Ask HN: Going Unemployed?

[SqMafia]

I'm currently employed at a large software corporation that treats me well but where I am incredibly bored by the things I do. The environment doesn't fit my personality. I have learned so much more on my own time reading and hacking than I have over the past couple years at the company. Ultimately, my eventual goal is to start a company or work at an early stage startup. I don't see my current path leading me there. I'm considering quitting my job so I can devote my time to learning new things and starting/joining a startup. My biggest worries are: 1. Resume gap 2. Healthcare

I've been good about saving money and living frugally so I can go at least a couple of years without a paycheck.

Should I make the move and just quit? How do you go from a corporate job to a startup? Am I right in thinking that I will be challenged and learn a great deal more about technology, management, and business at a startup?

[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?

[hga]

Check to see if your state has a individual health care program for the uninsured. 36 do as I recall, although you might not meet the requirements for your particular state's program.