Planning vs. Preparing

I promise, we are going to get on with approaching your mission.  We have just a few stops: the first was about money, this one is about the futility of predicting the future and the next one will help you deal productively with that futility.

Let’s talk about planning vs. preparing, two ways to attempt control of the unknown that we call the future.  While they may seem like interchangeable words, they are starkly different.  You see, the future is unpredictable, no matter how much we want it to be predictable.  Sit with this for a while because your belief in your ability to predict the future is likely core to the way you approach the world.  

In your daily life, at home or at work, you likely ignore black swans, stick to averages, and use the past to plan the future (even though your investments warn you not to!).  Dinners, projects, goals, trips, children, careers, etc.  The essence of the planning philosophy is this: The future is predictable, cause and effect are known, and you can anticipate your future desires properly, therefore you simply list out all the things you want, know how to do and go do them.  This can work for simple plans with short time horizons quite well. Although, how many times have you had to cancel a dinner scheduled only days prior?  The real problem is that the future cannot be accurately predicted. And yet we stress.

Think about the last time you tried to predict the future. If you were right, in how much detail?  Were your predictions specific and quantitative or vague and qualitative (things will get better, later).  If you were right about what would happen, were you right about when it would happen?  And even if you have a killer example of a specific, time-bound prediction that you’ve made, how many can you think of?  I bought Plug power at 2 and sold it at 50.  It was awesome and I haven’t done that before or since, yet I cannot help but share that story.  Similarly, how many times have you been completely wrong?  Were you similarly honest about your ignorance, or did you simply blame your poor prediction on external factors?  How hard are you working to maintain the central illusion of control over your life?  

Again, sit with this, and come back when the last paragraph no longer triggers intense defense and denial.  You may even want to read some great books on the topic (Antifragile, 4000 Weeks). Until you accept that you cannot really predict the future, you will continue to plan, your plans will continue to fail, and you will be frustrated.  If you need a little help to think differently, remember that every time you make a new plan, you do so at the point of maximum ignorance about that plan.  Your process of execution is a process of learning, so your plans should constantly change and update.  

Fortunately, there is another way to approach the uncertain future: preparation.  If the essence of planning is predicting the future and moving through it efficiently, then preparation is predicting many different possible futures and moving through them effectively.  You already prepare, all the time, you may just not realize it. 

Think about the last time you packed for a trip.  Did you bring a raincoat?  Did you do so because you knew it would rain from 3:07 PM to 4:22 PM, or simply that it might rain and you did not want to get wet?  Similarly, if it did not rain, were you annoyed at the wasted effort of lugging rain gear, or did you simply rejoice in the bad thing not happening?  This is the essence of preparation– thinking about what might happen and having a way to handle it.  Think of preparation as making many mini-plans in parallel.

Preparation has a definite negative connotation – you don’t want to get wet so you pack a raincoat, but then are delighted when it does not rain.  Planning tends to have a positive connotation – “everything going to plan” feels like a victory (despite again, maximum ignorance).  Planning is actually easier as it only contemplates one reality (not 10 or 100), and therefore the sense of control you gain feels great.  “What about?” becomes an annoying question, degrading your sense of mastery, rather than the core of your approach to the future.  

So how to prepare?  First, consider your desired outcome: where do you want to be? Next, think about how you will know you are there. Then, think about everything you believe would need to be true for things to go right.  This happy path was formerly known as your “plan.”  Planning for success is crucial as it reveals dependencies, deficiencies and long lead times that get in your way. Perhaps even more important, planning reveals your assumptions of cause and effect.  Realizing that you are making assumptions, which first appear as iron laws of reality, allow you to begin to consider that you might be wrong or that things may go wrong, opening the door for true preparation. 

For example if you want to go to Aruba, you may assume that you must fly there and you begin planning a plane trip.  You then may prepare for any failures in that trip– books to fight boredom, snacks for hunger, and maybe even how you would handle a canceled flight.  The key to creative preparation is to remember that what you want is to be in Aruba, not necessarily to fly there.  Given enough going wrong, it may make sense to take a boat! Considering these possibilities, weaknesses in your plan allow you to prepare for ways around them.  Do it enough and you may just end up with my brand of crazy preparation.  

In the next post, we are going to unpack the assumptions we make all the time when making plans, preparing, and setting goals. The mental shift from steps in a plan to hypothesis in preparation is incredibly empowering.  Until then! 

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