I'm 36, and you sound exactly like me when I was 31. Same situation, surrounded by a team who was on average 10 years older than myself married with children,

I'm 36, and you sound exactly like me when I was 31. Same situation, surrounded by a team who was on average 10 years older than myself married with children, working on mostly legacy stuff. Nobody seemed to really care much about their jobs, just wallowing in skill rot. When I was 32/33 or so I was offered to go into management. I turned down that management offer, kicked butt where I could and got promoted to a principal engineer. It was at that point I realized I was in a dead end job, went nuts in my free time reading book after book, tutorial after tutorial... and two years later finally summoned the courage to do a Rails project pro-bono on the side for a small local marketing firm; for about 4 mos I was putting in 60-70 hour weeks between my day job and side gig. Now I have another Rails project lined up for a NYC fashion site that pays about 15% more per hour than my day job and I've been contacted for no less than 5 full time Rails positions, one of which I interviewed for and turned down. The demand for this stack is fierce. And you know what? I'm madly head-over-heels in love with the latest and greatest the web has to offer (ie. meteor.js gives me goosebumps, and at the very least in the near term I want to do a front-end mvc project ala backbone). I'm not great - yet - but I feel like for once I'm really in the game. It's exhilarating. I feel more alive than I have since my early 20s. This NYC contract is about to be signed, and once that happens I'll be saying goodbye to the windows world altogether, join a co-working space, build a network, go to local tech meetups, etc, to ensure I have a steady stream of work. It also helps to have at least 6 mos of savings in the bank to mitigate risk. Seriously, go thru easy/free books like Learn Python the Hard Way, Eloquent Javascript, Michael Hart's Ruby on Rails Tutorial, the tutorials on the W3C site. You should be able to do all that in a couple months, and that's probably 50% of the battle (okay - there's alot more, but once you have some foundation the rest will be much easier). EDIT: Wanted to mention about the full time Rails positions, 3 were for small startups, 2 for larger companies. Naturally the small startups you can expect to take a pay cut if you're mostly maxxed out in your compensation in your respective area. But the 2 corporate Rails gigs the recruiters wanted to put me in at or slightly above my total compensation package at my current job (partly due to those being a mixed environment and needing someone with both C#/C++ and Rails skills).