Ask HN: Am I committing career suicide?
I've been working in IT as a software engineer for almost 12 years now. Half of that in Europe with J2EE, the latter half in the Bay Area as a web developer in .NET.
I'm starting to become more and more bored with work. I started to look around for other opportunities, but I feel it's hard to do that while working full time. Also, my problem does not seem to be with that particular job, it's with the whole corporate world. Being forced to sit at a desk the whole day. I'm still motivated to work on my own projects after work and on the weekends. I still like programming. I just don't like coding stuff for other people.
Long story short, I'm preparing to take a time out. Maybe one year, maybe two, maybe only six months. My savings could probably sustain my current lifestyle for 5-10 years, if not more. My plan would be to crank out mobile apps, maybe one every two months, see if any of them can make some money. If it doesn't work, I could use them as a reference to get a mobile dev job, hopefully at a company with a product I can be passionate about.
Am I crazy to give up a six figure salary just because I don't feel like being employed anymore? I'm in my mid-late thirties, will I even find a new job with a gap in my resume like this? Any first hand experiences? I'm single, no kids. After a decade at the same employer, I was completely burned out -- I had worked 60+ hour weeks for many years, with nothing resembling a "real" vacation since ~2004. I didn't enjoy the bulk of the work. I wasn't learning anything applicable outside of my employer's niche. I was being given projects that I was completely unqualified to work on (but I was the least unqualified person, so they fell to me). After one particularly brutal day that didn't see me home until well after midnight, I did some serious soul-searching. I gave my (pretty generous) notice the next day. I did the math and figured out my vacation payout + vacation time I had lost over the years due to the yearly cutoff was about three months, so I planned to take a three month vacation. Sleep all day, learn a programming language, drive to interesting places, read books, play video games, whatever sounded interesting that particular day. Recharge the ol' batteries. And that's exactly what I did. After my three months of R&R were up, it was time to start looking for a job. I applied for interesting-sounding jobs that I thought I was qualified for. Silence. I contacted some friends and asked about opportunities, then sent CVs to the few that said, "Yes, we have positions you should apply for!" More silence. I continue(d) to apply for interesting jobs, resisting the urge to just scattershot resumes at everything I'm qualified for. (I think that's tacky, and I'm not that desperate yet. Plus, I don't want another job I'll hate and/or burn out on.) My three months turned into six months...and then nine months...and now stands at 11 months. I haven't been able to get a single interview -- phone, e-mail, in-person, or otherwise. My savings and expenses are such that I'm okay for another two years or so, but I will need an income of some sort eventually. Maybe my skill set is crap. Maybe my CV is crap. Maybe it's my employment history gap. Maybe it's karmic retribution. I can't be certain, but my money's on the gap. tl;dr: Your mileage may vary, but I'm pretty sure I Darwin'd my career by taking time off without doing anything that I could put on a CV to explain the gap in my employment history. Thanks for sharing your story. I remember reading something similar a few weeks ago here on HN. It may be the combination of 10+ years at one company, plus a gap. It could be something else. Have you asked those friends for an update what happened after you sent your CV? In my (limited) experience, even though people say there's a shortage of qualified software engineers and it's a great market for them now, it's always hard to find a good job. Key word being "good". Unless you're a "rock star" that has written a book and is being hired to speak at tech conferences. Companies are still being picky, even if they can't afford to be. Ok, I remember at least two of your HN posts, the zsh and university hacking. That makes you stand out if only in this little world Trust me, your problem is not a three month or 11 month hole in your cv. I am guessing its the wrong marketing. A cv is not a way to find a job, it's a piece of paper used to fiddle with during an interview Try (and this is really wild guesses based on your posts) - there are hundreds of (tenured) academics who would