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I quit my job, and I'm excited about a more independent life (danielhough.co.uk)
170 points by basicallydan 1492 days ago | hide | past | web | favorite | 113 comments



It's great that the author has taken the plunge and I hope things work out well for him.

I'd caution others away from such a drastic move though. 6 Months is an incredibly short amount of runway to go from 0 to paying your bills by "starting, and finishing new projects".

My own experience was similar. I had a secure job with a good salary, but something was missing (first world problems). I was looking for new challenges and quitting my day job seemed like the best way to live the dream.

I'm risk averse, so instead of quitting, I talked to my boss and arranged 6 months leave without pay. It turned out to be the best decision I could have made. Even though I had experience with building a couple of larger side projects in the past, I drastically underestimated how long it would take to finish my first project. The 80/20 rule is no joke (might even be closer to 90/10).

To top things off our hot water heater needed replacing and a roof leak led to some emergency renovation work. By the end of my 6months leave I had a 90% finished product (great!!) and a $10k credit card debt (not great).

It's been a year since I took leave, and even though development has slowed down, I shudder to think how things would have turned out if I had quit.


This was fairly similar to my experience - 4 months into my time off I received a letter from the government saying that due to a problem with my employer last year I owed them thousands of pounds of tax. I might not be that risk adverse but this shocked me, and as soon as you see the end of your runway it becomes difficult to concentrate on a startup.

Also, London is expensive, remember that.

Edit: I will rinse and repeat but I definitely recommend getting a product to MVP stage before cutting your cord, as well as also having the necessary funds for this funemployment strategy to make sense - are you expecting to immediately start making enough money from the project to bootstrap it or are you going to go and get investment with your team?

Also I recommend getting into the habit of being honest and quantitative with yourself, which means getting into the habit of knocking out an excel document for your own living expenses and the commercial viability of any ideas you have.

Personally, I found myself ultimately fighting far too many battles many of which I was untested in, creating an iOS prototype while: sitting in cafes running customer development (I spoke to at least 50+ people), arranging meetings with people in the industry I wanted to disrupt, trying to attract the attention of Angels that I had connections to, getting my friends to help out with design/tech work, etc. It's a hard game and probably worth it for the experience. Something I realised was that you can't be perfectly self-sufficient - you might be an A player at a couple of things and a quick learner in others (which is how I felt) but you're going to be trying to hold so many things together that you will need a structure that supports you: finance, friendship, focus, partners. I fragilized myself by not being fully prepared for this - and also didn't have the financial situation to bide my time.

There are pools of water in the desert but you need enough water to reach them.


> Edit: I will rinse and repeat but I definitely recommend getting a product to MVP stage before cutting your cord, as well as also having the necessary funds for this funemployment strategy to make sense - are you expecting to immediately start making enough money from the project to bootstrap it or are you going to go and get investment with your team?

No I do not :) I have no team, nor any big business idea that I'm going to pursue that requires 6 months of work, like I said in the blog post. I have a few ideas, and maybe one or two will lead to something but maybe not. The key thing here is about learning a lot of new skills and becoming a bit more independent. Maybe I'll sacrifice that independence if/when I run out of money, but maybe I'll make money by some other means in a way which doesn't force me to sacrifice my newfound independence.

I am a developer, and a lot of what I will be doing will be for fun and learning first, and for money-making reasons second

Thanks for the advice though, I do appreciate it, and I will follow a lot of it. If I do decide that something might be something I want to make commercially viable, don't worry - I will take that part of it very seriously.


Risk is recoverable. The (admittedly high) chance of failure is not a reason to avoid the experience. I'd recommend anyone dissatisfied with their work/life situation do attempt this, even with the full knowledge that it won't amount to a "job" or "business" or anything.

Because, the risk is not a real risk. If you have friends and family who care about you, if you live in a 1st world country, you're not going to end up starving on the street. No, that takes mental health issues and a government that ignores the problem. Merely running out of cash on which to live when one is perfectly capable of working does not wind one up in the chow line.

What is the worst that can happen? He has to move in with a friend for a few months and get a "real" job. Basically, he'd be back to where he was before he quit. That's not a "risk".


> "I'd recommend anyone dissatisfied with their work/life situation do attempt this"

I agree wholeheartedly. Taking 6 months off to build a project was one of the best things I've ever done.

My advice for others is simply to consider asking for leave instead of handing in a resignation. If your boss accepts then great you've got your 6 months off with the added security of a job to come back to, if they say no then that's OK too because you were ready to hand in your resignation anyway.

Hedging your bets is never a bad thing.

> "What is the worst that can happen?"

speaking from personal experience, you can end up in a deep financial hole very quickly. Some expenses just cant be postponed.


Heh, well, I guess I haven't ever really left places on the best of terms. Usually, I'd get to a point that I was so depressed that I had no intention of ever stepping foot back in that place. The pattern was simple and happened frequently: work hard, do great work, see my work go unrewarded, slack off, get in trouble for slacking off, redouble my efforts, do even better work, get dinged for something petty, quit out of spite. Part of that was my own fault for not picking better places to work and not managing my work-life balance better. But part of that is that common management culture thrives on exploiting people who have difficulty managing their work-life balance.

But a "deep financial hole" isn't the worst of problems. The first time I did an extended time of intentional unemployment, I made the huge mistake of using credit cards. But after racking up my own 10k in credit card debt, my net worth was still significantly better than when I graduated from college.

Our assessments of the dire nature of such things is all in our heads. What was the worst that would happen? My car would get repossessed? That's bad, but is it "I'm never going to recover" bad? I always thought I needed that car, but it turns out that when it was finally taken from me (by a flood, not a bill collector), it was the first step to my own, much longer-lasting independence.

It felt awful at the time, but that was all in my head. Credit card debt is a problem of spending, not a problem of income. Oh, so I had a 17% interest rate that meant I was going to spend a lot more on the interest than I ever spent on the original goods. I sucked it up and took my lumps. I eventually got out of it by making my income much, much less reliable (I got rid of direct deposit and got lazy about depositing my paper checks). When bill-pay is automated, you always think you have money. When it's manual and you know you're unreliable, you never think you have money. So then you don't spend it on movies and bar tabs. You can actually force yourself into a healthier lifestyle by making other aspects of your life much harder on yourself.

But that's a story for another day, I'm kind of getting off topic here.


I most definitely agree with this.

There's risk either way -- opportunity cost if you don't take the plunge.

I feel like ux-app did it well, too, though, by mitigating the risk since he was able to take the 6-month leave. If a person can do something like this, or gain some free time (Fridays off, work from home, etc) to at least build out a first version of a product to market before quitting.... it's probably a good way to go, too.

Of course, not everyone has that opportunity. If you hate your job and want to work for yourself, and your boss won't let you do what ux-app's boss did.... then yes, quit your job and go for it! Like you said, moron4hire -- worst case scenario? You go find another job and you're right back where you started.


I too had a similar experience. I had been working with a company for 11 years. Started off as an SoE, ended as a VP/Dir. It was a great career. Awesome pay, awesome benefits, awesome people. But for the past few years I was just getting less and less happy. I'd come home exhausted, lethargic. Kind of felt like I was perpetually stuck in traffic... just slow and annoyed. In the end I just outgrew it there.

