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Comment by dunkelheit | Hacker News Reader

Recently quite a few articles appeared on HN about escaping the rat race for a while and taking some time off. As someone who has a little savings and who is a bit burnt out I've been toying with the idea myself quite a bit. My biggest fear is that because I have only a vague idea of what I want to do with my time, I will fritter away my sabbatical, not accomplish much and end up pretty much at the same point (but with less money). OTOH maybe my ideas about what I want to do are vague precisely because I don't have much time to flesh them out.

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I did this, and unfortunately your fears became reality for me. Like you said, I only had a vague idea of what I wanted to do (including traveling, starting my own company, continuing education, side projects, etc). Almost 2 years into it I ended up just barely dabbling in each. I traveled for a few months, worked on some side projects, and learned some new things, but didn't really do anything "big" or traditionally "worthwhile" with my sabbatical. I look at my friends and colleagues who in this time period have gotten promotions, new jobs, MBAs, etc and I start feel like my time has been wasted. People keep telling me that once I join the workforce again that I will look back fondly on this time, but right now I definitely don't.

The most frustrating thing I have experienced is that society in general is still not accepting of people taking "sabbatical" in their 20s. While about 10% of people think it's cool that I quit my job and am flying by the seat of my pants, the other 90% hear that I'm unemployed and treat me like a pariah. It's been very eye opening to me just how linked your personal identity is to your job. And I don't mean job as in "I am a programmer", but specifically the actual name of the company you are employed by. I've had people be very interested in conversation with me at social events when I talk about work-related things, but when I actually say the words "I don't currently work anywhere and am taking some time off", those same people have literally picked up their drinks and walked away.

It's particularly bad with recruiters now that I'm ready to start looking for a new job again. Even though I left my company on extremely good terms (they literally begged me to stay!), recruiters seem to see that I left [insert major well respected company here] and assume that I must been have fired. Most still seem to think Google et al are some extremely coveted workplaces and can't imagine that someone would willingly leave them. It is a very tough hurdle to get over.

About accomplishment, maybe the thing you wanted out of escaping the rat race was to take a break from feeling like you constantly did have to accomplish something.

As long as there isn't something seriously wrong (such as depression that leads to inability to enjoy pursuits), maybe that is OK. It could be important to be able to accept that you don't always have to accomplish something, and that your life doesn't have to be about maximizing how much you can accomplish. (Which is a different thing than saying it's OK to never accomplish anything or OK to consistently accomplish very little.) You don't recover from burnout or whatever else by driving yourself crazy with worry and guilt over how you aren't living up to some standard.

About the weird reactions, I've been through that after making a similar choice, and I've found that with some people, they are just not even slightly open-minded about it and they are going to judge you instantly. You can't do much about those people.

But with other people, their reaction will depend on how you present it to them. You've just told them you're doing something far outside the social norm, and they're going to be thrown for a loop and wondering why and how to understand it. They don't know if you're a lazy, broke, aimless loser or a person who has a plan and is doing this for some kind of purpose and real benefit to making their life better overall. You're going to get a whole different reaction depending on whether you say "Uhh... so yeah, I'm not working anywhere right now" or "I was fortunate enough to be in a good place financially, and I really wanted to take a year off, so I am". The second one signals that you're in charge, you're content with what you're doing, and your successful enough to give yourself the opportunity.

Thanks for making this comment. You did a good job of putting into words what I have struggled to express to myself. I resonate entirely with your comment, but unfortunately for me, my problem is that it's a lot harder to actually put these things into practice.

>About accomplishment, maybe the thing you wanted out of escaping the rat race was to take a break from feeling like you constantly did have to accomplish something.

100% yes! In fact, when I first left my job, this was exactly what was foremost on my mind and I intentionally took a one-month period where I essentially vacationed and didn't "accomplish" anything. I was very proud of having escaped the rat race, and felt good about it. After that is when I started to "get back into it" and work on side projects, etc. I was still confident that taking time off was a great decision, even if I didn't come out of it with an MBA or a startup.

