Support needed for funky colours

Mellissa
I feel so silly, at 29.5 years old I should know myself better, however I find myself insecure about adding fun colours to my hair.
I added an under color an statement piece about a month ago, it was taken well by family here in Canada. And I think it needs to be fille out a bit more.
It's not for work, no bosses to impress yet... we have decided to take the summer off and beach bum camp and ride the waves in Oregon for a month. Before coming home and finding new contracts and the colour will be made a more presentable then... 
I have the bleach and color just find myself stalling for days... I am worried about a culture shock, if it's appropriate for what i'm doing or will just make me look like an angst ridden teenager?