6 months ago, I too took the plunge. The way I looked at it was... this is an investment in myself. If after a year I am waddling, not learning anything, not generating (or on the path to) income... well... it's easy for a geek to become a W-2 worker just about anywhere.

I could go on about what I'm doing... but what's most important is that I feel I have grown and experienced more in the past 6 months than I could have imagined in the next 6 years at my old career. And to top it off, I'm energized, I'm happy and I'm in control of my happiness.


I'm sorry to hear about your debt and hot water heater. I do hope that such stuff doesn't happen to me, and believe me I did not take this decision lightly. I think even if shit hits the fan, I hopefully will still be okay.

Thanks for your good wishes.


In an industry like ours where finding a job is easy six months is quite reasonable. If things aren't going well after four or five months you just find a new job.


I'm always interested in reading about how people have managed to gain some personal and financial independence. But I find it hard to relate to this article. I guess if you have the runway to just sit around and discover what it is you really want do, then cool. But there's no real plan here, just "oh maybe I'll do freelancing too..yeah that sounds good." Maybe I've just been fortunate, but I've always worked in jobs where I feel I'm getting paid to learn skills that I know will be highly valuable whenever I decide to do something on my own. And I try to work on my own stuff, putting in 10-15 hours a week while still working a full-time job. I'd love to just leave my job, but I don't see why setting aside some solid hours each week isn't enough to get something off the ground. So, unless you're absolutely miserable in your job you shouldn't just leave it unless there's actually some other "thing" you're working on that actually requires your full-time attention. Again, maybe a lot of this post just reflects a sort of path of personal discovery, but it's hard for me to relate to. To me, the lesson is more about finding a job that is fulfilling enough and still leaves you enough time to work on your other stuff with the hopes that your other projects can eventually become self-sustaining and lead you to greater personal and financial independence.


There's an entire book about why you're right and the OP's approach is generally the wrong one, called So Good They Can't Ignore You. The OP is exhibiting the classic "passion mindset" - you search your soul for your passions and if you plumb deep enough, you'll magically unlock some cheat code in the world and people will start paying you.

The book is a light intro into the field of Self-Determination Theory and it's filled with examples of people following their passion for 6 months before flaming out because no one will pay them for the thing they like to do.

Another way to put it is that making money takes practice just like playing the piano does. You're probably not going to wake up one day and realize that an empty calendar is exactly what you need to learn how people will pay you for something that nobody told you to build.

http://37signals.com/svn/posts/1985-making-money-takes-pract...

http://www.inc.com/magazine/20110301/making-money-small-busi...


Sounds like a business school approach, and certainly valid. But to imagine its the only workable approach is silly. Everybody entrepreneur quits the job at some point to take the risk. This guy may (that's the important word) succeed at his own idea, or join someone else's project, or find a group of like-minded people and follow some idea to its conclusion. And sometimes this works.

In fact, there are so many examples of this working. Its a mindset: a person with non-entrepreneurial temperament can't imagine trying it, I get that. They go so far as to project their non-risk-taking onto others and claim they're making a mistake.

I think of it this way: entrepreneurs are swimming off the beach, splashing and surfing and diving and sailing small boats. A cruise ship comes by, people leaning over the rail and shouting "Get out of the water! You're getting all wet! You'll drown! The tide might go out! There may be sharks and stingy jellyfish!"

You can try to calm them, tell them "It's ok, I know how to swim, the water is not that bad, come on in with us!" But its pointless; they will stay on their cruise ship and shout and shake their heads. And that's ok.



That's a totally fine approach. That said, there's something to be said for burning your bridges. Well, burning your ships, is the better but less known metaphor.

I left law school a couple of years ago with a lousy plan to post on American craigslist listings, advertising LSAT tutoring. American rates were far higher than what I could charge in Montreal, Canada.

That plan was a total failure. But I was determined not to go back on the path that I was on. I wrote blog posts about the LSAT, and stayed in touch with people in my field. Eventually, an opportunity to be listed on the major blog in the niche came up, and later a chance to write explanations for the LSAT in return for royalties. I also set up a relationship with a company to teach classes for them, something I could not have done if I had still been in school full time.

I'm still doing all the things I started in the first dismal 3-4 months after leaving school. I couldn't be happier with how things worked out. If I had just tried it on the side, I never would have gotten so deep into things, and would have missed the opportunities I got. I HAD to find opportunities, because I had left myself no easy road back.


I've always romanticized the burning ships metaphor and will embark on my journey in a few months. Graeme ... did you move to the US? I'm a canuck in the US (established, have a decent job) but moving up to Canada in the near future. I don't have any concrete ideas about what I'll be doing ... just want to do something independent like the blog author. You describe your first few months as being dismal. Any advice you care to share?


No, stayed in Canada. I do a lot of Skype tutoring now, and sell books to Americans. There would be some advantages to being in Manhattan, but also dramatically higher rent for an equivalent apartment.

I like Neil Gaiman's moving towards the mountain metaphor. I had two objectives: earn recurring revenue, and earn enough in the meantime not to need to take a job. I just kept looking for opportunities that would move me in the direction of those twin goals.

Almost everything good that happened to me in the early (and later) days came as the result of talking to people. I emailed a few of the leading blogs in my niche. I cold-called a small company that taught the LSAT, and offered to help them expand to Montreal.

There were about five people writing explanations for the author of the leading blog. I contacted all of them. One of them founded a startup in the niche. I worked with them for a while, and still have a good relationship with them. That wouldn't have happened if I hadn't said hi. Talk to people.

Always look for opportunities. I got into Reddit early last year. I thought, "too bad there's no LSAT subreddit, I could post my stuff there". Eventually reframed that thought as "why don't I start a subreddit for the LSAT?". That subreddit has now become very popular within the LSAT niche, and it's been very helpful being the moderator there.

Think about what skills would help you towards your goal. "If I could do this, what would I know how to do? How would I do it?". I've learned book publishing, enough html/CSS to run a website on Wordpress, and some basic programming which has really helped speed up web page creation.

Nothing needs to be permanent. Don't say no to an opportunity if it's not what you want to be doing in five years. Is it useful to you today? I also do SAT tutoring. It doesn't hold much interest for me long term, but the money helped me through several rough patches.

Hope that helps. Think about what you want to achieve, and what skills you have to offer that will help you reach those goals.

http://www.uarts.edu/neil-gaiman-keynote-address-2012


That's kind of my whole point. If you're pursuing the kind of venture that simply won't work unless you have 100% of your time to work on it, then this makes sense. I just think that this is the case far less often than people think it is and it's certainly not the case for OP.


It's also useful for ventures where 100% time is not necessary though. The 'burning your ships' approach can be much more effective in reaching your goal. Not always, but often, to the point where I err on the side of, uh, burning.

And 'burning your ships' usually isn't quite as drastic and irreversible as it appears anyways.

Let me use friendships and social circles as an analogy. I've had periods in my life where I felt stuck socially. I kinda liked my social circles, I kinda liked my friends, but I yearned for something new or better. I didn't know exactly what though.

At first I tried to go to meetups and activities to meet new people. That worked at first, but it turned out to be very difficult to keep up. Because if I had the choice of meeting a bunch of perfectly fine friends on a Friday evening after a busy week, why would I opt instead for a bunch of strangers that one day might, or might not, become new friends? So at some point I just moved to another city, which for me was not such a huge deal, but still a pretty big step. And it worked very well. I had to go and make new friends. And it turned out that I didn't lose the old friends, not the ones that mattered anyways. In fact, those old friendships got a new shine and freshness.