love to setup "institutes" or other vehicles for their favoured area - you have years if academic, IT experience so you talk the safe language and also know arse from elbow. - co-run / co-start these institutes - one conference, with the professors network attending, you supply IT and find sponsors. I am guessing they will eat your hand off. Maybe I am way off base, but honestly it does sound like you are looking for another replacement job - if there is one thing I have learnt here, anyone on HN does not have the "right attitude" for employment That really sucks. I can weigh in and say it has a lot to do with the 10 at one. The gap just adds to it significantly by confirming their suspicions. Start starting your own business. See if you can pick up contract work at the old place. Anything to show the world your still employeable. You have no contact information on your profile. Your twitter tag line is kind of pessimistic. You bring years of experience at whatever you decide to put your mind to. Show it. Do it. Your savings exist precisely for that sort of situation. Take time off, and figure out what you want to do. Maybe it'll be freelancing/indie development. Maybe in 6 months you'll want to come back to the tech world. Or maybe you'll just say "fuck it" and go teach high school mathematics or help out with IT infrastructure in third world countries or whatever. The point is: you only live once, do it. Perhaps good advice for HORRID reasons. Anyone spouting "YOLO" or any such thing should be ignored out of hand. "You only live once" used to be perfectly fine before a bunch of kids gave it bad connotations. Once upon a time it used to be a way of saying that you only have finite amount of time on earth and you should make the best of it. Somewhat similar to "Carpe Diem" and "Momento Mori". The fact that a bunch of kids that use it as reasoning to smoke alot of dope and do stupid shit doesn't change the original meaning in the eyes of many folk. The Lonely Island did a parody song/video about YOLO where they made it about living well, but they took it over the top. https://www.youtube.com/watch?v=z5Otla5157c The YOLO phenomenon isn't limited to getting crazy, but it sure seems to be the most common use of it. 5+ years bankrolled on savings from working full time? Well done. I mean damn, well done. You are not crazy to give it up. I can't speak from experience; I am in my early 30's and gave up a lower rate about six years ago to good result, but that's just anecdotal. It seems to me you have a very strong position: You have serious industry experience and, from your description, very strong financial responsibility. It's almost irritating that this should be impressive, but it is: You are a whale among greedy remoras. ;) It is certainly obvious to you that this is a risk. Being single and without dependents does help, but that also brings to mind the question of priorities. You're in a position, now, where you earn enough to wrap up your retirement reasonably early, if this pace keeps up. If that is what you want, then you might consider that starting a family -- if that's a priority for you -- could actually make your current income sources very, very valuable in a meaningful sense. If your primary goal is work satisfaction... then yes, I would say this is an excellent opportunity to step out of your current environment (calling it a rut or anything else would paint a biased picture, I think) and potentially do something more rewarding, in terms of personal fulfillment. I would not go into such a venture with the expectation of more lucrative results, though. You seem to be in a good position. There are certainly many startups that succeed, and that won't change. But the reality will always be that more fail. Be careful. You are in a good position, and you seem to know it. My suggestion would be to try and decide what it is you would be happiest doing, or at least deciding on things you want to accomplish. If you can manage that, then you will at least have something interesting to work towards. If not, then you may need more time before you can do something new and expect it to end well or at least satisfy you. You summed up my inner dialog perfectly. I used the retirement calculator my brokerage firm has on their website. According to their Monte Carlo simulation, I have about 10 years to financial independence (90% chance that my money doesn't run out before I die), income, savings rate and expenses remaining at the same level. That happens to be around $1 million in savings in today's dollars. It's tempting on the one hand, but