Dilemma Flipping
Ability to turn dilemmas
which, unlike problems, cannot be solved
into advantages and opportunities.
_ _
The test of a fi rst-rate intelligence is to hold two opposing ideas
in mind at the same time and still retain the ability to function.
One should . . . be able to see that things are hopeless yet
be determined to make them otherwise.
_ _
Holding “two opposing ideas” in mind will be even more
important in the future than it was when Fitzgerald observed this
in 1936. In fact, there will sometimes be more than two opposing
—all of which have some validity. Leaders will need to learn to
like this space and make decisions, even when they cannot succeed
by problem solving.
More volatility, uncertainty, complexity, and ambiguity means it
will be harder to see through the mess. The dilemmas of the future
will be more grating, more gnawing, and more likely to induce feel-
ings of hopelessness. Leaders must be able to fl ip dilemmas over and
nd the hidden opportunities. They must avoid oversimplifying or
pretending that dilemmas are problems that can be solved. Dilemma
ipping is the recurrent skill that leaders (many of whom were trained
as problem solvers) will need in order to win in a world dominated by
problems that nobody can solve.
Many people will fi nd it hopeless. Certainly, we all have those
—and looking ahead ten years may spark more of them—
but the lesson for future leaders: nurture the ability to engage with
hopelessness, learn how to wade through it to the other side, and fl ip
it in a more positive direction. Dilemma ippers turn hopelessness
into hope.
My de nition of a dilemma is a problem that cannot be solved
and will not go away. The traditional defi nition of a dilemma was
the choice between two equally bad options (often referred to as a
“Hobsons Choice”). The challenge for leaders is to fl ip the dilemma
into an opportunity. At Walt Disney World in Orlando, for example,
standing in lines has always been a dilemma. Nobody likes to stand in
line, and there is strong evidence that the guests are less patient than
ever. Still, Disney doesnt want long downtimes when there is nobody
ready to ride, so they make the waiting experience as pleasant as
possible. They have made a number of attempts to ip the waiting
dilemma, including video entertainment and indicators about how
long the wait will be from a particular point. Another interesting
innovation is Pal Mickey, a stuffed Mickey Mouse doll that entertains

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