I totally get that. I've had the Bose Sport wired headphones and they worked/felt great. To be honest, the original Google Pixel Buds had a similar design and it worked well for me also. Sadly, the newest Pixel Buds don't work for me, and the upward facing tip isn't adjustable or replaceable on those. Bummer.
I take it you prefer an open-ear design with your headphones?