I think in the long run you'll be fine. Red flags are a lot less important than ability to solve the company's problems. As much as it pains me to say it, once

I think in the long run you'll be fine. Red flags are a lot less important than ability to solve the company's problems. As much as it pains me to say it, once you move out of the startup arena into large company territory time off matters even less because most people who will interview you know very little about specific technologies and just want the hiring phase to be over with. Some won't even ask you about your time away from work. Those that do will give you a "heh, that's interesting" and move on to the next question. Generalizing is usually pretty pointless but if I were banking on getting a programming job, were debt free, and okay with not being especially picky about what company I work for after the experiment should it come to that, I wouldn't worry too much about possible red flags. In life you have to prioritize things. If your highest priority is running your own business or taking time off from work to try something new, then your next job after that really has to fall down the priority list. You can't have everything assured and hope to be successful. Edit: MOST PEOPLE can't have everything assured and hope to be successful. Of course there are exceptions to every rule, but most of the time you do have to experience trade-offs to be successful. I'm not advocating taking huge risks, and most of the time there are smart ways to mitigate risk, but in the end I think a lot of people are arguing you should mind your red flags and try to stay focused on getting your dream job after the hiatus. I'm simply saying that isn't realistic if you want to focus on being successful in a different line of work. I've always believed you can really only be truly committed to one career at a time.