What would you do if you were me?
I feel as if I'm stuck in a no-win situation in my career, and I'm wondering HN readers, what would you do if you were me?<p>Here's my story: I'm in my late 40s and have been involved in information technology professionally for my entire adult life (and even did board-level repair of early personal computers when I was in high-school). For the past 20+ years I've been involved in IT audit and information security as an auditor and consultant, and as an information security manager. I'm technical enough that I'm currently a security-architect / sales-engineer for a large telecommunications vendor. I've tried two startups in the past (mobile robotics and security consulting). Neither were overly successful, but I learned a lot. I currently live in the upper midwest, am married (for 20+ years), have three children (ages 12-18), and make a decent living. Sounds great, right? I should be happy.<p>Here's the problem: I'm not making anything! I'm not creating! I strongly feel I'm a "Maker", a "Developer", but I may have realized this too late.<p>During the evening, I program for fun (mostly Ruby on Rails, these days, but Lisp, Python, C, and micro-controller assembly in the past). I'm not the greatest programmer, mostly because I can only do it a few hours each week (let's say ~10 hours per week), but I can get by. And, I really enjoy it. So, I'd like to do more programming. And, I'd like to do another startup. I have SaaS B2B application in mind. But, it seems at my age it is going to be impossible to shift from my current career to a programming career or to do another startup because the lifestyle change (read "drop-in-income, at least for a while") will be intolerable, especially for my family. Does that mean I'm done? Game over? At this point, am I doomed to sitting on the side-lines and only watching or being a cheerleader to other developers and startups? What have other professionals who have been in my situation ("golden handcuffs") done to get around this? I've had a successful career (especially for someone who didn't complete college), but with three teenagers, it's not like I have a stash of cash available to make the transition.<p>What would you do if you were me?