From Law School to developer: An interview with Andy Zhang
hireart.com
hireart.com
The fortunate thing about online education today (coursera/udacity to name a few) is that it strips away a lot of the tough/complex issues, offers you a bite-sized problem, and breaks it down into a manageable chunk that a non-tech person can solve. It's not unlike how a management consulting case interview might go - you can't possibly know everything about an industry/space, but you can (1) break out a facet of the problem, (2) ask some questions, and (3) distill the incoming data. You develop understanding incrementally.
I'm a big fan of incrementality (also in writing software). Everybody starts out writing "Hello World!"