A guy's biggest style mistake is definitely trying to look too cool. As long as you've got a good pair of jeans, a good pair of boots and a few good shirts, you're fine.
Imagine if you had baseball cards that showed all the performance stats for your people: batting averages, home runs, errors, ERAs, win/loss records. You could see what they did well and poorly and call on the right people to play the right positions in a very transparent way.
Also, I need deadlines, just like everybody else, especially coming from magazines, newspapers, and stuff like that. I need daily or weekly deadlines to get stuff done, or I continue to do things and not go off on a year of unproductivity.