That's usually a red flag to me -- feels like the scummy side of the Internet.
Doesn't take away from the point (mostly) - that the Internet is enabling a new type of remote-working lifestyle - but I can't get over my spidey senses tingling about the underlying...
Just yesterday I was feeling jealous that a friend posted on facebook he has locked in a contract with the Tonga tourism board and is currently sailing his yatch to Tonga to start the contract. After sailing to New Zealand for the Hobbit premier. I met this guy wiring up financial web services between banking mainframes in Singapore and some reporting companies. Not exactly what I'd call scummy side of the internet.. unless you have a very low opinion of financial traders LOL.
Once while on a diving boat in the Red Sea I was chatting talking to the others divers before our next dive and it turned out 3 out around 7 of us where free lancer software developers. I have been told by people that Britain does have an unusaly high work from home rate for IT workers (never verified that statement though).
As for rich though... I used to get paid a hell of a lot, but in all reality I burnt a hell of a lot of cash really quick. I think the aforementioned diving trip was £2000 for 8 days for example. And there was a lot of down time as well. I had some contracts that took over a year to finalise.
Loneliness was never an issue either. I was doing all this around the age of 25, and particularly working in London you could literally waltz down to a pub, use the free wifi and chat to the locals. If you choose a decent pub the culture there is amazing and the local bar flies will introduce you to every person in the neighborhood.
The only time I ever suffer from loneliness was living in Northern Ireland, anyone that knows the history of NI can piece together why that place can be a harsh on strangers.
It's popular, and provides value within that niche.
There are TONS of legitimate business possibilities that are entirely remote. Software is a big one. I've met lots of developers who travel and work remotely.
I personally have a pretty decent side income in book royalties, from Amazon and a couple of affiliates. If I can ramp that up a bit, I'd consider traveling.
I'm developing a real online business in Medellin (mentioned in the article as one place becoming popular) - and have run across a bunch of Timothy Ferriss groupies that spend their days perfecting the art of SEO, for businesses that they fully know bring in cero value to society.
They consider the internet a fool's playground, and their mission seems to be that of profitting from its fools.
... Well, to be fair, it is.
Though, it's also important to keep in mind the opposite bias: if someone happens not to live the described lifestyle, it's also fairly possible that that non-transient person also doesn't have a representative sample of the general population among his or her friends.
It seems difficult to even design a way to scientifically study this and how widespread it is, too.
Cut it out. The difference between you & Patrick is literally just "desire to be like Patrick".
I don't mean to disagree, per se, but I don't think this is exactly a fair statement. Making a successful business out of selling bingo cards to teachers on the Internet is actually pretty ambitious as far as I can tell. Yes, the bingo card production itself is basically RNG on Rails, but that isn't what made him successful. I could put up a precise clone of Bingo Card Creator and it wouldn't even pay for its hosting.
Put another way: If I picked some crappy niche and put up "Hello World" attached to a built-in algorithm, do you really think I'd do as well as he did? (I don't think desire is the difference, as I certainly desire for that to be true, in much the same way I desire for ice cream to not have any calories.)
He did an amazing job with practically nothing — do you really disagree with that? It's obviously not impossible, but it's certainly not normal or the preceding statement wouldn't be true. Painting it as impossible is wrong, but trivializing it has the opposite effect of what you want: It makes it look more impossible than it is, because it isn't actually trivial.
$$\ $$\ $$$$$$$$\ $$$$$$\ $$\
\$$\ $$ |$$ _____|$$ __$$\ $$ |
\$$\ $$ / $$ | $$ / \__|$$ |
\$$$$ / $$$$$\ \$$$$$$\ $$ |
\$$ / $$ __| \____$$\ \__|
$$ | $$ | $$\ $$ |
$$ | $$$$$$$$\ \$$$$$$ |$$\
\__| \________| \______/ \__|
* Keep at it for a year or two, in your scarce spare time, and
* Carefully study how best to present your offering to your target market
You know what? I'm going to do this, just so I can settle this once and for all and be right on the Internet. I'll throw up a crap product, work on it like five hours a week, and we'll see how far in the hole I am from hosting costs.
