I don't do messes very well. I try - I try really, really hard - to not let that affect allowing my "kids to be kids". In fact, these days I'm the parent in the household who is more apt to let them go outside barefoot or get all their toys out and spread them all over, so yay, me! I just make sure everyone and everything gets cleaned up right away.
I'm weirdly proud that I let Little Lady go at some 'real' painting at just over one year old. It took me a few more months than that to let Mini Me go at it the first time. Little Lady still loves to rub food in her hair so I was prepared to deal with painted hair.
We taped a piece of card stock to the table cloth, she chose the colors she wanted, I dabbed some paint globs on the paper, and she smeared, examined, poked, and tasted.
She was painted from her fingertips to her elbows, but it cleaned easily. The end result is really pretty (I like how the tape left a little 'frame' around the edges) and I felt a little ashamed that I don't let the messes happen a little more often. So... since this first attempt we have been doing some messier things a little more and it's fun (and good) for us all.
I just love that as my children continue to grow and learn, I do, too!