Tom Leinenweber, 46, attorney

( Beth Rooney, Chicago Tribune / September 7, 2012 )

He says he's weighed down with an overflowing briefcase because he's delivering two giant textbooks -- American history and college algebra -- to his high school son. Leinenweber made a tactical mistake, having the online retailer send the books to his office when he should have had them sent to the house.

What's right: Not much. He's so hard on his briefcases, even when not carrying high school text books, he has to buy a new one every year.

What's wrong: The bag is digging into his shoulder; wearing it cross body would distribute the weight.