That said, I did try a less drastic approach at first, and perhaps that's generally a good idea. But there's no substitute for forcing a change, because doing so incrementally can be quite difficult.


Hey xwowsersx! I hear your concerns, thanks for sharing them with me.

So, don't worry: I'm not just sitting around. I've been working on a small side project which is nearing completion, and I have another couple that I'd like to start. Plus, there's another long-term project I would like to do as a learning exercise in game design & development over the course of a few weeks. I should be able to get some time for that very soon. Furthermore, I'm a busker on the London Underground, which some people do for a full-time job and I hope to dedicate more time to (I have a financial goal there, too) which includes learning new songs and becoming a better performer. Finally, I do have a short-term (3-4 weeks) freelance project which is looking to be greenlighted coming up, which in itself will also be a learning opportunity.

The point is, there's loads of learning happening - and I'm really excited about all of that!

"I'd love to just leave my job, but I don't see why setting aside some solid hours each week isn't enough to get something off the ground." - I did this for about a year and a half and I just don't find it satisfying anymore, but I think part of that was because of the job I had.

It could be that this is just a short path of personal discovery, and I quickly change my mind - but I kind of want to find out for myself. For a long time, the whole "But Dan, you don't have a startup that is taking up more time than you can handle right now!" thing bugged me but the truth was, a large part of me wanted to quit for a whole multitude of other reasons, which I hope I have expressed somehow, at least between the lines.

Anyway, everybody has their own path. Mine, perhaps, seems a bit foolhardy at times, but I've been through some rough patches in life and come out the other side a better person, so even if this turns out to be a huge mistake, I do hope I look back at it and say, "well, that was a useful learning experience."

But I don't think it will be a huge mistake ;)

Thanks again, I appreciate the realistic viewpoint and honest opinion.


It varies from individual to individual. Some people can't focus well on a side project while working full-time, either because the full-time work eats up all available energy/time or because dissatisfaction at work leads to a low-level depression, making it hard to get motivated to do anything else. (I've been in both situations.)

Sure, finding a job that is both rewarding and non-all-consuming such that you can work on side projects too (ignoring any IP ownership issues) is a great solution, but not everyone is in that situation.


Totally agree. If you actually do have the passion for an idea, then you will make it regardless if a job. I work full time and work on three startups on the side. Granted, one is a bike shop that my partner mostly runs but the other two are saas style websites. The saas products aren't done but I put in at least a few lines of code a day. Sure, I could finish quicker without a job but I don't care, I think and work better with a bit of security.


What makes me bitter is not having this type of freedom as an H1B worker. For all intents and purposes, I'm a slave to my employer. Sure, I could quit at any time, but that would mean having to go back to my home country, which I have no intention of doing. The USA is just a better place for all sorts of things.

Will I be able to maintain my sanity until I get my green card? I have no idea. I've already become quite bitter and cynical about my job. I don't have anyone to look up to, the work is not challenging and the company is grossly mismanaged.

If anyone has any advice, I'm all ears...


Start a company on the side. There's never been a better (easier) time.

Can you start a company while you are in the US on an H1B? (Obviously, many people do.) There seem to be two schools of thought about whether this is legal with the IRS - research it, and maybe talk to a street smart immigration lawyer.

What if the company you start isn't actually incorporated, but is a side project allowing you to expand the skills you will need as a startup CEO - funded by the cash flow from your job? Or perhaps your company is incorporated outside the US?

Also, for anyone dissatisfied at work, I highly recommend the test at JOCRF.org. It's well worth the money.

Source: I've been in your shoes, and this is the advice I wish someone had given to the younger me.


I looked into this and it is illegal. Basically the law quite specifically says that while you can start a company, you cannot work for it, because your H1B explicitly prohibits income streams outside of the company that sponsored your visa. So if you start a company, you can only be a completely passive investor (meaning you would need a co-founder to act as managing partner/CEO). At first I thought the "income" part is a potential loophole, but then I asked around and was told that doing the work at no pay (under the guise of "volunteering") is also not allowed.

Trust me, starting a company is my plan when I get my Green Card. Until then, I'm trapped.


You obviously have more concrete experience here than I do, but my instincts say there's a vast gap between "working on a side project you hope to eventually work on full-time" and "form an official registered company with the IRS".

If you go to the IRS / your state's department of commerce and say "hey, we JUST TODAY started a BRAND NEW COMPANY that happens to already have X million users and we want to incorporate", do you know if they'd snoop around and accuse you of having "started" it prior to talking to them?


No, the laws around H1B are pretty clear on this. You can launch something, but can never charge for it legally. So, that rules out B2B. You can of course launch a social app or something, hope that it grows like a wildfire and then try monetizing it later, but that's such a bad idea for a bootstrapper.


How does that make sense? If you create a C corp, you are under no obligation to disclose that on your personal tax returns unless a taxable transaction happens and all the money earned would be inside the C corp which is its own entity.


The E-2 Investor Visa allows an individual to enter and work inside of the United States based on an investment he or she will be controlling, while inside the United States. This visa must generally be renewed every five years, but there is no limit to how many times one can renew. The investment must be "substantial". Investor visas are available only to treaty countries,[1] which include countries like Albania and Senegal, but do not include Brazil, Russia, India and China.[2]

http://en.wikipedia.org/wiki/E-2_visa

Just did a quick search for Canadians, so it might be different for other countries, as stated above.


I believe that the E2 visas require you to demonstrate "non-immigrant intent" (or however they phrase it). They want you to show that you plan to leave the US eventually, and any time spent in the US can't be used towards applying for citizenship, etc.

Confusingly, http://www.peerallylaw.com/en/content/view/517 says that some government departments allow dual intent on the E2...

In summary: maintaining correct visa status in the US can be hard.


How about starting a company, and than have that company sponsors your H1B? There would be some grey -ish part during the transition from the old H1B (of the old company) to the new one, and I think you would need a co-founder/ investor such that you can't have control of the company (ie. less than 50%). Would it be feasible to do it that way?


This is very, very difficult to pull off. You not only need to prove that your company has the financial standing to reliably and consistently pay you a full-time salary (which, for most startups, isn't always possible), but you also cannot have any controlling interest in the company. This means two things: either own less than 50% of it, or have a board of directors that has the power to fire you.

In other words, a total pain in the ass.


IIRC, when you do the visa transition, the government does a fair bit of due diligence to make sure this isn't what is happening.


Another option is to find a new employer who is willing to pick up your H1B. I was on the hiring side of that process at a startup a few years ago; it was a bit more of a hassle than the normal hiring process, but absolutely worthwhile.


I looked into that too, but if I switch employers now, then I lose my place in the Green Card queue and have to start that process over, which means losing at least a year and a half. (That is, if my new employer even agrees to file a Green Card petition.)


Start an offshore company, maybe?


I looked into this as well. Basically, depending on where the company is located, accepting online payments becomes a huge issue. A lot of countries (my home country included) just do not have good financial infrastructure to be able to handle online payments.

There's also the administrative overhead and weird tax laws that come into play. Basically, if I start something elsewhere, it would be the opposite of "lean."


If payments are an issue, maybe someplace like Ireland? There are well trodden paths here.


