiness), which is fine for a while, but the pleasure will appear in diminishing returns and will in all likelihood, over time, engender cynicism, dissatisfaction and boredom.

Much like many people’s experience with the 9-5, in fact. Ironic.

The Meaning of Life

The secret to a happy life is really no big secret at all: Find a purpose and become a craftsperson. This purpose, as we’ve seen, should be greater than yourself but still in line with your core values. Often, it doesn’t necessarily involve a need to escape: simply a re-evaluation of what it is you’re doing versus what it is you want to do. It’s not easy, but then nothing worth doing in life is.

People who tell you otherwise want your money.

I’m still working on my purpose, but here’s what I have so far:

I do web design and development because I believe in the power and potential of the internet. I believe that the internet is the ultimate demonstration of a pure meritocracy and is showing us a new way of managing ourselves without unnecessary authority. I believe that it can remove the power of many of the unelected and unwanted gatekeepers of culture and provide a more equal opportunity to succeed for anyone with the desire to create and produce, whether for the sake of creation itself or as a principal means of survival.

I don’t think that a person should be prevented from owning their own space to demonstrate their creations within this democratic environment just because they don’t have the time to learn the design and development skills necessary to create this space: that’s why I’m here.

I can facilitate their involvement: I can give them them the power to express themselves as freely as possible and in whatever form that expression takes within the confines of digital technology. I believe that the more people that are encouraged to create and express themselves in this way—to find their audience—the better the world will be for it.

Even if that expression takes the form of videos of their cat jumping into a box.

Cultivate the skills that you want to cultivate; aim to be the best at what you do and do it with love first, whatever it is. Make pursuit of success and money a byproduct of this love. Understand that, at times, it will be hard and be ready to bear this suffering with all the dignity of a Greek hero, like Viktor Frankl (and if the price of a taxi ride is getting you down, read his book for some real perspective).

Finally, escape if you want. Just make sure you know where you’re escaping to.


1 Seinfeld, Jerry; Comedian; Miramax; 2002 (Back)
2 Pirsig, Robert M.; Zen and the Art of Motorcycle Maintenance; Harper Perennial; 1984 (Back)
3 Frankl, Viktor; Man’s Search for Meaning; Washington Square Press; 1984 (Back)
4 Pirsig, Robert M.; Zen and the Art of Motorcycle Maintenance; Harper Perennial; 1984 (Back)
5 Frankl, Viktor; Man’s Search for Meaning; Washington Square Press; 1984 (Back)
6 Ibid (Back)
7 Ibid (Back)
8 Pirsig, Robert M.; Zen and the Art of Motorcycle Maintenance; Harper Perennial; 1984 (Back)

Are you planning your next travel adventure? See our Travel Resources page for our favourite tools and gear to help you plan the perfect trip. 

  • Share:

Enter your email to sign up for our monthly newsletter and free ebook South America Highlights.

33 Comments (1 pingbacks)

  1. Reminds me a story of Willie the Bird. Decided not to fly South one Winter. Started getting Cold. Then started getting Real Cold. Decided to fly South. En Route, wings froze and Willie plummeted to the ground. :( Willie thought “this stinks, I’m gonna die.” Then a Cow came and plopped on Willie. Willie thought “this really stinks, I’m gonna die covered in Sh%*!” :( :( But the Plop started warming Willie’s wings. Willie thought “this is great, I’m gonna make it!” Willie started Chirping. Jethro the Cat heard Willie chirping, came along, dug through the plop and Ate Willie. Moral of the story… those that Sh%* on you aren’t necessarily your enemies, those that get you out of Sh%* aren’t necessarily your friends, and if you’re Happy Lying in a Pile Full of Sh%*, don’t Chirp about it. So… if you’re Happy, Relax and Enjoy it. If you’re not Happy, Change Things. :) Doesn’t get much more complicated than that. (story not relevant, I just like it)


  2. Hi Simon,

    I discovered this post while organizing posts for the upcoming Gen Y Travel blog carnival (which I have the honor of hosting this time around at

    But yes, I was pleasantly surprised at this article. This part especially hit him for me:

    “For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s personal dedication to a cause greater than oneself”

    It’s true, at least for me. True happiness only happens when you’re straddling that sweet spot of “not too easy to be boring but challenging enough to be interesting”.


  3. How nice to read a thoughtful, refreshing post that steps away from the lifestyle design mythology. A good definition of happiness is the Aristotelian one of purposeful motion towards a goal, and it does sound like you’re getting there.


  4. Thank you so much for this essay. I too, have longed for freedom and I found it in travelling. In learning about other people’s cultures. Like you said, it is the journey that matters. My most wonderful memories are those of our misadventures, the wrong bus we got on, the moments when we almost didn’t make our flight, the trivial conversations with the other bus passengers.

    My hubby and I just got married and while we thought marriage would effect to a changed lifestyle…somehow we haven’t found ourself slowing down. The desire for freedom is still there. I guess we just have to find out what our passion is…as it is…we work to afford to travel..It’s early days yet..I’m hopeful that sometime soon..we’ll find our purpose and become craftpersons.

    Keep these interesting articles coming…

    =) Val


    • Thanks Val. It’s good to have that positive, go with the flow attitude when things go wrong: I think that’s kind of when you know you’re on the right path. Like my man Baz Luhrman said, “the most interesting people I know didn’t know at 22 what they wanted to do with their lives, some of the most interesting 40 year olds I know still don’t.”

      I know I’m still working it out.


      • Some days though I’d rather be boring and know what I want to do with life. Then again, the beauty of life lies in its uncertainty, that life as we know it could change in an instant is what makes it wonderful.

        Hubby and I are going on our first trip abroad as a married couple on Thursday. I’m sure it’ll be a period of discovery. Wish us luck. Oh and thanks again, you and Erin are an inspiration to us.


        • Knowing what you want to do with your life is important and ‘boring’ is totally relative. If you’re happy where you are and feel like you are on the right track, then ultimately that’s all that matters.

          Good luck with your trip and have a wonderful time!

  5. really thoughtful post. As a long-term traveler myself, I can see a lot of this in my own line of thinking (and seem to recall we talked about some of this stuff at dinner a few months back). Hope all is well.


    • Thanks very much Mike, appreciate it. I’ve been playing with this for probably as long as we’ve been traveling and I’m still working it all out. Hope things are good with you too.


  6. My dream is to actually become a Greek Hero. The only problem is that there isn’t much money in that right now… Any suggestions?

    Thanks for the shout out. It’s an honor to be mentioned in the same line as Kristy, Dan and Audrey.


Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.