my hair plan

so, i have a hair plan (yes, i can get vain, bored, and overthink simple things sometimes):

1) grow out my hair to about the length it was in high school - a little longer than shoulder length. i want to be able to put my hair in a low ponytail. i imagine the growing-out process will be painful, but perhaps if i consult a professional along the way, they can help me?

2) keep it that long until it starts really going gray (which may not be that long) - or until i have a new plan.

3) when it's mainly gray, i hope to cut it into a bob - chin-length-ish in the front, and shorter in the back. my thought is that it will be more wire-y and thus get a little more crazy-voluminous than it even is now at this length. i'd like to have the same hair that this lady who coordinated a day-long zen retreat that i went to back in college.