Incidentally, it's the second part ("Carefully study how best to present your offering to your target market") that I believe to be tremendously difficult and that I don't believe I will have much chance at. From where I'm standing, one of three things happens:
1. You get lucky and happen to be very good this.
2. You get lucky and happen on the right approach without actually being good at this in general.
3. Your product earns back nearly 10% of its expenses.
I'm confirming too many people's biases by commenting on a 'patio11 thread about 'patio11, but the deliberately assumed helplessness of HN'ers when it comes to business is one of those things that drives me fucking bananas. In this case, so bananas that I have deployed ASCII art on HN for the first time ever. :)
Lots of hackers like to build things relevant to their own hobbies, but the problem is that if you make (say) a WoW character builder, some other hacker will build another one for free. (I don't play WoW so I don't know if my example made any sense, but you can fill in the blank for one that does.) They need to find something non-hackers want.
I don't think there is any list you or 'patio11 has of these things, or else the niche would already be filled. But I think that's what HN'ers want: "tell me what to build!" And they don't know what to build.
2) Talk to those people about their problems. Find out what really scares them, pisses them off, or simply takes too much time.
3) Build something to fix that problem. Keep talking to real people who have the problem you're fixing as you build it.
This is the methodology I've heard quoted by a dozen successful entrepreneurs, from Jason Cohen to Naomi Dunford. It's also extremely close to Tim Ferriss' recommended approach in Four Hour Work Week.
I make money in slightly different ways to this - at present - but as far as I can tell, it works. If you follow all the steps.
(Note: building something for WoW players fails at step #1. The market simply doesn't support spending a lot of money regularly.)
Although once you start evaluating, you'll rapidly find there are plenty of markets that fit the bill. Golf. Soccer fans. Airplane enthusiasts (RC, amateur pilot and planespotter alike). PC building enthusiasts. Almost any business. Martial artists. Re-enactors and RenFaire enthusiasts. Almost all the alternative medicine areas. And that's just off the top of my head without mentioning any of the markets I'm actually considering entering one of these days.
Even if you don't have a better product, you can still make sales by being more visible, being the first product people find/try when they begin searching. If they like the product, they might buy without even knowing there was a free competitor. It's a less noble strategy than having the best product, but more profitable than having a perfect product no-one ever finds. (Ideally you should have a great product and high visibility, of course.)
I ran across a rather good quote on this subject the other day - "Don't worry too much about being different. Just be good. Good is different enough."
Exactly. Just look at Google & Facebook. Both were late comers to their respective businesses (search engines & social networks). Both now have oodles of money.
They'll build the same products. Over and over and over again. Not bad, per se, but a massive opportunity for someone with development skill and a different set of interests.
Ask the non-hackers in your life what little pieces of software they occasionally have a big enough desire for -- big enough they'd pick $30 at the time. Then tell me. :)
Nonsense! Just look at bottled water. The definition of selling something that everyone (not just hackers) can get for free.
Without this market conditioning, I don't think many people would have been interested. So they are selling something valuable to a lot of people: water that won't make you sick, which is much different than the alternative.
In a word: marketing. Finding the right ways to efficiently reach his target market. I've tried marketing before — it's hard! Many BigCos seem to have the same problem. I can write whatever software I want, and I can study people for hours on end, but that doesn't mean the study will actually teach me the things I need to know to get the people to use the software.
There is a super power at play here, but it doesn't take a radioactive spider to get it. People who can simultaneously speak "customer service" and "technology" are rare. Many of the world's most successful software businesses have noticed that and achieved billions just by arbitraging a trivially corrected ineptitude common to programmers.
> There is a super power at play here, but it doesn't take a radioactive spider to get it. People who can simultaneously speak "customer service" and "technology" are rare. Many of the world's most successful software businesses have noticed that and achieved billions just by arbitraging a trivially corrected ineptitude common to programmers.
I agree, this is one thing that really benefits him. But from the standpoint of someone starting out with nothing, I'd say shoddy customer service is a pretty good problem to have — it means you have customers who need serving! If you can't do customer acquisition, customer retention becomes a moot point. Dutifully serving two people who each pay $20 a month will not make you billions of anything.
Patrick actually mentioned this on his blog some years back: He had a tiny customer base and knew he needed to find a way to grow it. The conclusion of the story was something along the lines of "I did marketing and then it was OK." That's where a lot of people's stories would have gone differently.
No, that's the awesome thing about software sales: You absolutely can be!
Step 1: Price software at $20
Step 2: Assume hosting costs of $10 per month
Step 3: Convert at a ratio of 200 views to 1 sale 
Step 4: Profit!!!