What does it take for a foreigner to own a LLC-like company in Ireland (LLC is a see-through entity so individual just pays standard income tax)? For e.g. how easy is it to set it up compared to a Delaware Corp, which can be done in a single day?


Currently you need a minimum of two directors to setup a company, so it probably isn't great for this. Ireland isn't really a great location for traditional companies, but great for multinationals due to the double taxation loopholes. There are EU countries with lower corporate tax rates, but they don't have the loopholes.

In the UK you can register a company online [0], however you need a UK address. There are various formation agents that will register the company and provide an address for a small fee (<£100) [1]. If you want a business bank account I think you'll need to do it in person though. You will probably want to get an accountant too which will be ~ £1k/year, although you can do it yourself.

Further reading:

http://www.bdb-law.co.uk/media/440379/settingupbusinessinthe...

[0] http://www.companieshouse.gov.uk

[1] https://www.theformationscompany.com


It's also really, really easy and cheap to set up an international business corporation (IBC) in well known offshore locations like the British Virgin Islands or Gibralter. It's just because of the payments issue that I suggested Ireland.


Do you have any more specific resources on the matter? I've got a lot of hearsay from researching but it's quite hard to know exactly what's wrong and what's not - it seems like there are more speculation than advices from people who have actually done it. And why would it be a problem with the IRS? I would have thought the main road block would be from USCIS.


I know MVP is all the rage (and for good reason) but what about developing a product in complete stealth mode until you are legally able to launch it and make it publicly known then?

Keep your codebase clean (and ideally covered with automated tests) and be prepared to add and subtract a lot of features once you are able to get feedback from real customers.


Unless one actually needs the corporate structure to distribute equity or hire, why start a company when you can just start a side project, and convert it into a company if it happens to take off?


My jeweler has been in the US without a 'green card' for 20 years. He works for himself; no problem.


How about this?

1. Setup a company in the country you're from. 2. Outsource the work from your US company to company from point #1 3. Profit!

If that's not allowed, then build the product on your own (personal expense), then "grant" it to your US company, then keep the company running until it's making enough profit to legally hire you to work in the company.

How about that? (Looking for feedback, I'm in similar boat)


Yup ... that's me. Except my home country is Canada and not that bad. I am moving back. A few years ago, I had tons of ideas. Just no freedom to achieve them (apart from the H1B restrictions, I have a very restrictive IP arrangement with my employer). Now that it is time to leave, I feel a bit lost. Looks like all those years not thinking has atrophied the innovative part of my brain. I'm hoping it can be rekindled.


Congratulations!

I quit my job about 19 months ago and had the luck to get immediately re-hired by my former employer as a freelancer for a few months on a much higher rate (http://steveridout.com/2012/12/30/a-welcome-delay.html). This, combined with living in Madrid now instead of London, has given me enough runway to live cheaply for another 2 years if needed.

I've been working on my current SAAS project http://readlang.com for 11 months now and despite showing a lot of promise it's still not even ramen profitable. I'm still feeling very hopeful about it though and while it's looking promising have every intention to follow through to see where it leads. May write a blog post about this as it approaches it's 1st birthday.

I'd say your 6 months is on the short side for creating and selling a product of your own, and would recommend you try to find consulting gigs to save up some more money first if this is the road you're considering. If you just meander and hop between a bunch of projects for a few months I fear that in 5 months time you'll be looking to take for a normal job again, perhaps running back to your old company! (I've actually done this before - I took a year off with no plan, didn't focus on a project, and ended up re-joining the same job I'd left.)

Anyway, good luck, look forward to see what you can create!


This is exactly what I was looking for! I recently moved to Germany and I'm learning German and I'd love to do it through reading. I was about to sit down and patch together an epub reader to do this, but now I don't have to.

Here's some feedback if you'd like it :)

I just subscribed to the $9.99 per year version. However, I was mentally preparing myself to pay more, since it was very useful. I would have liked to try it out for longer though. The most useful part of it were the multi-word/phrase translations and I could only try out a very small number before it popped up the "subscribe" notification.

So to sum up, I signed up because it was just $10 a year, but would have paid more if I'd gotten to try it out for a short while longer.

All the best!


Thanks, yes I'm always very happy to get feedback, especially from paying customers :)

The current pricing is partly an experiment to see if people will pay, and it turns out that 1 in 30 of those who sign up do at the moment. It's also to ensure that if the site explodes in popularity I won't lose money through Google Translate API costs. I plan to increase the price at some point (but not for current subscribers) although not sure what it should be exactly. What would you think of $4/month or $30/year options?

I'll think about increasing the 20/day phrase limit, I really need to dig into my analytics a bit more to see what the usage patterns are on this. Roughly how long did it take you to reach the limit and how much longer would you have liked?

Thanks again!


It took me about a minute before I was prompted to create an account and another minute before I was prompted to sign up for a subscription. I'd gotten through about 4 sentences in total (I clicked a fair bit since I'm still learning the language).

I'd happily pay $4 a month / $30 a year. I really like the Chrome extension as well. Here are some of the features I'd thought of adding to my (now cancelled) project:

Being able to see the meaning and usages of a word with a hover of some sort. I find it annoying to keep clicking on the right hand side to pull up the definition. Additionally, a number of definitions are just not available.

Something I find myself doing a lot is selecting and trying to right click. The 8 word limit on phrases means I'm stuck with typing stuff into Google Translate. For longer sentences context gets lost and so the translations are not accurate.

Being able to collect personal word lists. This is great for learning which is my primary intended use.

Keep in mind that I'm a beginner and the requirements of someone at an intermediate level might be very different.

Hope this helps and I'm looking forward to using it even more!


Adding a hover pop up after selecting a word/phrase could be a nice feature. It would be easier to implement if I had my own database of definitions/translations instead of relying on external dictionaries in an iframe like the current sidebar. Note that one of the reasons I've avoided implementing important features on hover so far is to ensure that everything works well on touch devices.

Not sure how to enable selecting text in a nice way given the current UI. Would probably need a way to temporarily disable the current word selection feature. Hmmm... actually one way would be to add a keyboard modifier to temporarily enable native OS selecting for advanced users without cluttering the UI for regular users.

Personal word lists: I've avoided tagging, folders or lists for organising words so far because I don't think I'd personally use them, but it's certainly something I'll consider for the future, especially if enough people request it.

I'll keep your suggestions in mind, and if you want to encourage the development of any specific feature please add or vote for it on the uservoice page: https://readlang.uservoice.com/forums/192149-general/filters...

Thanks again!


>I wasn’t totally happy with the way my job was going.

This needs more clarification. Everyone, as in every single person on this planet, has reservations from time to time about their job. That is normal. What is not normal is quitting for fleeting reasons. And I think that's a symptom of hipsters the days. More kids are growing up with helicopter parents and told they are the best at everything they do. Those same kids get a mid life crisis at 25. Quitting your job because I am not 'totally happy' with your job sounds like an irresponsible decision.


In many ways, I totally agree with this.

It is very dangerous advice to go around and tell people to "work less, live more", or "quit your job, go live life". This isn't a one size fits all message (I'm not saying the OP is giving out advice. Or saying he thinks everyone should follow suit. He is simply telling his story, which I found to be a very interesting and enjoyable read.)

I got where I am at because I work(ed) my balls off. Late, Late nights and grinding out solutions to problems in coffee shops and hours and hours of reading and hacking.

