It seems we do share some things in common. I eventually built a comfortable upper middle class lifestyle for myself, but had I been more motivated in my school age years I had potential for a lot more than that. I was simply too much of a procrastinator to qualify for any kind of scholarships, and my parents would have really struggled to help put me through an expensive university education so tech school ultimately made sense for me. A nice benefit of that was the ability to step into the workforce after only a few years of extra education without having to take on massive amounts of student loan debt
I recently worked my way into the top 10% of Canadian earners as well, but it wasn't necessarily due to underemployment in my case. It took me a prolonged time of putting in my dues working my way up the chain over the years.