Enjoying your watch

Do you guys ever feel like the price of your watch holds you back from enjoying it sometimes?

So i recently went on a 2000 mile motorcycle road trip and was between wearing my Seiko Turtle or my Tudor BB58. I took the Turtle because I didn't want to risk damaging or losing the BB58. During this trip i did things like zip lining, rafting, etc. Throughout the whole trip I kind of wished I brought my BB58 instead.

The BB58 was my first expensive watch purchase, and i know if something would have happend to the Turtle I wouldn't go crazy but part of me says i should just use the watch I feel i will enjoy.