The "Rework" approach comes with a huge caveat lector!

However, I wish this guy the best of luck. More jobs for the poor, smart, and hungry...


If they are responsible only to themselves, and have money in the bank, then there is no 'irresponsibility' in the equation at all.

Some folks value 'safe' corporate jobs. Others make their own way. In America, 50% of us work for ourselves. Its not crazy or irresponsible; its normal here to not have a corporate job.


> In America, 50% of us work for ourselves.

Do you have a citation for this? It sounds very high to me, and the most recent info. I could find with the BLS[1] puts that number closer to 11%.

[1] PDF - 2009: http://www.bls.gov/opub/mlr/2010/09/art2full.pdf


You're right. Even in my state (Iowa) its only around 25% I guess things have changed a lot since I last looked.

Sad in a way. Folks think now somebody has to 'create' a job for them. Used to be, you bought a truck and a sign and some tools, put an ad in the yellow pages, and you had a job.


That's awesome. I can relate to this story. I quit my job around 5 years ago because I was unhappy with what I was doing. I took the planning very serious and paid off all my debt and saved enough money to travel around the world for a year while just working freelance and running various businesses I was starting. After five years though I'm finding that I work way harder and much longer hours than I was working at an office. It's almost impossible to ever open my laptop and not work. I miss that when I got to work, I worked, and when I went home, I didn't. I don't have that luxury anymore. But I have a ton of other awesome perks. I can live anywhere in the world so I generally live in places where the dollar goes a long way. It's been a pretty incredible experience.


I did this and it was great way to fuck myself. My wife was sick, so I have no other option but to quit and bootstrapped my consultancy business from home.

- most of my friends were in work, so I lost those

- zero unemployment support + paying health insurance from your own pocket. If you are bootstrapping and need some decent runway, this matters (especially in EU)

- Big hole in your CV

- if you stay in metropolitan expensive area, your savings will run out fast...

- traveling while bootstrapping? you can pick only one

- if you never worked from home, your productivity and working habits will sink like a rock

I think better way is to gradually prepare yourself while working. Start some open-source stuff. Learn new language at your work. Do standup comedy over evenings, whatever.

Also try to bargain with (or blackmail) your boss. Workers who are actually qualified, are rare and generally underpaid. Retention is HUGE problem. You could start side project at work, with silent agreement from your boss. You could get work from home (and build working habits for your startup). You could even get location independence for reduced salary.


- You only socialised with your friends when at work?

- I am sure you can have some, even minimal, support as an unemployed person in the UK.

- Big hole in his CV, one of the most exciting times in his real life?

- True, but he knows what he wants to do so he 'll have to play with those rules.

- Maybe true.

- You can't say, he might be more productive from home.

Hope your wife is okay now or getting better!


> traveling while bootstrapping? you can pick only one

Decidedly not true. Probably you feel that way due to your situation, sick wife etc.


I did precisely the same thing last month. I had a great job, challenging and meaningful work, but there was something missing. Here's my experience six weeks in.

I found enough freelance work pretty much immediately to pay my bills, and didn't have to drop my rates. That said, my wife has a successful small business, and I have over a year's runway, so there's much less pressure.

It forced me to become more 'social', and attend meetups (including HN London) and other events. Although I'm getting some work through meetups, the major benefit is in staving off the loneliness you may get from working remotely/at home/from a coffee shop. Coming from working in a great team, my experience is this hits you hard.

Meeting lots of new clients and potential clients has been seriously fun. I wasn't expecting that. I even dipped my toe in Elance, which has been a surprisingly positive experience so far.

I've never been busier or more motivated. I wake at 5.30am but now walk the dog, make time for my wife and take time out to explicitly learn new things when I like, not when a schedule dictates. That alone was worth quitting. My advice, for whatever it's worth, is to be rigid about dedicating 'off' time. (No mobile!) Even just half a day a week has safeguarded my mental health so far, and it's very, very easy to skip it.

I've been able to work on my startup[0] a good three days a week, as well as launching a couple of other smaller side projects already. If possible, I strongly recommend having a big project so you feel like you've got an anchor, and can make forward progress whenever you're at a loose end and you might otherwise be checking HN.

Quitting full-time work has been the best decision I've ever made.

[0] http://databasify.com


Congrats on taking the leap, enjoyed the post a lot. I did this almost 2 years ago, and never looked back - as soon as I fully committed myself to life without a job, https://openexchangerates.org took on a life of its own and remains my primary focus.

FYI, it took about 8 months to start making money (could have been much sooner, but I dragged my feet a lot) and another 6 months from first paying customer to totally covering my lifestyle and making enough to reinvest.

If you'd be interested, we have some freelance engineering tasks coming up - shoot me an email (josscrowcroft at gmail) and we can discuss further. I'm in London for a few more weeks at least.


So, you're going to go through some changes. Be ready to forget what weekends mean. You'll probably start getting frustrated with weekends, because you'll wonder "where the hell did all of these people come from?".

I highly suggest adopting an alternate wake/sleep schedule. Or rather, I highly suggest not resisting the change away from the "normal" 9-to-5 schedule that everyone else accepts upon them. I personally went to bed at sunrise and got up around noon. I also put work at the end of my day, rather than the beginning, which allowed me to pay attention to my health in a way I've never been able to accomplish otherwise. You have no reason to work their schedule, yet you'll end up A) getting stuck in their lines and traffic, B) paying their restaurant/bar/movie rates, and C) missing out on one of two amazing worlds: extreme late night or extreme early morning. The people you will meet there will be the most fascinatingly unconventional people in the world and they will inspire you to do great things. The fact that you are on this journey probably means you're one of them anyway. Go find your people. The people of the night are a close-knit community and help each other out in ways you can't imagine.

Now that I'm married, that doesn't work out too well, but I'm working on getting her to eventually be able to take the night as well :P

You'll probably end up working constantly. Learn how to take a day off: honest-to-goodness unproductive time (it takes you out of the fight-or-flight mode and gives your body a chance to recover). You probably won't be able to stand more than one day of it, as you'll get antsy and start feeling a need to make something. But it's necessary to unwind. Play video games all day. Go to the zoo. Watch movies. See your friends.

Don't think you can extend your runway with credit cards. You can't extend a blanket by cutting off the tail and sewing it to the top.

Stay open to opportunities. Make sure you keep meeting people. People are where the opportunities come from. Nobody is going to hunt you down and give you a chance.

It's better to take part-time work that pays the bills than it is to take full-time work that gives you lots of disposable income. Your time is far more valuable than anything any employer will be willing to give you. That's kind of the point, if your time were actually worth $80,000/yr, then they'd probably only hire you at minimum wage. Keep your time for yourself. If you live in a big city, you might be able to get by on bartending in a popular place on weekends. It's better than sitting in a cubicle farm.

You probably won't make it. Unfortunately, 6 months just isn't that much time. Oh, I think it's enough time to build just about anything, if the resolve is there and the freedom to work however you want (work tends to fill the time you give it, and most slowness in projects is the bureaucracy from which you are now free). But you'll learn that there is a lot more to making a project happen than the build phase. For example, if you haven't done any marketing yet, before the product is complete, you're already very behind schedule. You'll have to learn how to do all of those things that aren't programming, because otherwise you won't know what to look for to hire an effective person to do it for real.