Admittedly, your profit for the first month will be $40 - $10 = $30, and your hourly wage will be $30 divided by however many hours you worked on the thing.
But let's say the software, like BCC version 1, is basically "a random number generator attached to a GUI" (as I vaguely remember patio11 describing it once), so you didn't put in too many hours. Now if you can manage to maybe triple your daily uniques to an entire 120 views a day and keep converting at that ratio without putting in too many more hours, you already have a business that'll pay for your pizza, forever, without really all that much effort on your part.
Now, if you assume an opportunity cost at google salary for working on this, of course it'll never be profitable. But if I assume google salary opportunity cost for my work, I'm losing money at an incredible rate by being a doctor, too.
 Someone who actually sells software for a living could probably give you more realistic numbers here, but these don't seem entirely unachievable to me.
200 views to 1 conversion is a little high, but not completely impossible. 1000 views to 1 conversion may be a bit more realistic. However, if you've got 40 uniques a day, that still means you're selling more than 1 copy a month, and are thus in profit!
(This is why SEO plus software or other product sales work so well, btw - the CPM you're getting off your views with a well-targeted match between content and product is far, far higher than you'll ever see anywhere outside of poker blogging. )
It's not rocket science, and most people on HN could do it. As tptacek has said several times, it just takes a couple of years' worth of persistence and willingness to look at what's actually happening and adapt for it.
If you are serious about this, start reading his blog from the beginning. He gives a blow-by-blow account of how he got there.
And I predict that having a self-defeating attitude will greatly impede your success.
Of course, the product improved greatly over time as well, so I really don't mean this as a criticism. If you want an example of a true minimum-viable-product, Bingo Card Creator 1.0 had to be it.
I totally missed the resize thing for the first several versions for the same reason my customers did: I don't resize things.
Fine, it's a poh-tah-toh.
> If you are serious about this, start reading his blog from the beginning. He gives a blow-by-blow account of how he got there.
I've actually read his blog for years. I've learned lots of useful lessons from it, but one of my takeaways is that Patrick is just very good at marketing.
But yes, I am serious. I'm considering setting up a blog documenting the process so everyone can point and laugh, but I'll have to figure out whether my ego can take it.
> And I predict that having a self-defeating attitude will greatly impede your success.
What a great hedge! If I succeed, you can say you told me so, and if I fail, you can still say you told me so.
But no, really, tptacek just said desire and a modicum of effort were the prerequisites. I can do those. If pseudo-religious faith is required as well, then I guess I will fail. But there's nothing to be done about that, is there?
If you do decide to do this, I'd be more than happy to offer help and advice if you think that'll be valuable. I'm not patio11-level successful at this stuff yet, but I have a certain amount of knowledge, particularly about marketing. Email's in my HN profile!
As I understand Patrick's story (someone please correct me if I'm wrong):
* He accidently found something that produced small profits.
* He built on that and iterated.
* At no point was BCC insanely lucrative.
* But at every point, it made sense for him to work on it.
* He didn't need to put in many man-hours to increase returns.
* If BCC's ROI for time invested ever became negative, he could have stopped.
* Once he hit that point, he put it in maintenance mode
* Based on his BCC case studies, people wanted to hire him.
* Consulting is where he makes most of his money.
1. Find a niche where you can make some amount of money.
2. Work at it, intelligently, until you hit a maxima.
3. Talk about the good stuff you do.
4. Look for logical extensions of your business where you can leverage your new
experience (more lucrative niche, consulting, better job, etc.)
That's true, but it was consistently making about enough to pay my rent one year later. I would consider that to be an astonishingly good return on just a few hours of work per week.
> 1. Find a niche where you can make some amount of money.
I suppose that "some" there is the important part. I don't think finding a niche where you can make $500 a month profit right out the gate is that easy. It's not a ton of money, but I'd consider that very encouraging.
Obviously, most HN'ers haven't established for themselves the career Patrick has. My point addresses why that is.
I'm arguing here with the same mentality that says 37signals advice only works for 37signals, "because they got to start with a hugely successful blog".
A lifestyle business is one that you build to improve peoples' lifestyles (including your own) rather than to make billions. You can give one a 70-hour-per-week effort, or you can automate yourself out of necessity and get passive income.
You don't have to burn lots of hours and take degenerate risks to be passionate about something. I see Valve and Github as lifestyle businesses (proving the culture, not making the global rich list, is part of the goal) but I'm sure the leadership is quite passionate.
