I started my journey with the buying of a beyer dt770 80 ohms and a radsone es100.
It pleased me for 3 years, and I felt the need to try something else. So I watched reviews for getting a good sound. I finally bought in early 2021:

• a Hifiman he400i 2020
• a senn hd6xx
• a topping dx3 pro V2 (for the ldac capability I never use)

Then I fell in the iem rabbit hole, and bought:

• a Blon bl-03 that left me unimpressed
• a kbear ks1 because it’s so cheap
• a moondrop aria as “serious business” iem

From this experience, I think I lean towards bright sound signatures. I need a minimum of soundstage, and I place imaging and instrument separation above everything else. That view could change through the journey, though: part of the fun is trying new unexpected things.