First: I am technical, and there are still technical articles (or conversations) that leave me in the dust. I was reading about advanced memory management tech

First: I am technical, and there are still technical articles (or conversations) that leave me in the dust. I was reading about advanced memory management techniques the other day and it was very apparent I was out of my depth. So it's a spectrum, not a switch. You will never understand all of them. But you can increase the proportion. My suggestion would be to just give yourself permission to play around. Look something up on wikipedia---when it gets boring or hard, stop. Install python on your personal machine. Now install another version. Now you hate pip, and you too are a Real Engineer. Trick is avoiding the temptation to work hard. "Courageous play" is the phrase to keep in mind.