[obviouslygreen]

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.

[skurry]

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.

[obviouslygreen]

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. ;)

[skurry]

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.

[obviouslygreen]

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.

[wnight]

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.