So you are 27 years old (same as me)?! For how long have you been working now?
I'm asking, because I am also thinking about when to quit my current job and what to do next. What holds me back are just two things. First, its the paragliding course I already paid for but didn't finish yet. And second its the feeling that leaving my job would be too early right now. I have been promoted as teamleader just one year after graduating.
But still I envy people like you who are able to simply quit and start a new thing.
You will always be able to come up with reasons not to take risks, and they don't have to be particularly good ones as long as they give you an excuse to wait a little longer. There will never be a right moment. I recommend you evaluate whether you're happy with your current situation, and if not, then seek to change it. Your choice isn't simply between keeping the job and quitting it; perhaps you can find a different way.
I was in a similar situation as you are; running a small programming team at age 27, with no real commitments. I decided to stay because the opportunity seemed too good to pass up, but I'll never know where I'd be now if I took a risk back then. Over those three years it seemed like everyone I interviewed ran their own project. Many popped back and forth between working as part of a team, and running teams several times in their career, so it's not as special an accomplishment as I'd thought at the time. Now it's three years later, and I've gone part time and started telecommuting so that I can travel wherever I want and have time to figure out what I want to do next. Your choices may vary. Good luck!
Actually you cannot travel "wherever [you] want", because in most countries you also need a work visa to telecommute. That's particularly the case in the US.
I'd like to re-enforce that life passes quickly. Higher hurdles develop as the years pass so that simply leaving a job without a plan has higher costs. Once you "settle down" you have to consider how to pay the mortgage, keep health benefits for your child(ren), and provide for your family if something happens to you. As you move closer to 50, your retirement becomes a factor in simply quitting your job.
Settling down was NEVER a consideration for me until I met my wife sometime around when I turned 31. I thought that I would always have plenty of time to change careers, explore interests, etc. (How wrong I was.)
It sounds like we're both fortunate enough to live in cultures in which changing careers and pursuing interests is a possibility. Don't dally! You can always take up paragliding again. You can always be a team lead again. Time you can't get back.
