The time I spent with the organizer was both. I wanted to cry a bit (luckily he had big shoulders to cry on). And, my husband was there helping too (and he ALSO has big shoulders).
Things I learned:
1) People are different. My husband, my assistant and I all were around for this and we were all immediately diagnosed as ADHA, OCD & pregnant, respectively. Totally nailed it. We all have such different styles of what to do with stuff and HOW to deal with it.
2) When everything from one closet is out on the floor in piles you will probably want to give up. If you are really lucky and have someone there to help, they won't let you.
3) You might not finish in a day. These projects can take some tweaking over time. Be hopeful, but flexible.
4) You have more shit than you ever thought possible.
5) Trash day doesn't happen nearly as often as one might like. So, remember to plan in advance for the throwing stuff out portion of the process. I didn't plan well enough for this. So, a few days later we still have a section of crap to deal with...
6) Old paint smells really, really bad.
7) Drink a lot of water.
THIS LINK: DIRTY LITTLE SECRETS OF TIDY FAMILIES really reminded me that LESS STUFF is GOOD.
THIS LINK: MAKING SPACE CLEANSE sounds like a great way to begin and set intentions for some serious process.