Painful? Maybe a little, but the rewards you get should far outweigh the pain you experience, so it is a net positive gain. If anything you're doing feels like torture, then it's not worth it. After the first couple of weeks, there should be no pain, just growth.
Most importantly, you don't have to follow everything Steve does and try it yourself. If something doesn't resonate with you and it feels like torture to do, you're completely free not to do it.