on the other hand: 10 damn years!! I don't know if I can do it. It's weird, I'm hoping that the decision is somehow made for me. My company being acquired or forced to downsize, offering severance packages... But alas, it doesn't seem to be in the cards. Ha! Yes, ten years feels like a very, very long time just lately. ;) There's nothing wrong with coasting when you know you're moving in a good direction, which it seems clear you are. In your situation, you have the chance to sit back, observe, and carefully consider the environment (in addition to consulting whatever oracles you consider the most wise) and then decide when or whether you should strike out with any given idea. Unless you're throwing yourself on the mercy of an incubator on the strength of your resume, which in my opinion is a laughable gamble for kids who don't know better, you will want to think long and hard on what you want to do and how you want to do it. Once you can answer those questions for yourself (as you are the only one to whom you answer, and you'll never find a more forgiving situation), you'll have your direction. Once you take it... well, that's another story. ;) My lease is running out in November, so that's the time frame I've given myself to see if it gets any better. The good thing is that time doesn't run against me. Okay, maybe opportunities for indie devs in the mobile market may be shrinking, and it might be harder to find a job in your forties than in your thirties, but I can wait a few months and carefully consider all the options. Points well taken. Yes, indie opportunity is not what it was, but it's most certainly still there. I can't speak to ageism in the market, though we all know it exists... hopefully your skills speak for you. My best weapon in the last decade has been the interview; if you enjoy and excel at that, plan on getting most of what you want. :) I don't know what your qualifications are, but if you are interested in freelance web/Android work, please drop me a line. Info is in my profile. I have nothing waiting at the moment, but I do get a fair amount of leads. A couple thoughts, some more depressing than others. You could probably get three to six months off pretty easily. If just asking wouldn't work, you could hint a relative is on their last legs and make a firmer request? A few months would probably clarify the issue in a way we can't for you. Consider looking for a new job. Partly to judge the market, and the market's take on you, and partly to actually look for something much better. You could negotiate a six-month late start and have a vacation while you decided if the job really was for you. Maybe you could already afford to retire - in Costa-Rica or Thailand for random example - and could buy and rent property there as a fallback nest egg in case this really was your retirement, but otherwise not costing so much as to hurt your savings assuming you'll want to try to retire here. And lastly, what's the chance that retirement savings is going to be here when you want to retire? Are you paying attention to where it is enough to avoid the next bubble? Land would still be valuable to live on, rent, while currency-denominated assets could easily hyper-inflate. Some assets can be seized, or lost in war, others - or remotely stored ones - perhaps less. All that said, do it! Don't make any commitments, just start by taking vacation, ask for leave when that's out, and quit when that's done if you still want to stay away. > My savings could probably sustain my current lifestyle for 5-10 years, if not more. You're successful, > I'm single, no kids. and you don't have obligations. Considering these, I'd quite safely say this is a game you are not likely to lose. While it's a decision you need to make by yourself, your worst case scenario is better than lives of most people in the field. Plus, taking a year or two to work on startups as far as I can see is quite normal and even seen in a positive light in many places. I may be echoing others, but I to say to go for it. As for the "gap", this is simple. Start a business. If you're going to be making and selling mobile apps, you'll want a basic corporate entity behind you anyways. Now, instead of being "unemployed guy building apps" you're "Founder of Mobile App Development Consultancy" or something along those lines. Given what you stated about not liking the corporate world, that's completely understandable. I certainly prefer smaller companies, even startup, bootstrapping level ones. J2EE and .NET aren't strongly used outside of the big enterprise-y corporate world. Given your