Long post
I know it is good and I have been guilty of this too, to take as much gear as you can. I sent to Japan with 35/50/85 primes too thinking I will miss some shots and in the end as I suspect like I always do, I took 7600 shots on my 35mm and 200 each on the 50/85. I should have just taken my 35mm.
In the past I use holidays as a testing ground for my new lenses, whatever I just got, I would just take that, make the most of of it, be it a 35mm, 50mm, 45 Tilt Shift. There is no better time to use a piece of gear non-stop but without pressure. Just go for it, you learn the limit of you, the lens and you pick up what situation it is good for, what situation it isn't good for, it improves your improvisation skills and you come away with the best images you can achieve with that lens. Because the situation forces you to work your hardest if you really want to photograph something, you will work at it, so inadvertently you end up with an better thought through image, a better image than just point at something with a zoom. Using a prime forces you to think.
Learn to let go, this will make you learn what you can take instead with what you have and you will come away with better images and as a better photographer.