The short version: "I Love Lucy" was a lifestyle business dreamed up so that Lucille Ball and her husband could have children. It was easier to revolutionize an industry than have a two career couple and family, so they did. In terms of technical innovation, the show was the "Star Wars" of its day, which is part of why reruns of it still get played to death to this day.
Nope, you're mostly just concerned with your own lifestyle. That's fine, of course. But there's no need to try and make it sound any more noble than it actually is.
As I write from the rooftop pool bar at Bangkok Hotel.
I pretty much live this lifestyle, though I wouldn't say I'm all that connected into the nomadic community. For instance, I was not aware of the Tim Ferris conference. I tend to socialize completely outside this scene actually. Perhaps I should get more connected.
Loneliness is indeed the major issue, fortunately for me often sated by my adequate social and dating abilities.
1) 50% Web Services Providers (Owners of firms or freelancers) - Devs., PPC, SEO, Graphic Design and Similar.
2) 20% Owners of Hard Goods or Software Products
3) 20% - people with larger businesses who have "made it" and now pull salary and travel full time (or part time) and invest in new biz or projects.
4) 10% - Consultants or remote work arrangements.
Like attracts like and all, so the fact that nobody at our conference was sketchy might not mean much, but I didn't feel uncomfortable about anyone's biz and there were 80 or so attendees.
Mark isn't representative (in my experience) of this new digital nomadic class because his business model is so difficult: he makes money from his writing. Which is fantastic (I love reading his articles), but it would be a lot easier for him to provide paid for PPC services.
My business, by the way, is selling custom designed products (like cat furniture) from ecommerce stores. I'm now started a new biz throwing these types of conferences for this growing remote-working scene.
I don't share Mark's lament in this article, but I enjoyed reading it.
"Mark Manson is an entrepreneur, writer and perpetual world traveler. He writes about unconventional living and self development at his blog Postmasculine.com."
For example, if I spent 6 months on an app, I doubt it would pay rent, because there's a lot I'd have to learn and it would probably (?) be amateurish. On the other hand, if I cut out 18 months and kept iterating, I'm sure I'd do better, financially, than I'm doing at my day job.
I haven't won this game yet (I have a fairly typical day job for a top-5% programmer of my age) but it seems like the trick is to find an avenue where you can rapidly get better, invest heavily in yourself when you find it, and eventually be independent.
This is exactly it. At his last job, my (now) boss started a project on the side. Eventually he had to quit, not because he was making lots of money, but because he didn't have enough time to support the side project. It was bringing in money at this point, but not enough to match his previous salary. He kept at it though, and eventually the revenue grew. Twelve months later, there are 15 of us and money in the bank :)
having no boss is nice in theory, but i suspect that in practice it'd become a drag because i'd have to personally fill in for all the value-add that my boss (and her boss, and so on up the chain) now provides.
It seems to me that the scary part isn't the month or few without income, but the risk that you can't get back into your old gig (or something comparable). That's a very small risk of course, because developers are in high demand, but enough to give pause.
One month to try something cool is a small cost, but quitting your job usually means you can't go back in the same standing.
You aren't likely to go back to your previous job, but even a failed startup should qualify you for a better job.
If you have the oppertunity, go for it. You regret the things you didn't do more than the things you did do.
Yes, good programmers can generally get better jobs quickly, but there is a point some people get to where the "job hopper" image starts to hurt them. Most people, if they see a string of 6-month jobs, assume this person is constantly getting fired.
On the other hand, "Because I'm broke and need a paycheck right now" is probably the most common answer, and those are exactly the people who get bit by this stigma. Because no company wants to permanently hire someone who is only applying out of temporary financial need.
I think that as a society we need to create the political and economic conditions necessary to make freelance consulting a more viable career path for skilled individuals. There are a lot of obstacles and frictions that could be reduced.
It's somewhat self-reinforcing, I'd imagine. Because of the stigma, people are less inclined to leave jobs, and therefore a higher percentage of departures are negative.
There's also a "can't win" dynamic from short job tenures. If you're obviously moving up, you're a mercenary. If you have a lot of lateral moves, you're unsuccessful.
Additionally, I think few people actually want to be job hoppers. I'd love to find a 10-year fit. On the other hand, it's uncommon that a I find an environment where I keep learning for long enough to justify more than a year or two.
