Life on the road was not for me. Sure I loved seeing the world but ....

1. Always having to make plans for the next place to sleep was stressful for me. I'd arrive at some city and have to start planning the next city else I'd be homeless once my hotel/apartment term expired. I started booking longer (4 weeks, 6 weeks, more) but even then just the fact that I have a place I don't have to think about is less stressful for me.

2. No hangout buddy or really close friends. Some people are great at making new friends and I did make a few in certain cities but I'm at least a little introverted and felt pretty lonely quite often.

3. There only so much tourism I can take. At some point it just got boring seeing yet another old church, yet another museum, etc. Some recent book claimed you should take several shorter vacations than fewer but longer ones. They recommended no more than a week at a time.

4. Not being able to buy/own anything. That might appeal to some but not to others, it means no shopping, something that many people enjoy while traveling. It also means no PS4, no Vive/Oculus, no gaming rig, no tools, no food supplies. Sure if I rented an apartment I could go buy a few things to cook but when I have a permanent residence I have tons of utensils and spices and other things in my kitchen that I just don't have the time to gather in a temporary place. Similarly I had drawers or closets full of parts and tools, something I didn't have digital nomadding.

Of course that's all just me. I've met others who really enjoy that lifestyle. Good for them!

Number 2 is a big one for me. I've considered a digital nomad life a few times because I love to travel, love to see new places, love to meet new people and all the rest, BUT...

I hate solo travel. I'm naturally very quiet, introverted, socially awkward and get social anxiety, so travelling alone is stressful and I don't end up exploring new places much and meet rather few new people because I find it incredibly hard to just start a conversation with strangers (doubly so if there's a language barrier).

I'd love to go on extended travels, working from coffee shops while exploring new and interesting places, seeing new things and meeting new people, but to feel comfortable doing that, I would need someone to join me and I simply don't know anybody who would do it with me. :(

I just moved back to the states after 8 years doing the digital nomad thing and while I totally agree taking a friend or SO with you is ideal, you develop the skill of feeling comfortable opening up to strangers. I used to be completely unable to do this and now I can chat up anyone anywhere. Unfortunately I find that most people can't reciprocate, increasingly so these days. I was severely disappointed when I moved to Austin and got nothing but cold shoulders when trying to start conversations with people in public (I had formed the impression that Austin would be a friendlier place than it is in reality; people talk a big game here but when it comes down to it they are just as self-absorbed as people in any other tech hub). The first six months are brutal but eventually you will get over it out of necessity. I don't want to downplay how rough the adjustment period is, though. It sucks and it reduced me to tears nearly every day.

I am not a Digital Nomad but an expat, and IMO it's not just about being able to open up to strangers but being welcomed by them, I've had people literally tell me they just expect me to leave after one year because that's just what people do here, they are protective, they are okay socializing with me but they don't involve me within their circles because I can't speak the language.

Find yourself some "real" Austinites. Something like 4/5ths of Austin's population is "foreign", and this figure is pretty close to literal. It's a big east-coast city in Texas now. But there are "real" Austinites that are every bit the wonderful stereotype you've heard. They have started moving out of Austin lately though, to cities like Elgin, San Marcos, New Braunsfels, or Fredricksburg. There's still some local flavor south of the river in Austin. But everywhere else are just Los Angeles and East Coast transplants that brought their road rage and shitty attitude along with them.

Thanks for the reply! Very much appreciated.

> There only so much tourism I can take. At some point it just got boring seeing yet another old church, yet another museum, etc. Some recent book claimed you should take several shorter vacations than fewer but longer ones. They recommended no more than a week at a time.

I just finished a two week honeymoon less than a month ago, and we did it as a traveling and sightseeing vacation. We started with a week in New Orleans and the surrounding area (and mostly did sightseeing instead of partying, it was a honeymoon), and were going to head up through Atlanta and see more of the South. We decided after that first week we were not looking forward to more sightseeing in the humidity, so we made a beeline for Florida and went to Disneyworld for a few days instead. Even though we were a little underwhelmed with Disneyworld after building up expectations for so long(we go to Disneyland often, and I would say they are comparable depending on the type of vacation you want), we didn't regret it.

Like many things, the wonder becomes commonplace if you are subjected to it consistently for long enough. That seems to start happening for a lot of people around about a week.

