I'm 23 and have been fishing since I could walk.
Much like you, everything I had was "good enough". Spinning rods and worms, maybe a mepps inline spinner. Then when I turned 18 and started actually bass fishing and wanting to be not just a angler, but a great angler, I realized I had to get serious. Through trial and error I realized some stuff just can't be done on an ugly stick with a spinning reel and 10lb line. That's when I got my first baitcaster. It was a cheap walmart one, so definitely not "good" gear. I luckily caught on within a few days and was hooked. I started saving every penny I had to buy more bass lures, and moved away from live baits or the standard senko wacky rig. When I was 20 I realized fishing the bank was fun, but there are so many more fish in the lakes that I cannot possibly run my lure past if I am on the bank.
So I saved every penny I had and bought an old bass boat. Even with the boat, fishing was rough for two years. I was stuck in my shore fishing habits of throwing wacky rigs 24/7 and spinnerbaits. Sure, I caught fish, but I didn't catch quality, and sure didn't catch limits like I thought I would by owning a boat. This is when I feel I got "serious". I started watching fishing videos 24/7. I was watching every video put out by every pro. Every tips and tricks video on youtube. This is when it clicked. I learned patterns and forage times for bass and where they are more likely to hangout and what mood they will be in.
I haven't really had the dough to buy nice gear until two years ago. Boy does it make a difference. The only reason I don't regret having crappy gear until as of late is because even if I had it, I would have had no clue how to properly use it. Now, I don't own $500 rods or reels, but most of my set ups are in the $250-300 range, and I find these to be practical for how serious I've gotten without going broke. Still paying off those college loans... lol
One of my best purchases fishing wise was a decent sonar... I use to just aimlessly cast lures not even knowing what was below the water or what the depth was. Man were my eyes opened when I got the sonar. I went from throwing spinners and texas rigs at the bank to drop shotting downed brush piles, or picking apart that 10x10ft hole that nobody would ever know was there if they didn't drive over it with sonar. I feel like I am just aimlessly typing now so I'll stop, but I just wanted to say... I relate. haha