Unfortunately, ~20 months later, things have changed. I've gotten enough negative reactions in those 20 months, and enough rejected job applications and negative conversations with recruiters regarding my employment gap, that I really start to question (even if only subconsciously) the entire situation I put myself in by quitting. I've started to lose that confidence that I initially had, and once that confidence starts to erode, it's been really hard to get back.

First I want to thank you for your honesty. It is so refreshing to read, in this sea of self-promotion of Medium posts that go around here.

You may want to talk to a coach about this. I'm sure you can find someone specialized in finding jobs. You make it sound like you somehow let yourself down, and if that shimmers through in an interview, you won't leave a good impression. I think you need somebody to help you with finding a good way to frame this time in a better light. Not only for your next application, but also for yourself. What started as time off might have turned into involuntary unemployment, with all the negative weight that this brings.

>I've gotten enough negative reactions in those 20 months, and enough rejected job applications and negative conversations with recruiters regarding my employment gap, that I really start to question (even if only subconsciously) the entire situation I put myself in by quitting.

That's a challenging position to be in. Essentially you're facing what most people with new ideas face. I could tell you that everything will be okay, and that you'll be better off in the future...

Those comments are hollow until this passes, and expecting people in general to empathize is impossible. What I can suggest is to keep at it and re-evaluate periodically. You'll find someone(s) who will understand.

Not sure who your friends are but where I am half the young people are creatives or otherwise not traditionally full time employed and my experience has been people are far more likely to avoid you for being a boring banker/lawyer/accountant in a suit (which I used to be) than unemployed with a good story about what you are doing, which could spark a decent conversation.

I live in Dallas, which is notorious for being pretentious, not very creative, and pretty "corporate", so that probably contributes to the experience I've had.

Hear here.

I don’t know. I’ve had to actively hide my unemployment as well to get people to take me seriously. Even switching to ‘I am a freelancer’ makes you so much more desirable as a conversation partner...

That's actually a great way out of this situation. Recruiters know that there are many gems among freelancers, so working on side projects or on short paid projects should put GP in a whole different category.

What the fuck is a "creative"?

An encompassing term for artists, designers, illustrators and other profession where your job is mainly to get original ideas and implement them.

So does that mean using engineering and math as the basis of building bespoke software is not creative in that sense? Just curious, not criticism - because I always thought of designing the architecture of a large software system, making it work within constraints, codes, making it easy to work on, fit withing design constraints, a beautiful UI, even a new programming language as creative.

As far as I know no. I do agree with you that programming (and many other professions) can be/are creative. Still having the term "creative" as profession does not mean that other professions are un-creative. People like to put people in bins and give them labels, and I suppose that creative is the main ability these professions require.

Maybe one thing that is specific (at least from when I spoke with people employing creatives) is that they have more leeway on what to do.

yes, exactly. Its an offensive term to say the least. Scientist are the ultimate "creatives" as they create fundamental things that all other fields depend on. But somehow they don't describe themselves as "creatives". Calling yourself a "creative" at best doesn't make any sense and at worst makes you look like a jerk.

I'm guessing it's "not like a boring programmer"?

> the other 90% hear that I'm unemployed and treat me like a pariah

Are you sure it's that, or could it be because they find they have trouble relating to someone who is in such a privileged financial position to do nothing for two years, when they themselves may be financially insecure?

People relate through shared struggle and experience. When you say, "I don't work and I don't need to", you've dashed any sense of camaraderie a stranger, or even many friends, might have felt.