experience with Java, I'd say you might find Clojure to be a great move and still be able to leverage your Java past. Go for it! Get yourself an LLC or similar and build some apps. If you have 5+ years of financial runway, you should certainly be able to find something self-sustaining in that time. :) Jump and don't look back! That's exactly what I'm already working on. I have a domain name secured, an app in the Android app store, and if I do make the jump, I'll change my LinkedIn to "Founder, <company name> LLC" or something like that. I could use my C# skills to port the app to WP7/8, and I might even buy my first Apple computer and learn Objective C. Exciting prospects! No advice as to whether you should do it, but if you do, stuff like this will be useful to cast your adventure as "legit" if you want to return to the standard world later. I'd definitely work on leaving a trail/portfolio of your work as you go. Do it, and come to Malaysia. Savings that lasts 5-10 years in the states would lasts you at least 20-30 years here. Most people here speaks English fluently, and the startups/hackers culture here are vibrant and growing. My good friend quit his cozy programming job in Canada and spent a year travelling and hacking in Malaysia + Singapore. He left with more money than when he started (took very very few consulting jobs in between). Oh, and tons of great (food) memories: http://malaysianfoodporn.com/ I have to agree with Cheng. Malaysia is probably your best bet for somewhere in between if you are looking for a balance between the developed world and stretching your savings. KL is a pretty laid back place to be with awesome food! And with AirAsia being based in Malaysia, you could pretty much travel anywhere in Asia for cheaps. And if you ever decide you are running out of money or are bored, there are a multitude of companies/startups you can start consulting for! Btw, bearwithclaws, how did your friend end up with more money than when he started? I'm curious. I occasionally did some consulting jobs. Put it this way, some people make about $500 a month in Malaysia (which is more than enough to survive comfortably on). When you charge $100+ an hour you can make more in a day than the locals make in a month. Having been in Malaysia on and off for the last few years: you can survive with $500 a month. But you don't wanna put a guy in his late 30s in the kind of accommodation you'd have to put up with for that budget. Let me put it this way. A 1000$ rental gets you much more luxury than the same amount would get you in the west. But a 500$ monthly budget is pretty poor lifestyle in the long run even in South-East Asia, though I agree not quite as desolate and impoverished as you'd be in Europe or America :)) I had some super interesting housing arrangements the whole time I was there. One of the more interesting ones... http://richerd.com/2011/09/03/sleeping-on-the-streets-of-kua... Yeah I heard of your sleeping rough back in the day from bearwithclaws :D So yeah we're definitely in agreement. You can survive for $500 easily -- if you find a 'bed' that costs $0 ;P 100+ hour? How do you get these gigs? I wouldn't mind repeating your experience :) I think those "very few consulting jobs" was enough to offset the expenses I could probably move to Ecuador or Cambodia and retire outright. Trust me, I've been considering it. But there's something about the developed world that I enjoy. When I traveled through Asia, I like Japan, Singapore, Hong Kong, South Korea. But Singapore seems to be even more expensive than the US? What's beautiful about Malaysia is that it's somewhere in between. The major cities (KL/Penang) are like developed world, but the living costs are relatively (way) lower. Also Singapore is just around the corner, if you need some (very!) First World living for a change. There are also plenty of high paying corporate jobs available in Singapore, in case you ever need to fall back on one. And start-ups. I moved to Singapore from Britain last year. I only have 4 years of experience in the field. ~3 years at a big social network in europe. We got beaten by Facebook. Then I switched to Consultancy work, yes the J2EE weblogic corporate mangers-all-over-the-place kind of work. But after a year I stopped and joined a startup in the mobile industry. I coudn't be more pleased. To you:
- Do it!
- The gap doesnt matter, if you can explain properly
- Dont start working fulltime alone, either have a companion, work somewhere were similar people do the same thing, or have a second job on the side. This is mostly for social reasons.
