“How I Knew I Wanted To Become a Digital Nomad”

“How I Knew I Wanted To Become a Digital Nomad” post image

“If you’re going to take on this lifestyle you can’t have an employee mindset. You’ll end up broke or bored– trying to sustain the lifestyle by scrambling for remote work” – Jon Myers

One of the biggest misconceptions about the digital nomad community is that we are all a bunch of glorified backpackers (of course, many of us are–  I don’t think there is anything wrong with that).

One such example recently got popular on Hacker News, and an interesting discussion ensued. In short, the author had a hard time adjusting to “life on the road.” Fair enough, life on the road isn’t for everyone. (And what follows isn’t a reaction to the author, just my thoughts).

If you want to sustain the location independent lifestyle for many years, I wouldn’t suggest using your freedom of time and mobility to travel around and see attractions.

What I’m attracted to is something I’ll call lifestyle business design.

If “lifestyle designers” are those who live like millionaires without having a million bucks, then “lifestyle business designers” are those who spend their time like wealthy people before they are wealthy.

How Lifestyle Business Designers spend their time:

  1. Embedding themselves in a community of others who are having the type of success they are seeking.
  2. Increasing their cash runway by baselining their expenses in environments good for work, health, and networking.
  3. Regularly attending relevant conferences and meet-ups (regardless of location).
  4. Leveraging their flexibility to gain access to influencers.
  5. Learning how to set up financial entities in foreign jurisdictions (They are a micro-multinational of one).
  6. Building distributed teams that are globally optimized for cost and performance, and then meeting them in person.
  7. Visiting their manufacturers regularly. They might even live in the same city while in prototype or production phase.
  8. Identifying mentors, meeting with them, and going to work with them in some capacity.

How Lifestyle Designers spend their time:

  1. Visiting temples.
  2. SCUBA diving.
  3. Going to Thai islands.
  4. Living the dream.
  5. Volunteering

(Please don’t get me wrong, I love these things, I’m just bringing up the issue of focus and priority). I see remote working arrangements and the like as golden opportunities, and I sometimes wince when I see aspiring entrepreneurs squander them.

Here’s what Jon Myers had to say about it (full comment):

“[this article] makes being a “nomad” seem like a wandering soul hopping gig to gig taking advantage of low cost locations without much strategy or purpose.  The whole point of being location independent… is that you can be more strategic about your location, expand your network by being exposed to serendipitous opportunities that would have otherwise not presented themselves, and grow your business.The opportunity to expose yourself to places and people on an upward trajectory, and how you can add value to those situations and take advantage of them should be a priority at the top of the list.”

I’m focused on being able to have “lifestyle design” freedoms for the rest of my life, not for the next 6 months.

Sure… it was temping to take my first remote working agreement right to a bungalow in southern Thailand, but I’m glad I didn’t.

I bet I had a lot more fun because of it.





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Published on 09.24.13
  • So so happy you are blogging again mate, great stuff!

    Big ups for #’s 2 & 6

  • Jesse Lawler

    Fantastic distinction here, very well defined. One extra bonus point on the quality-of-life upsides to “Lifestyle Business Design”…

    The lifestyle designer is going to meet mostly vacationers. Nothing wrong with that; interesting people vacation. But the lifestyle *business* designer will meet international business folks. And no contest, hands-down, the average international businessperson is more interesting company than the average vacationer. Even if you have no intention of ever doing business with them. Exceptions (of course) exist, but on average this is overwhelmingly true. And what’s more quality-of-life-y than interacting with interesting people?

  • That blogger does make one good point, the illusion of location independence. We use the phrase location independence because we haven’t accepted the internet as a location. When you have to have a fast internet connection and a laptop to make money, you are tied to the online location. Long term this doesn’t matter (true internet ubiquity) but right now… it can be a distraction.

  • +1

  • charlesmpiche

    Love your perspective on this and I can relate. What most of us want ultimately is live life on our own terms. Location independence doesn’t necessarily mean moving every week, unless that’s what you want…

    For me personally: Moving to a new country of my choice with a one-way flight, immersing myself to a new culture, doing weekend or week long trips to surrounding cities/countries, moving when I feel like it. Add the Lifestyle Business Designers list to that and you get:

    A Location Independent Lifestyle Business Designer?

