Let me put on my Project Management hat for a moment. I think you first need to enumerate, at the highest level what you want to achieve, should be one sentence or less. Maybe its "Become a world class python oriented Data Scientist". Under that you can break that down into four-ish domains you need to learn, in this case, Statistics, Python, Data Science, Data Visualization. From there break it down into subjects under those domains, each one being maybe 20-200 hours of work. Continue to break it down until you get to something you can accomplish in one sitting. One sitting is different for all people, for me it's about 50 minutes. Then when you sit down you don't have the cognitive overhead of trying to figure out what to do, it's already been done for you. From there, just knock out tasks one after another. Every few months re-examine to make sure you are on course. As far as tools, I use Trello to do this personnally, but there are others out there.