I suspect the last time Personalized Learning was great when Plato was learning what he wanted (philosophy) from who he wanted (Socrates).
Personalized learning is often equated to learning with a computer or technology-based instruction and while technology has an important role to play, it should not replace or overshadow a structural reform of the educational system. This is how I envision an ideal future for my son, who will be in high school in 2030. His strengths, needs, skills and interests are regularly assessed through a series of interviews by one or several educational psychologists who create a personality profile. This profile will be updated by each of his subsequent teachers. It is used to help him choose a direction in his education as well as individual courses that fit that direction. There are no mandatory courses. For each individual course, he gets to choose his own teacher (since technology allows it, maybe even out of thousands of teachers across Canada) or even multiple teachers. Perhaps that is how he also gets to choose what he learns in that course. Let’s say if it’s Psychology, he gets to pick individual theories he is interested in. No more memorizing useless information for tests. I doubt that Socrates was giving multiple-choice tests to Plato and grading him. Abolishing tests altogether might not be a bad idea. For admission to higher education, a comprehensive personality profile built over 10 years of school can be used along with a series of interviews and oral presentations of accumulated knowledge.
Is this likely to happen in Canada? Not in 10 years. The inertia of the existing system is too strong to overcome. It can only happen in a built from the scratch alternative system. If it does happen in the distant future, who is more likely to take the risk, a public system or private enterprise?