I recently got a pair of Red Wing boots for the first time in a very long time. I had a pair several years ago but lost them after playing a show. (Long story short, don’t let a merch guy pack your personal items, especially when you’re in a rush.)
Day one was of the most uncomfortable days my feet had experienced in a very long time. I’d forgotten how much fresh leather hurts. The instant gratification of comfort is not an option when it comes to breaking in real leather boots. Everything about my feet hurt, the arches, the soles even, my toes.
It’s currently day seven of wearing them constantly (possibly falling asleep in them a couple of times. I’m pretty sure I burned a hundred calories). The leather has softened and there are creases from using them like they should be.
The good things in life will take cultivation and time. At some point, durable things will involve pain but if you can last through it, it makes it all worth it.