- If you want to work in the startup world, try to do something apart from j2ee. But I see you want to do mobile dev, good choice! You should think twice about what your motivaions are, do you want to become an entrepeneur? Or you just want to be happy with your job? Dont make the wrong choices for the wrong reasons. > You should think twice about what your motivaions are, do you want to become an entrepeneur? Or you just want to be happy with your job? Dont make the wrong choices for the wrong reasons. This is a great question. I think my main goal would be autonomy. Being able to go hiking in the morning and then work through the night. I never understood why we're forced to spend the days pent up in office buildings. The other thing: Since I was a kid with a Commodore 64, I've been wanting to develop games. Just small, quirky, but fun and captivating games. This might be the chance to go after that childhood dream, as silly as it may sound. Did you work at Hyves and are you now working for Bliep? I know a few people who did :-) If you are risk averse (assuming you are because you have lived corporate life for 12 years) I'd recommend working for a small company first, for at least 6 months. There are many aspects of running the company and your own product which you don't see in a corporation. This will help you prepare for launching your own enterprise. I'd probably try to emphasize "left to go do a startup" on your resume, whether or not it works out, whether or not you approach it as an 80 (or even 40) hour/week thing, rather than "took time off". But, otherwise, this is absolutely good for your resume, I think. Assuming there's no huge change in the market, you should be as employable if not more. Maybe try to stay involved in the .NET/J2EE developer community once a month or so, keep in touch with former coworkers, etc. in case you decide to go back to that instead of mobile, though. Neither you are crazy nor you are the only with such feelings. I am a 3x entrepreneur, have sold 2 companies and 25 years old. I am working for the acquirer of my last company for last 14 months and I am already tired of writing code for someone else. I am all set to leave my six figure salary and keep hacking & building products that inner me wants to build. Believe me, getting a job at the same pay scale will never be a problem for you. Go ahead and start working on your own ideas full time. Lets me tell you my story, I was in UK working for a small consulting company as .Net developer, then I decided to come back to Vietnam and started my own company , outsourcing back to the company that I have worked for. The company has started ok with 4 people, but over the last year or so, besides doing outsource, we stated several projects but none of them has gone well so far. Further, the company has been hit by the economic crisis as many other companies, so its finance hasn't been in a good state. Due to my personal financial need since my marriage, I have once again got a corporate company working as PM/Developer with an high pay ( in Vietnam), but at the same time try to keep my business alive. It has been one year since I started working here, and even though I don't think I have done a bad job with the salary increase, but I honestly never have been enjoyed a single day of it. I am determined to quit the job and get back to my business as it has started to pick up again, we also preparing to launch a mobile product shortly. All in all, I think the stories that you guys have put here is such a good inspiration for me to get back to start up world, enjoying every day of coding and hacking. Hopefully, one day my product will make to the top of hackernews. Do it, and make sure to use your time off wisely. You have enough savings, you're single. If you're gonna do it, now is the time.
I'm in a somewhat similar situation. I've been working in the Bay Area as an ASIC validation engineer in a big semiconductor company for the past few years. I'm 30 years old. I've also gotten quite bored with work, so on the side I've been doing some mobile development (Android then iOS). I just very recently (Friday) started interviewing and it seems that the demand is pretty high. (I've gotten several requests on linkedIn before even publishing any apps). The transition for you should be even smoother since you have a background in CS. I feel that you can't go wrong by taking some time-off, work on your own projects then decide whether to join a company or start your own.
I don't have as much savings as you, so my goal is to quit my job and find another job in Mobile Development, while working on my own project on the side.
In all cases, best of luck! Here is the app that I released about a week ago (shameless plug): https://itunes.apple.com/us/app/dish./id648176152?ls=1&m... I just gave my resignation notice about an hour ago (no joke).
