I've been in your position, quit, and failed horribly. My primary weakness as a programmer is lack of focus/tendency to get distracted and as such I was forced to recognize that I work best in a (preferably small) company. As such, here's my advice:

Hack after hours and put it on github so people can see the commit history. If you're not motivated enough to write it in the evenings after working a full day, you're probably not going to be motivated enough to do your own startup/freelancing setup successfully.

Once you've made something interesting, find companies that interest you, email them and describe why you're interested in them, that you're looking to get out of the corporate world, and that you made this cool thing, are they or someone they know looking for a programmer. You'll be mostly unsuccessful, but having a job gives you plenty of cushion and it only takes one yes.

If you're really serious, fly out to SF for the YC open house coming up. I have no connection to YC aside from rooming with a guy in the program but can attest that getting an in on the YC network will at least get you under consideration at a bunch of places.

I had a similar history. My startup was beset by the fact that 90%+ of the time I was alone. I was the only one doing the coding... and to be honest, it got hard to stay focused. Working with someone, especially who is depending on me, I can work huge days for weeks at a time. Drifting alone for a month at a time... not as much. The experience raised my respect for pair programming tremendously, if nothing else.

Since you mentioned lack of focus/tendency to get distracted - do you ever wonder if you're not "startup material"? I mean this not as an insult, but an honest question, since I know I wonder it. I figure the "startup people" who are stuck in faceless corporate jobs are still working at the insane pace necessary for startup life - if not at work proper, then at home. Is there any truth to that?

What does someone who is "motivated enough" look like when taken out of a motivating setting? Are they typical overachievers throughout life or do they seem lazy without the tremendous urgency of that lifestyle? Some mix of both, something else?

He's got a really important point here: Lack of focus / effort is going to be your downfall if you're weak. Assuming you're a competent programmer, there's no shortage of clients willing to hire you as a contractor if you need the extra cash to pay the bills. When I went full-time, I loved it immediately and I know it was the best possible thing for me but I consistently have to work on my effort and concentration to keep producing and being able to work on my projects. (I work on my own projects/apps & design/front-end to pay the bills.)

You didn't really fail because you learned more about yourself and where you work best.

"but my life is miserable".

Why are you settling for that? You may think the easiest option now is to stay where you are. Sure it's stable but this is probably the best time to actually give your entrepreneurial dreams a shot!

Sure you won't be getting that paycheck but you're not needing that much money at the moment anyway. Plus you still live with your parents so you don't have to worry about rent, food etc. You'll still live.

++ You are still young, in your 20's. It's so much harder to make that plunge when you're 30,40 if you have a mortgage to pay off or a family to support.

What's the worst thing that can happen? You build some cool apps, try to make a business out of them but don't get enough traction? So what? You've taken a correct path in your career by doing something you enjoy. You can always go back to corporate. Plus you tend to meet so many more people if you really immerse yourself in the whole entrepreneurship community.

Take a big breath, quit your job and go do the stuff that makes you tick. By the sounds of it, you're in a pretty good situation to do so right now.

+1 for these comments as well. Better to do something crazy now, knowing you can always fall back and recoup your losses, rather than finding yourself down the road with more serious responsibilities you can't ignore at the same job hating yourself/wondering what could have been.

Thanks. I think one of my biggest fears I have is the impression that once you leave corporate you can't go back (or it is much harder to go back). Is this even remotely true?

As long as you keep developing your own skills as a hacker, you'll still be a valuable hire for any corporate. Experience is experience - whether it be at someone else's company or your own.

As long as you have the skillsets that corporate require, they are mostly likely to hire you back. Not to worry, I quit my job some time back in 2006 to start a biz, failed, got a job, my pay was increased by 20%.

As long as you are young with no major liability like loans or credit cards debts, you should really just do it now! You never know, later on in life there will be family commitments, housing loans, insurance, etc. Definitely more restrictive.

