It sounds like the problem you're grappling with is what to do with your life. You stated you tried to start numerous "software businesses" over the last 20 ye

It sounds like the problem you're grappling with is what to do with your life. You stated you tried to start numerous "software businesses" over the last 20 years and you're currently implementing a programmable PostgreSQL proxy. Do you want to be an entrepreneur or an engineer? What is it about business that draws you to it? Is it the freedom and independence and not wanting to work for someone else? Or are you passionate about producing something that will improve the world and solve a problem that could benefit many other people? As for "I'm 37 and we're looking to start a family" ... what do you value more, starting that family or whatever "not getting a job" represents. The issue I think you're facing is that the value of "not getting a job" is undefined. Keep in mind that "becoming entrepreneur" is not the only alternative to "not getting a job." If you're passionate about engineering but you want more flexibility and freedom than a 9-5 then maybe consider becoming an independent contractor? I haven't heard anything in your question that implies that you're passionate about business and being an entrepreneur or that there is any specific vision that you have for something that will improve the world that you can't wait to get to market.