Whatever you decide to do, best of luck! Some more data points and thoughts: - I have 23 days of PTO per year, which is generous for the US. I did several two week trips the past years, mostly to Asia. My job is fairly low stress, I work less than 40 hours per week. But still, as soon as I set a foot into the office, it feels like all life energy gets sapped out of me. Maybe it's the fluorescent lighting? The crappy HVAC that oscillates between freezing and muggy? The open office plan we moved to last year? The constant sitting? As soon as I'm on my bike on the way home, I feel better. - Worst case, if I do it: I get lazy and don't do anything during my time off, and won't have anything to show for at the end. But that's entirely in my control, and I won't have anyone to blame but myself. - I read many blogs and comments about this. A recurring theme is people saying "I'm afraid I wouldn't be able to bring myself to go back to work after taking such a long time off." While I can see the point, aren't they implicitly admitting that there is something wrong with their current situation? > The constant sitting? Try to get a standing desk. It worked wonders for me. I've been talking to my manager about this. The problem is, after moving to an open floor plan, paradoxically we don't have room anymore. I'm trying to work standing up for a bit. It does help, but of course is far from ergonomic at a regular desk. It probably also looks ridiculous, me doing a semi-split to get low enough to reach the keyboard and mouse. Try using a few reams of copy paper (or books and boxes etc) to prop up monitors and input devices. I had such a makeshift setup at first. Also, have you tried working from home? Orthogonally, negotiating a four day work week 4x8h (at 80% pay) might help you enjoy yourself more. Managment might not be too happy, but if you insist and tell them that the alternative is 0 day work week at 0% pay (i.e. you leave), they might see the light. Not sure if this is a popular sentiment, but the Bay Area is expensive. I would probably move to a cheaper area for a while if I wanted to work on cool stuff on my own for a while without taking a nice salary. If you are smart you can live in Bay area with under than $800 per month everything included (rent+food+bills+gas+insurance). That's what I am doing right now and working on my start-up at the same time. I guess you can start by living in one of a three-bed apt. in Sunnyvale! I've been thinking a similar thing. It's probably not very smart, but one idea would be to move to Honolulu. Same cost as the Bay Area, but much more beautiful and no tech echo chamber. If anyone has a suggestion about equally beautiful places in the US that are cheaper, please share! Virginia Beach? Fort Lauderdale? Would it be possible to make a few apps on the side, see if they get any traction and then decide whether or not to jump? You could try taking a month off (without resigning) just to work full time on this. This way you could figure out if you're passionate about mobile apps without actually giving up your job. I have a line of Android apps that have a few thousand downloads. So far I've made about $30 in half a year with ads. But I'm positive that it would be a different story if I could dedicate myself to that full time. Cool, so it sounds like you know what you're doing and you've got a pretty long runway. Go ahead, jump. This will probably end well. Oh wow, I'm actually trying to make that decision right now too. Thanks for posting this. I've been building something in my spare time and between freelance gigs. It's at a good working prototype stage. I just want to spend a solid month polishing, plugging in minimally required data, release it and see what happens from there. At the same time, I've just been offered a new contract which will put my project on the slow track for a good half year but it's money coming in. Being able to focus on something that I'm interested in is amazing. My creativity flows and I see results occur at a pace that keeps motivated even more. Yet, I don't know what decision to make - Financially sound status quo or happy pipe-dream. but... I'm reading everyone's comments with great interest. No, you don't. I think it might help to change the way you look at this. It is not only a problem but also a big chance to find something that fuldills you again. I went to the same situation but with lot less savings. It was damn hard and still isn't all sunshine, but i do not regret leaving my boring well paying job at MS for a second. Problems will occur but they are also solved on the way. Read Books on the topic, make a solid plan, and then learn to trust in yourself and let go. Might sound oversimplified but sometimes you have to make a change in order to get what you really want in the end. You're not alone in this. There were thousands that did the move. Best of luck. People here have given great motivating responses. But In don't think anyone has answered the whether it would be hard to get an job again after a big gap if you decide to get one again. It seems like you want to continue coding in some form, so really there will be no gap of experience in your resume. If anything finding people who have built products themselves and put them out there is great to see and are hugely valuable to an enlightened organization. Whenever I interview people this is always a fun part of the conversation. I find that those people are very likely to be tuned to building great products and are the kind of people I want