  • right


  • Short, but great article. I love your definition of lifestyle design vs. lifestyle business design.
    It’s interesting how you can live the lifestyle design without living the lifestyle business design and it’s great, although you would be miserable if it were the other way around (so location independent working without the awesome time spending). I guess this shows which one is more important, right?

  • Lifestyle design is, essentially, a SHORTCUT to a semi-retired kind of lifestyle, defined by and filled with whatever makes you tick.

    And shortcuts don’t work in the long-term.

    They have an expiration date.

    You probably could sustain your designed lifestyle on freelance-type work for years, but I think eventually it will get somewhat old. Not to mention the kind of rollercoaster it is to always hunt for work – work – hunt again – work – hunt some more – work.

    If that’s how you make a “lifestyle design” life work, then it has an expiration date.

    But if you defer the temples and beaches for a while to work on creating a viable business, then you’re building something long-term.

    See? There’s that “deferred life” thing coming back to bite you in the ass.

    But not really.

    The point is to defer somewhat of a lifestyle do the right kind of hard work and not chase shortcuts that leaves you high and dry.

    All those points you mentioned would be “hard work”, so to speak.

    Or simply: “do the work”.

  • Youssef Mobarki

    Nomads gotta Nomad. But yeah…thanks for clearing that up, Dan.

    Oh one little thing to add, you don’t have to travel to SouthEast Asia to experience Lifestyle Business Designer…#justsaying

  • Ian

    100% Agreed.

    To me the digital nomad lifestyle is about being proactive in life.

    Pat Flynn is a great example of a digital nomad, and he’s been in San Diego the whole time!

    Lewis Howes is a digital nomad even though he’s got an apartment in Hollywood.

    Maybe I just make digital nomadery an all encompassing thing, but to me, it’s about identifying an optimal life and going after it.

    The deceptive element is that most people who go for it, find that Thailand is a great place to start… then the visa runs kick in…


  • Andrew Jacoby

    i left the states for full time travel may 10th 2010. Until april 15th 2011(tax day, not salient to the story but an interesting, if unconscious choice of dates) I did the work one hour on the internet and basically sit on a beach bum around life. I was a lifestyle designer. I had reached what I thought was the mountaintop. Then I got bored. I realized that the most interesting thing I could do with my time was to put full time effort into business. I graduated to LIfestyle Business Designer. Now instead of a few grand a month it is over 5 figures but that is the least interesting bit really. The thing that shifted was a realization that full engagement in my business was more interesting than another day at the beach, even if that beach was somewhere really cool. I have come to believe that the lifestyle design part is, or at least was for me, like a gestation period before becoming the lifestyle business designer. There is obviously alot more to be said on the topic but very enjoyable post Dan.

  • Love it, Dan. Especially this line:

    “I’m focused on being able to have ‘lifestyle design’ freedoms for the rest of my life, not for the next 6 months.”

    I personally couldn’t stand the “hunt for work – work – hunt for work – work” cycle that Sam Woods described in his comment, which a lot of non-business-building digital nomads follow. Some people can pull this off and love it, finding it an adventure… for me it’d be a constant source of worry. I crave stability.

    It’s funny how “stability” in the majority culture is defined as settling down in one place and having a “secure” job (as if those really exist). Whereas “stability” for me (and probably most LBDers) is having a business/businesses supported by multiple table legs, so to speak, so that if one breaks, it’s a bump in the road and not a complete disaster.

    “Stability” means my business keeps being profitable whether or not I’m physically able to work, as Amy Hoy fantastically describes here. And that I have the time/income freedom to travel whenever I want, which I can utilize as frequently or infrequently as I wish.

    Now I wish people would quit saying “You’re so lucky” to be able to do XYZ, and instead say “Congratulations on following through on the steps you decided to take to construct your dream lifestyle.”

