Encouragement-bombing goes here: toturi. Every bit helps =)
I think he feels like he needs to write a technical blog and be super interesting, drawing a huge readership, like Raymond Chen. But a large part of the difficulty is that he can't say much about Work. He's very hesitant about writing technical stuff.
I can totally understand that. I stay very skirty and vague about Work too, but even without talking about Work, there's fantastic journalling fodder in a lot of things he says to me. He has great stories to tell, really funny and interesting things that he says. And he's a really good writer.
I keep saying, "you SO should blog that!" and "see, that's the kind of thing you should be writing in your LJ." But he always says that I'm the only one who finds it funny/interesting/whatever.
I've even threatened to post his non-Work stories and funnies here in my journal, without his permission, for all the free world to see. I was trying to get him to write them up on his own so that I wouldn't mangle them beyond recognition.
But he's not biting. Maybe I should just make good on my threats.