It's funny you ask that, because I was just in the middle of writing an addendum to my comment about how people will react to observations I have about my sabbatical due to my "privilege", and "how dare you complain about being financially secure", etc. It's interesting to see just how mean/jealous some people get when they hear that I'm able to financially survive without a current source of income. Like the author did in his first paragraph, it seems that every time I talk about being unemployed I have to caveat it with some "I know I'm privileged etc etc but hear me out..." because otherwise people will summarily dismiss anything I say. You haven't explicitly done so in your comment, but others in this same post have (see bottom of the comments in particular), and I've even had people in real life maliciously accuse me of secretly being a 1%-er (I'm not even close).

To answer your question more directly: I've considered it, and that's probably the case for some of those interactions (see above), but the majority of the ones I'm specifically thinking of are interactions with people that I know for a fact are much better off financially than I and make just as much (if not more) than I do/did.

Even financial peers may nonetheless view your position as privileged, because they may not be able to give up whatever it is you did to be able to leave their job. Perhaps they are burdened with debt, or have a family to support, or may simply lead an expensive lifestyle that is not socially tenable for them to curtail. It could even just be that their partner – or potential partners if they are unattached – would be uncomfortable with them taking a two-year unpaid sabbatical, so even if they wanted to, they couldn't do so in good conscience.

To put it another way – who wouldn't take a two year sabbatical if they could? The fact that it's rare, even among well-paid tech workers, is a good indicator that it's not within the realm of relatability for most.

I also don't think it's necessarily a judgement of privilege. Consider the reverse scenario: a party of people enjoying their sabbaticals, and one person with a desk job. No-one's going to hold a conversation for long with that person, simply because their day-to-day experiences are not relatable. The sabbatical crowd will want to talk about long-term travel, how to stave off boredom, and the interesting startup ideas they're working on. No-one wants to hear this one guy's stories about scrum drama, getting a promotion, and taking their kids to the recent company outing. His stories may be positive or negative, boring or interesting, but no-one else can commiserate with their own current experience. For anything topical you're left with sports and the weather.

Your point is well taken, but when I mentioned people that "I know for a fact are better off financially", I was taking all of those things (debt, family, lifestyle) into account. Again, I'm sure for some interactions, those things apply, but I've had similar interactions with people that have no debt and have no family to support (and in fact, actually receive monetary support from their family/parents).

>To put it another way – who wouldn't take a two year sabbatical if they could?

It seems a lot of people, actually. Again, I can't speak for everyone, but even many of my close friends, who I know a lot about their financial situations and have actually had this conversation with, have even said that they could take time off just as I did and have no financial issues at all, but still would not do it because they feel too pressured by societal expectations to always have a job.

>I also don't think it's necessarily a judgement of privilege. Consider the reverse scenario: a party of people enjoying their sabbaticals, and one person with a desk job. No-one's going to hold a conversation for long with that person, simply because their day-to-day experiences are not relatable. The sabbatical crowd will want to talk about long-term travel, how to stave off boredom, and the interesting startup ideas they're working on. No-one wants to hear this one guy's stories about scrum drama, getting a promotion, and taking their kids to the recent company outing. His stories may be positive or negative, boring or interesting, but no-one else can commiserate with their own current experience. For anything topical you're left with sports and the weather.

There is far more to talk about than just sports/weather and work-related stuff. Even when I was employed, most of my friend group was not in the same industry and we were still able to have lengthy conversations even though most of the group didn't even know what "scrum" is, or never had to worry about a promotion, or never considered startups.

My experience has been that the topics of conversation or ability to commiserate isn't the issue. I've been in situations where I have had lengthy, wonderful conversations with a person where we clearly connect and can relate to each other, but as soon as I drop the "I am currently unemployed" bomb, their entire attitude toward me will change for the worse. (FWIW, I've also been in situations where their attitude has changed for the better, but I find those to be rarer)

I experienced similar when I didn’t have an ability to support myself. I had nothing immediately after college and couldn’t find paying work for nearly 5 years. I had the misfortune to graduate from college at the start of the Great Recession in ground zero of it. Society really does not treat people well. I was constantly made to be aware just how worthless everyone thought I was.

I genuinely wish no one ever had to experience anything similar to what I experienced.

