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Comment by nlh | Hacker News Reader

Anyone else have their "sketchy" filters activated after reading this article? Author mentions how he travels around the world and how he's meeting up with friends / colleagues at this conference (and that he knows them from email lists / online forums), but there's no talk whatsoever in the article about what businesses any of them run.

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...

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I did this for about 5 or so years, earnt great money building corporate web services, general business automation stuff, and web sites. I stopped as I grew bored of dealing with large enterprises and general depression from the repetition and changed tact. Seriously considering returning to doing though just for the amount of freedom you get.

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.

Being from Belfast that last line makes me pretty sad. For what it's worth there are plenty of good people and somewhat frequent meetups/tech talks etc. Usually organised through various groups like ruby users. There's also Laverys..

Its all good I definitely don't hold the place or the people to blame. I was living in Cookstown at the time traveling around meeting long lost relatives. I met more than a few good people, but also some of the worst (a few fisticuff incidents stories not appropriate for here, and being questioned as to why I had just wandered into a local pub). It just took a long time to gain peoples trust after that you where treated like royalty.

Ah, Tyrone. I had stupidly assumed you were in Belfast.

You can google him. He runs a site that focuses on relationship, fashion and related issues, catering to men.

http://postmasculine.com/

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.

Recent podcast interviewing him http://foolishadventure.com/audio/work-from-anywhere-by-buil...

One of his blog posts was actually posted on HN ~6 months back and attracted a lot of discussion: http://news.ycombinator.com/item?id=4214480

I can attest that it is indeed the 'scummy side of the internet'.

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.

"They consider the internet a fool's playground"

... Well, to be fair, it is.

It may be, in the most darwinian sense. In the same sense that warlords justify genocides.

FWIW: You could have written essentially the same (fairly value-free) article about a buddy or four of mine, who have roughly the same lifestyle, with the financial support being a software business.

It's a useful data point, but owing to patio11's unique situation, his friends are probably very non-representative of the general population.

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.

The idea that Patrick's situation is unique is one of the dumbest and most damaging emergent memes on HN. Patrick is literally the textbook story of how to get to this point without having a unique circumstance. He started from the worst job in software, and clawed his way out with (all due respect to Patrick) possibly the least technically ambitious product in the history of commercial software development.

Cut it out. The difference between you & Patrick is literally just "desire to be like Patrick".

There is a world of difference between saying it's impossible to accomplish what he has and saying that he, at this moment, has developed a place for himself that relatively few people, even here on HN, have. The former is obviously wrong, just as much as the latter is obviously right.

The point is that if Patrick can do it starting as a Japanese salaryman, you can most probably do it from whatever position you're starting from even more easily.

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".

I suspect that there's not much difference between what you're saying and what I believe: I also suspect I didn't phrase my original meaning clearly enough, because I think we're speaking at cross purposes. No disagreement with what you're saying, but I was attempting to talk about who Patrick is likely to know given A, not how difficult or easy it is to achieve A if you commit to going down that route.

> He started from the worst job in software, and clawed his way out with (all due respect to Patrick) possibly the least technically ambitious product in the history of commercial software development.

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.

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?

    $$\     $$\ $$$$$$$$\  $$$$$$\  $$\ 
    \$$\   $$  |$$  _____|$$  __$$\ $$ |
     \$$\ $$  / $$ |      $$ /  \__|$$ |
      \$$$$  /  $$$$$\    \$$$$$$\  $$ |
       \$$  /   $$  __|    \____$$\ \__|
        $$ |    $$ |      $$\   $$ |    
        $$ |    $$$$$$$$\ \$$$$$$  |$$\ 
        \__|    \________| \______/ \__|

You missed only two extra details:

* 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

Oh, snap. I just got ASCII-arted by tptacek.

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.

Curious: apart from methodical patience, what super power do you believe Patrick was "very good at"?

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. :)

> Curious: apart from methodical patience, what super power do you believe Patrick was "very good at"?

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.

I think the marketing you're thinking of when you think about Kalzumeus --- blog posts, year-end summaries, podcasts, email newsletters, video courses --- is stuff that did not matter when he was bootstrapping. There you'd be confusing cause with effect: the adept marketing you see today is a product of his nuts-and-bolts execution selling a product as a microISV and paying close attention to what was working.

