Misconceptions of the Work-from-Anywhere Lifestyle

Scroll down ↓

Today launches my Summer Festival of Guest Posts…aka…my way of slacking off while I’m in Bali and pleading with friends who have amazing voices and insights to share their genius with you.

Kicking off this new “every Friday” feature is my friend, Chris Guillebeau. Many of you know Chris already, but if you don’t, he’s the guy who travels the world and writes for a small army of remarkable people at The Art of Non-Conformity. He is also the Chief Troublemaker of UnconventionalGuides.com.

And, he’s also about to become an author with the release of the forthcoming book, The Art of Nonconformity. I’ve seen an advance copy and it’s fantastic, reserve your copy today at amazon.

So, without further ado, I’ll turn it over to Chris…


There goes that Jonathan Fields again… heading out to beautiful Bali while the rest of us hold down the fort with guest posts. What a lucky guy. I’m guessing his schedule today looks something like this:

10am: Wake up in the hammock

11am: Eat banana pancakes, Jack Johnson style

1145am: Quick email check

12pm-6pm: “Brainstorming time”

6pm: Post a TwitPic of the hammock

615pm: Quick email check

630pm: Begin drinking beer

8pm: Bonfire and barbeque prepared by the local Career Renegade staff

That’s how the “work from anywhere” life goes, right? Yep, that’s the life… of pretty much no one I know.

Plenty of people will tell you about the benefits of the work anywhere / location independent / off-the-grid lifestyle. Fine. But most of them will leave out the hard parts. (Most of them haven’t actually done it either, but that’s another story.)

Before you join Jonathan and co. in the Indonesian treehouse, here are a few things to keep in mind.

Misconception #1: Work Anywhere, Make Money.

I’ve been location independent for nearly ten years, but I could actually make more money (a lot more) by staying in one place instead of roaming around all the time. Working in North American time zones is more profitable than Indonesian time zones. Despite the welcome presence of the banana pancakes, money and working from Southeast Asia are not correlated.

Misconception #2: Passive Income = Cha-Ching!

Wake up to the inflow of funds before heading back to the hammock—what a life. Actually, Jonathan’s already been over this before… better take that post down quickly, man! (Unfortunately, he’s right. The reality is that most of us work pretty hard for that “passive” income. We have to feed the funnel, keep prospects coming in, and be available for clients or customers no matter where we are in the world.)

Misconception #3: If You Build It, They Will Come.

All you need to do is open a storefront and put out your shingle. W00t! Except not. Viral marketing means “spend a lot of time talking to everyone you know and hope they’ll do the same.” Building your project is 50% of the task; spreading the word is the other 50%—and that’s hard to do when you’re working from the road.

Misconception #4: The Whole World Is Wired.

Alas, “wired” means different things in different places. True, I had a surprisingly fast WiFi signal in Erbil, Iraq—but I’ve also been at a loss to get online in Tokyo, supposedly one of the world’s most wired places. I also spend a lot of time worrying about internet connections, especially when doing video interviews or uploading large files. If you need to rely on a constant, consistent pipeline to the world, you’re better off at home.

Misconception #5: You’ll Spend Your Days Chillaxin’ in the Hammock!

OK, this one is real… sort of. Here’s where we get into the reality of working from anywhere. By far the main benefit of establishing your plan of freedom is the ability to go anywhere, sometimes more than the actual going.

Remember the words of the Mad Hatter from Alice in Wonderland: “If you don’t know where you’re going, any road will get you there.” With that in mind, here are a few things to think about before you book your Thai Airways flight and head out across the Pacific:

  • What are you really after? What’s the goal?
  • How will your business bring joy to your customers?
  • What does freedom look like to you?
  • How will you build sustainable practices into the biz, so you can actually book that flight… or do whatever else you want?

Don’t get me wrong…

Location independence is awesome! Sign me up. But the best part of a freedom business is the freedom itself. You can be free wherever you are, or you can be stressed wherever you are. Better to solve that problem first…. then, start picking out your dream hammock.

When this post goes up, Jonathan will be in Bali, and I’ll be working from the road in West Africa. Sign me up for some banana pancakes! That’s no misconception.


Chris Guillebeau travels the world (without a hammock) and writes for a small army of remarkable people at The Art of Non-Conformity. He is also the Chief Troublemaker of UnconventionalGuides.com. Reserve your copy of Chris’ forthcoming book, The Art of Nonconformity, at amazon now.

Join our Email List for Weekly Updates

And join this amazing community of makers and doers. You know you wanna...