Just to cover the whole gamut of human lameness here, let's also mention the opportunists. Someone looking to meet somebody at a desirable company, to advance their own prospects, would, upon hearing you don't work at any such place, conclude you're of no use to them.

txcwpalpha, some portion of those who "treat you like a pariah" are probably these people. The good news is that such people are of no use to YOU, and you just dodged a bullet.

I don't want to necessarily promote a cynical view of the entire world, because these people are still thankfully a small portion of the total. My bigger point is that a surprising number of people whom I experienced as rude, standoffish, nasty, etc. turned out later to also have been dishonest, hiding something, and/or actively engaged in wrongdoing (be it right there, or in some other part of their lives). Not sure whether the stress of being deceptive leads them to be shitty toward others, or if a shitty worldview leads to both... probably the latter... but in short, shittiness is rarely confined to just the one area of a person's life that concerns social interactions. And rarely does it have anything whatsoever to do with you. It has to do with them - in fact I would say it's a marker, a fog beacon calling out "BEEEEP - this person is shitty in this observable way and probably other currently-unobservable ways - BEEEEP." Just think about it like this: if talking to someone feels like you're talking to a gangster, or like you just went to prison, that's probably because that person belongs there. I highly recommend spending time around some scumbags just to get the flavor.

As someone who has "taken a lot of time off" to spend time _on_ the things I think are important, may I suggest answering the work question with "I'm currently working on _____" or "Right now I'm spending a lot of time on _____". There are a hundred ways to direct the conversation somewhere productive and fun, but "I don't currently work anywhere and am taking some time off" does sound like an embarrassed euphemism for "unemployed." Don't be embarrassed.

I appreciate that advise, it's something I've been trying to do more recently, and I've noticed it does help in conversation.

The funny thing is that, even though my original comment hints at how regretful I am now of being unemployed, it didn't use to be that way. I used to be very proud of having left my job and being unemployed! I thought I had made a great decision and it didn't even occur to me until months later that people would see "taking time off" as an "embarrassed euphemism" rather than something good.

You should be proud. It shows that you have at least some financial discipline and ability to save, which is not something everyone can say.

It really helps to work on something interesting, even if it's very part time, and purely for fun. That might also help with your recruiting woes.

Also, sabbaticals don't seem that uncommon in the Bay Area, at least among people I know. Maybe it's a regional culture difference thing that makes it seem so taboo in your area?

It is sort of the job version of "All the good ones are married." A currently employed individual with talent and a great job is a highly desirable candidate. Everyone else is, at best, a bit suspicious.

However, how you present that info can make a difference.

> those same people have literally picked up their drinks and walked away.

I think it might be attitude personally. I am 26 and have been making it on my own for the last two years, and I think I'm so excited about what I've been doing and sharing it that people always seem curious enough to listen. Be able to hype up what you do! Whatever it is. That's a skill for sure.

> but when I actually say the words "I don't currently work anywhere > and am taking some time off", those same people have literally picked up their drinks and walked away.

To me, this sounds like a good filter. In fact I have been using this sub-consciously with girls when they ask me about my day job. I don't answer with "serial killer", it is screaming "I'm unemployed and unsecure". But rather "I don't really work or have anything right now".

Start getting rid of useless people. The sooner, the better. It is very hard to get rid of people if they are opening discussions so this time they just disappeared away.

Thanks for sharing your experience. Specific information about the downsides of this path is very valuable for me (and others, I guess).

> "I don't currently work anywhere and am taking some time off", those same people have literally picked up their drinks and walked away.

Wow. Really. Fuck them. Whats so great about talking to ppl with office job.

Seriously. What a great filter for people you wouldn't want to grow close to anyway. "If we can't talk about corporate servitude, why talk at all?"

/s, hilarious.

I thought the same thing! And I'm tempted to say that if that was their reaction, I probably wouldn't get along with those people very well anyway. Still, it was very jarring when it happened, because it was clear that it was my statement of unemployment that turned them away.