I would definitely do it again. Soon actually... hibernate mode

I am in a very similar position:

1. Have an IT Java job that I despise.

2. Want out of that job to work on my own apps for profit.

3. Still live with my parents, but am in my early 30s.

I am currently working on these for-profit apps on nights and weekends. It's not easy, as that time goes very quickly. The only reasons I haven't quit my job (as I figured I can always find an equally miserable Java job if I was desperate):

1. The suckiness of the job can be a great motivator to keep me plugging away on my side projects.

2. 4 weeks of paid vacation/year means I can afford to go to some interesting developer conferences and quickly recoup the cost. This allows me to get to know people who are already where I want to be.

3. I can use the paychecks to bootstrap my company-to-be. Not that it takes a lot of money to start a company, but I like the idea of a substantial rainy-day fund.

When I can make enough money from my side business, I'll happily quit the day job. Enough money means I can consistently make around 70% (or more) of my paycheck's gross amount.

Please keep us posted on what you ultimately decide to do.

Wow you hit it spot on. I do hack in my weekends/nights but the time just goes by so fast, and it is so draining staying a computer so much of my waking time.

Yeah. I am also saving now so I at least have a small nest egg once I get the guts to take the dive.

I'll let you know what I do for sure.

You and probably a lot of other people aren't going to like this advice, but here it goes...

You're in your 20s with a full time job and still living at home? Fix this immediately.

Honestly it sounds like you need to learn some responsibility. You have a full time job, but you don't like it, so you're going to quit. You have the parents to fall back on.

Maybe a start up will give you responsibility, maybe moving out and financially separating from your parents will give you responsibility. Maybe both with give you double secret responsibility.

I'm actually shocked no one has said this until now. Someone having a full time job but still living with their parents (unless for special circumstances) speaks volumes about their maturity.

Time to start living in the real world. I say jump in and begin your startup. Best case scenario you succeed and end up doing what you love, worst case you took a shot (hopefully one of many) and got out of a job/lifestlye that is making you miserable.

Well in my defense I only live at home because I am so confused. My parents are nice about it. I can easily buy/rent but the stopping factor is that I don't know what to do. I am located on the east coast, and want to go to Silicon valley, etc. so I see no reason to invest in a 1-year lease or mortgage if I am trying to change my lifestyle! :o

Based on this reply, it sounds like you want the easy way out. It's time to "nut up and make a decision" (Liz Lemmon).

If you want to go to Silicon Valley, go. If you want to stay at home, time to become an adult and not rely on your parents for everything.

Maybe you'll tell me it's the smart way out, but it is a compromise I will not make.

Yes, you can save 6-8 grand each year by living at home, but you're living at home. I guarantee that your friends that went out and are living on their own are mocking you behind your back.

Sounds like you are looking to leave one job to get another job. Take some time to think about why joining an as of yet unknown "startup" would be better than the job you currently have. If you don't know where you would be going, then it might just be filling in imaginary holes.

One of the biggest things that's different between a big corp job and a startup might be that you are "closer to the metal" of the business part. What you do has a much larger effect on the ability for the business to succeed or fail when you are part of a small development team. Perhaps you could go even further and build your own business. This might prepare you better and give you an idea of what it is about a startup that you really would give up your current job for. Perhaps your new business would even do well enough to provide the income when you quit your day job.

Not to be too critical, but some of the trailing comments brush on this - are you turning joining a startup into a strawman cure for a lack of structure, motivation and focus?

I'd grind any bullshit for 22 hours a day if it was heading towards something I wanted badly enough. A change of product, codebase or setting isn't going to suddenly change your internal drive or other subjective factors. Even if you hit a startup thats on cool platform X, it will become background noise to getting something delivered / ploughing through the bug list / etc etc.

Your decision to quit isn't progressing because its arbitrary - you're not leaving your job for any specific reason or because you have a clear goal in mind. If you have a strong reason (eg, passion for a project, monetary goal, cancer, whatever), decisions like this normally happen pretty fast.