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'm actually thinking more of his bazillions of well-chosen targeted landing pages (e.g. "Dolch sight words bingo"), his ability to rank highly enough in search engines for the right words that interested visitors flow into his site (you can't be profitable with 40 uniques a day) — that sort of thing. In essence, yes, you need to pay attention to what is working, but first you need to find something that works in order to pay attention to it.

> 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.

I have a certain amount of expertise at the type of SEO Patrick used to bootstrap BCC - I've used a similar technique to get my last public web project to 400k-ish uniques/month.

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.

you can't be profitable with 40 uniques a day

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 [1]

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.

[1] 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.

I don't sell software (yet) but I do Sell Things On The Internet.

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. )

For a lot of programmers, or at least for me, there is a mental wall that comes up whenever attempting to analyze the responses of other humans to one's own creations. Scaling that wall is not impossible, but it's difficult and draining, and the same mental effort has to be expended every time the wall is approached. I think when people are saying that Patrick is uniquely good at marketing, they're saying that for him, the wall is not there, or at least he's a lot better at climbing it repeatedly to iteratively improve his marketing.

There is a lot of money out there for hackers who want to make stuff for non-hackers; but I think a lot of HN'ers have problems figuring out what those things are.

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.

If you're only willing to build things you like, I've got no help to offer you on microISV product businesses. For what it's worth, I have the same challenge. For people like us, my recommendation is: find a way to align what you like with something that is lucrative as a service. You can make a lot of money wanking around with suave ways to get pixels onto an iPhone screen.

And therein lies the rub. If hackers build things relevant to their own hobbies, and "hackers," as a group, tend to have really similar hobbies...

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.

I meant was that hackers build those things because they are familiar to them. Patrick had some interaction, somewhere, that led him to realize that people need bingo cards.

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. :)

My auntie was telling me this weekend that she has to keep running Windows to keep an old Quilting application running. There are newer/cross-platform ones available but they can cost thousands and she doesn't want to change.

1) Identify a market that you know something about - not necessarily much, but something - and where a medium-sized number of people spend a fair amount of money with minimal resistance, regularly.

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.)

Doesn't elementary school teacher fail at #1 too?

You might think so if you know schoolteachers only by reputation, but actually, they spend a ton on teaching materials. They will go to Barnes & Noble, scour the educational section and plunk down $200 without blinking.

Well, my wife is an elementary school teacher, and I promise she doesn't spend 200 at BN without blinking. She does spend some money, but not tons.

Most people in every profession fail at #1.

Hence why you need to find the ones that don't :)

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.

Having competition, even free competitors, doesn't have to be a deal breaker. If you have a superior product you can still make sales.

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'd go further - having competitors is a very strong sign that you're onto something good. It's when you enter a niche that should be teeming with competitors and isn't that you should start being concerned!

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."

Having competition, even free competitors, doesn't have to be a deal breaker.

Exactly. Just look at Google & Facebook. Both were late comers to their respective businesses (search engines & social networks). Both now have oodles of money.

the problem is that if you make (say) a WoW character builder, some other hacker will build another one for free.

Nonsense! Just look at bottled water. The definition of selling something that everyone (not just hackers) can get for free.

The success of bottled water is the result of a, eh, educational campaign. Namely, that tap water is full of yucky stuff.

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.

True. Every domain I've ever worked in, I've seen huge opportunities. Alas, I suck at seizing those opportunities. I code something up (the fun part) and then lose interest at the startup / marketing & sales / money stuff.

So Patrick did not throw up a crap product--it was just a very simple product.

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.

> So Patrick did not throw up a crap product--it was just a very simple product.

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?

Reading this "challenge" unfold here has been interesting and perhaps oddly, inspiring. If you do go through with something, please pass a link my way :)

I really hope Patrick won't mind me saying this, but... that initial downloadable Java version really was quite bad. You could resize the Bingo window smaller than it should be, causing all kinds of bugs that made the bingo cards completely unusable. Only quitting the program & restarting would fix it, resizing wouldn't. I remember this because I kept looking at his program at the time, wondering why it was successful, how those bugs slipped through whatever beta testing he did. I assume the marketing (especially SEO) is what filled that gap, as well as understanding what his customer demographic would tolerate.

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.