While about 10% of people think it's cool that I quit my job and am just flying by the seat of my pants, the other 90% hear that I'm unemployed and treat me like a pariah.

The trick for getting around this is to form an LLC and say that you were freelancing. No one will ask questions.

And, after all, it's true. You would have taken money in exchange for services rendered, had a sufficiently-enticing opportunity presented itself. So it's not even a lie.

Because these are all the excuses people give when they were fired and couldn't find another job. Especially after 2 years, when the unemployed person has likely given up on the search.

But seriously, if you enjoyed the job so much, why leave? Why not just take a quick vacation and keep enjoying the job?

>Because these are all the excuses people give when they were fired and couldn't find another job. Especially after 2 years, when the unemployed person has likely given up on the search.

Yea, I'm aware of that, and I don't necessarily blame the recruiters for that, but it does suck for me.

>But seriously, if you enjoyed the job so much, why leave? Why not just take a quick vacation and keep enjoying the job?

I didn't enjoy the job. I worked my ass off doing 60-70 hour weeks in a position I disliked with co-workers I didn't respect because I knew that sticking it out would get me early promotions and bonuses, which is what gave me the financial security to take time off. In doing so I guess I also proved that I am a good employee, which is why my company tried so hard to get me to stay (and has even tried to re-hire me a few times). But I didn't enjoy it, and would only go back as a last resort (unfortunately, because of the reasons mentioned in my original comment re: recruiting, it seems I may have to go with that last resort).

The specific company I worked for is actually known internally for being a place that people commonly work hard for 3-4 years, take the payday, and then quit to go do something else. But externally, it has a reputation of being a great place to work and I've had a lot of recruiters express surprise/disbelief that I would willingly leave it.

> I knew that sticking it out would get me early promotions and bonuses, which is what gave me the financial security to take time off

Nice; good on you for playing the game and walking away with the prize you wanted.

Honestly sounds like Amazon.

Amazon does not have a great reputation.

Well it did at one point, and still does in the eyes of software development employers

"If you can survive there, you can survive anywhere."

Hopefully other employers believe they can provide better work balance.

Why did you work so hard when you hated the job and coworkers so much? Why not find a similar role at a place you enjoyed more? Have you talked to a counselor about workaholism?

>Why did you work so hard when you hated the job and coworkers so much?

I think you might have good intentions with this question, but it seem a bit silly. You could ask the same question to anyone about any job. Why do you think the millions of investment bankers or consultants or lawyers or medical residents work long hours? Why do people work long hours in shitty retail or food service jobs? Why do people work in sweat shops? Not everyone has the opportunity to work somewhere they "enjoy more", but they keep working anyway because at the end of the day we all need a paycheck.

>Why not find a similar role at a place you enjoyed more?

That's precisely what I'm trying to do now. If you mean "why didn't you find a similar enjoyable role to begin with?", because those enjoyable roles don't pay nearly as much, and I wanted to build up a decent-sized savings so that I could take time off, travel, and work on side projects. My "plan" was to spend a few years working hard, build up a nest egg and a resume, and then transition into something more "enjoyable" though lower paying. The first part of that plan went swimmingly, but the transition part has been a little rocky.

> Why do you think the millions of investment bankers or consultants or lawyers or medical residents work long hours?

I thought lawyers worked reasonable hours. The medical industry is it's own special situation. Those investment bankers must be bad at math - for overtime-exempt employees, each extra hour worked past 40 reduces your hourly pay rate by 2.5%.

Retail, fast food, office, IT, software development - all jobs pay 150% pay after 40 hours, and 200% pay after 80 hours. At least in WA State, it's the law for non-exempt employees.

Aren't sweat shops illegal?

You did have the opportunity to work somewhere better. Were you suffering out of a solidarity with the less fortunate?

At least you admit this was your plan from the beginning.