43 responses

43 responses to “Misconceptions of the Work-from-Anywhere Lifestyle”

  1. […] This post was mentioned on Twitter by remarkablogger, A.R.Karthick, Santi Chacon and others. Santi Chacon said: Misconceptions of the Work-from-Anywhere Lifestyle: Today launches my Summer Festival of Guest Posts…aka…my way of… http://bit.ly/cceX4g […]

  2. Hey Chris,

    Cool post here and a good wake up call. I recently decided to take the plunge and cut back my offline business to what I could do “remotely”…. all so I could move to the mountains and go skiing.

    First three weeks, I made it up the chairlifts ONCE. Lifestyle businesses sure can be hard work! It’s all a learning experience though, and I now measure my “success” by how many hours on the slopes I clock.

    This post gives me some good ideas of what else is in store for me, so thanks.

    PS Jonathan, if you’re reading this, don’t think you’re gonna get away with not updating us 😉 I wanna see some Bali pics man!

  3. Sweet on point post Chris thank you.

    Very rarely is there such a thing as “passive” income in just about any venture. I think that’s why it’s so important to “love what you do.”

    Awesome real post. Too many people are selling the plug & play and relax all day type of online businesses. That’s just not what it’s about for me anyway.

  4. Carl Natale says:

    “Location independent” is my favorite phrase of the day.

    Although I’m not the worldwide roamer you are, I recognize the challenges. I found once I decided what will be the proper balance of revenue generation and hammock chillaxin, things fell into place. Sorry, that makes it sound easy. It’s not but it becomes easier when you have guidelines. They will need adjustment from time to time. But it works.

  5. Matt says:

    Oh shit, back to the drawing board 😉

  6. Dude, thanks for having me on CR – hugely honored. Hope all is well over there!

  7. Oops, I meant “A@TW” or JonathanFields.com – not CR. But I’m still honored. 🙂

  8. Sandi says:

    Great post Christ; I’ve always been a little suspicious of “passive” anything, let alone income! Like Tony’s comment I believe it’s more important to focus on what you love to do. That’s what makes it all so juicy, no?


  9. Joel says:

    Love it Chris! A little bit different type of post from you this time, but very good and I love when you let your sense of humor come out =).

  10. Jeffrey Tang says:

    Makin’ me laugh and think first thing this morning – love the post! I was surprised to hear about your wi-fi troubles in Tokyo … one would think Tokyo would be one of the least likely places to have bad connectivity.

    I’ve often wondered how you’re able to keep up lines of communication while jumping in and out of time zones. Would be cool to see a post about that on AONC 😉

  11. Andy Fogarty says:


    It’s all about the freedom to have the freedom, but that freedom isn’t free 🙂

  12. I confess–I’m absolutely no good at working and writing while traveling. Not that I’ve tried it very many times; but I have tried. A few times. Once for six weeks. I just can’t concentrate when there’s so much stuff going on around me, even if it’s just cool scenery whizzing by on a train.

    I’ll have to give it another try someday 🙂

  13. Hmmm… if Chris Guillebeau is admitting it’s hard out there being an uncoventional entrepreneur is there any hope for the rest of us? Thanks Chris (and Jonathan) for an honest, yet strangely uplifting, take on the realities of generating passive income and working from the road. Why do I say “uplifting”? Because after reading this post I feel much better about my own struggles… Even though you guys make it look easy, it’s good to know you have your frustrating moments too.

  14. Tom Bentley says:

    Chris, thanks for the insights and the smiles. I lived on a Micronesian island 5 years ago, with dial-up Internet access—and intermittent at that—and my pals in the US would send important 3MB photos of their cats with baseball caps on. That download would take a mere 45 minutes or so.

    I was a teacher at the local junior college, and though the snorkeling and diving was extraordinary and the sights dazzling, things like the supply boat being six weeks’ late and the inscrutable politics of the island brought my traveler’s floating head some gravity.

    But then again, me and my gal are looking for another stint somewhere now…

  15. John Sherry says:

    Location independent is a cracking phrase Chris. I guess we all seek freedom from normal pressures so the work from anywhere choice is a lifestyle that goes, “neh-neh-neh-neh-neh” at the normal working ethos.Still this is a sobering reminder that there is no magic pill or dollar bill to money making…..on the road or not. All roads don’t lead to roam!

  16. Christian says:

    The whole “what are you really after?” bit is really essential. It’s so much easier to borrow someone else’s vision, instead of discovering your own.

    I had a mentor back in the day that made a really nice point that stuck with me. He said he loved the fact that he could go out and pay cash for a new Ferrari right now. If he wanted to, he could. He had the option. But he didn’t. He just liked having the option. Having the money didn’t mean he had to spend it. For him, making that purchase would be an attempt to live someone else’s vision, not his own. His vision was simply the attainment of that level of freedom.