to work with. I'm not an expert or anything, so take my personal opinion with a grain of salt. If you aren't happy, do something about it. Otherwise, in a couple years, you will wake up miserable feeling like you have cheated yourself out of the most precious thing we can never get back - time. You are the CEO of your own life. Enjoy your journey, take risks, and don't be afraid of being a little foolish - so long as it is in a smart way. Good luck! (FWIW I skipped out on traditional job offers after getting my masters to begin a startup) You're definitely not crazy. I am not as far into my own career as you, but I would even say that it seems the crazy thing to do, in your position, is to do nothing. You want more from life? Get it! You will be able to find a job later, guaranteed, especially if you kept hacking after leaving your big-co job! (Do re-adjust expectations, though. A start-up will not pay you nearly as much as your last job did, although you should get stock. You know all this, but it will still be a big change.) Do it. The kind of people who will look down on you for taking risks are not the kind of people you want to work for. In general, it sounds like you've taken a very safe / corporate path with your career. Pays well, but it's boring. That might be the problem. I did a year in a big company and haven't worked any sizeable since. I know guys who earn six figures a year working at banks, but the crap they have to put up with -- what's the point? So just as everyone else has said in this thread -- sounds like you have enough of a cushion to do just about whatever you damn well please for at least 2 years (taking into the account the possibility that you decided to live as a rockstar at ~5x above your current means) What I do want to say -- and I'm really unsure that I should be saying it at all (since I'm not your dad, but then again, this is the internet) Maybe you should start at least considering settling down somewhere? I don't mean settle down somewhere and enter a company you hate for the rest of your life just for job security, but more like pick a place (or search for) a place you want to be in for a long time With IT/software skills like yours, I doubt there are many people who won't see your value at a technical company, and that will enable you to get a job in most places, but being transient forever (even if you're writing awesome software) doesn't seem like a wholesome plan I'm definitely assuming too much, and I don't know anything (outside of this post) about you or your goals, but just figured I should at least make the point Also, your Honolulu-as-a-place-to-live idea sounds amazing Your assumptions go in the right direction. I think the Bay Area is an amazing place to live, not the worst place to raise a family. But somehow I don't have much luck with the dating scene here (living in the South Bay). San Francisco might be a bit better, but it's almost impossible to find an apartment at the moment. And even here it gets a bit too cold for my taste sometimes, which is weird to say for someone who grew up in central Europe. Maybe another move will make me a more interesting, well-rounded person. Maybe an environment that's not dominated by technology might be a good place to recharge my batteries. At the very least it's an adventure and a cool story to tell. Yeah, I've only visited the Bay area & California in general, but definitely finding a place you want to be in is what I was going for -- it seems you're already thinking about that, which makes sense. Maybe some places that recently had tech booms might be good idea? Though I don't know where you'll find better general weather than California -- Seattle? Austin? New York? Dallas? Chicago? I live in Texas, but I do have to warn you, it gets cold here from time to time when the wind blows in the winter. sometimes [EDIT] - Of course, outside America might be a good fit too, there are so many places, and it seems like you've got pretty much free reign -- you've got a pretty rare chance I don't think many people get (though we all decide our daily lives, I don't think many people get as clear a decision point as you have right now), enjoy it I don't think you're committing career suicide. Sticking around indefinitely while you're miserable will not only suck the life out of you, but your drive to do well at work. Might I recommend a book called Quitter by Jon Acuff? He's done a couple of books about making the leap from the corporate world to a more fulfilling "dream" job. It was a good, quick read. If you've got the savings and a decent plan, I'd say go for it. If you are a decent programmer, you should be able to find some sort of satisfactory-paying work even with the "gap" you describe. And if you truly have 5-10 years of savings, you have more than enough cushion to try working for yourself for a year. Try to retain some discipline as you go. If after a year or two you're not able to make anything work, consider looking for a boss again. Come live in Asia for 6 months. Cut your costs, have a break. Word of warning - Its easy to take a break and end up getting nothing done. Set boundaries. I am right now going through the similar stage that I wanna do something for myself. I am just 4 years in this carrier and have no savings. Still I thought to take a chance, but my friends didn't allowed me to do it. So right now I am working for myself during the nights, sacrificing some of my sleep. If I where you or have some saving, I will definitely go for it. You're absolutely not