I started without a savings buffer, and have managed to do alright. But there were many moments where having spare cash could either have let me outsource certain work, or avoid having to do work to earn money in the short term.
If this was just a temporary choice of one thing over the other, I'd say 'go for it, and enjoy yourself', but I wonder if this sort of lifestyle, done long enough, can really be put down. By the time you want a spouse, a family, and a place to put down roots, will the temperamental changes brought on by your nomadic living even make this possible? The guy at the end of the article who's lonely and wants a home - he might want it, but I'm not at all sure he'll be able to get it or keep it.
Perhaps I'm completely full of it. It certainly wouldn't be the first time. But I'm sure I'm not the only one who knows a long-term womanizer who can't manage to settle down, even though he now claims to want to. These guys might be setting themselves up for the same sort of problem, with 'new experiences' taking the mental place of 'new partner'.
Surely I can't be the only woman on the planet who ever viewed my husband's "nomadic" career choice as a feature not a bug.
There's also people who aren't strictly speaking nomadic but do take long (multi-month) trips and work from there.
The only quibble I have with this article is the use of the word "rich". No-one I know with this life-style is really rich, they have good upper-middle class incomes doing jobs that are easily done remotely and they leverage that to live in a way that other people cannot.
I think that as these guys get older most will start to move from nomadic to semi-nomadic to "takes long working vacations", but some may indeed live like this forever.
It's good stuff.
The flip side is I work 24x7. When I'm on a push to get a product out, I've been known to forget what day it is. And I have had to limit myself to doing all my marketing work after 7pm. I do customer service from about 8am-9:30am. So that's a lot of hours in a week.
Wait. How's that different from a startup where I own only a small equity stake instead of 100%?
Something I had to learn myself. Something, I did learn and it centered me, gave me context and a lot more happiness.
So I am happy for everybody living that way. If it does please them and does not hurt anyone else. But I know for me, that this is not my style of life.
I'm so, so thankful for the experiences in travel that this lifestyle has afforded over the last three years. I also think that in some ways, being constantly on the move has made me a better worker, but it's time for a change. I start a full-time sit-down-in-an-office position in February, which I chose to do for exactly the reasons that the article outlines. I echo the parent comment - it's a cool lifestyle that you should try if you can, but it's not for me any longer.
I suspect many nomads are following similar SEO consultant/"passive income" schemes, but I also know from previous HN threads that there are a fair number of members (many of whom I assume are programmers) living an expat life overseas:
Do you want your kids to grow up in hotels and short-term rentals, never having been in one place for too long? If the answer is "sure", talk to people who grew up in military families who were shipped all over the world -- it's not fun.
If the idea is that you're going to travel, and the family stays put, understand that the cost is that you won't have a family at some point. Road-warrior consultants generally aren't the happiest people.
So true, I did similar kind of "on-the-road" consultancy for a 9 month period in a previous role and that was enough. Saved a load of money though as I had no accommodation expenses of my own in those 9 months.
Here  is a family of 7 driving from Alaska to Argentina... because they want to.
I met many similar family expeditions during my drive  and it was always a joy to meet the kids - who were all bi or tri-lingual.
One of my favorite quotes from a ~10 year old was "I don't like homeschooling.. I like WORLDschooling".
* Where did you decide to live?
* How do you support yourself and family?
* What do you do for school, is it expensive?
* How's it working out? Any regrets?
I guess it's similar to how visas work for writers. There are artist visas for writers, but they seem to exist so the artist can stay longer.
Many countries grant citizens of wealthy countries 60 or 90 day visas pretty easily.
I personally find the topic interesting for various reasons. For once, because i've been living a "nomadic-founder" lifestyle for the last 17months (sidenote: rather "nomadic broke" than "nomadic rich" :) and because my startup creates a platform that tries to free more people from classic employment and enables them a global "workdesk".
My whole journey was inspired by someone's travelling-story on reddit, which is why i'd like to share mine here. Maybe someone thinks about doing something similar, in which case i hope my story can give insights/inspiration as well.
