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Recently I posted on how freethinkers are obstacles to innovation, by being both undiscriminating on ideas and undesirable as social associates. Today let me outline how best to be radical, if you must.
Freethinkers who work on a radical idea or project tend to shoot themselves in the foot by trying to be radical on as many dimensions as possible. For example, if they manage to get funding for a startup pursuing their radical software product, they try to also be radical on software tools, project management, office location and organization, personnel, compensation, meeting times, work hours, marketing, and so on. In their personal lives they try to be radical on romance, household organization, medical care, education, clothing, music, and so on. This freethinker strategy of being radical on every possible dimension pretty much guarantees that something will go very wrong with at least one of these dimensions.
To have the best chance of succeeding in a radical project, you should instead choose just a few related dimensions on which to make radical choices, and then make conservative conventional choices on all the other dimensions. This strategy minimizes the chance that some other project dimension will go badly wrong and take down your central radical idea with it.
While all-dimension-radical freethinker projects have little chance of success, their looming wreckage can be a great place to look for promising radical ideas to pursue – many a successful radical project idea was "stolen" from freethinker predecessors. So if you are shopping for a radical idea to pursue, make friends with ambitious freethinkers – but don’t pick up their undiscriminating habits.
How to be Radical
"Another personality defect is ego assertion and I'll speak in this case of my own experience. I came from Los Alamos and in the early days I was using a machine in New York at 590 Madison Avenue where we merely rented time. I was still dressing in western clothes, big slash pockets, a bolo and all those things. I vaguely noticed that I was not getting as good service as other people. So I set out to measure. You came in and you waited for your turn; I felt I was not getting a fair deal. I said to myself, "Why? No Vice President at IBM said, `Give Hamming a bad time'. It is the secretaries at the bottom who are doing this. When a slot appears, they'll rush to find someone to slip in, but they go out and find somebody else. Now, why? I haven't mistreated them." Answer, I wasn't dressing the way they felt somebody in that situation should. It came down to just that - I wasn't dressing properly. I had to make the decision - was I going to assert my ego and dress the way I wanted to and have it steadily drain my effort from my professional life, or was I going to appear to conform better? I decided I would make an effort to appear to conform properly. The moment I did, I got much better service. And now, as an old colorful character, I get better service than other people.John Tukey almost always dressed very casually. He would go into an important office and it would take a long time before the other fellow realized that this is a first-class man and he had better listen. For a long time John has had to overcome this kind of hostility. It's wasted effort! I didn't say you should conform; I said "The appearance of conforming gets you a long way." If you chose to assert your ego in any number of ways, "I am going to do it my way," you pay a small steady price throughout the whole of your professional career. And this, over a whole lifetime, adds up to an enormous amount of needless trouble.When they moved the library from the middle of Murray Hill to the far end, a friend of mine put in a request for a bicycle. Well, the organization was not dumb. They waited awhile and sent back a map of the grounds saying, "Will you please indicate on this map what paths you are going to take so we can get an insurance policy covering you." A few more weeks went by. They then asked, "Where are you going to store the bicycle and how will it be locked so we can do so and so." He finally realized that of course he was going to be red-taped to death so he gave in. He rose to be the President of Bell Laboratories....Many a second-rate fellow gets caught up in some little twitting of the system, and carries it through to warfare. He expends his energy in a foolish project. Now you are going to tell me that somebody has to change the system. I agree; somebody's has to. Which do you want to be? The person who changes the system or the person who does first-class science? Which person is it that you want to be? Be clear, when you fight the system and struggle with it, what you are doing, how far to go out of amusement, and how much to waste your effort fighting the system."
Richard Hamming, "You and Your Research" http://www.cs.virginia.edu/...
Robin, your "free thinker" whose "negative self-definition seems to have more force" on him than rationality is a character I recognize from conversations, accusations, and sour opinions of my own, but not from real life. I don't think that's anybody's actual central motivation. I don't think that characterizes the middle of the clump of "free thinkers."
I remember people with strong individual ideas, styles and approaches, and sometimes strong ideas about how to judge truth or falsehood. And of course all of these have ramifications. I remember cranky, lonely and broken people. Also I can think of lots of rationales for respecting or pursuing unconventionality per se in certain contexts.
I agree a lot of us have a reactions against conventional ways that we should watch for. "Shooting yourself in the foot" is a good metaphor for depriving yourself of a safe support while making a risky grab.
I suppose my main problem with this advice is that, to a weirdo, it's not weirdness but conformity that seems problematic and to require deliberate effort. The idea that he's turning up the weirdness knob and just needs to ease off... might have more truth to it than weirdos like me like to admit, but if so it's hard or elusive.