That doesn't mean the time isn't worth while, but you need to know how to use it wisely and not become despondent if/when you finally cave and get a "real job." Use this time to learn as much as you can. Specifically, try to learn about yourself, i.e. how to motivate yourself to work on a consistent and regular schedule, how to get yourself out of ruts. You'll learn what you're capable of pulling off, even when you weren't sure what to do at the beginning.

And if you do "fail", pick up the pieces, dust yourself off, and get ready to try again.

This experience will change you. Try to let it change you as much as possible.


I agree with most of this. I also woke up around 3 today and usually work more towards the midnight-7am time period.

The only big problem is that you don't seem to have much of a plan to make this sustainable in any way dan. I think you should try and do some contracting since that is the easiest way to transition away from the 9-5 full time job trap. While you do that you should also be making your own stuff that you think could generate some revenue and also plan a kickstarter for a separate larger initiative. Basically do not put your eggs in any single basket but have a larger portfolio to mitigate risk. The only thing is that you should've been doing these smaller projects on the side for the last year to give you more of a cushion.

This is basically exactly what I did in the past year and all of these strategies succeeded for me so I have gotten into a pretty good position. I now have a thriving contracting business with 2 other employees, a successful kickstarter(we raised around 150k) with 3 other main partners in a separate company, and between $500-1000/mo of passive revenue from some of my smaller projects(to be fair though I have been working on those projects on the side for the last 2 years, originally they made significantly more than 500-1k/mo, they have just slowed down a lot). I spend my days mostly on the kickstarter.

The most important part of this is that any one of them can fail at any time and I will not freak out. Some of what you do will fail, even if you feel in your gut 100% sure it will succeed there is still a very real chance it will fail. Some of my smaller projects failed spectacularly. You need to be prepared for this and have a plan to mitigate these failures.

It is not easy to escape from full time work in a sustainable way. You have to work at it and you have to have a plan. You also need some luck.

Also if you live in san francisco, new york, dc or london you need to seriously consider moving away. The problem with selling products on the internet is that your earnings in no way reflect your geographical location, and it is much harder to succeed when you are spending way too much on everything.

Edit: Apparently you live in London. Trying to bootstrap in the most expensive place in the world is very hard, I would advise trying to contract locally where companies will be more willing to spend above average for developers.


He says "in islington" which is in London.


By a staggering coincidence, I know the telephone number of an Islington flat, where I once went to a very good party and met a very nice girl.


Hey moron4hire. There's a lot of good comments in this thread but yours made it to the top for good reason: thank you for your blunt, honest advice and thoughts.

I am especially glad that we are agreed about "It's better to take part-time work that pays the bills than it is to take full-time work that gives you lots of disposable income. Your time is far more valuable than anything any employer will be willing to give you."

As for failing: yeah, you're probably right. There is a high chance that I will not be able to keep this up forever. Part-time work and freelancing may sustain me for a while, possibly even extend my 6 month runway - but I need to find something more stable and/or large in terms of amount-of-money-to-live-on.

But I'm glad you also agree that even if I do go back to a 9-5 job, I will find a lot in this lifestyle which I enjoy and can learn from. And maybe if/when that happens, I will be excited about returning to that lifestyle I formerly had. After all, there are many enjoyable lifestyles and the "9-5" can be one of them.

I promise I won't rely on credit cards, and I promise I will stay open to opportunities. The man who I mentioned in the post, Mike Rugnetta [1] told me "Say yes to everything you can at first. Then, eventually, you will be able to say no." - I hope he is right.

Finally I love your suggestion about alternative sleep/work patterns. Personally I think I'm likely to adopt an early-riser thing. I'm very into bouldering, and the best time to go to the climbing wall is in the morning at 6:30am. I would love to get to a point where I regularly get up at 5am, but I'm not quite there yet. I guess we shall see where this takes me.

Thank you, moron4hire - I appreciate your honesty and your well-wishing :)

[1]: http://twitter.com/mikerugnetta


You know... I bet you could go indefinitely on freelancing in addition to building your projects. I don't know what your lifestyle is like or what kind of expenses you have, but I do know that if you're a software guy, there's a demand for it out there. If you're focusing on your projects and just freelancing enough to pay the bills, you might not have much expendable income, and you might even have to scale back your expenses.... but if it affords you freedom, is it not potentially worth it until you get your other projects going?

That's my plan at least: replace my day job with a freelancing gig, which should afford me enough time to build out the ideas I have. I actually wrote a blog post about it recently [1] and I have high hopes for it! Hopefully I can be like you some time next year and take the plunge!

[1] http://blog.mcdougle.net/creating-acquiring-software-assets/


Your wording suggests a subconscious viewpoint that is similar to how people view "dieting". The common view is that the diet is a special case, a difference from the norm. This ultimately sabotages the effort because it makes it an effort, a contrivance that must be maintained.

The successful diet--and the successful non-traditional career path--rests on accepting the new lifestyle as the norm, as natural, as default. That which was the old way must become the exceptional case.

The journey through the wilderness requires many skills. You can't be thinking about the river you crossed to get to the desert, and you can't be thinking about the mountain you'll climb once through the desert. Be present in your work.

I still have family members who think "this freelancing thing" is just a temporary stop-gap until I find "a real job". They have no concept that the freelancing could be an end unto itself. I don't want to be a freelancer for the rest of my life. At some point, I'd prefer to get out of services and into products. It might not even be software, I have been receiving more interest in my artwork this year than I have ever in all previous years.

But that's down the road. Right now, I'm a freelancer.

Okay, flowery language aside: unfortunately, it's really easy to take on too much freelancing. It's really easy to rationalize, "oh, the client needs the extra effort right now, and at least they're paying, but we'll go back to normal after this, because they're paying." Well, clients are as adverse to change as everyone else is. It's easier for them to keep paying that extra rate than to accept the lesser productivity.

Plus, as far as your body and your mental willpower is concerned, the work is indistinguishable from your project you hope to pull off. You'll be working hours for your clients be right back in the situation you're in working for The Man: not enough energy to work on your side projects, beholden to someone else's schedule.

That's why I suggested completely unrelated work for temporary sustenance. Bartending, cooking, dog walking, what have you. They usually lack the ability for you to decide to work more. The very nature of the work prevents you from sabotaging yourself.

Incidentally, that's why I'm pouring more effort into the freelancing. I'll turn the freelancing into B2B consulting. I've got a couple of subcontractors working for me. I manage their work directly. My clients don't even talk to them. They know about them, they know that they are paying me and I'm paying someone else to do some of the work. But they also know that it's the only way they're going to get more done on the project in less time. Right now, I personally am the biggest chunk of what the client receives. If I can build this large enough, then taking myself out of the coding, at least, shouldn't have that big of an impact to the overall workflow.

So for now, I'm a freelancer.


That's a very interesting take on it.

I don't think I plan to do freelancing simply as a "stop-gap." We'll see how my mindset changes as time goes on, but I do hope to actually build a business out of it -- make a good living myself for a while, then hire teams, work on bigger projects, etc. Like I say in my blog post, I will be just creating another job, but it will hopefully be a job on my own terms, essentially. There are the issues you mention -- easy to pick up more work, etc -- but I can do it at my own pace and on my own time.