I'm in my mid-20s, IT-guy for >14years, YC alumni, don't have kids, speak 2 languages (english & german) and in the process of learning spanish (thank you duolingo!). When i started, i moved out of my apartment, gave away all my belongings but a backpack of clothes, my camera and thinkpad. I had only little money on the side and apart from my role as a startup founder, not really any perspective on regular income in the near future. Never had plans for more than 1 month ahead, sometimes plans would completely change in matters of hours. I was expecting to be living very low profile and in case money runs out completely, find some simple job to get by. Money and materialistic belongings became my lowest priority pretty soon. On the upside you gain a completely new sense of freedom. (A particular quote from "Fight Club" immediately comes to mind)
So moneywise, in the first few months i was still employed and working remotely for a befriended company as a programmer. But that ended soon, because i wanted to focus more on the startup. One of my co-foundes had some funds from his former startup with which he could support the team for some time. Not overly much, but enough to get by without much luxury. Earlier that year i got the opportunity to build a funded art-installation that won a price and some money. But to be honest: I'm constantly broke, but somehow there's always a way if you want to.
You'll learn to enjoy your life with the little you have. You get creative eating healthy for little money (have never eaten so much good fruit in my life) and finding places to stay. Mostly i stayed in hostels or i could live with people i met on my journey. Sometimes only due to their hospitality, sometimes in exchange for work (small IT stuff, built a hostel, crafted a "designer locker", gardening and so on). When you stay in inexpensive hostels (my only requirement was wifi), you'll also meet interesting people that are in a similar situation and learn new ways to get by.
For the last 6 months i've been in south america. Life here is comfortably cheap. Most of the time you can easily get by with 10$ a day or even less. And if you're schedule is flexible and you're not in a hurry it's easy to experience some of south-america's incredible nature for little or no money. And you will meet interesting people and life-changing moments travelling outside the usual touristic way of moving around these countries.
What i'm trying to say: If you feel your situation is similar and you maybe even have some money on the side for the beginning: do it. You will not regret it. Don't be scared and never give up. Just always remember that, even if hard times come, there's always a way and surviving those will only make you stronger. You'll find a simple way making money on the side for food & shelter (heck, here in south america you could just be making and selling bread or cake on the street for some hours a day and get by).
Needing only your laptop and wifi to work is an incredibly enabling gift. Pretty much everywhere i went i had access to wifi and could work on my startup and communicate with my co-founders. Take use of that gift and you will have a life-changing experience. Founding a startup in such a globalized way _is_ possible with some coordination skills. Our whole team is spread around the world for the whole time being and we successfully launched a couple of months ago.
Shameless plug: We are building a plattform that enables many many more people to live a location-independent lifestyle like ours. Our vision is that you'll be able to work directly on our site, offer your expertise and/or being presented with jobs directly targeted at what you're good at, always knowing how much money a finished job will make you. We're still in the process of collecting feedback and iterating. Getting a two-sided marketplace off the ground is hard :)
If you have any questions about the story or feedback on our startup, i'd be happy to answer them here or contact us at firstname.lastname@example.org
I'm in a slightly different situation and wonder what advice you might have.
I'm not on the border of going broke. I work for myself from home, alone, and have a comfortable income that I expect will continue for a while. Definitely enough to travel with. So I'm not afraid of not having enough money.
But I am afraid of simply not knowing what to do. Typically when I take vacations it's pre-planned, a week-long thing with a specific destination or event, and then it's over.
A part of me really wants to go "nomadic" and travel lots of places, but I just don't know what I'd do with myself. How to choose where to go to next, how to get the most value out of where I'm at, etc. It seems like constantly moving and trying to get something unique out of each place would take so much consistent planning and work as to be a second job, sucking attention away from where I'm at so I can plan where I'll be.
I don't work with anyone else (even remotely) and I don't have friends scattered across the country/planet. It's extremely unlikely that I would be receiving random calls from people I know, deviating me from my path and pulling me into unexpected interesting places or scenarios.
So my fear is that I'd end up wandering aimlessly, missing the good bits for the obvious ones, not getting a whole lot out of it, and wondering what I'm doing. Is this a legitimate fear? Is there a way to prevent this?
1) Pick a place. Let's say Paris.
2) Go to hostelworld.com, sort by highest review, choose the first hostel in your price range, book a week stay.
3) Sit at a large table in the common room, nurse a beer or coffee, work on your laptop, wait for others to wander by.
4) Strike up conversation, ask about where they've been, what they've done, and what they recommend.
It really is that simple.
Talked to a few folks at hostels, found out what was cool to see in Spain, and used the web to figure out how to get there. Ended up traveling all around Spain for a month, just by getting somewhere, spending time, plotting my next step, and then going.
It might be a little intimidating. It should be. The uncertainty is what makes the journey so much more worth it.
