One type of person is naturally organized and can self-manage easily. Sometimes the lessons are learned after making mistakes in real life and we adapt our behavior easily and quickly after one or a few mistakes.
Some people need monitoring to get into a groove.
Some people seem seriously challenged with self-managment and need to be directly told some things that may seem intuitive or common sense to the rest of us. Put your book in that spot when you are finished. Keep your papers in one place in an organized manner. Know what you did with your homework assignment. Know your schedule. Update your schedule when changes occur.
New systems such as getting used to a new internet platform for an online class can be a big challenge for some people.
I seem to have kids on the opposite side of each spectrum. I am more mature than they are and the way I am today is not the way I was when I was young. I am wiser and more organized and neater now than I was when I was a preteen and a teen. It is hard for me to shift gears from what I know is best (that sometimes borders on perfectionism) and what is reasonable to expect and then to figure out how to deal with each kid to shift gears to teach them these things without sounding like a critical complainer or a nag.
Homeschooling more rigorous academics in the junior high and high school years is a challenge. I thought that outsourcing some of the teaching to others this year would be less of a burden on me but so far it is more work for me! I am happy to report that the classes I selected are rigorous which I wanted, but they are harder than I thought, and this is a both a blessing and a curse. My kids are being pushed to do hard work, (and some busy work in some cases). They are doing some quality learning too, of course. They have to comply with external deadlines, report to an authority who is not me and take quizzes, tests, and get graded by unemotional third party teachers. While this does not seem unreasonable to those who live the school life you need to know that my kids have had an alternative education using unshooling, then Charlotte Mason, then an eclectic largely "learning by doing" experience. All those things were the polar extreme from reading boring textbooks and answering homework questions and memorizing the periodic table and being tested on terms.
I can't say my kids are at a place where they are doing learning for the sheer joy of learning in all of their classes. They are being tested and tried by the rigor. They are both doing a college prep program, one is the classical education model. These are basic courses that will more than fulfill high school graduation requirements. They are learning and they will grow their minds in this process so it is worth it. They are doing these things in order to keep the door open to seek the career of their choice. They are doing these things because they have to if they want to do those careers.
The last thing that remains a challenge for both of my kids is having a full academic load and continuing to play a four season sport plus do Boy Scouts. My older son is also juggling participation in the year-round FIRST Robotics team. I don't want them to not fulfill their passions, to not have a social life, and to not do the sport they love which also has or is getting them into top physical condition.
If my kids had it their way they would narrow their academics to their passion areas and skip doing what they hate. They would avoid history as they think it is meaningless in their lives. My sophomore says he would like to spread his academics over six years (not four) so that he could do the robotics at a high participation level, do Boy Scouts with its leadership roles and for the fun of it, and do the sport at an intense competitive level which he now craves for physical fitness and for the full social life it provides.
But we live in America where high school is supposed to be only four years and where colleges still want (practically demand) that students enroll as freshman at age 18. So we are trying to squeeze our alternative education kids into the cookie cutter as much as we can while still allowing them to have time to do the extracurricular activities that provide them the personal fulfillment they love and which helps make them the unique people they are developing to be.