I have struggled, and continue to struggle, with a lack of focus in my learning projects. My focus tends to cycle between some 6-7 subjects. In an effort to tame this, I have come to believe in the power of (a) concrete milestones and accomplishments, and (b) external accountability.
For example, I have wanted to learn Sanskrit for some time. Rather than pick up a book and work through it yet again, I enrolled in two correspondence courses that gives out certifications. I also have classes roughly once a week with an online tutor.
Similarly for Mathematics and Physics, I am preparing for and plan to write a nation-wide exam meant for MSc/BSc students in India as a minimum validation of my knowledge. I am also doing a correspondence course in BSc Physics/Maths from an accredited (in India) distance learning institution. Their assignments and exams, while easy, provide a basic timeline for my progress.
For Machine Learning and AI, I have completed several courses on Coursera and edX, but I found that even though I earned high grades in many of these courses, my grasp of topics - especially the theoretical side - wasn't satisfactory. I am re-doing some of those courses again, and intend to work through a standard text or two for the ideas to truly take root, but we'll see.
I am also interested in philosophy - both Indian and Western - and have read some material on it over the years, but I don't know what milestones are suited for it. I have considered writing up reviews of fields (such as ethics or epistemology) as a summary of my own understanding, but right now I don't have the bandwidth for this.
This was in addition to several other learning projects, such as Karnatic music and functional programming. For Karnatic music, I had a weekly session with a music tutor, and for functional programming, I forced myself for a while to commit programming exercises to github. I later quit both these projects to make room for the other learning projects.