I transitioned for 3 years.
Yes, seriously, 3 years. I did my mini-chop right before my freshman year of high school, and though now I have the self-confidence to rock short curly hair, I didn't at the time. (Which I kind of regret... it's really flattering on almost everybody I see it on.)
My hair was really never straight past the first shower when I had a relaxer though---it was always awful at holding the straightness, and it takes waaay to long to straighten my coarse/dense hair. Also, my hair keeps growing new layers, so I got a complete under layer of ringlets after my 2nd year transitioning, that basically made me do half-up, half-down styles alllll the time.
I didn't figure out how to manage my hair until after I chopped it off, and my hair actually looked decent. By chance, I had also switched to cone-free condish (GTFN, which is no longer cone-free), and it had worked miracles on my cone-hating hair.