I was exposed to a really compelling version of design stance at an early age, since I somehow discovered Victor Papanek's Design for the Real World at the public library (quite possible heard about it via Whole Earth Catalog). This was an eye-opening and intense book, as Papanek excoriated the profession of industrial design for spending its energies on trivial things while the real problems of the world are begging for creative solutions. At the time I read it I probably had no idea that there was such a thing as industrial design, but now I not only was aware, I had strong opinions about it.
The Dispossessed was a big influence on me; it turned anarchism from an abstract idea into a living image of a better world. The genius of the book was that it was not a utopia; it depicted an anarchist society struggling against the obvious natural human tendencies towards selfishness and power.
Ted Nelson is a famous computer visionary, best known for coining the word hypertext. He was not the first person to see the huge potential of computers to enhance human thought, but I certainly learned about that from him – his book Computer Lib / Dream Machines was an early influence.
See Stewart Brand. The Catalog was a major early influence on me, particularly in its stance that one could be interested in anything and pursue anything. There was a Whole Earth Bookstore in Evanston, IL where I grew up, which is where I found both the catalog and Ted Nelson's Computer Lib/Dream Machines. When I went off to MIT I managed to fall in with a bunch of Whole Earth-friendly fellow students who were into alternative energy and other alternatives; later I got to actually share an office with SB himself in the early days of the Media Lab.
One of my main influence s. I learned a lot from Phil, who despite being a grad student in an engineering department seemed to have read widely in philosophy, sociology, and other exotic subjects. But the main lesson he taught was a stance-related thing; that one could do technical work while at the same time having a rigorously critical attitude about the work, the field, and society. Probably his essay Towards a Critical Technical Practice is the best explicit articulation of this, but it's a quality that comes through in much of his work.
The Dispossessed, Le Guin. This belongs on my list of major influence s; it's rich portrayal an anarchist society in all of its contradictions and problems really made the ideal alive for me, for a time.
A big influence and so far the only one that isn't a person (John McCarthy invented the first version but it's grown quite beyond his original concept). I learned Lisp by hanging out at the MIT AI lab with some of the Symbolics founders, and have been using it as my main tool ever since. The Lisp Machine remains at the pinnacle of environments for programming as a design activity; I don't know why the state of the art hasn't advanced since then.
David Chapman (aka @meaningness) has been a major influence on my own thinking. His work at the MIT AI lab with Phil Agre made a deep impression on me when I was trying to figure out my own academic path. This included a critical take on the standard cognitive science view of the mind, which is pretty much Rationalism minus the more cultish and cartoonish aspects.