We did spend a day in Savannah after that though, and that was gorgeous. Mixing up the vacation probably let us appreciate it more.

Regarding 4, did you ever consider trying a gaming laptop? Razer is coming out with some pretty insane builds at very small form factors.

As for tools, yea that was always a bummer. Some cities have hacker barns or whatever but it really depends on where you are. As always, I recommend digital nomads that like buildin shit to check out Taipei, the maker crowd is HUGE there (relatively).

As an expat(who doesn't know how long until I might move again) it's not just about gaming IMO.

Anything you buy is just more weight to move to the next place. If you enjoy technology and novelty it hurts, think about all interesting that can come out of IoT, you can't just get a new thermostat or put a smart mirror in a place you don't own and need landlord approval.

It gets worse if you are living as a hardcore nomad moving from place to place within a few months, you need to have a limited supply of clothes, shoes and other similar things.

Funny though, that's exactly what attracts me to the lifestyle :) I love the aggressive minimalism.

Clevo and Sager are great too. The performance gap between desktop and laptop GPUs has been closing so rapidly that imo there's almost no reason to get a desktop rig even though gaming laptops were godawful even 5 years ago

They still lose hands down in the performance/dollar metric. Also, CPU performance is not in the same ballpark. Similarly marked parts (eg. desktop i7 vs laptop i7) have widly different performance characteristics, mostly due to thermal budgets.

But you CAN game in a laptop that doesn't require a backpack-sized power adapter now, and that's great. They're just not the most economical choice.

I haven't even got into the upgrade angle.

1 & 2 are basically the reason we started Hacker Paradise, to make it so you can travel the world without having to think as much about logistics, and while immersed in a tight-knit community.

Sounds like you're pretty set on being settled down, but if you ever do choose to travel again, definitely check us out! I myself have mostly settled now, but still like to get away for 1-3 months per year. A large segment of our community has that mostly-stationary lifestyle accented by stints of medium-long travel :)

Oh man I've wanted to ask you guys for ages (politely) - how do you justify the cost of your program? I'm sure you've heard it before, but everything you offer I can find on my own, at a hostel cost of 10 bucks a day and a coffee cost (for wifi) of like 1-2 dollars/day, in SE Asia. Your program seems to be charging several hundreds/week for establishing housing.

I love the idea, yet I need to say that $700-$800 for a week is pretty steep. The 4-week offering is a bit better, but still a lot of money, considering flights and food are not included.

Your are right, traveling to much, all the time, you end up having no bonds. This is not good.

Why are you and your grandparent conflating a lifestyle business (== not a try-extremely-hard business) with digital nomadism?

Where's the connection?

One group of people it can work a bit better for, in terms of living somewhere you have a real connection rather than living an expat lifestyle, are people who are themselves from somewhere with a lower cost of living, but can't find good jobs there, so moved elsewhere. It lets you sort of halfway move back to your home country while retaining some of the income advantages of the wealthier country. I have a Greek friend who does something like that, running a small business that is mainly economically based in northern Europe, but because he has a flexible working environment, he's able to spend a significant portion of the year in Greece, which he left in the first place only because there were no jobs, not because he wanted to leave.

In some formal sense the mechanics are very similar to an American running a lifestyle business from a beach in Crete, but culturally it's different from the "digital nomad" lifestyle.

I have a friend from the U.S who lives in Argentina and works online doing tech stuff. He lives with his Argentinian girlfriend and makes enough in two months to make TWO years living expenses! He does speak fluent Spanish though. He went to the doctor and spent 45 minutes with her and it cost him $12. This is not digital nomad, but really immigration with the intent of not returning home, but it does represent another option.

yep been doing Arg for 10yrs now. 1/3 the cost same time zone as NYC clients. great-lifestyle down here.

How does this work if you're not a citizen of that country? In this case your friend is an EU citizen, so that unlocks lots of options (like in this case work from Greece). I'm especially curious as Brexit is promising to ruin a lot of opportunities that would otherwise be available to my fellow Brits and I.

In the case of the American running a business from Crete, how does that work in terms of taxation and residency? People seem to get away with it in the far East, but (mostly) you can't just stay in a country indefinitely, mooch off the cheap system and pocket the difference.

I've studied the rules for Greece specifically. Currently for non-EU visitors, ~$24,000 in a bank account will get you a 'self-sufficiency' residence permit for 1 year. There are other permits available for buying property, marriage, and such, but thats probably not what a nomad would do.

