^I think it's best if you find out which tones best suit you. I've noticed most times it's not about how dark or light you go, it's about finding the right shade of whatever color you want. So look if warm tones suit you or if you should aim for cold ones..
Going a light brown route can be good as you'll gradually get used to the darker hair and from then on you can slowly go darker.
Going a light brown route can be good as you'll gradually get used to the darker hair and from then on you can slowly go darker.