> Those investment bankers must be bad at math - for overtime-exempt employees, each extra hour worked past 40 reduces your hourly pay rate by 2.5%.

It's not about the OT pay working at an IB; it's about the bonus -- which is often a multiplier of your base salary.

> ...must be bad at math - for overtime-exempt employees, each extra hour worked past 40 reduces your hourly pay rate by 2.5%.

Not really. The first one does, then the effect is getting smaller with each hour.

Enjoying the job? Office jobs are not exactly milkshake.

I was in the same place as you. When I started my sabbatical I had some vague ideas, but mainly just planned to drive around the western US and experience the outdoors. After a few weeks I realized I missed thinking about technology, so I started doing the CryptoPals exercises (https://github.com/wskinner/cryptopals). I learned a lot, at my own pace, and didn't come back feeling like I wasted my time.

Those first few weeks of unstructured time were essential. Not framing the time as having to accomplish something is important - I found that my intrinsic motivation came back on its own anyway.

A lot of people confuse the pursuit of entrepreneurship woth just wanting a break. They are two different things. Entrepreneurship means killing yousrefl with more work than in a day job.

If you’re looking to take a break, then just do that like the OP. Take a break and do some light coding only if you want to.

If you want to do entrepreneurship Then you need to cut down the risk when you are going full time. So have some momentum for an idea - Ie you’ve vetted it, built it and charging at least 5 people for it. Something that lessens your risks.

Also make a commitment on a timeframe after which you would quit and start looking for a job. Eg: if I have 0 revenue after 1 year I will quit.

"Entrepreneurship means killing yousrefl with more work than in a day job."

It doesn't have to, a lot of the people I know started their business because they wanted to get away from that culture.

In my experience as someone who started and ran a small business for a few years now- entrepreneurship carries a lot of risks. Financial, social, and emotional. If you have a business background or previous professional experience with a valid business model - in that you can just execute building a profitable business from the get go and delegate the parts needed - you're set. But if you don't have capital or experience delegating, it can be a very painful process because you are now responsible for everything from hiring/management, operations, finance, product, etc.

I feel like not being sure what you would do with your time if you weren't working is one of the surest signs you're really truly burnt out. For the intellectually curious, the world has an endless supply of fascinations to explore. For the civic minded, there's countless causes and people who could use your help. For the pleasure seekers, there's a rainbow of experiences left to live. And what better time then when you're young and healthy.

Consider broader definitions of "accomplishment" and "wealth" than "job" and "paycheck."

I speak from experience on this. A few months into a year-long sabbatical my brain had rewired itself and the burnout healed. I started finding enjoyment in the small quiet moments again. 4 years later, I can say that the sabbatical was the best career move, the best financial decision, and the best personal decision I have ever made. It led me to a new home, a new career, and much new wisdom.

I'm intrigued by your sign of burnout. I have over 100 hours of vacation time left that I need to use before 2018 ends. I've been indecisive on how to use it. I don't know if it's because I'm a workaholic, unimaginative or burnt out. I feel like not knowing what to do with free time could be a sign of any three, I don't know how you would figure out which though.

I only realized in retrospect that it was burnout. I "felt fine" at the time. I remembered being passionate about things in college but it seemed like I was just too busy for that kind of thing anymore. Sometimes I'd sit and think, "hmm, strange that nothing seems to excite me anymore, maybe that's just what getting older feels like."

I knew I felt weary, but everyone around me seemed to feel the same. I was honestly surprised when the color came back. I was almost too busy to notice it was missing.

Now that I know how my own burnout symptoms manifest, I can keep an eye on my stress and work-life balance to make sure I don't get so far gone again.

Just sleep and read books, it simply can't go wrong. Books and bedtime help more ideas come. Do lots of cooking if enjoyable.

> I have only a vague idea of what I want to do with my time, I will fritter away my sabbatical, not accomplish much and end up pretty much at the same point (but with less money).

This is what I did for 2-3 years.