That said, there it is not difficult to overstay the standard 90-day EU visa and simply pay the fine when leaving / on the next entry.

As far as taxes go, I would wager that any American in Greece is only paying taxes in the States. The Greek tax system is notoriously insane.

> That said, there it is not difficult to overstay the standard 90-day EU visa and simply pay the fine when leaving / on the next entry.

Don't do this. Customs officials really don't like it when you show a flagrant disregard for their laws. Also, you can create permanent problems for yourself if you ever decided to return.

I certainly did not imagine doing this on my own, nor have I tested the limits first-hand. The self-sufficiency permit isn't that difficult to obtain for a committed nomad, as I see it.

But the chatter in the Greek expat forums specifically describe the purely financial nature of the Schengen zone penalty: pay-to-play. The punishment comes in the form of the fine amount, which in a range is left to the discretion of the customs agent. Evidence of "flagrant disregard" or an otherwise spoiled attitude might get the maximum fine, whereas an honest mistake (or an engaging attitude) might cost only a few hundred euros.

If you don't have a visa, then you get 90 days in the Schengen Area every six months. You can head up through the Balkans (or elsewhere outside of Schengen) when your time is up. I used to go to Greece for three months at a time and then head elsewhere, like Argentina, Taiwan, etc.

I'm more interested in "short" long term options, e.g. a year or two. For pure tourism, tourist visas are more than enough.

Canada, for example has a Working Holiday visa which lets you remain for up to two years, travel and find employment (if you wish). There are restrictions: age, nationality and there are a limited number, but it's essentially a free ticket for 24 months.

Many (most?) countries have working holiday visas. The rules and availability depend on your own nationality and the country offering the visa, but generally they are for under 30's for up to a year. Some have a higher age limit, some are longer (as you point out), and some can be renewed for a second year if conditions are met.

If I'd known about this when I was young enough, I would have spent year in each of a dozen countries.

Make a name for yourself in some industry. The last time I looked for a job (around age 39), I sent out an email newsletter to about 9,000 subscribers and got back serious job offers in seven countries. I was sponsored by a company and immigrated to Austria on a work visa for technical workers. I would have gotten permanent European residence after five years, but returned to the SF Bay Area before that. There are ways to do it.

It looks like for the UK, you have the choice of CAN/AUS/NZ, Singapore, Hong Kong, Taiwan, Japan (pleasantly surprised to see that) and South Korea. There's also summer camp work in the US via BUNAC (which you pay for), but why bother when you can get a visa waiver for 90 days?

This sounds fascinating to me. I'm looking at doing the same thing - launch a product for global audience while relocating back to India.

Any idea how long your friend took to gain traction? What do they do to find a community of fellow techies/dropshippers/SEO mavens/whatever in Greece? Do they ever talk about moving back to north Europe?

I don't keep in that close contact, but as I understand it he hasn't precisely moved back to Greece. The business is incorporated in northern Europe and he has his legal residence there. It's just that since there's no office to go into there's no real need to be physically present most of the time, so nothing stopping him from doing much of the work remotely from Greece. It probably does help that Europe is fairly small and flying back and forth is not too difficult.

Great spot. I spent over a year (over many trips) working remotely from Greece, including Crete.

Question... Legally, how does the digital nomad thing work? Specifically WRT travel visas. Are you entering countries on a holiday visa and just working anyway? Establishing some sort of residency? Are you taking contracts in those countries, or working for US-based companies? Or, just blogging on your own and making a living through affiliate links, etc? Where do you pay income taxes?

To me traveling with a laptop and working is neither traveling nor working well. Im sure there are ways to eeke it out to make a ramen diet more pallatable overseas, but you arent really connecting with locals and local culture if youre online "hustling".

I suppose it depends on how you do it. I worked from a beach town in Costa Rica for a month last year. I worked very well, being unusually productive (I think due to lack of stress and a change of scenery). I worked ~6-8 hours a day/5 days a week, and got more done than I had over many more hours back home. That left me plenty of time to meet and hang out with locals, so scuba diving, swim in the ocean twice a day, cook with local fish and ingredients, make new friends, etc... It was fantastic!

