When you say you're working 50-60hr/wk and want to load more learning on top of that, I feel concerned for you. You've described a sure path to burnout. If you

When you say you're working 50-60hr/wk and want to load more learning on top of that, I feel concerned for you. You've described a sure path to burnout. If you're doing this for fun, well, make it fun. Take it easy on yourself. Just work on side-projects when you have time and energy. No one cares whether you're an expert in something that you just do for fun. If the goal is more to make a career switch into some kind of IT or computer profession, I can say that I've never encountered anyone who expected me to know everything. We're all grownups and we all understand everyone has different strengths and weaknesses. When we're looking to recruit, we want someone who is helpful and can learn fast, not someone who is already an expert in our whole stack. You'll be more likely to get the job you want from networking than from already being an expert in techs a, b and c. When networking, it's nice to be able to talk about what skills or side-projects you've been working on, but think of these more as ice-breakers than as things which need to be perfect. To focus on the question about analysis paralysis, try inventing side-projects which align with your goals. Setting a short-term goal will help you figure out what skills you need. If you want to get into game dev, either build a basic game from scratch or start modding existing games, it doesn't matter what. You'll figure out soon enough if you need to learn more theory.