The first time I tried playing by ear was when I took a jazz improve class, again in college. I was the only strings person there, and I felt quite out of my league playing with a bunch of experienced jazz musicians. I did my best, but in the end I felt like playing by ear was just not something I could do. Fast forward a few years, and I took a class in Suzuki Method. There, we were expected to at least give playing by ear a try, and since most of the songs we were working on were fairly simple, I took a deep breath and gave it a shot. For the first time, I felt like it was okay to try and fail, and to my surprise, it wasn't as hard as I'd thought (I think years of aural skills training had definitely helped by then). I still don't feel like an expert in playing by ear, but I've found it can definitely be a fun and exciting way to practice.
I think the key to successfully playing by ear is listening. It's much easier if the music you're trying to learn is deeply embedded in your memory. For example, I'm a huge fan of the TV show Game of Thrones. Since I watch it regularly, it's easy for me to hear the theme song in my head. So the other day when I was practicing, I decided to try and play it by ear, instead of looking up the sheet music. It took me a few tries to find all the notes, but eventually I did. It was fun to play, and my daughter loved it! I've tried playing similar songs by ear as well, including the Misty Mountain song from the Hobbit Movie and simple folk tunes.
When I first started playing by ear, I found it very intimidating. It wasn't how I usually practiced, and I felt insecure without a music stand and sheet music in front of me. I was uncomfortable with making mistakes and feeling notes out (or listening for them) instead of knowing exactly what I was supposed to play. But I think that's one of the things playing by ear helps us to let go of. Instead of relying on sheet music, playing by ear makes us explore music more, thinking carefully about how it sounds, not what notes are on the page. What's more, it's good for music students to learn to take risks, and sometimes making mistakes is an important part of that process. That's what learning to play by ear has helped teach me, and it's a lesson I hope to impart to my students as well