A friend recently asked, “How comfortable are you with uncertainty? How comfortable would you like to be?”

And that sparked a number of reflections:

  • It depends on the kind of uncertainty. It’s one thing to improvise when the plan goes out the window, but another to live with little or murky sense of a plan in general.
  • With any kind of uncertainty, there’s a difference between risk tolerance and risk capacity. If you can tolerate more risk than you can afford, proceed mindfully.
  • Comfort with uncertainty can be built with practice. Taking on enough uncertainty to feel stretched — neither static nor stressed to death — can increase comfort over time.

Most of all, it emerged in conversation that life in general is a lot less certain that we tend or want to think. Planning is indispensable, but resilience and flexibility are priceless.