I worked from a small beach town in Costa Rica for 6 months a while back, and I have to agree with the parent. The novelty kind of wore off and we had to work a _lot_, it became more of a nuisance with bad/spotty internet than a WFH paradise. We took off 3 days one time the week we left to be just like regular tourists for once; that was great.

I concur. I did the same in the Mediterraneans, working from a beach for a month; whenever I felt like I took a little swim in the sea, being refreshed, and it did wonders to my productivity. Not sure why wouldn't you do this if you could...

Full disclosure: I work for the author's company.

I agree with you! Back in March I finished a 15 month trip around the world while working full time. I travelled to 40 different cities in 15 countries and while some places where difficult to adapt to and the conditions where I worked from were challenging, I can say that my productivity didn't diminish.

Since I came back (I live in Barcelona) I've attended retreats in the Alps (Austria for skiing + Italy for hiking just last week) plus 2 weeks in a very nice countryside house 2 hours from Barcelona where we worked together with 10 people from the office and in the afternoons we did hikes, wine tastings or went to the beach.

Thanks for joining the discussion. I wonder how do you keep business running (bigender claims an outstanding support) while in retreat ? Does only a part of the company goes on retreat ?

>To me traveling with a laptop and working is neither traveling nor working well.

Well, regular working is not traveling at all on the other hand.

To GP's point, at my office, I have a desktop with 2 monitors, at my home office, I have a desktop with... 2 monitors. Traveling, I'm stuck with either a VERY heavy 17" laptop or a less heavy 15" laptop, or an incredibly light 12" laptop. Any way I go about it, I don't have my dual 27 inch laptops.

So? Unless you are a graphic designer, why would that matter?

It might be convenient, but hackers for decades had just had 14" (or less) monochromatic monitors and they've built masterpieces on them.

If "dual 27 inch monitors" are so important to your work, then (a) I don't see how you'd be able to be a programmer in the 80s and 90s when those things either didn't exist or costed a fortune, (b) fine, don't travel.

The "very heavy" part (for the 17" laptop) doesn't matter, as you're not supposed to backpack everywhere with it. Just keep it at your hotel/rent house/bangalow in the different cities you visit and work from there. You can still visit the city and explore all the other hours.

Besides, if it's that important, then anywhere you go and stay for a month or more (and nomads can spend several months on each country or more), you could buy a $200 24" monitor -- and then just give it away to some friend you've made, charity or sell it.

I wouldn't be able to program in the 80s and I don't want to go back to the 90s. I'm sorry but having my IDE on one half of one screen, debug console on the second half then browser on the other monitor is a big convenience that I have gotten used to.

Its like saying, oh you like your power steering, and automatic transmissions? Well then you couldn't drive a Model-T.

That viewpoint that progress makes you weak is a very bad way to view the world. Progress makes us all better at what we do by making us more efficient.

>Its like saying, oh you like your power steering, and automatic transmissions? Well then you couldn't drive a Model-T.

No, I think it's more like saying "most of those efficiencies are probably cargo cult" especially since programmers with just a 12" laptop and Vim can (and do) run circles around people with double and triple monitor setups and fancy IDEs.

So nothing especially efficiency improving that wouldn't be trumped by simply more skills.

(Not saying that you don't have skills. You might be better than Linus. Saying that multiple monitors are not the reason for that).

Yes, it's nice to have a big screen, but not really essential. As for the second screen, it gets all marginal returns from there.

You can use an iPad as your second screen. Not as good. But that's not the point. The point is good enough for know the world while you're still alive.

Understood that especially in front-end work, dual screens are pretty much necessary for testing & debugging and just being able to work efficiently.

FWIW, a 24" monitor in original box will fit in a checked bag-- takes up half of the medium-large hardshell luggage I have-- and yes I've traveled with an extra screen.

I wonder if good a VR headset would some day change this.

I can only hope so. Ever since I played with a Virtual Boy Headset in the mid-late 90s, I have wanted a VR world that would replace my physical desk.

Just bring them in checked luggage. As another comment points out, you're not backpacking.

Consider it like traveling with a bicycle, which people do quite successfully.

As a front-end dev, the extra screen is a nice productivity boost. You shouldn't lug around extra monitor, too many kgs/lbs.

Get the portable Asus MB168B+, goes in your backpack. Lugged this bad boy around 13 countries over the past 2 years. No Flux support though!!!

Yea you could probably argue there are better economies of scale doing all of your working in large chunks and then all of your traveling in large chunks.

