Is it Better to Plan or Prepare?

What's the difference between planning and preparing? Are they just semantic variations of the same thing, or do they greatly affect results and outcomes?

I'm into Dungeons & Dragons in a big way. I've been a Dungeon Master since 1980 and believe that it's a big reason why project management has been a key component of my professional career. I'm still learning, though, and a few years ago I was taught a valuable lesson in the difference between planning and preparing.

That lesson, and its application in my professional career — and, I think, its application to the business world in general — is valuable.

Here's what happened.

I had designed a grand adventure that pivoted around the group of players making a specific choice. D&D players being what they are, the group figuratively decided to go west instead of east. My plans were shot and the campaign ended right then and there.

I planned but failed to prepare.

Have you ever had an experience in your professional career where you thought your plan was rock solid but the effort bombed because you failed to prepare?

Planning

At a fundamental level, planning entails a certain amount of expectation. You develop a plan to achieve a specific outcome, and hopefully that plan is good enough that the method and means you use to achieve that outcome are predictable.

No battle plan ever survives first contact with the enemy. – Helmuth von Moltke

What happens when your plans go awry and your desired result is not achieved? Was the effort itself worthless, or could the journey still yield something of value even if you never reached your intended destination?

Sometimes our plan is quote-unquote successful because we achieve the desired end result but we had to improvise along the way. Or maybe the plan required a bit more funding or effort than was originally anticipated. You built that bridge but it cost 1.5x as much as you'd budgeted.

Not all plans that fail to achieve their stated objective are failures.

Preparation

Unlike planning, preparation doesn't focus quite as much on the outcome. You may have a desired result in mind but you assume that the process you go through will have some variability.

Variability is the name of the game when it comes to preparation.

Change is the plan, and you plan for things to change.

"Whatever may come, we're prepared," says the smart homeowner before the storm arrives.

From the outside, the steps taken before kicking things off might look surprisingly similar between planning and preparation. The research shares a lot in common and the resources acquired have a great deal of overlap.

The key difference between planning and preparation is in the expectations for how it will go and how it should end.

Lessons Learned

I run the teens D&D program at my local public library. The players are a very enthusiastic and high-energy group. Anything can happen, and trying to get into their minds and predict their likely behavior is about as reliable as forecasting the weather on the dark side of Venus.

I've learned from past experience and present observation that trying to plan a grand adventure that will have a predictable path and a reliable outcome is foolish. Instead, I prepare various adventure hooks and locations and enemies and allies and let the group discover them — or not — based entirely upon their choices. I'm prepared either way.

The plan — I do have one, actually — is for the players to have fun. The preparation means I'm ready for whatever path they choose to get there.