  • Danica Ratte

    Thank you Dan for sharing Jon Myers quote “If you’re going to take on this lifestyle you can’t have an employee mindset. You’ll end up broke or bored– trying to sustain the lifestyle by scrambling for remote work”. This really resonates with me. I am in the beginning stages of creating a “Lifestyle Business Design” and have only 8 months until my move to SEA. I have been flip-flopping between continuing to work remotely for my current employer once I move or to go full-time into building out my online business. This quote answers my question!

  • Adrijus Guscia

    Damn. Very timely post. I’ve just hit the place where I earn full-time income from my freelancing and that has been making me too relaxed and spending more time just hanging around with friends etc.. Too soon as you say. Need to get back to the grind!

  • Cool post. Reminds me of the discussion about the hamster wheel versus the flywheel. It’s good to step back and see which one you’re on. And, if you find you’re running around like an aimless furry rodent, figure out what it would take to spin that flywheel and build some sustainable momentum.

  • Ben

    Great discussion, love your list of 8 valuable tips. My viewpoint is simple, I aim to acheive the point where I don’t have to be a wage slave. And many people are thinking something similar; doing something different down the line. Some are business savy and quickly set up profitable businesses, others need to travel and experience other things first. There are many roads to Rome.

    I think geographical arbitrage can be a first step towards an independant lifestyle. I work in Australia as a professional 2 weeks per month and live in S-E Asia the other 2 weeks. Gives me some time to plan, strategise and implement, while still maintaining an income flow for the family. It would be faster not having a j.o.b. at all but this is the best I can do while I get myself up and running. Leaving behind the polticial and admin. headaches of full time work has been, better than I ever could have imagined! Need to work more on implementing online businesses though. Cheers!

  • Josh Stanton

    When people back home ask me what I do all day my answer is always something like “90% of the time I work. The other 10% is for play, but that’s not why I’m here.”

    To be honest, sometimes I lose a little momentum and feel bad about not taking more advantage of the things to do and places to see in Thailand. But then I always come back to the same conclusion, in that, I didn’t come here for a holiday, I came here for business.

    Thanks for putting things into perspective man and I can’t wait for DCBKK!

  • Dan

    haha word, nomad gonna nomad. :) makes me laugh

  • Dan

    Only if you define “shortcut” as synonymous with avoiding the work, the most interesting parts of lifestyle business design is that there are some real efficiencies, or hacks, or shortcuts presented.

    your differed point is interesting: those who do the work are always differing something!

  • Dan

    not for me, i guess it depends how much you like your work. i love the opportunity to wake up every morning and focus on the work i choose…. i’d live a lower class lifestyle if it meant i could do the work i wanted.

    i wrote about that once: http://www.tropicalmba.com/rice-and-fish-heads/

  • Dan

    i agree with your comment!

  • Dan

    thanks brother man

  • Dan

    when you gonna put that tongue in? :P

  • Dan

    it’s been a rockin’ one so far, looking forward to catching up soon.

  • Dan

    haha, this reminds me of Seth’s quote “the risky thing is safe and the safe thing is risky.” I do think LBD is a pragmatic approach to security in the 21st century, but that’s a complicated argument to make!

    perhaps a few more countries tanking will help us make the case for hyper agile internationalized small businesses as good investments.


    thanks for the link too, i’m going to go check it out.

  • Dan

    do both! best of luck with the move….

  • Dan

    haha :) rock on…

  • Dan

    +1 many roads and arbitrage as a hack to get more runway. the only fallacy i see is people taking a lot of time to ‘figure things out’….. most people who figure things out are just shipping, breaking, shipping, charging, rinse wash repeat.

  • Dan

    haha… these terms are getting out of hand! we need a style guide :)

    I’d say Pat Flynn is location independent, but if he doesn’t semi-nomad I’d not say digital nomad.

    it’s a degree and mindset thing i guess too…

  • Dan

    yeah buddy totally agree. there is no shame in focusing on your work.

    nobody is busting on Steven King because he doesn’t go to the local craft show every weekend. He does his thing.

  • Dan

    this is a very good point. locations are not even close to arbitrary in terms of how they impact your life/business.

