Can anyone help this man?

Readers! Help me play agony uncle to Chris.

As you'll know if you have been following my blog -- and I apologise if not, as some of this won't make much sense -- a number of themes have recurred many times already, and will continue to recur. They include setting ourselves personal challenges and working on them collectively (as seen in the Ten-Year Self-Improvement Challenge [TYSIC:], which I will be summarising later this week); embarking on bizarre team efforts (like the iPod, which...