I've quit a few jobs. In my experience, when you're thinking about quitting and asking other people if you should quit, then it's time to quit. I have tried to stick it out before and I wish I had just quit instead of trying to work through it.

How have things turned out for me?

My last employment gig that I quit was about a year ago now. I quit, then worked for a month full-time on one side project. Then a company I previously worked for needed someone for a few months, so I went back to them at 50% more pay since it was contract.

Then I took another month off to complete another side project. These projects didn't make money so I started looking for some remote, contract work. I found one pretty quickly that was using Zend Framework, which I had experience in due to using it on one the above-mentioned projects. I accepted this, at an increased rate of pay from my previous contract.

Now, that contract is almost up so I'm looking to take time off to work on another idea but am also applying to some contract gigs that interest me. I've sent off three applications so far, and I've had three interviews (the third coming up on Monday). Also, the place I previously worked at/contracted needs someone again for a few months so I have an offer in my back pocket.

As a capable programmer who can take the initiative to build your own stuff, it is incredibly easy to find work. Quitting your first job is the toughest though. But then afterwards, you wonder 'Why was that so difficult?'

This will be a great opportunity to learn more about yourself. If you quit and take time to work on your own stuff, you will learn a TON about your work habits, how productive you are, your focus levels and whether the entrepreneurship route is for you. This is incredibly valuable information to learn about yourself in your 20s. You may find after a few months, that you prefer the structure of the corporate world. Maybe it's tough for you to understand that now, but I can definitely understand why some people would prefer this.

And, if you take time off, build some stuff on your own, and highlight that in your cover letter and resume, it will be very, very easy to find work should you wish to return.

Have fun!

Not quite the same thing, but I'm leaving a PhD program that's been making me miserable to join a small supercomputing company. In my opinion, being happy trumps everything.

Keep in mind, though, that you have more choices than your current job and a risky startup. There are undoubtedly other stable jobs out there that might make you happy.

If you do decide to strike out on a startup, use your amazing-paying job to save up a bit and give yourself a good runway. This might help you be less miserable all on its own, as working towards any goal you find meaningful may lift your spirits.

I didn't see a word about /what/ you want to build. Most people leave their jobs and pursue startup life, which is not glamorous, because they have a burning, necessary passion to build something and solve a problem. And it's that passion that will get you through the ups and downs of startup life.

That said, if you just want to build cool stuff using new technology, there's always the chance you could just up and move to SFO and get a job /at/ a startup depending on your skill-set.

You say you have a fine job and amazing pay. Why quit? I would quit when my startup is earning more than my current job.

What do you do when you are at home? You can spend your extra/free time on your startup until it grows big enough. At least you only have to work 8 hours a day. In my previous job I worked 9.6 hours a day :P

(Disclaimer: I quit my job almost a year ago but I have not gone fulltime doing web apps. I still enjoy coding while at home. I found a new hobby. :) )

Since you have no significant financial obligations (and I'm assuming some good savings), this sounds like the best possible time to get out there and try something. I did it at 30 (after a layoff) with a mortgage and a car payment, and it was ridiculously hard.

Did good come out of your move though? Or are you still looking right now?

I sold my company, took a job working for someone else, and I'm now actively planning to start another company. The reason I suggested that you're in a good position is because most of the issues I had were cashflow-related - having to cover my existing expenses on substantially reduced income (I had to pick up all kinds of distracting side projects to pay the bills). If you're living at home and you have healthy savings, you can really focus on building the product.

Echo those other comments, I'm in a similar scenario. My email's in my profile if you want to exchange ideas. My thoughts: happiness comes from loving what you do. I guess you have to choose the right moment and hopefully find something you love.

For those of you who quit and then returned back to the work force, did you have any difficulty finding work or explaining the gap in employment to potential employers?