Growing out short hair to long is kind of a nightmare... I would know - I've done it 3 times in my life. The last time I did it I was fortunate enough to be pregnant 2 times and took weekly pictures of myself. I won't bore you with the weekly progress, but here is my hair over about a 3 year period. You can see how short it got (the bleach blonde) and then where I went from there. The two hardest stages are getting it from a short style to bob style and then from shoulder length to past the shoulders. I think those two are the hardest because those are the points where I always want to cut mine back off.
March 2005: just cut off my bob length hair
April 2005: cut off like Keira Knightley 's hair on the cover of Elle Magazine (and no I'm not drunk in this picture just really happy with my cut)
June 2005: cut off to almost mens length (the back and sides were clipper cut) and bleached blonde. I cut it this short so I could get this blonde.
March 2006: colored dark again with highlights and getting closer to bob length. When I grow my hair out, I change the color so I don't get bored with it.
August 2006: cut off to a shag since I didn't like the mom bob thing I had going (and being almost 9 mo pregnant I needed to feel cute). BTW this is just a couple of days before my son was born :)
February 2007: still dark and grown into a bob length again. Bangs are pretty wispy from the "after-baby hair loss."
August 2007: 1 year since I cut it off into a Shag. Now much lighter and shoulder length.
February 2008: 6 mo later almost past the shoulders and even lighter. I cut heavier bangs to change up the style and help with my hair boredom.
August 2008: finally past the shoulders, still rockin it light with the heavy bangs. About 4 weeks before I had my daughter.