Ugh, I've done so many dumb things.
Most of which involve mindlessly wasting money and trading really nice gear to the local shops for substantially worse gear to satisfy my need to be more metal.
ugh.
Started off on cheapos, but once I started playing in a *shit* n00b band playing nirvana/godsmack/deftones covers and shitty derivative originals........I had to upgrade.
I had a real nice setup.....unknowingly......MIA Strat, Laney GH50 head and matching 4x12 cab. (worked a lot in high school to afford these things)
At the time I didn't know what a tube amp was. I just thought it sounded good in my bedroom.
Wasn't loud enough. Wasn't clean enough. Wasn't heavy enough.
Traded the Laney head for a Fender M80 head. DOH!
Although, I actually used that head for a very long time with various shitty metal pedals. Ibanez Smash box, Guyatone Metal Monster, DOD Death Metal
The other two that jump out at me is trading off my baby....the first bought MIA strat for a Epiphone Explorer (which I hated and traded to a friend for a florescent yellow Kramer super strat). ouch. double ouch.
Next was a Gibson Les Paul Classic I bought new in 2001. Dream guitar. Jimmy Page sunburst.
Had it on a stand in my bedroom. Had a party at the apartment, woke up to it knocked over on the floor and a fracture in the neck (not even through the finish).
Immediately tried to unload it because I was afraid I'd be stuck with a broken guitar. Got like $600 for it. ouch.
Currently are worth more used than I paid for it. doh.
With all that said, I spent most of my guitar playing life buying, selling, and trading.
After my phase of losing money to local shops, I realized I could flip gear for profit online. I'd seek out good deals, and flip them on HC, TGP, and TB.
I spent at least 8 years doing that.....til the markets tanked.
Got to try a lot of gear. Probably ended up breaking even in the end, but at least I have some gear I really enjoy leftover (lifers). imo.
Then it all came around and hit me. I'm done with that buy/sell/trade shit now. (though I could use to sell a few more things I don't need anymore. Iceman anyone? lol)
happy with what I have and realized I sound like me through everything.
In retrospect, I should have spent a lot more of that time practicing and getting better as a player........rather than focusing solely on the gear.
That's what I'm doing now, 18 years later, practicing and focusing more on my playing.

works out eventually.