Wow...I have transitioned 4 times in the past, this is my 5th and last.
First time: I was 15 years old, had no idea what my natural hair looked like; mom relaxed me at 5! Didn't know anything about hair boards just stopped relaxing, and rollerset my hair for 13 months with mini chops the whole time. Relaxed after 1 month natural.
Second time: Transitioned for 5 months, had a big event to go to in the summer, my hair was looking CRAZY so I relaxed and regretted it.
Third time: Transitioned for 9 months, bc'd hated it then grew to love it as it grew longer! My hair was the healthiest it had ever been, grew to nearly BSL. After a year or so I couldn't take the tangles and relaxed again.. regretted it that day.
Fourth time: My hair was longest it had ever been (almost BSL) a stylist overprocessed me and clumps of hair broke off in the back and I made the decision to go natural. I had to cut my hair to an inverted bob to blend the damage... this cut was NOT the biz on 5 months post hair (required too frequent heat, since I couldn't wear a pony) so I relaxed.
Fifth time: Currently almost 9 months post, and I'm sticking it out for at least 3 more months! This has been the toughest transition since I started with short hair, every other time I had hair that was at least SL... but I'm trucking though!