So the thread on quantifying your gear purchases got me thinking about when i began understanding how important learning to listen is in this hobby. I was in Phoenix Arizona spending a whole Sunday w/ my HiFi dealer. We had breakfast together and then he opened his store at around 11am to his regulars and set-up a spread of snacks and various Japanese fine alcohols. The first person to come visit was an older gentleman dragging along 2 milk crates full of records, each hand selected for it’s premium qualities that audiophiles find important.
By noon there were a dozen regulars gathered, picking favorite albums and playing particular tracks in order to listen for particular qualities to pick apart the equipment.
In particular cables were being picked apart that day, from regular $10 RCA’s, power chords and speaker cables to Nordost cables whose cost was in the excess of thousands of dollars each. Terms like, air, blackness, depth, height, width, fullness, thinness, color of tone, and other characteristics i was not familiar w/ were being discussed and folks were listening for particulars. Later that evening at dinner w/ my dealer as we spoke I understood i had no idea what i was doing in this hobby as i had heard very little that day that was able to discern no matter how hard i tried, it all basically sounded the same to me. This was almost 10 years ago, i made fun of the fact that i spent the day listening for air, height and weight. Today is a different story and this is my tale of the day i learned to listen like an audiophile. It’s been an expensive and at times stressful and painful journey for me but once the bug sunk its teeth into me the virus took hold and still drives my actions and any spare funds i manage to cobble together 
Feel free to share your own stories or experiences. Happy listening to all 
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I kind of did the whole learning to listen thing in easy mode.
When I first got to University there was a group of about half a dozen of us who got into Hifi, because we were all from different parts of the country and most of our gear was sourced in different brick and mortar shops we all had very different systems.
Many of our upgrades came from the same shop, so later Rega and Linn turntables were in all the systems except the one with the Revolver.
We’d spend hours listening to the systems and discussing them, sometimes swapping components, to better understand synergy between components.
We also spent an insane amount of time during the week at the local hifi store, often multiple afternoons a week. We were friends with the staff and as a group we spent significant money there and the staff would let us listen to stuff that was traded in.
As a result I heard a LOT of different components, but it was the long hours of discussions, that really taught me to listen.
The only interesting thing in my journey was I fell into the measurement/as the artist intended trap years after that. When I moved to the States none of my gear came with me, and when I did get back into it, there wasn’t a lot of overlap with gear I was familiar with, I didn’t have friends who were into hifi, and I went down that rabbit hole and spent the best part 5 years not really liking my system.
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I kind of did it the hard way. lol
As long as I can remember I would listen to music deeply, whether it was my parents big credenza sized record player with built in speakers or my self customized car stereo I was always enthralled by the listening experience.
My first job was in a bodega and when I got my first payday I bought, well not bought but put my first $5 dollar payment towards a JVC boombox that the bodega owner had taken from some guy that owed him money. lol
My father at the time worked in a factory in Newark NJ that made loudspeakers. Big 3 way 1970’s speakers the size of a college refrigerator. For the life of me I couldn’t remember the brand but when I finished the 7th grade I asked for a pair of speakers and he brought me a pair of the speakers he helped to make they were returns or 2nds or whatever but I was ecstatic. I then proceeded to drive them with the JVC boombox. When I finished the 8th grade and was going into HS I asked my parents for a stereo as my graduation present and I got a Fisher integrated receiver. Joy.
It was always solitary though as I never had close friends that would move mountains like I did to chase great sound.
I’ve self taught listened but never great gear and true world class sound until this latest reiteration of the hobby which started a year or two before Covid.
So I’ll rephrase the subject a bit ans say I’ve always appreciated good sound and that was my first step into listening like an audiophile. But to truly hear what you’re listening to, you need experience, lots and lots of experience.
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