About me: I am very entrepreneurial and believe I would do well working solo as a consultant and possibly hiring help. I do want to do that at some point. I love to learn and a good challenge. Please help me make this decision! Current job (I am there for about 4 years): Pros: secure job good pay (I guess I am 80 percentile for my level/geographical area) large corporation - main business is not software excellent health insurance for low cost to me, pension, 401k matching, 6 weeks paid time off per year small dev team use of latest technologies (mostly WPF/silverlight) low supervision (I can do personal things all the time) I get to do a lot of moonlighting and my goal was to go solo full-time in a year or so. Cons: small team of non-professional devs 50% of my time I do things I don't enjoy projects are not meaningful to the organization If I left it wouldn't be too hard for them - business would resume as usual. Nobody besides my small team of 3 has any idea about software development whatsoever. Prospect job: Pros: small/agile software company same salary as current job same size dev team but all are very sharp (I would probably be the weakest of the team in the beginning) technology used is outside my comfort zone (latest cool web technolgies such as html5/jquery/...) - I am not a web dev and they know that. ton of learning opportunity Start-up - possibility of stock option/partial ownership of some sort Cons: Small office space - not able to do personal things as often (may be pro) No room for moonlighting less benefits (but salary can compensate for that)