When teaching myself as a kid, I quickly realized that win32 was way over my head. However, web stuff seemed easy enough, so I started teaching myself web development instead. This was in the early 2000s, before everything started moving to web applications. It certainly managed to pay off!
This was also me as a kid with the Mac - we got our first home computer in 1993. Pascal? WindowPtr? Compilers? Yikes - I'm only 9 years old! I'd done some QBasic and Logo at school but couldn't wrap my head around the 'abstract' GUI stuff: If I tell the turtle to go Forward, it goes forward...
Then I discovered HTML - much easier to wrap my head around at the time.
I never did learn win32...