The album's legacy is mixed, precisely… [because] opened up a whole new path of freedom to jazz musicians: Those who had something to say thrived; those who didn't, noodled. That's the dark side of what Miles Davis and George Russell (and, a few months later, Ornette Coleman, in his own even-freer style of jazz) wrought: a lot of noodling—New Age noodling, jazz-rock-fusion noodling, blaring-and-squealing noodling—all of it baleful, boring, and deadly (literally deadly, given the rise of tight and riveting rock 'n' roll). Some of their successors confused freedom with just blowing whatever came into their heads, and it turned out there wasn't much there.
We often associate freedom with creativity, and assume that the more of the first you have, the more of the second you'll have. Our tendency to see creativity as sudden inspiration; as something that young people are better at (witness Silicon Valley's fetishizing of 20-something programmers and entrepreneurs, or our assumption that young children are more creative than their stodgy parents); and as an activity that's nearly impossible to formally promote (you can't manage creativity, as one article put it; you have to manage for creativity), combine to make it seem like the best way to encourage creativity is to just turn people loose.
But as Kaplan points out, usually that's not quite the case. Lots of creative moments combine preparation and training with serendipity or the creativity that emerges out of responding to in-the-moment challenges or opportunities (travel, biking, workshops and cooking are all examples). Other creative acts are grounded in, or push the boundaries of, the nature and limits of the media you're working with (this applies equally to crayons or Lie groups or reinforced concrete). The tinkering movement recognizes the fundamental materiality of most creative work, and puts engagement with stuff at its center. And as Matthew Crawford and Richard Sennett argue in their books, the creativity of everyone from machinists to musicians is tested and tempered by the demands that their materials make, and the traditions in which they work.
In other words, thinking of "creativity" as mainly an expression of a psychological gift– a capacity to be creative– is wrong. Or it's incomplete. People aren't creative when they're free to do whatever they want. They're creative when they're free to experiment, to try out new things, to fail at the boundaries.