It's certainly enjoyable to switch on and off from work and live off savings, but then you eventually get to the point where you can't find a job to switch back on to, and your savings are all gone...
Saving for the future conflicts in part with the desire to live a full life today.
Taking sensible care of your money is wise, spending a bit less than you make is wise. Trying to get lots and lots of money and giving way too much to your work now in hope that you can then, at some time later, retire and finally start living for real is an illusion. Because you never know what's in the future and you never will.
If you haven't learned how to live and let go before you retire, you sure don't know how to do that when you actually do retire -- in fact, you're going to spend most of your remaining days learning just that. Most people seem to fail in that, because transitioning from a "drone" to live a full life is hard. Really, really hard.
Living now doesn't mean careless, extravagant spending and ending up broke. But all the work you've put into your savings needs to be periodically extracted out and enjoyed by yourself because that's what life is.
You can never control life to the extent that you could be certain you won't run out of money, even if you try. (Well, one way would be to kill yourself as soon as you have lots of money -- then the money and security has outlasted your own life.)
I've learned that the only thing you can do is force yourself to trust that you will always get enough money somehow, somewhere, for everything you really need in your life at the time. If you try to think something else, it's an illusion. Life is at stake in many ways, all the time, there are endless ways it could change or end each day and each hour. And you won't have a say about it should something happen.
You can only trust that your life finds its own way and that's all. The rest you can choose to learn to enjoy.
Anyway, I like the fact money is really unimportant in my life. I can eat out and it does not break the bank yet I also don't care if I get laid off or fired. Next time I am unemployed I could eat out less spend and spend less money, but getting a job a little sooner is not that big a deal and people look at you funny when you have long stretches of unemployment plus I never really found much in the way of a mid day social life.
PS: If in a few years I have 50k of non retirement money sitting around I could take a year off, do a start up and not feel as cash strapped, or whatever but retiring mid 40's is also a reasonable goal based on my spending habits and and how much money I will probably make with a few more years in the field.
I'd be willing to bet that, for the current generation at least, that will never happen. (But I still max out my retirement account, just to be safe. :-)
I am 40 and have been programming since I was 12; almost always on the bleeding edge. I can assure you that there is a point of being "too old".
Unless you are quite a different person that I, I highly suggest you keep maxing out that retirement account. ;)
I can't speak directly to the IT guru part, or to getting burnt out on new stuff. I can tell you that my dad is almost 70 and has never enjoyed his work more. I'm 35 and I'm still always itching to learn new things. And given the rapid advance of technology, I'd be surprised if the usual 'grow old and die' scenario remains 'usual' much longer. In the not-too-distant future I expect longer lives and continual renewal to be the norm, and I for one am looking forward to it.