A Tour Guide
Photo Courtesy of Jamie Trueblood / AMC
Don took his kids to see his childhood home at the end of Season 6, which got us thinking: he would be the best tour guide ever! He's a great public speaker but doesn't talk too much, he's handsome, and he can tell really sad, creepy stories about each location. He could even do a "Whorehouses of Pennsylvania Tour." Too far?
An ASPCA Representative
He loves puppies. Hell, who doesn't? Caring for some helpless creatures would teach Don some compassion, and he could use a new furry best friend. Besides, who could say no to Don when he pleads for a loving home for a poor animal?
Don Draper thinks he's the voice of a generation (or something) and has a lot of compelling stories to tell, especially of his fucked up Dick Whitman childhood and his time in the Korean War. Besides, he blew his cover (and his career) when he told the truth to the folks at Hershey and his co-workers. Might as well get it all out now and make a buck at it.
Remember how well he nailed "Father Abraham" with his son and ex-wife at summer camp? The man's a regular Fred Astaire! Imagine all the possibilities!
No one knows the value of a nap more than this guy - he sleeps all over the place: at home, the office, mistresses' homes, and hotels. The dude knows mattresses. He'd be able to sell them just as well as all his pitches to Heinz, American Airlines, Jantzen, and London Fog. (But hopefully better than his pitch to Hershey. Wink, wink.)
Now. Hear. This.
Beautiful women don't intimidate Don one bit. He has some experience in casting models at the ad agency, so this should be a piece of cake. All he has to do is hang at the right bars, and they'll come to him. Cha-ching!
Don may not know how to make a ton of different drinks, but he knows the science of an Old Fashioned better than anyone. Plus he has a bartender's personality - just watch how effortlessly he makes Conrad Hilton a drink, while simultaneously listening to his problems.