Building software products are, to me, like investing -- building a separate source of income. I'd love to have many different sources of income, one of them being freelancing. I assume once my "investments" can sustain me -- and, as time goes on, I end up with more responsibilities (like a family) I may cut back on the freelancing thing. But for now it sounds great.

My point for the OP was that I do think he can sustain himself indefinitely on things like freelancing or part-time jobs that allow him more time to focus on his projects. You do have a point though -- it might not be a bad idea for someone in his position to pick up an unrelated job like bartending.


As I said in another comment in this thread (and I think you get this concept), the existence risk is not reason enough to avoid an experience. Or rather, most things that we judge as "risky" have a worst-case downside that is actually quite easily recoverable. If it doesn't work out, you'll have an empty bank account and be working at a desk on someone else's schedule. Sounds just like all of college and my first 8 years of my career. In other words, distinctly not selling my body for another rock of marijuana to snort.

Even if everything every naysayer says is 100% true, it's still worth the experience. It's still worth testing yourself.

I personally found that I work hardest for myself. I work best when I understand the rationale for doing what I'm asked, and when I ask myself to do the thing, then I completely and fully understand the rationale. The surest way to get me to not do something is to tell me "because I said so." When asked why I won't, I'll most likely reply, "because fuck you." To me, the two are equally legitimate and reasoned arguments and are completely deserving of each other.

I also was not personally able to do the "side project" thing. "Just work 10 to 15 hours on top of the 70 you're already working for The Man and the 10 you're commuting and why don't you spend any more time with your friends and what is wrong with you and your health, why can't you take care of yourself and get enough sleep and eat properly and exercise and setup time to talk to this financial planner I've been telling you about for the last 3 days, you just seem like you're drifting." (can you tell I lived at home too long?) If something is worth doing, I believe in spending my entire effort on it.

Mistakes are meant for making, because most of the time they aren't mistakes.

My best friend just started this journey for himself as well. He is married, they are upside-down on their mortgage, and they just had a kid. He quit his job in finance to become a photographer. It sounds like the absolute worst mistake he could possibly make. He got his first sale inside of a month. He's received a few accolades for his work. He would have never gotten there while still working for The Man. Even if he has to get a job in a couple of months, he knows his metal now. He knows it's just a matter of time before he gets to do it again.

And that's called hope.


Taking a day out now and then is the best advice I think you can give - if you're the sort of person that's always hustling you sometimes get guilty about it, but that one day on the sofa playing video games a month will keep you sane. (Or watching films, reading, whatever you use to take your mind off things)


I'll try not to take this resounding agreement as a cue to spend all of today playing GTA5 :)


Your time is far more valuable than anything any employer will be willing to give you.

^^^ that


As many others mentioned, six months isn't a lot of time so my actionable advice is to do everything you can to increase that runway while maintaining the independence you crave. I suggest ranking your ideas based on three criteria: how long they'll take to build, the likelihood that they'll produce an income stream, and the amount of ongoing maintenance and effort it'll take from you if the idea seems to be working. Find the one with the best ratio of the 3 (easy to build and likely to make passive money) and build that first.

Also, I recommend you give yourself a hard deadline for launching each idea you work on. It's incredibly hard to launch. It's much easier to push back the launch date so that you can put in just one more killer feature, tweak the look and feel just a little bit, and get that copy perfect. It's much better however to just launch and improve as you go. It's a lot easier to determine which features are actually the killer features when you introduce them one at a time instead of all at once.

Once you set a date and time to launch, stick to it no matter what. You can always improve on your idea and launch again. The generally held belief that you only get 1 launch is a fallacy. If the first launch goes poorly, nobody will realize you launched twice anyway.

Obviously how long you should give yourself to launch your idea varies on the idea itself but I highly recommend something absurdly short - like this time tomorrow. That's enough time to put together an minimally viable product. Plus it would make for a catchy title when submitting to HN.

Good luck with your adventure!


I did exactly this in July. My colleagues and friends were surprised that I didn't have something else lined up, but I needed to take a full break from the 9-5 world. Funnily enough I had about 6 months of runway too.

Several comments in this thread have mentioned how it's hard to get a side project to profitability in 6 months, but that's really not the only route to a sustainable lifestyle. Freelancing, consulting and other income streams (hurrah for busking!) are all perfectly good ways to try out new projects, learn or improve skills, and bring in some cold hard cash.

I've personally found that far more doors are opening for me now I'm open-minded, available, and willing to have conversations. When I was equated with the tech company I worked for, people would not have approached me about the things they do now, and I certainly wouldn't have considered some of the things I'm considering! It's taken a few months but I'm happy with where things are going, excited about the various projects I'm doing, perfectly satisfied not to have a complete prototype of a fundable startup idea yet, and definitely still overwhelmed at the sheer amount of branching futures ahead of me.

Good luck!


Hey jlees, I totally agree about being open-minded and not being attached to a company. It could (and already has) opened up doors for me which I didn't realise were there, which is hugely exciting.

I think the mistake a few people in this thread are making (although I do really appreciate the advice) is that I am trying ti build a business. I may end up trying to do that, but that is not the goal in mind here :)

Thanks for the good luck!


I left my job a good paying job a little over a year ago after building up about a year of savings. The work environment had deteriorated a lot since starting there and honestly I was to the point the money wasn't even worth it. So probably worse off than the author says. A year later I can say I haven't regretted it at all. Keeping up on freelancing has really been my key to keeping a positive cash flow while working on my long term projects. I rarely turn down any web/consulting work, unless it has serious red flags.

The thing is about a startup project is that it might take a while to get going. Some things I launched a year ago have just now really shown the work I put into them was worth it.

Balancing time where work stops and relaxing starts can be difficult when you are on your own. There is always something to do hanging over your head. I've had to be disciplined on this to avoid burning out. I spent a fair amount of time doing accounting, projects bringing in money, clients paying, monthly invoices, etc, it does consume a non trivial amount of time each week.

My one concern in the article though is quitting without a plan. I had a pretty concrete plan which I'm still moving towards.


Congratulations! I made a similar jump about 20 months ago.

My only advice to you is to keep doing the freelance gig thing on the side, as I see you are doing based on your comments.

The things I've learned about surviving:

1) As one commenter said, 6 months is basically no time at all. It will FLY by. Launching your side project to a state where you are comfortable with the project or can at least try it out in the market will take about 6 months.

2) For Freelance gigs - People will only pay you for what you're good at and you have experience in. It's no different than finding a real job. No one will pay you for what you think you are good at, if you don't have proven experience in it. This is good to know if you get in a money crunch. Always go back to your real strengths and the money will follow.

3) Always plan for Plan B. Build your professional network weekly if not daily in the industry where companies are willing to hire you if this venture doesn't work out for you.

4) It will take you at least 3 months to find a job once you start looking, assuming you have the right marketable skills. It shouldn't take that long, but it does. Plan accordingly.

5) You will need help about 3 months from now. You'll be lost as you try to find yourself. Don't be afraid to ask someone for guidance. You could be asking someone you met in Austin or someone you met recently. You never know.

6) Start a personal / professional mailing list. Allow people to have an insight into what you are doing. People like this kind of stuff. This allows you to stay in touch with lots of people fairly easily.

7) You never know. Jason fried wrote an inc article I believe about how he ended up writing for inc through a series of events & connections. Keep an open mind as I think you are doing now, and keep your relationships up to date.


