Lots of selective memory and faulty reasoning here. Take his first example: "Took art classes in high school instead of working out with the football team. I design for a living now." It's easy to retroactively give a positive interpretation to any life choice you might make, but consider the alternative. Had he chosen football instead of art he might be looking back thankfully that the decision lead him down the path to becoming an NFL star, or sports announcer, or whatever.
Similarly, the folks who took risks, ignored the common wisdom, and failed miserably may not be writing blog posts extolling risk taking and ignoring the common wisdom. IMHO there's no sound generalization to make about risk. Sometimes it's good, sometimes it's not, and plenty depends on our attitude towards it.