Some thoughts on the art of planning

Last night, on our way home from work, my daughter mentioned her desire to spend some time sleeping in on Saturday. Actually, what she said was something like, “I hope no other plans happen so I can sleep in on Saturday.” Being the loving father that I am, I rushed to correct her. (That was sarcasm!) I pointed out that she did have plans: sleeping in. Certainly, if something else came up, she was perfectly free to adjust her plans, but this would be a change of plans, not an imposing of a plan on unstructured time.

As I reflected on this conversation, I realized that I’ve come to understand a lot about planning. So, I figured I’d inflict some of what I’ve learned on all of you. This is mostly going to be stream-of-consciousness, so I apologize if I get rambly. Also, depending on how much material I generate, this may turn into a short series. We’ll see.

That’s right! I’m creating in public without a net!

Anyways, some thoughts on the art of planning.

The Value of Planning

What’s the point of planning? Why do it? One reason that we plan because of finitiude. As created beings, we do not have infinite resources at our command. I have only so many waking hours. I have only so much money. I can only be in one place at a time, technology notwithstanding. Therefore, I am always having to choose to where to allocate my resources.

I’m writing this blog post on my lunch break. As I was preparing my food, someone approached me, wondering if I’d be available to play a game over lunch. I politely declined, because I had scheduled myself to write this blog post. If I use this time on a game, then I can’t use it on a blog post.

It’s when you’re planning that your values become apparent. Continuing with my example, I had decided that it was important to blog regularly. I knew that meant giving up something else, because there’s only so much time in the day. I decided I would give up lunchtime gaming on certain days to allow me to blog. That way, I could easily make decisions like I did today.

Planning for Outcomes
“I think a plan is just a list of things that don’t happen.” –Mr. Parker, The Way of the Gun

Having just explained why plans are good, I must hasten to say that plans never actually work as written. I think that this is where many people begin to work with planning and then get frustrated. They put together a plan, begin to execute the plan, and immediately run into roadblocks. The instinctual response is to try to continue to execute the plan, but, of course, it’s not working now. Either they fumble through the steps of the plan, becoming increasingly frustrated and dissatisfied with the outcome, or they abandon the plan altogether.

Instead, it’s better to see this as just another form of finitude. One thing that we’re short on at the beginning of planning is knowledge. We don’t know what parts of our plan won’t work or what events in the world will go wrong and interfere. Furthermore, there’s not way to know. If we did know, we’d make different plans, right?

This leads into a basic reality that we must face when we plan: uncertainty. I actually consider this to be a fundamentally spiritual point. We often live under the delusion that we control much of our world, but if you stop to think about it, there is so much that is beyond our control. Even our own bodies refuse to bend to our will. Planning in a way that ignores these realities is egotistical, though reality will assert itself in time. However, planning in humility acknowledges our lack of control, which changes how we consider our plans.

James speaks to this well in his letter:

Come now, you who say, “Today or tomorrow we will go into such and such a town and spend a year there and trade and make a profit”— yet you do not know what tomorrow will bring. What is your life? For you are a mist that appears for a little time and then vanishes. Instead you ought to say, “If the Lord wills, we will live and do this or that.” As it is, you boast in your arrogance. All such boasting is evil. (‭James‬ ‭4‬:‭13-16‬ ESV)

Therefore, since we cannot guarantee that our plan will actually be effective, we must be sure to at least understand the objective of the plan. What are we trying to accomplish here? That way, when (not if!) the plan goes awry, it’s possible to adjust the plan to something new to still be able to achieve our objective.

Remember: we’re never planning for the sake of planning. That’s silly. Rather, we’re trying to make sure that something happens. In a way, as long as we accomplish our goal, who cares how it happened?

I’ve read this in enough places that it’s almost a proverb: Planning is invaluable, but plans are worthless. Planning is invaluable, because the process of thinking through the plan helps reduce uncertainty by developing enough knowledge to support your improvisation efforts when you have to adjust course. But plans are worthless, because woodenly following a plan is not guaranteed to bring about the results that you want.

I think I’ll tie this post up here. Hopefully there’s been something of value here. But my lunchtime is over, and there are other things that I’ve planned to do today that I need to get to.


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