Am I the problem?

Hi everyone. I really struggle with managing reports who need a lot of structure, because to me, micromanaging is the highest form of disrespect.So I'm looking for some resources on how to manage someone who needs frequent check-ins, help structuring their day, and to-do lists that we create together. As someone who's extremely autonomous and self-directed, and excels in ambiguous situations, I personally find it insufferable when my higher-ups try to give me direction that's anything more than high-level guidance. I'm really struggling with one of my (fulltime) reports in particular because he isn't productive unless I'm (for all practical purposes) micromanaging him and keeping himself accountable by showing small bites of progress throughout every workday. He seems not to mind, or possibly even like this structure, but I'm having trouble knowing where to draw the line. And at some point, it ends up taking a lot of my own time to be doing this too. For months I was giving him much too much freedom and his productivity was really low. This stressed him out and it stressed me out too. Finally, for the last month we've been doing a system where he and I write out word for word what he'll be delivering during the week, and checking off the boxes as he goes, and this system is working better, but I still personally struggle with how much I should check in on him to keep him on track. Whenever I ask him during the day how things are going, he brings a bunch of things to my attention that he's blocked on. It's almost like when he's stuck, he's just not doing anything! And that he doesn't know how to ask ambiguous questions (like when you're stuck on something but you don't really know how to go about getting yourself un-stuck). And, when he does ping me for a question, if I'm in a meeting and I can't respond right away, I have a feeling he just stops working on stuff until I answer, which can sometimes be hours...instead of working on something else in the meantime. Sorry if this wasn't very structured. Any ideas would be welcome. Is my management style the problem? Is he the problem? This is my first report so I'm much more inclined to think I'm the issue here, and I just want to find ways to remedy this situation.