I greatly enjoyed Barry Berkus' "How to Think Like an Architect" videos, and have been searching in vain for an industrial design counterpart. To have a creative designer walk you through, in plain English, a design as it unfurls is immensely edifying, but I can't find an ID guy who's done it.
I did, however, luckily stumble across Field Notes man and Curiosity Club veteran Aaron Draplin breaking down a graphic design project. Learning website Lynda.com tasked Draplin with designing a logo—something that can take months—and condensing it all into a sit-able video. Not only does Draplin render his process completely transparent, there's a bonus starting around 15:00, when he discusses what happened after he decided to go freelance.
Aaron Draplin Takes On a Logo Design Challenge from lynda.com on Vimeo.