    Freedom means that…having the option. You can be location-independent and stay in one place. I think somehow a lot of people miss that.

    We think we’re SUPPOSED to be in a hammock. We think we’re SUPPOSED to be in Paris…and next week in Milan. And if we’re not, we’re not successful. We’re compelled in other words…to live someone else’s vision. Of course, actually being a world traveler has it’s benefits. There’s nothing wrong with it, but it also has it’s costs.

    Most of us are a lot freer than we think. Want to go to Italy for a month? Really? That’s what will make you happy? Or are you just convinced that’s what you’re SUPPOSED to want?

    • Christian,

      Love the devil advocate approach to the “typical” perspective of “the dream”… We all have our particular perspective on what that vision is and pursuing that is what is most important. Freedom (to me) is the absence of stress… Nothing more, nothing less. A lesson learned from the perils and experiences of life.

      Cheers brother!


  17. Daniel says:

    The truth is everything worth doing is hard in it’s own way. (Seems like I’ve heard that somewhere before.) I’m just starting down the entrepreneur’s golden road. 🙂 But, for the last several years I’ve worked for a company remotely from my home. Earlier this year I took a 2 week road trip where I worked from the back of an RV over a verizon connection almost the whole time. It was cool to get away, but staying on task and worrying about connectivity was a bit stressful.

    It’s funny. When people learn that I work from home, they immediately say something like “OMFG that must be awesome! I would love to do that!” Then their eyes glaze over when I tell them that it’s not always all that and a bag of chips. It can be very isolating due to the lack of personal contact, you don’t get a sense of what associates are really thinking from their body language, and even the ‘holy grail’ of not having a boss breathing down your neck can be a challenge because you have to motivate yourself even when you don’t feel like doing $#!t.

    Obviouslyl there are really awesome up sides as well! But, as stated above, everything comes with a price.


  18. Best Beloved and I are taking our show (and our 6-year-old) on the road. We’re fortunate to have two parallel worldwide networks; one professional, one personal. Also fortunate the our work is largely asynchronous; time zones have so far been a boon rather than bane.

    We’ve been very clear on the fact that this isn’t going to be a life of ease, a perpetual vacation. If I were independently wealthy, I might not travel as much as we’re planning to, but at the moment, our work seems to want us to go to it, rather than vicing the versa.

    We’re checking carefully to make sure there’s water in the pool before we dive in, but I think when we get back from Vancouver BC in 8 weeks, we’ll have a much clearer idea of when we’ll be letting the house go and how we’ll be living better without all this STUFF.

  19. The ability to work anywhere definitely doesn’t replace hustle 🙂

  20. […] Chris Guillebeau’s excellent piece on the realities of working from anywhere. […]

  21. Ah, good to see you here Chris!

    As you know, we’ve been traveling the world as family since 2006 and we find it an awesome life, so we have no plans on stopping ( nor do we miss North America). Yes, there are some sacrifices and challenges, but well worth it if a person does it with their eyes open, is adaptable & plans well.

    I’m writing this from Barcelona where we’ve been for the last month, soon to mosey over to France and I think the Europeans can teach Americans much about “quality of life”, especially for families.

    Time equals wealth in our book, so that is what we enjoy most about our lifestyle…having the time together as a family and time in that hammock looking at the beautiful blue Med sea. 😉 The educational, cultural & social benefits for our very fluent trilingual/triliterate child have been outstanding. She was 5 when we began and will turn 10 this fall.

    Also, we can travel the world & live luxuriously (even in expensive countries) for MUCH less than we ever could live at home ( on just 23 dollars a day per person).

    Jonathan and family just might not want to come back! 😉 It’s an addictive lifestyle because it’s about giving yourself permission to be free!

    Oh, the internet connection IS one of the most frustrating things and you never know where you will find it good or totally maddening when you need it. We had great connection in the middle of the Sahara desert in Morocco, but one heck of a time finding any thing in central LONDON! We even went to 3 MacDonalds but none of them had working wifi. Finally we found a delightful luxury hotel that let us sit for hours sipping a drink while we used their great connection. 😉

    • Hey, Jeanne D!

      There’s where we’ll luck out in London, ’cause we’ll probably spend time with friends who I *know* have ‘net access.

      • Hi Joel!

