What the Study of Chess Experts Teaches Us About Building a Remarkable Life
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Does anyone have a system for answering this question?
There may be literature out there on this -- please tell me if you know of any.
You probably want to look at examples where this has been done and try to abstract a method out of those. Neil Strauss's The Game (about pick-up artists) is a marvellous example. And Colvin explains in Talent is Overrated how Abraham Lincoln deliberately practiced writing by analysing, simplifying, and trying to reproduce others' writing.
If I were to attempt an answer, I'd try something along these lines:
1. Figure out what an excellent outcome is.
For writing, this might be a collection of articles/books. Tricker for entrepreneurship. Are Page and Brin examples of excellence for entrepreneurship? Could you model them and be successful without being in the specific situation they were in? Is Branson a better example? Is it likelihood of success, imapct, or profit that you want to optimise? It's worth noting that many things that have a tradition of deliberate practice -- chess, music, and sports -- have simple measures of excellence (win, make it sound nice, win).
2. Break out the outcome aspects that matter.
Good writing not only has clear and lucid prose, but a storytelling structure that engages and entertains the reader. Entrepreneurship involves, amongst other things, identifying a solution, producing the solution, marketing to customers and investors, inspiring employees.
3. Compile specific examples of the aspects.
Get articles with excellent prose and books with excellent stories. This is harder for entrepreneurship, but probably doable.
4. Modify the specific examples into exercises.
Rewrite the article into bullet points so that you can later write the prose from those. Split the story into pieces and write on cards so you can later practice arranging the story. Specify the requirements for a web-app that's a solution to a problem so that you can practice implementing it from that.
5. Perform the exercises and evaluate your performance. Repeat.
This is where the deliberate practice takes place (though performing these steps can also be a form of deliberate practice -- for meta-understanding of performance improvement in the field). The time-span of each exercise can vary enormously -- from seconds to months (for some things that can't be easily simulated).
Of course, this process should be iterated and refined. I think it would be much easier to do this with a partner that have similar goals.
What are your thoughts on this?
Robert Silverberg in his essay " The Making of a Science Fiction Writer" (originally published in "Worlds of Wonder" and later in "Reflections and Refractions - Thoughts on Science Fiction, Science and Other Matters") explains in great detail (40 pages in my edition of R&R) how he used stories of writers he admired as raw material for extracting the principles of "how to write well" (enough to be be awarded the Hugo and Nebula and sell everything he wrote) and the results of his applying these perceived principles to write stories embodying each technique.
Quoting from azgolfer's comment above, "In music, one huge factor is copying people. Stevie Ray Vaughan not only knew every Albert King lick, he knew them well enough to use them in new ways. To be a good musician, you need vocabulary and facility. Learning to play other peoples licks will help you with both."
Silverberg copied writers he admired. But the principle is the same - study a "work" that has already achieved your desired outcome, extract a principle or technique by analysis, embody it in your work, get real world feedback on its effectiveness. Rinse, repeat.
Caveat: I am not very sure how this would apply to entrepreneurship.