Part of it's the writing. Take the headline. "Finding the unjustly homeless, and teaching them to code."
So, uh, who exactly are the "unjustly homeless"? The piece doesn't really say. The closest it gets is this fascinating sentence meant to explain McConlogue's interest in this particular homeless person: "Before you think this is some weird 'fish bowl' experiment, you can just tell when he looks at you" — "he" being the homeless man in question — "that he lost a series of battles."
So the justly homeless are the people who look at you and you can just tell that they ended up on the street after a series of triumphs?
The piece's most objectionable quality is McConlogue trying to absorb this homeless man — a real person, with an actual history that McConlogue can't really intuit by looking into his eyes — into his precanned, triumphant programmer narrative.
The reason I keep saying "homeless man," for instance, is that for all his big plans — and despite already writing about him on the Internet — McConlogue hasn't bothered to find out the guy's name, or even talk to him. "I will call him 'The Journeyman Hacker' until I discover his true name," McConlogue writes. McConlogue has written this guy's story before even saying "hello."
But if McConlogue's help is ham-handed, it's still an effort to help. He's still — assuming he goes through with it — actually doing something more than quickening his pace as he walks by this guy.
I think the question is whether McConlogue follows through. It's easy to write a blog post about your good intentions. It's harder to walk up to the object of your heroic fantasies and actually deal with their reality. But if he does, he might learn something. And since he clearly wants to help, he might end up actually helping — even if it's not in the way he expected.
It's easy to be offended by his tone-deaf post. And it's easy to mock it. But as Slate's Will Oremus tweeted, "what do you do when you pass a homeless guy on the street every day, and are you sure that's so much more helpful?"