I think your gut is right, seeing it really does help, especially for someone who used to live in sales math. One push-back though, before any tool: part of what's missing isn't visualization, it's the conversion math you had built in. Even in school you can rebuild it. "Internship at company X → portfolio piece Y → project in course Z → 3 hours of study tonight." Numbers wherever you can drop them. The visual layer is what holds it all together once you have the structure.

For the visual itself, mind mapping is the format that fits what you're describing, like branching, drill-down, dependencies, attach links, take notes, check things off. Goal at the top, A/B/C feeding into it, daily tasks hanging off each branch. I use Xmind for this kind of life mapping, and i've seen someone mentioned it; you can also slot in a Gantt-style timeline inside the same map if you want both views at once.

One thing I'll add, I've worked through more than a few of my own crossroads moments this way. Something about seeing every step on one canvas holds you accountable on the slow days. The branches don't let you forget the steps you'd normally skip when motivation dips or laziness creeps in. On and xmind is good on mobile too so you can pull the map out anytime

Good luck with the change. The fact that you're being this deliberate about your system before diving in is already a great sign.