You're not nearly as harsh about the Java version as I am. The relevant comparison, though, is not "BCC as released" versus "BCC as could hypothetically be implemented by someone with a Jobsian level of attention to detail", it is "BCC as released" versus "45 minutes with a straightedge, construction paper, and incipient carpal tunnel syndrome."

I totally missed the resize thing for the first several versions for the same reason my customers did: I don't resize things.

You should see what he can do with ANSI.

I really hope you do try this out, and blog about it - it'll be REALLY interesting for all concerned.

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!

I guess it might be a little bit more complex. For example I have todoteria.com (shared todo lists service + app). It is up for 5 months. I doubt that extra 7-19 months will change anything for me. I have ideas/plans but it would be interesting to hear your opinion on that.

It's not like Bingo Card Creator let him quit his job overnight. In fact, if you look at the profits from BCC (not revenues) it's far from his main source of income.

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.

Steps for someone wanting to replicate:

  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.)

> It's not like Bingo Card Creator let him quit his job overnight.

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.

I think Patrick's point is that his friends are not some kind of transient scam artists.

The Lifestyle Business and Tropical MBA podcasts give some insight into this world. Basic idea is to set up "lifestyle business(es)" that provide you enough financial freedom to travel, etc. Downside is that the lifestyle is your passion, not the work you do, and it has a definite non-hacker approach.

I don't like this idea that "lifestyle business" != passion.

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.

I agree with you and wrote about it more than a year ago: http://www.novemberwest.com/blog/2011/07/02/lifestyle-busine...

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.

I tend to agree, but I was latching on to the commonly accepted definition, as Wikipedia defines it: "A lifestyle business is a business that is set up and run by its founders primarily with the aim of sustaining a particular level of income and no more; or to provide a foundation from which to enjoy a particular lifestyle."

http://en.wikipedia.org/wiki/Lifestyle_business

> A lifestyle business is one that you build to improve peoples' lifestyles (including your own) rather than to make billions.

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.

I could see taking a hacker approach to it if you do periodic technical work that does automate things. I don't necessarily think you need to work constantly on the technical thing to be a technical person doing interesting things. But I do agree that most of the examples I find aren't along those lines. The guy in this story is a self-help/lifestyle blogger afaict. But maybe that's because the lifestyle bloggers are more likely to blog about their lifestyle, whereas the people doing it via technical work are more under the radar? No idea.

What would make you think this is not possible?

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.

I hosted a similar conference for digital nomads in October and the basic breakdown off the top of my head:

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.

I think there's an exponential return on efforts for a lot of this work. Most people can't take away enough time from their day job and responsibilities to get good at it, but people who do and take an investment mentality (investing their surplus time back into their skills and contacts) can take off.

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.

If it's something you want to do, my best recommendation is to save a large percentage of your income.

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.

> 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.

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 :)

May I ask what this project was? How did he know it was worth it to leave his current job?

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.

If you really can't get a job anywhere as a good developer, or as a freelancer, you probably should check what you are doing wrong.

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.

What you say is all true, but there's one thing that probably hasn't hit most HN readers yet: the job-hopping stigma. It sucks that it exists, but it can catch up with people after a certain point.

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.

I don't think employeers worry these people got fired. I think companies are concerned whether you're just a hired gun (not that there's anything wrong with that). But if I'm a young company and I want someone to come on board, I'm not making the decision lightly. I want a long-term partner. So yes, a lot of short term employment would be concerning.

At 6 months, literally "fired" is unlikely because most companies don't act fast enough. But the assumption people make based on a lot of short job tenures is that the person was unsuccessful at all of them. Most unsuccessful people don't stick around long enough to get fired, but that's irrelevant.

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.

On the one hand, if you are in need of work (maybe you quit to do a startup and then your startup failed) and you do you have a resume that is starting to throw the "job hopper" flag, it might be time to ask yourself why you're even applying for another company and if you'd be better off reinventing yourself as a freelance consultant instead.

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.

i've come to realise that there are people whose passion is figuring out what to do, and people whose passion is figuring out how to do it, and that as a "how" person i will probably always need/want a "what" person or company to be working for.

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.

If you scroll to the bottom, you will see this bit:

"Mark Manson is an entrepreneur, writer and perpetual world traveler. He writes about unconventional living and self development at his blog Postmasculine.com."

Read the Four hour work week, where Timothy talks at length about the kinds of businesses they run.

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