I used to know a guy who would obsess about ‘breaking in’ a pick and it would sometimes take months. Luckily, for me, I like them straight out of the box. Jim Dunlop. Gator Grip. 2.0. I use the blunt corners (not the sharp end). I think this comes from my younger days when I couldn’t afford picks so I used to use 1p pieces. I got a big sound, but they were always metal shavings on my guitar and I used to break a lot of strings!😂