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I feel a similar way, and I'm a little bit older with a fairly strong desktop/web/mobile dev background. My focus was heavy on Microsoft technology before moving 50/50 to Linux.

I look at industry as a series of different waves happening where I just need to get on one so that I can find the next. A wave is going to cross the startup world before it moves into established business. If I time it right then I can hang in there for a while. It doesn't help with my anxiety, but I've done this before so I know I can do it again. I suspect I'd find the same pattern in a closer examination of your background.

There are very few people learning all of these technologies because time is required to learn the basics, as well as put it into practice within industry. That's deep learning. A lot of people are lucky to work in places that will put unproven technology into production. The number of places willing to take this risk is increasing because cool technology is a requirement for attracting top talent. If you are in a more risk-averse organization it may seem scary to move to a faster moving, less risk-averse one, but you might find they actually have more leeway for mistakes and learning.

I watch for particular patterns around how a technology is hyped and who is applying the technology. Thoughtworks publish their perspective (https://www.thoughtworks.com/radar) and I try to read this, plus other analyses to understand what direction things are moving in. You have to take a longitudinal view. It's not good enough to just compile your research and make a decision. You need to know how a technology has moved over time. Once you start doing this you start to develop some "spidey" senses when you see something at the top of HN - and you don't have a ramp-up cost each time you have to make a switch.

Other than that focus on a few fundamentals, including one programming language reasonably well. I'd strongly suggest learning Python and having an incremental two year development plan so you don't half-ass it. A lot of the Linux world is built on stable skills. Rather than focusing on AWS, or Azure networking learning networking and TCP/IP beyond a cursory level. There are a lot of folks building cloud infrastructure badly, slowly etc. because they don't understand these fundamentals. The references are old and boring like TCP/IP Illustrated Vol. 1.



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