I slept in everyday, went to the gym or for a run, rode my bike around, read books, went to movies, watched TV, shopped for groceries, cooked most of my meals, went on dates, and pretty much never left town.

Eventually I only had like 6 or so months of expenses in the bank and got another job.

Wasn't a waste to me, I loved it.

How did you get back into the job world? I'm in a similar situation and wondering how to spin my time off (which I've loved).

This was back in 2012 that I started working again. I just looked at Craigslist and got lucky when I saw an ad that was the intersection of my previous 2 positions. Applied there, got it, and stayed for a bit more than 3 years.

My background is writing/marketing though so it’s not like my skills were particularly out of date.

That sounds like a healthy life. To bad things aren't setup for the majority of people to have time to care for themselves.

In my experience having done this a few times, I find that while I'm working I can't come up with new ideas because I'm too mentally exhausted or just don't have time.

Usually I take a week or two letting myself experience calm and boredom, and then reading what others are doing inspires some ideas.

Usually I then write myself mini proposals like you'd do for your boss or a grant, clarifying what I think I know, what I think might work and why it works be interesting, how the problem I'm considering is done best now, and how I'd go about developing that problem into a project.

It takes maybe a day or three per proposal, but saves months of chasing bad ideas like a new electronic device that solve a technical problem in a cool new way (but does it worse than the current solution.

It just takes a different amount of time and introspection and recovery for each person. There are so many ways to live a good life, and many are better than what we thought we wanted in high school or college. Don't be afraid to explore things that seem silly, no one is watching and it's the only way to learn.

But boredom while alone is critical. Perhaps the most important part to redeveloping curiosity and processing what we think we want is silence.

I've been in that boat. My situation ended up being similar to what you're worried about— wasn't able to develop any idea or business substantially. My advice from my limited experience is: if you want to go it alone enough, you should be able to create at least a very simple version 0.1 before you strike it out on your own. We often think work is what's holding us back, but lack of disclipine and direction could be just as limiting.

I've found lack of direction to be my biggest issue. I've got a job that, thankfully, gives me a decent work-life balance (if not a great pay to go along with it), but I just can't bring myself to do anything during my time off because I don't know what to do.

Though, that's not to say discipline isn't an issue as well. I've had several ideas, and never really followed through because of lack of discipline/not seeing how it's going to help me earn money, etc.

Do nothing, live. There will come a time when you get passionate just go with it.

It's a serious risk. If I'm ever in this situation again, I think I will have an idea, and possibly even a very bare-bones prototype before I quit my job.

Also, if you're going to use this opportunity to learn a new language/framework/etc, I'd dip the toes in the water now.

I’m in the same boat. However the thing to realize is that you’ll be better off even if you fail, you’ll have a lot of new skills. You’ll also have time to network.

I quit my job to work on a project (http://ngrid.io). I’m close to being done but in the process I’ve met a lot of people and I have three job offers lined up without interviewing.

The trick is always to go TO somewhere not FROM somewhere.

Sure, but finding a worthwhile direction in which to go (and not just another soul-sucking job not much different from your current one) takes time and energy and these can be in low supply because of full-time responsibilities and burnout.

I think the idea of taking a month-3 month vacation is a better goal, or perhaps a year to do a masters. I've seen people quit to learn and experiment with stuff but its difficult - better to get a job where you can learn stuff.

I will fritter away my sabbatical, not accomplish much and end up pretty much at the same point (but with less money).

The best part of doing this myself was to become comfortable with this. At the end of it, you feel more free than most people. Or at least I did.

Becoming ok with not being defined by money or accomplishments is one of the nicer parts of growing older. You can finally relax and shed some of the angst from youth.

Everyone needs money, but ultimately if you live a simple life with simple tastes then you can still afford some gadgets to satisfy your hacking spirit.

It takes at least a year just to decompress, and then another year to become comfortable with not having anything to show for your time. That is the growth.

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