Should I dye my hair even tho it's damaged?

I've always had light hair which of course requires a lot of bleach the thing is that in the summer I dyed my hair sooooo much and it felt my hair feeling dry and having so many split ends. I dyed my hair one last time close to my "natural hair color" which is like a dark brown. Everyone says to dye it back light because it looks better but my hair is sooo dry and I want glossy shiny healthy hair. What should I do.