        Yes, having friends there helps a lot and we did use friends on other visits as we have been a few times. ( We tend to stay for long periods, so do not want to burden friends who have their own responsibilities.) We also had an apartment the last time there that came with wifi, so it was easy then. 😉

        We try to always get free ( if at all possible) or cheap wifi, so that impacts. Mostly we DO get free wifi and usually it is decent…but there are moments…often right at the wrong time. 😉 We thought for sure it would be easy in London, so had let things accumulate while unplugged before arriving, so were caught by surprise.

        Sometimes it is quite surprising on where you can and can not find free wifi as my example show. Plus sometimes it is just a LOT slower than one would want it to be…or more expensive. BUT rarely do we HAVE to be on and we like to have time off the grid, so we’re lucky in that.

        Flexibility is key I think for such a lifestyle and I thrive on an improv kind of life, so don’t mind the challenges. A tightly wound kind of personality that needs a rigid routine, would probably not be as happy.

        • I remember reading up for our Ireland trip; everyone said “don’t be in a hurry” and we thought “hurry? on vacation?”

          We prefer to tell time by the sun (or the seasons) rather than the second hand on a clock. That business of not needing stuff urgently helps out.

  22. Chris… Love this brother!! While I’m still a baby on the location independence of just over a year, I have found many hours of work a real scenario. While the first question of my friends and family on the phone is “what state are you in”? … they have little idea as to the amount of true time and dedication it requires to make it a day to day… While the evolution of thoughts and projects continue onward, I stand firm in belief that banana pancakes and freedom of any stress will soon come… Embracing it’s reality as I write.

    Thanks for the rockin post brother!

    Patrick Hitches

  23. Daniel says:

    Wow I wonder if Jon would be surprised by the conversation that’s going on here. 🙂

    Chris is spot on with the points here. Loved the one about passive income. All of us still do work, only that the results start coming in like much later when something’s being sold.

    Like way way later, when the getting it viral part gets into motion once we “start talking to anyone we know about it and hoping they do the same here”.

    Thanks for holding the fort Chris!

    • Jonathan Fields says:

      Hey Daniel,

      Not surprised at all, you guys always bring so much insight and experience to the conversation. And, I love how Chris lays it bare, then says he’s in anyway…BUT, truth is, I don’t look at either Chris or me as being truly location independent. Yes, we CAN work almost entirely virtually, but we also have very definite fixed home bases that we operate out of. And, at least for me, I like it that way.

      It’s a lot like entrepreneurship, tons of people want to be entrepreneurs, until they become one…then a large chunk of people realize the trut is very different than the dream

      • @Jonathan – So happy to see you popping in from Bali! I’m so excited about your adventure and glad that you and Chris are sharing all the pros and cons.

        You are so right too that having a home base in one’s home country is very different than being a perpetual traveler (although many perpetual travelers also have regular home bases in various other countries so not really a “homeless” experience). There are advantages and disadvantages to both styles, but the first option is easier I suppose and why it is most popular. Lines are blurred today.

        Semantics get in the way I think, as we are all in the process of learning new ways of being/traveling/working/schooling thanks to the “new economy” and tech. Just the fact that you and Chris “CAN work almost entirely virtually” make many consider you “location independent” or “digital nomads”.

        I love it that you are exploring this option as a family and taking us with you through the process as I think extended travel is true gift for families that more will be doing in the future. I am hoping you all have the time of your lives!

  24. First of all yeah for you and this post smells of integrity and honesty. Everyone preaching easy and fast…their sales will be down.

    A comment on #2… once the cash comes rollin’ in there’ll be the temptation to continue working like a maniac in fear of losing it.

    Or the addiction to fame and stayin’ on top with other gurus one will keep them from chillaxin when in fact they could because of the systems they set up will bring enough income to live on forever.

    # 3 So true…ask realtors and construction workers about that one;)

    My daughter works for Southwest so we can travel free anywhere. We visit friends and family all the time. I bring my laptop but ask me how distracted I get from everything else…just ask me.

    I bow down to you for your authenticity.

  25. Hi Chris.

    I like to read pieces like this that discuss the misconceptions that folks have about a certain lifestyle. The hard material is often left out, and I’d say the greatest benefits are often left out. People usually talk about the middle-of-the-road material regarding any venture in order to prevent competition and seem to be more average than they are.

    That message about how if you build it, they will come, only attributes to certain specific ventures that are right on the money as far as the time they were launched, as most items that are built require active grabbing of people until a high threshold amount is reached, and even then it can require effort to maintain.

    The phrase “passive income” sure does work well to lure in folks. It is analogous to “profiting easily”, which goes against the concept of money being earned by work, and so it fools many.

  26. I think you nailed it with it’s the “ability to go anywhere, sometimes more than the actual going.” I love knowing that I can work anywhere, but I’m not always so keen on actually working anywhere…mostly!

