I'm a late bloomer. I had close encounters with audio for years before I fully succumbed to the hobby. Initially, it was via coworkers who told me their Sennheisers and Grados were better than the Sonys and Bose I knew (back then) as the epitome of audio quality. I was curious, but frugal, and didn't end up getting my own pair of Grados until 5+ years later.
I went another 5+ years without buying more headphones, faithful to my Grados and developing an open-back superiority complex. On occasion, I would be interested to buy another headphone, but being eternally frugal, I knew that it didn't make sense to own multiple pairs.
But in 2017, Bluetooth was ascending. Apple had just released AirPods. Headphone jacks were vanishing. And I suddenly had the excuse to overcome my frugal tendencies: I had to have a second pair of headphones that was Bluetooth.
Long story short, the "one Bluetooth headphone" turned into insatiable curiosity that turned into me starting a YouTube channel to justify buying more things than I need. And the interest in Bluetooth headphones… well it quickly ran into my open-back superiority complex. After almost a year of the YouTube stuff, I finally bought my first pair of IEMs after seeing their name pop up on Reddit's /r/headphones enough times that I got curious.
Even then, in 2018, I hadn't really committed to the audio hobby. My YouTube channel was a hodgepodge of topics, reflecting my varied interests. Headphones. Motorcycle parts. Transformers toys. Computer accessories. But around that time, I started working with someone who was genuinely deep into audio. Like, owned-two-AKG-K1000s deep. We ended up taking over an empty desk at the office with audio equipment we hauled in, me providing the various Chi-Fi IEMs I had acquired, him supplying all manner of amps and headphones.
By that point, my headphone monogamy was destroyed. I succumbed to the hobby, and in 2020 officially dedicated my YouTube channel to hifi personal audio. My collection of IEMs is senseless. But it's fun to share.