The Education of the Self Taught Designer

A Rube Goldberg design.  The term "Rube Goldberg" has come to mean any overly complicated contraption.  I think Rube was drawing parodies of products produced in the gizmo enamored society that he lived in.

Someone once said that you can't design a thing that you've never built before.  Experience has taught me that this is true.  What that pronouncement means is that to design a thing, you know ahead of time how each design decision will affect the performance of the finished product.  The rub is that until you actually build a thing for the first time there is little chance that it will actually work.
You can of course go to a school where they teach you how to design stuff and you get the benefit of someone else telling you what works and what doesn't so you don't have to figure it out for yourself.
But as I recently observed with the business of designing kayak paddles,  there's nothing like building something that doesn't work to teach you why you should build things that work.  Building things that don't work draw the border on what is possible.  Stray outside that border and you get stuff that doesn't work.  Stay inside the border and you get stuff the works.
So mistakes and bad designs are important because they provide the designer with a better understanding why stuff that works works.  If everything worked then there wouldn't be a need for designers. Designers, good ones at least have a good mental map of the territory of what is possible and what isn't.  The more things the designer has actually built and failed at, the fewer bad designs he / she is likely to pass off on customers.