It's kind of interesting to follow someone else's audiophile journey from their first high-end component to the present day.
Mine began with a B&O Turntable system decades ago. This was safer than continuing to sneak time

on my father's McIntosh System (turntable, reel to reel, etc. - it was nice ...) when he was at work.
Some years later we went with a Krell Int with B&W 802s (in cherry) and a Sony ES SACD. A set of Grado Headphones joined the package as well. We had a few multi-channel systems thereafter that NEVER fully satisfied my two-channel craving ....
Now we're patiently waiting upon the delivery of another two-channel system.
Whether long or short, what's your audiophile journey been like?
You asked from first component to present day. A whole system was the beginning, in 1990:
Cambridge CD-3 CD player
Stax SRM-T1 tube headphone amp
Stax 'Professional' electrostatic headphones
Siltech cables
One and a half years later, I switched to a speaker system, with then my third CD playback system (Meridian 602/606) and Audio Innovations Second Audio parallel push-pull triode monoblock amps, powering Ensemble Reference monitors. I kept the amps for 26 years (going through heavy modifications and supplement with BorderPatrol MB external power supplies) and the speakers for 25 years (re-foaming in 2005).
Development of my system:
CD playback:
Cambridge CD-3 > Meridian 208 > Meridian 602/606 > Wadia 8/12 (kept for about 20 years) > Berkeley Alpha DAC2 (with switching to Simaudio Moon 260 DT CD transport after the Wadia 8 gave up) > Schiit Yggdrasil DAC v1 > Schiit Yggdrasil DAC Analog 2
Amps:
Audio Innovations Second Audio monoblocks > Octave RE 320
Preamp:
diverse passives > Pass B1 (buffered) > Octave HP 700
Speakers (all monitors):
Ensemble Reference > Reference 3A MM DeCapo BE > Reference 3A Reflector
Subwoofers:
REL Storm III (purchased in 2000) > JL Audio F112v2
Cables:
Ensemble/Siltech/MIT > Monster Audio Sigma 2000 (IC/SC) > ZenWave Audio D4 interconnects / SMSG speaker cables (digital AES/EBU cable, MIT)
Room treatment:
Tube traps/ sound panels/ SubTrap, then window plugs, then ceiling diffusers (all ASC), absorbing panel from Acoustics First. Changing through diverse carpets.
***
Now I'm essentially done. While I have regular exposure to other kinds of systems, I will always remain a monitor/sub guy. I can hardly envision any more meaningful upgrades within this type of system that I have, except perhaps the DAC. Yet given how spectacularly it performs -- it really came into its own with the preamp upgrade --, there is no hurry, i.e. not within the next few years. Good on my wallet, I have other things to take care of. Don't be surprised if I have the same DAC five years from now, or longer.