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To be fair, it is pretty difficult to imagine his situation. It is such an outlier example that it is needs more information to fully understand; information which is lacking from the article.

At 29, he's had 15 solid working years behind him. Not a single job in that time? (less a couple of short contracts - which are still jobs, so the headline is a bit of a misnomer) The economy hasn't been bad for that long, and arguably still isn't that bad, at least in Canada.

I get the impression that he decided to spend the first 20-some-odd years of his life focusing on himself, which is fine, I respect that if done without any illusions, but now he's scrambling to catch up thinking he should be at the same level as his peers who have spent years focusing on their careers. The world doesn't work that way.

If that is not his situation, it wasn't clear from the article.