[W]hen it came time for Obama to leave home he reversed what his mother and father and grandparents had done: he turned around and moved east. First back to the mainland, spending two years of college in California, then farther, to New York. He ended up in Chicago, back in the Midwest, from which his mother’s parents had fled, embracing everything they had escaped—the constriction of tradition, the weight of history, the provincial smallness of community, settling for your whole life in one place with one group of people. He embraced even the dirt, the violence, and the narrowness that came with that place, because they were part of its memory.
Obama's decision to move to Chicago to become a community organizer itself seems to speak to the sort of longing for entrenchment that Macfarquhar describes. I found this all very interesting because for me, whether it is better to work on setting roots or to try and continually explore is a nagging question. It is easy to imagine exciting places and happenings from afar and to believe that somewhere else is better/more interesting/dazzling/full of smarter people than here, and it is a destructive generalization because it is unconfirmable and usually just leads to despair wherever one is. On the other hand, curiosity is difficult to quell--and for a reason. I admire Obama's thoughtfulness about his parents' lives though, as it reflects a wise maturity on his part:
“What strikes me most when I think about the story of my family,” Obama writes, “is a running strain of innocence, an innocence that seems unimaginable, even by the measures of childhood.” Innocence is not, for him, a good quality, or even a redeeming excuse: it is not the opposite of guilt but the opposite of wisdom. In Obama’s description of his maternal grandfather, for instance, there is love but also contempt. “His was an American character, one typical of men of his generation, men who embraced the notion of freedom and individualism and the open road without always knowing its price,” Obama writes. “Men who were both dangerous and promising precisely because of their fundamental innocence; men prone, in the end, to disappointment.”
It is a tricky thing, this balancing of freedom and rootedness, though the two aren't necessarily mutually exclusive. At the same time, the former tends to be the more glamorous route for a 20-something. The latter perhaps carries us further in the long run, but again, such approaches don't seem mutually exclusive to me.