Earlier quoted context omitted.
I'm actually fairly serious. I've been bored before, so I hear you. But, I guess I'm kind of surprised that you chose to jump into nothing rather than parlay your way to something else. Seems a little impulsive. Impulsive is a red flag, despite what many on HN think (you can be impulsive, but you better be brilliant too). Now you've got to explain a gap in your res to a potential employer (should you choose to go tha…
I tend to be fairly transparent and vocal. Sometimes it gets me into trouble, but usually it works out for the best. If a potential employer asks why I left my job (which I entirely expect), I will be straightforward. Heck, I'll even send them a link to the blog post. I'll tell them how I don't think sticking to what is easy is the best approach to building a successful business, even though it feels safe. I'll tell…
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.