Sidecuts for curly hair + growing it out?

I am interested in changing up my hair pretty drastically. I am pretty sure I have 3A/2C hair (I'm new to this classification so not entirely sure), and have had pretty much the same haircut for the last 14 years: long (generally mid-back at least), with either very long layers or none at all. I know how to handle this and I think it looks good, but I'm tired of it and would like to try cutting it short and/or getting a side cut (or both!)My biggest issue with a sidecut is growing it out, because I know eventually I won't want it. I've gotten opinions about this from friends who have done sidecuts, but all of them have straight hair. Has anyone done a sidecut and grown it out? What was the experience like? Manageable? Not worth it? How did you handle it?

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