To me 1-2 week vacations per year though is not a large enough chunk of time off. I sometimes wonder if I'd rather forgo weekends, accumulate all of that time and then take 2-3 months off all at once.

It depends on a lot of things. In a prior life, I took some month-long vacations with effectively no communication back home. (it was pre consumer Internet.) It's definitely qualitatively different from my more typical week or two intermittently online trip these days.

That said, I get antsy if I'm "in the office" (physically or otherwise) for too long and, when traveling, there does come a point where I'm ready to get back to my house rather than living out of a travel backpack.

These days I find it much more practical to take a couple of 1-2 week vacations and spend some time around business trips than to take a huge chunk of time off. But circumstances will vary.

That's kinda what I did. I wasn't head down on trying to build something, but I did write a novel while we were traveling, along with some freelance. We'd travel, moving from place to place frequently, then settle in somewhere with decent internet. We travelled through Peru and Chile, but lived in Buenos Aires for a month.

Travelled through much of SE Asia, but lived in Thailand for a couple months. India (travel) Spain (living) and so on.

This is what I have found. When I travel, I want to travel deep, so to speak, and suck out all of the marrow. I have tried to do work while touring by bicycle and, while work could easily finance my trip indefinitely, I was seeing much, much less by bringing it along. Better to save up for shorter trips, free to wander as I will.

I love backpacking but it seems fundamentally incompatible to tour by bike and work simultaneously - as the pleasure of traveling slowly means there isn't time to fit both any significant distance and work time within the same day.

Planning to work remotely laster this year and will definitely pick a spot and stay parked there for weeks.

When I think about Lifestyle business, I don't really think it mean traveling.

I personally want a lifestyle business but for my lifestyle. That is wake up late, enjoy the day, maybe go for a road trip or hike, work in the evenings, work till midnight or so. Or if I feel like it, take a day off.

Go on vacations but not worry about return date. Bring the laptop and if needed, work. Otherwise just enjoy the vacation.

This in so many ways, this. I have a bunch of ideas. If you can build stuff, we should talk. lol

I'm also what you call a digital nomad. I find it tough to work while "on the road". It's stressful, you want to get out and see places, meet people, but you still need to work. This is why I prefer to move to a city for a few months at a time and slowly do all the touristy things.

Also about what you said about others not being very interesting; I completely agree.

> you'll still find yourself missing the familiarity of people from your own culture (or similar, Western cultures, assuming you're a Euro or American)

I didn't find that to be true. I miss foreign people and cultures after settling back down. If you want to find people from your own culture while on the road, stay at a hostel or take a break from roaming at any backpacker/nomad/tourist trap.

Stay out for a year or so and you will likely want to mingle with some westerners. Or maybe not! Everybody's different.

The expat pockets around the world have their own culture going on. Suddenly you're hanging out with the embassy staff, some UN people, some interns and backpackers and other random people. I'd say it's very interesting in itself to experience and not the same as meeting people back home.

That's precisely my point. Except that SE Asian expats are boring af on average. There are exceptions to be sure (I made several good friends while traveling) but on average they're shockingly boring, but they're as good as you're gonna get for that Western fix.

Maybe that's what I should have been more clear about. You'll end up hanging out with boring people because you miss home after a bit. Before I went traveling I would have expected that community to be a lot more interesting than they were.

Get off the beaten track to find interesting travelers. The locals tend to be friendlier too.

Sigh. That's the most obvious of knee jerk responses and the most naive. I hear stuff like that a ton from people who are chasing that old illusion of authenticity.

16 months on the road through the backwaters of SE Asia and India as well as the expat nests is plenty of time to get the "authentic" experience and mingle with locals. rolling eyes emoji

I was on the road on and off for over 10 years. I still wanted to hang out with foreigners even after getting back.

The human mind wants freedom and to have options. That's why the grass is always greener. Spend a month traveling and being back at home will sound ideal. Get stuck in an office and traveling sounds perfect. Finding the right balance is the key. In my case though I have had the freedom at times to be anywhere I still gravitate to keeping a home base.

Why do we need to equate a lifestyle business with traveling the world full time? I run a lifestyle business and I go abroad maybe once a year for about a week and I am very happy. I think the point is that the lifestyle business lets you do that if you want to, but at the end of the day you can still do whatever you want.