Contingency Planning

  1. Contingency Planning
  2. Contingencies: Commander’s Intent
  3. Contingencies: Plan a Graceful Exit
  4. Contingencies: Making Peace with Probability
  5. Contingencies: The Chrysalis Cycle

Plans are worthless, but planning is everything.— Dwight D. Eisenhower

With the launch of Jonathan Fields’ new book Uncertainty, I’m thrilled to see so many people discussing their strategies for dealing with the roller-coaster that is life. Because life is uncertain. And to deal with that, people often spend an inordinate amount of time trying to make their lives as staid and unchanging as possible in order to bolster a false sense of security. Hardly any time is spent getting better at rolling with the punches. Standard advice on this topic is “build a buffer (of time or money),” “buy insurance,” or “plan ahead.”

You Don’t Need a Degree in Actuarial Sciences

To be clear, I am not advocating that you relentlessly plan and prepare for every possible contingency. Not only is it impossible and hard on your mental health, but it’s not even necessary.   I once read a tip on The Simple Dollar, a popular frugality site. He said, to spend less on heating and cooling bills, leave your windows open for three seasons of the year. His reasoning was, the more time you spent in a non-temperature controlled environment, the more comfortable you would become in a wider range of temperatures.

It was a brilliant piece of advice, and I offer it to you now:

Practice getting comfortable with uncertainty and ambiguity.

There are pay-offs far beyond the obvious.   Of course, the main problem with uncertainty is that it’s hard to know what to do; conditions are always changing, or might change. You have to constantly adjust, and that’s an added stress we can all do without, right?


It doesn’t matter whether you deal with it or not; things are always changing. To argue that you’d be less stressed if you could just be certain of things is like arguing that you’d be be more productive if you didn’t have to sleep.   With the rate of change speeding up all the time, not being able to adapt on the fly becomes more and more of a liability.   Tolerating, embracing, and even thriving on ambiguity is possible.

All this week I’ll be releasing articles on strategies for dealing with uncertainty. Sign up to get the feed to your RSS or email if you don’t want to miss them!


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