When I was a kid, a friend of mine taught me the basics of chess. We didn't know about en passant and a few other fiddly bits, and we had a couple of rules wrong. But we played like it was the most important thing ever.
We played and played and played, and in so doing learned that we tend to lose if we start off doing certain things, and that no trap works twice in a row against the same opponent.
We adapted to favorite openings and learned how to finish the game when only a few pieces remained.
Neither of us had read any books, and didn't know terms such as "middle game". We just played with desperation. It was agony, and it was glory.
I almost always lost. And I quit the game after a while.
Then one day I found an old Reinfeld book that my sister had bought used. I read it from cover to cover, learning a now-obsolete form of chess notation, and I worked through most of that book. By the end I had gained a glimmer of understanding about how very much I didn't know about this game.
I began to make people work so hard to beat me that every opponent expected an exercise in frustration when it came time to play me. But I still lost. And I quit the game soon enough.
Years later I bought a version of Chessmaster for my Xbox and played through the Waitzkin instruction course that came with it. It changed everything for me once again, and clarified some tactical ideas with interactive exercises. I began to feel that I was far from competent but at least learning the language of the game properly after a couple of decades of blundering around on the board.
Now I began to actually win against some less-experienced players, and the game became less of a panic attack. But I gave it up yet again, because I felt overwhelmed by the whole experience.
Next time I tried my hand at the game, I had years of computer programming experience under my belt, and had trained my brain to power through logic problems in order to pay the mortgage.
I picked up a copy of Fritz and used it to learn how to document main lines and variations as I studied branches within games. And I switched to correspondence play, allowing me to take the time to really think and explore ideas before choosing my moves.
These days I find I win around half of my games. Sometimes I'm winning, and sometimes I'm losing. But I finally feel like I'm playing the game in a way that I couldn't imagine when I was a kid wasting a summer with my best friend.