Deep down, I hate surprises (ask the people who were unsuccessful in throwing a surprise baby shower for me when I was pregnant with my oldest; I was dead set to go to IKEA that Sunday and they basically had to sit me down to keep me from being absent). So having a plan is semi-essential to my being. My oldest is the same way; he always likes to know what's going on. 7 yo will quite often ask what's planned, too. With chagim, and a different schedule every day, and baby waking up at all hours, it was becoming a mayhem. My friend likens a good messy unschooling day to a great party. I like my parties slightly less rambunctious, where guests clean up after themselves...
One of my biggest concerns with our unschooling period was what to do with 9 yo, as he clearly needed more structure to get anything done. He is brimming with ideas, but he is very disorganized, so he is having hard time getting anything done unless it is put down in writing somewhere and then reinforced. We had many a night when just as I was tucking him in, the regret of all the things he wanted to get done but did not get to came out.
On my end of things, I am very lucky to be guided by a few veteran homeschooling moms. One of the threads that resonated with me is that it is easy to unschool and then it is just as easy to see where there are gaps. Then you are willing to enforce those areas. I have kept up chumash with the boys over the summer, so we never unschooled that. I have decided that math is vital, so that was also part of the schedule since August. I saw that 7 yo had hard time writing, so Printing Power joined the list of daily exercises. Finally, as we were getting further in chumash, I saw a need to work on more grammar, so we picked up Lashon HaTorah. 9 yo was so lost after not doing it for 6 months! We were in the middle of a unit of tense-changing vav, and he did not have those verb conjugations down. However, after a week of working on it ( and printing out a basic conjugation chart), he is much more comfortable. 7 yo knew his prefixes well, now we are working on those suffixes.
Finally, Rosetta Stone was my offer to the boys, and they both took it up, for now. I am worried about conversational Hebrew. I was kind of hoping for getting some exposure to native speakers in a casual setting ( a Hebrew-speaking babysitter, perhaps?), but it did not happen.
Now, on coming full circle, 7 yo asked me today to pick up history and science. While on the surface this is a request for even more structured learning, it is also a child-led inquiry. In this regard, that little unschooling experiment was a success: when they are interested and ready to learn it, they will ask for it.