> Is this a legitimate fear?
Perfectly legitimate fear. But none that cannot be overcome. Yes it takes some time to get into it, but the only way to get there is to jump into the cold water and get out of your comfort zone. Realize the fear but have the courage to just try it.
When relocating somwhere without knowing anyone, i usually start off by just checking wikitravel (now probably wikivoyage) and check the "Sleep Budget" section. Pick the Hostel that sounds nice (kitchen, wifi, artisanias, friendly personnel) and head there. Plan nothing more (well maybe just checkout some stuff you want to see eventually, while you're around the area.).
When doing so, the most important thing is to have confidence, that a flexible schedule and your freedom to move whenever and wherever you want will help you get where you want (wherever that shall be). Unplanned and spontaneous trips have been way better and fulfilling than any planned stuff. That's something you can only learn by experiencing it yourself.
And in case you really end up somewhere without finding contacts or get bored, just relocate :) Pick another stop and do it over again, don't ever get frustrated and keep in mind that there are tons of people doing the same as you and are happy to connect and share good experiences with you.
E.g.: At some point i was in peru and planning to visit bolivia. Looked up a really nice guy on couchsurfing (who ended up hosting me for a week). In his respond to my CS request he recommended a festival at lake titicaca that was going to happen soon. Went to the festival alone and immediately met incredibly nice and interesting people (with whom i spent a lot of time in bolivia and peru afterwards). This one clueless couchsurfing request ended in 3-4 weeks of fun and many new friends that i'm looking forward to meeting again at some point.
Another time i met a guy who was travelling with his '94 chevy van from the states down to SA since 2 years. We ended up crossing the salar de uyuni and the bolivian andes towards chile together in his van (and lost the muffler along the way on the rocky mountainpaths...).
So my advice is: Just plan the first step, be open for things to come and then spontaneously choose what looks best. Freeing yourself from the idea that you _need_ plans for a good time will give you the freedom to be open to what comes and lays the way for unexpected adventures :) The people you meet (travelers and locals) are probably the best "tour-guides" you'll find.
I've never had a lonely planet on the whole trip, so dunno how useful they are for this kind of travelling. Found the reviews on wikitravel/wikivoyage to be reliable enough, so far.
I'm currently working on the details of my next stint abroad.
I'd really like to see someone turn a cruise ship into a moving, floating tech city that would move about the world (possibly spending a week in each port, allowing inland travel) so people can travel but also have a stable support network. It'd even have a school for people with kids. It'd probably be cheaper than living in New York or the Bay Area.
I've looked at this (from even the mid-1990s), and it's really hard to make the economics work. Ships are expensive, both in capital costs and especially in operations costs. You can buy used ships, but they're never very efficient or suitable, and retrofitting them is expensive.
People who would be comfortable living out of a tiny cabin with limited services are almost always better off just renting a place on land for a period of time and flying in between destinations. It's only if you need a large, constant space that it makes sense, and doing that with a ship is expensive.
There's also a horrible scale problem -- you could maybe make this work on a per-user cost with a $10b world's largest ship, but a $100mm ship is probably 10x less efficient, and a $1mm boat is another 10-50x less efficient.
There's also the loss of freedom with a large ship. I'd rather just make enough to buy a $5-10mm boat of my own (or, ideally, $100-200mm), and have some guests sometimes, vs. try to coordinate when people get on or off or where it goes as a collective.
There's the regular cruise ship industry on the low end as competition, too. You can get deals and just book 90 days on cruise ships if you want, and get the scale advantages of a large ship; the downside is boredom and being around a bunch of old people (usually) or sometimes drunk college students. Block-booking (how most "gay cruises" or other special interests are done) works. Geekcruises did some of this.
What might make sense is a bunch of ships going on a specific route, with transferability across them, or big fixed platforms at sea where people can go to/from by air, boats, or bigger ships. Of course, now you're looking at many billions of dollars in capital and a very large minimum scale; it's really hard to be incremental in this market.
Recently I also took my kids to Kathmandu for a couple of weeks and mixed working with holidaying - so it's definitely possible. Of course in almost every major city in the world there are plenty of expat families raising kids successfully.
I guess you need to decide how nomadic you wish to be. Personally I think it's nice for kids to feel like they have some kind of home base so I'm more in favour of longer stints in places (e.g. not moving every 3 months) but that is only based on a hunch, and also depends so much on the personalities in your family.