crazy. I'm 30 and in the midst of traveling the US meeting with software developers for 5 months. Every minute, both the ups and downs, have been worth it. Check out my site codingacrossamerica.com and shoot me an email if you're interested in figuring out whether this is the right path for you. Ask yourself this- Do you want to work for anyone in the future that would hold this against you? You don't sound like you do. There will be no gap in your resume as long as you can exactly explain what you have done in these years. Get a business registration and try the self employment. If you fail your new employer will appreciate your "research" time in development and learning. Here's a dude who took a year "off" with his family and cranked out an iPhone app. http://www.npr.org/2013/05/20/183910777/seeing-the-northern-... Thanks for this link! I've been reading a lot of blogs lately, but haven't seen this article. I've seen the TED talk mentioned in the article, and it was an inspiration to my idea, along with the Four Hour Work Week of course. Quite a few people seem to be able to make a living as indie developers. But I wonder how many fail, without making their story public. People like to read about success stories, but not about failures. I've also read Ferriss. Interesting ideas but I'm not sure how applicable it'd be. I like the idea of work hard for 10 yrs and take "off" a year or two better. :-) If you ever want to meet up and chat, feel free to ping me. I've been doing indie development for ~3 yrs. I can't tell you where to go or what to do, but if you just hate what you do, might as well try to find something different. Many people in this world do not enjoy their jobs, but you appear to have the resources and the freedom to try to find the job you like. P.S. Here's an idea. Have you considered going back to school for a Master's, if you don't already have one? That could give you more personal time to explore side projects (as well as hopefully working on something cool for your degree), handily explains 2-3 years of gap in employment history, and you come out with a degree. Thus allowing you to hedge your bets in case you have to rejoin the corporate world later. I applied to SJSU, they have a Master's program with emphasis on mobile development. But after the budget cuts they seem to be really struggling, bureaucratically. I haven't heard anything from them other than "we received your documents, we'll process them within a week". That was two months ago. I haven't really followed up with them and asked what's going on, which I guess is a sign that I'm not really passionate about that idea... Sometimes you have to take a few steps back in order to achieve or figure out your so called dream job. Bare in mind cash is a limited motivator as it will never fulfill the drive and passion you have to achieve more. Don't take me wrong money is important but personally I would prefer having a mediocre salary for a while and know that I am on the way to achieve the "real" thing. You sound like you are having the usual symptoms of wanting to do your own thing. Remember that if you don't try you will never find out. This is me speaking from experience. Best of luck! Maybe. But if you don't do it now, it'll just become harder and you'll regret not doing it all your life. I did something similar, but I did it much before 30. Haven't regretted it so far. Go for it. I think you should go for it. I'm currently in a similar situation. I started learning how to program about a year ago and even got a job at a startup. I really want to learn iOS dev because just being a RoR dev will limit my career path real soon. I quit my job a few weeks ago and have been spending all my time learning iOS dev. My goal is to find another job after I'm comfortable with iOS. I can't speak to the resume "gap", but I can promise you that this will make you a better developer by a ridiculous amount. > I'm in my mid-late thirties, will I even find a new job with a gap in my resume like this? Certainly not at a big company. I'd suggest quitting your job and traveling around the world for a couple of months. Go to unfamiliar countries such as India, China, Japan, Korea, Peru,.... It will open your mind and give you life changing experiences. Stop working on some app...Go for something big. it will come to you If you've got that much money saved, you should be working for yourself, making awesome applications and changing the world. Don't worry about a gap in your resume, you'll probably make something notable on your own that could carry your career/life into a new direction. Do you think you would fare well at designing and coding app's for the iPhone or Android? It would be a shame to waste your skill, but you could put it to good use and make some $$$ at the same time, at your own pace? If you have 12 years of experience, are in the Bay Area, and can do mobile dev work, you should have no trouble finding a new job paying six digits if your entrepreneurial plans do not pan out. This might help. The Jeff Bezos regret minimization framework: http://www.youtube.com/watch?v=jwG_qR6XmDQ You know how to code. Take time off if you have savings. You will find a job if you desire going back to work for someone else. if anything, i feel like you should be more employable if you decided to pursue mobile development rather than continue on with .NET. a change is as good as a holiday....also sounds like there is a dearth of stimulating conversation at your current gig. Who, if not you (!!!), should do this?