  27. Thanks for sharing these misconceptions about the location independent lifestyle. I particularly love the point you made about ‘why are you doing this?’. It’s got to be a really compelling reason to add the extra stress.

    I found it fairly challenging to work while traveling as a nomad, and I have only done it in Europe and Panama.

    I found it hard to balance work time and ‘tourist’ time. When in London, Paris, or Bali, one must be out there exploring all the time, right? No, when you’re working, you have to find a rhythm that works.

    I recently spent three weeks in Paris doing research for my novel. For jaunts like that I put my workload on simmer, doing only the basics required to work with my clients and run basic ops. I gathered a lot of inspiration, and found it a perfect balance to return to Denver to develop more content for future episodes of my web TV show and dig into my novel revision.

    My rhythm in Paris was working in my ‘office’ in the morning with coffee and a croissant, then going out to explore or meet with friends. Later at night I’d edit videos and respond to emails. On the weekends I had full permission to unplug and enjoy Paris.

    On the business side, it’s definitely part-time work, and it definitely only works for awhile, if you’re intent on developing content. It was a lot easier on this trip, because I’d gotten some footing on it during my year traveling, but it definitely can take time to adjust.

    The stress of ensuring a good internet is no joke. It’s not fun and you really have to weigh the benefits of being abroad versus reliability in your delivery.

    Thanks for sharing these challenges. It’s not that it’s impossible, you just need a really good reason to try to work that way.

  28. “Viral marketing means “spend a lot of time talking to everyone you know and hope they’ll do the same.” 🙂

    I can see myself using that – with attribution of course. 😉

  29. Never mind finding it difficult to get online in Tokyo, I’ve found it difficult to get online in some parts of the UK and we’re supposed to be more advanced!

    Also, my experience is that there’s a whole lot of graft needed to get your online business and community to a point where you can make decent money. Separately, that you could spend your entire time online if you wanted to. This, for me, goes against all of the reasons I started out on my location independent journey in the first place. Why travel when all you’re doing is the same old stuff in different wifi hotspots? 😉

  30. Amy Putkonen says:

    Great post, Chris. Funny to see you out here because I just shared a link to your site the other day as I was talking to a friend about how you are doing the same thing she is. Her goal is to travel to 30 countries before she’s 30. Ah, to be so young again! (I’m only 42…giggle)

    Anyways, a great post. I am sure that doing all that traveling gets old after a bit. Still, a little freedom goes a long ways too and at least you guys have some of us working slumps dreaming a bit and chasing after something. Keep up the great work!


  31. LynnH says:

    Thanks for the thoughtful post. I’m thinking a lot about the intersection between what I love to do, what I’m excellent at doing, what I can do (must sleep sometime, for example) and making enough income to make it a reasonable situation.

    I live in a low-housing-cost city, and stay home most of the time. In one way, I’m location independent because I do not have a storefront, it’s all internet or I go on site. When I’m lucky, on site is far from home, but I’m happy to work in this field.

    It’s sort of funny, though. This old house has a great porch and there are a few tasks for my business that I do in fact accomplish on a hammock out there. I’m not snoozing, but the decor is about perfect when my task schedule and hammock weather coincide properly.

  32. Thanks for this, Chris. It’s good to hear something other than how wonderful it is to be location independent. I recently returned from a six month stint of working while in Australia and can say while I loved it, it had it’s drawbacks including being incredibly expensive. Having said that, I am looking forward to my next trip.

  33. Cath Lawson says:

    Hi Chris – Who would have thought you’d have connection problems in Tokyo,

    I’ve been thinking about this for a little while now and I’ve come to the conclusion that maybe it’s not that I want to travel to a new place every couple of months while I’m working.

    It’s more the feeling of knowing I have the freedom to work where I want, when I feel like it, as you described.

    Good luck with the book sales. I’m looking forward to reading it.

  34. Bill in Detroit says:

    I like the idea of being able to slip away from home for a week or two at a time to research material for a writing project. Too, I have family spread out over 3 distant states and it would be good to be able to see them each year instead of having to choose between seeing one of them or traveling somewhere intriguing.

    But my writing skills are not sufficient for that (yet).

  35. Ana says:

    It’s refreshing to get a different point of view. I admit to getting swept up in the “fantasy of the hammock”, and I appreciate the reminder that passive income…isn’t. 🙂

    Thanks for a great post.

  36. Karla says:

    Thanks for sharing informative blog like this! I find it very interesting to read and I also love the points that you expressed! Anyway, thanks for sharing and keep posting!!!