This is a healthy way to critique it. I think the most positive element is not any of the tangibles he mentions, but that he's consistently found ways to pursue

This is a healthy way to critique it. I think the most positive element is not any of the tangibles he mentions, but that he's consistently found ways to pursue battles of his own choosing, and to artfully spin failures into the launchpad for a new adventure. The hits he's scored are materially not so big, in part because he's avoided major commitments - and had he done more of the things he finds boring and stressful he would have more commitments, more hits, and probably be wealthier - but it's a sucker's game to get into comparative success. You don't get to have any of these experiences at all if you stick to the salaryman path, and that's the underlying appeal; the audacity of being able to strike out on your own and actually make it work for a while. It keeps a dream alive for a lot of clock-punching developers.