I've found it's been a natural progression for me. When I was young and didn't have much disposable income, it was whatever I could find to chuck a fly with - usually a WallyWorld or Crappy Tire combo special.
As I got older, and had a bit more play money I upgraded my gear (still not top of the line, but lower end of the "name brand" spectrum - I still own my first "good" rod and reel, a 2 pc Sage VPS 590 and a Lamson LP2 reel with a spare spool).
Then I got to the age where my income and living expenses where such that I could afford to spend even more, so of course I did, lol. Not being a hard core fly fisherman, my gear still pales in comparison to some, but it serves me well enough, although I caught just as many fish on my old Sage as I have on the more expensive rods and reels that have since replaced it in the cabinet. It gets hauled out every now and then for nostalgia, but rarely gets fished. Just relegated to a back-up 5wt role now.
I've met people who are the exception, but generally we live to our means. We make more money, we tend to buy a nicer car, or a bigger, nicer house, or nicer hunting or fishing gear. Doesn't make us better fishermen, just like being able to afford a Maserati doesn't make someone a better driver, but if you can afford it, why not enjoy the fruits of your labour?
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