What’s the Best Strategy for Learning Digital Logic?

I've been trying to learn programming for a few years but haven't had much success. I'm really curious about how computers and digital electronics work, though my background isn't very technical. I work at a software company where colleagues are generally helpful and willing to answer my questions. Over time, I've picked up some basics like very elementary Java and C++, realized what logic gates are, and experimented with Arduino and breadboards. However, I still feel like I don't fully grasp the concepts. Recently, someone suggested I go back to the basics and focus on understanding one logic gate a month—creating truth tables, HDL descriptions, and studying how each gate is constructed (like how an OR gate can be made from NAND and NOT gates). The idea is to make this knowledge automatic over time. I'm 38, learning out of interest, and although I secretly hope to turn this knowledge into a career someday, I'm not in any hurry and want to ensure I understand everything. What do you think of this recommendation? What would your strategy be if you were in my shoes?