Did you try switching to a sharper shovel? I kept having the same issue until I got one that was actually meant for digging, not just for moving loose soil.
Oh wow, that's one of those things that makes you stop and think lol. Last week I was trying to plant a bush and my neighbor came over and handed me this super pointy trowel he uses for cactus stuff, and it changed everything. @the_elliot is probably right about the sharper shovel being key, but now I'm just wondering how many other basic tools I've been using wrong my whole life lol.