  • Dan

    ‘The thing that shifted was a realization that full engagement in my business was more interesting than another day at the beach’

    it’s an empowering day when that happens, when you find something you love doing in the world, so much that you’d be willing to eat rice and fish heads or sleep on mom’s couch to get it done.

    if you ever write up your story please send me the link!

  • Dan

    “And what’s more quality-of-life-y than interacting with interesting people?”

    totally agree here this is perhaps the #1 upside of this lifestyle for me, have the flexibility and freedom to track down others (and spend a lot of time with) people who have the same projects…. not simply the same interests… as me.

  • Dan

    still love that metaphor!

  • Ian

    Yeah I guess Digital Nomad signifies that one does travel where as Location Independent Entrepreneur is more suitable for a guy like Pat. Lexicon improvement, Check.

  • Andres Zuleta

    Dan, always timely.

    When I first read 4HWW I dreamed of working little, traveling lots. Now, I dream of working my ass off doing what I love, and helping as many people as possible (all while traveling the world, too).

    This week is my very last week at my 9-5, and as of next week I am a full-time lifestyle business designer, heading to Japan first, then Vietnam, then South America… and then who knows where. But it is less about the travels, and more about being able to devote tons of time to the business I am passionate about – and the traveling bit is just ensuring that my business fits within my ideal lifestyle.

    You and Ian have been a huge inspiration, thanks for all you do.

  • Meddahi


    I’am eager to be a bachpacker , but I don’t think it’s easy to do for adults who are in charge of children. I think it’s something to do for youngsters and new graduate students.

    Thanks for paying attention to comments

  • Danica Ratte

    Really??! Question for you- how do you know when you are ready to make the leap to live a Lifestyle Business Design?

  • Dan

    I once had something similar to a remote working agreement. I went from spending 10 hours a day working on my job (give or take… sometimes more with commute and stress) to about 2 hours a day creating results.

    I then went even further and hired somebody to help me create the results I was paid to create.. so I got down to about 15 minutes a day or so. I’m not sure of the actual numbers, these are just from my memory.

    The point is, if somebody is paying you money keep at it and build something on the side!

  • You’re talking about “lifestyle _business_ design”, whereas my point was more related to “lifestyle design”.

    I’ll still maintain that basing your life and business on shortcuts will most likely come back and bite you sooner or later.

    Shortcuts are often taken because the motivation is to avoid doing work.

    I’m not denying there are efficiencies and hacks — I’ve made use of some of them.

  • kevkos30

    Good timing on this article as I am headed to Thailand for work and most people are telling me how lucky I am and how I’m living the dream, thinking that I’m going to spend 3 weeks on the beach drinking mai tais and coconuts!

  • Danica Ratte

    I do see your point! By doing remote work on the side, it keeps your options open, maintains good connections and will help with positive cash flow until the business is steady.

  • Great post, Dan, and just what I needed to read right now.

    As someone who is still struggling to get past the starting line in building his dream lifestyle, I think your first list works great as a set of goals for anyone new to the game to adopt. Which I’m going to do myself, of course.

  • Dan

    Cheers thanks Simon!

  • Dan

    haha :) a little bit couldn’t hurt

  • Dan

    cheers! yeah with kids a little tougher but i’ve seen it done many times

  • Dan

    congradulations Andres with you the best on your new adventure!

  • I SO get you. Me, I got tired of horseback riding, clubbing, margaritas, clubbing, beaches, clubbing, beach, clubbing, morning naps after the CNBC morning bell, clubbing, beach, clubbing…see a pattern? The change for me came when I volunteered at an orphanage in Northern during Christmas. I realized that being able to live that lifestyle was awesome, but I needed something more – I call it my maturity from Lifestyle Entrepreneurship to –> Impact Entrepreneurship, The best part of this transformation is knowing that you are truly doing on a daily basis the kind of work you find just as enjoyable as the lifestyles other people only lead on vacation. it’s pretty effing cool…..

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  • Chris Maltese

    Absolutely. Its also the fuel that keeps you going and gives you new ideas. I’ve had these desires for a while, but now that I’ve discovered this supportive community, its amazing what is happening and the connections I’m making and the creative ideas that have been inspired. What a trip!

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