When Things Don't Go According to Plan

Any thing worth doing is a thing worth planning. But though you must plan, don’t fall into the trap of letting the plan steal the show. The primary goal is to do the thing, not to make a plan about doing the thing.

I heard long ago in the Army: Plans are worthless, but planning is everything. There is a very great distinction because when you are planning for an emergency you must start with this one thing: the very definition of “emergency” is that it is unexpected, therefore it is not going to happen the way you are planning.

Dwight Eisenhower, at the National Defense Executive Reserve Conference, November 14, 1957

This quote is often used in its abbreviated form: “Plans are worthless, but planning is everything.” I’d like to highlight something else that Eisenhower touches on: The need to anticipate and plan for contingencies.

The first step is to create a primary plan of action. You need to be clear on what you want to accomplish, and how you plan to go about accomplishing it. And you need to know what is measure by which you will conclusively determine whether or not your goal has been achieved. Most of us get this far.

The second step is to anticipate the roadblocks. What are the weaknesses with your plan? How might things go awry? You are trying to anticipate, mitigate, and prevent, wherever possible. If you can’t mitigate or prevent, how do you account for it and work around it? Advanced planners will make it this far.

Everybody has a plan until they get punched in the mouth.

Mike Tyson

The last piece is a set of fallback plans, for when you cannot mitigate, prevent, or work around a show-stopping issue. What’s your secondary plan, in case the primary plan is untenable? Repeat step two, and find the holes in your secondary plan. Great. Now, what’s your fallback plan for the secondary plan?

Obviously, the end goal’s importance weighs heavily here. If the plan is to grab Thai food on your lunch break, but it turns out the restaurant isn’t open on Mondays, no problem. You figure out another destination on the fly, with the worst case being that you end up back at the office cafeteria. If your plan is to make it to your father’s funeral, however, you can bet you’ll be finding another way to get to your destination if your car breaks down en route.

A great plan involves a balancing act between spending enough time to account for contingencies, relative to the level of the end goal’s importance, and yet not spending so much time on the plan that you forget to put in the work required to accomplish the goal.