I'm close to that point at my current job, too. I feel like I learned lots, but that the learning and growth has plateaued for me, so it's time to move on. I would love to just announce my leave and head out in uncertain waters, but I have a rule that I always have to be moving towards something I want, rather than away from something I dislike. Leaving because I am unhappy with the work would break that rule (to my dismay).

From one Dan to another (Danny, actually), I wish you luck, and I hope you succeed in finding what you want to move towards!


> moving towards something I want, rather than away from something I dislike.

I loved this.


That's a good rule, Danny. I hope it serves you well, as mine do me :)

Thanks for the kind words!


Such an important and hard lesson to learn.


wow -- surprised at all the folks that just quit their jobs recently. We've got quite an HN job-quitting support group.

i also just quit in june of this year and it's a big change. i've always been motivated to work on projects on my own, but going to absolutely zero supervision (and zero income) took a lot of getting used to. it's easy to get paralyzed thinking that you need to work constantly and you end up not having fun even though you're super free (for a little bit) and have a really flexible schedule.

we're personally having our official launch at a trade show next week...it's going to be a real moment of truth for us and i'm kind of terrified.

good luck!


Congrats on making the leap! I've been waiting for the right time as well, and it has been too easy to continue kicking the can with reasons why not.

I am curious on the 6 months of runway. Have you found how many months others save up?


I did read a fair few other peoples' approaches. Some people said, "enough for a year", others said, "enough for 6 months" and some people said "enough for 2 years".

To be honest, there's no one amount. I felt comfortable being riskier. My family was very supportive of my decision since they've all done similarly risky things in life. This made me feel comfortable going in knowing that if it all completely went tits-up, I'd probably have a branch to cling to. But this isn't something you should use as a motivator to chill out and be lazy. You need to find ways to support yourself, one way or the other, otherwise you've just moving from one dependence to another.

Freelancing is a good place to start because it doesn't require complete dependence on somebody, and you can work on your own terms, and it helps to have a bunch of stuff you can say, "I did this thing" in case the time comes to get a job.

Good luck in figuring out the right time for you :)


"The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man." --George Bernard Shaw


Good luck. It could be 6 months you will never forget regardless of what happens in 6 months. Many work really hard chasing elusive goals and forget to enjoy today.


Congratulations, man! I did this 2 years ago when I quit the US foreign service (really stable job) and decided to learn programming. It worked out really well for me, and I have done some incredible things that I never would have had a chance to do otherwise.

It's not the easiest road, but you will have a great time, I am sure. Will definitely watch your blog for updates, and let me know if I can help at all.


Can you please elaborate on the programming from the scratch? Of course Codecademy is a great start, but what and how exactly did YOU start? Furthermore, what did you end up doing, where did you move from there and where you currently are?

I quit my finance job few months back (hello to everyone) for non-tech related start-up. Not that I have a better pay (almost the same), but I have more free time and finished JS/Python courses on Codecademy. I just feel a little bit lost now and would appreciate some advice or story from the fellow explorer.


Hey, good question.

I actually started out building stock prediction algorithms, then realized I had no idea how to do that (~October 2011). I was mainly coding in C# and Ruby, and picking it up from books.

I then found Kaggle, which has a lot of great machine learning competitions. They will post something like "predict bond prices accurately", or "score essays automatically", and lots of people get to compete to create the best solution. The leaderboard format really motivated me, and I met some great people and did very well. I learned a lot of the stuff I needed from online books, Khan Academy, etc.

Concurrently with Kaggle, I started a consulting business, and got a lot of clients through there.

After I spent a lot of time doing machine learning, I was found by edX (edx.org), an online education company that was looking for people to develop ways to grade essays at scale. I thought I knew how to program before, but I actually didn't (I was coding mostly in R for Kaggle, and not using classes or building resuable code, etc).

At edX, I actually learned how to test/deploy and develop properly. I also ended up doing 99% web development, which is fine, as I learned that skill, but got a bit bored due to not using machine learning at all. I learned Python, Django (the main web framework), and a lot of server deployment and other skills. I can't emphasize how invaluable working at a startup that did things the right way was in terms of my learning.

I recently left edX to work on some of my own projects. Currently, I am working on an android application, Happsee (www.happsee.com) that helps track, visualize, and discover what makes us happy (and can do a lot of cool machine learning with). I have also worked on an open source learning management system, Movide (www.movide.com).

The key for me to learn programming is to de-emphasize the programming. I don't actually care much about programming. I care about making things. I get a similar joy from snapping legos together and making something and from coding. So find a problem you want to solve, and start thinking of things you could make to solve that problem.

For me, data is insanely cool, and I have done a lot of random explorations on my blog. I just did an analysis of happiness (http://vikparuchuri.com/blog/what-makes-people-happy/), but I have also analyzed how much characters on the Simpsons like each other (http://vikparuchuri.com/blog/how-do-simpsons-characters-feel...).

Small projects like that are a great way to learn, and can get you exposure through presentations, blog, etc.

If you have any questions, I'm happy to help. vik at equirio dot com.


Loved the post. I'm in the exact same position as you. Have 6 months of runway and I've become an independent consultant. I'm also spending the time on my own ideas, like my newly launched https://www.silvrback.com

I wish you the best of luck. Like you said, life is too short not to take risks.


That's awesome! Good job with Silvrback, and thanks :)


"Now, here I am, sitting in a coffee shop in Islington with no fixed income, no employer, and no startup which I’ve just received seed funding for: just me, my laptop, and a bunch of ideas"

Where did you receive the seed funding from? I was hoping your post would be some sort of roadmap, but I miss that part.


I could be mistaken, but I believe he's saying he doesn't have a seed funded startup.


You're right. I read too fast and I thought "I have roughly 6 months of runway funds" means "I have seed funding for 6 months." Thanks for the correction.


Aw, crap. Word fail from me there. Thank you Loren.


So what if you don't have any ideas about a different life but hate 9 to 5? When I would take off I would immediately miss the feeling of doing something actually productive because I have nothing else but my job. Does this make me stupid or just uninspired?


Neither, really - it just means you haven't tried doing other things with your life. You might find that once you have that freedom you do all sorts of cool and fun stuff with you time which you, ultimately, consider productive.


On the one hand I feel a gut reaction "you fool!" for leaving a secure, stable paying job with good people (Huddle are just around the corner from here, I know some of them).

On the other hand, I hope you do something great with it!


Any chance we'll see Android support Go officially in the next 2-3 years?


Wrong thread, huh?


Be excited. Call me after 10 years of that ;-)


Truth. One does get used to this, once you got it working, fairly quickly. Still wouldn't go back to a regular 9-5 but that's because they're 80% not really more interesting than going it alone + some fair amount of travelling.


congratulations :) good luck with whatever comes next!


Great! Life is about risk-taking and discovering the things you love to do. When you follow your passion, then you become more inspired and more satisfied in life..


- I hope, pray and wish you the best.


Me too! Thanks David.


You have made a devastating OPSEC mistake. You have disclosed that you have around 6 months left of money. You have probably also stored it in just one bank account. If some weird transactions end up siphoning off your balance, you will have no money left to defend yourself. The secret service guys know this. The freelance crook at the bank knows this too. Be careful or you will be toast.


Tinfoil hat on a little tight this morning?


Can someone explain the above to me? My english fails me.


Good luck




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