[kishorenc]

Why don't you start thinking and also working on what you exactly want to do on the side, and solidify your plans once you feel confident enough to make the jump? The transition does not happen overnight.

But, yes, I definitely feel you will really have a chance to learn more in a start-up, since you will essentially juggling various roles, especially in the early days.

[SqMafia]

That's pretty much what I am doing now but it seems like a waste of time. Essentially I'm trading my time for some extra money and benefits while distracting me from where I really want to be.

My main worry is the so call "resume hole". Would I make myself harder to hire later by having a "gap" in my resume when I am not working?