I'm one of those people - I find any "in-ear" headphone/earbud to be outrageously uncomfortable.

Great news - there are a TON of alternatives! You're still an asshat if you play loud music without regard for your surroundings.

My personal pick? Get a bone conduction headset (ex: Shokz or cheaper alternative). Comfortable, lightweight, waterproof, you can still hear your surroundings.

Same problem with anything in-ear. I have two pairs of Shokz that I use for work (OpenComm) and play (OpenRun). I thought they would be a gimmick, but 3 years later, I love them and use them daily.

Fun hack: when I travel I prefer my over-ear noise cancelling Ankers, but they're bulky. So, for traveling light, I use Shockz and then silicone ear plugs to block out external sound on e.g. the airplane. Creates a little bit of a "swimming pool" effect acoustically, but works well and is tiny to carry.

I have a Shokz brand two-piece headset (the OpenFit 2+ i think?) that just wraps around the outside of the ear, with the actual speaker part held just outside the ear canal. I can't do in-ear buds either, but these just work for me. Doesn't even feel like anything's there.

I did try their bone-conduction headphones, but the quality was slightly worse and they didn't feel as nonexistent to wear.