Mindexplores one answer to that challenge: the cultivation of habits of
mind, or habits of thought, as John Dewey (1933) called them. The idea
is that we should have habits of mind such as persistence and flexible
thinking, just as we have habits like brushing our teeth or putting the dog
out or being kind to people. Habits are not behaviors we pick up and lay
down whimsically or arbitrarily. They are behaviors we exhibit reliably
on appropriate occasions, and they are smoothly triggered without
painstaking attention.
The very notion of habits of mind, however, poses a conceptual puz-
zle. By definition, habits are routine, but good use of the mind is not. The
phrase “habits of mind” makes for a kind of oxymoron, like “loud silence”
or “safe risk.” Indeed, the story of the young man in the convertible illus-
trates what can go wrong with cultivating habits of mind. Here you have
a habit of mind (being careful) played out in a way that misses the point
(the man looks for the train from the middle of the tracks). The very auto-
maticity of a habit can undermine its function. Habits like that don’t serve
us well on a literal highway—or on the metaphorical road of life.
Can one have a habit of mind that truly does its work? The resolution
to this puzzle is not very difficult. There’s a difference between the think-
ing required to manage a mental process and the thinking done by the
process. A habitual mental process does not require a lot of management
to launch and sustain it, but that process itself may involve mindful think-
ing. It may involve careful examination of alternatives, assessment of risks
and consequences, alertness to error, and so on. For example, I have a
simple, well-entrenched habit for the road of life: looking carefully when
I depart a setting to be sure that I’m not leaving anything behind. This
habit triggers and runs off reliably, with very little need for mindful man-
agement. But the behaviors deployed by the habit are highly mindful:
scrutinizing the setting, glancing under chairs for concealed objects, and
peering into drawers and closets for overlooked items.
In all fairness, the man in the convertible displayed a habit with some-
thing of this quality, too. It was good that he looked both ways with care.
No doubt his scan of the tracks was precise and sensitive. He certainly
would have detected any oncoming train. The difficulty was that his habit
included a bug, rather like a bug in a computer program. Although his
xii Learning and Leading with Habits of Mind