The Balance of Planning and Spontaneity

What We Can Learn From Bilbo Baggins’s Journey Through Mirkwood

David Kaplan
· 4 min read

Plans are like cars, they begin to depreciate the moment they are used. This does not mean you should not buy a car. It just means that you should not expect to sell it for its original price two years down the line.

Plans can have detrimental effects if they are chiseled in stone. We plan in order to accomplish a goal. We plan using our best anticipation of future events. However, predicting the future is difficult. The world is chaos. As predictions fail, the plan must be allowed to change in order to keep pushing toward the goal. In fact, it is beneficial to build spontaneity into your plan by setting times when you check the status of the plan and decide what to do next.

Businesses fail every year because they do not adjust their plan to new events and lessons learned. Blockbuster and Hollywood Video have become common examples of companies that tried to maximize their video rental business, failing to recognize and learn from the digital world evolving around them.

Methodologies such as Agile Development and The Lean Startup were created to combat this problem and make people think about business and organizational planning in a different way. The Lean Startup argues that the goal of planning is to learn. You must embrace your limited knowledge and strive to learn more. The only way to learn how events will unfold is to execute a short term plan and measure the results, like a scientist would in an experiment.

How do you build spontaneity into your plan? Okay here comes the geeky Mirkwood analogy that will help explain.

The Mirkwood Analogy

In the middle of the novel The Hobbit, Bilbo Baggins and thirteen dwarves entered the forest of Mirkwood. Their goal was to get to the other side (to the Lonely Mountain where treasure awaits). Their plan was simple: stay on the path.

As a side note, this plan was given to them by Gandalf, who did not actually go with them through the forest. Beware of any plan concocted by someone without any skin in the game. You should especially beware of wizards.

The longer they stuck to the plan, the more they started to doubt it. They were unable to measure their progress because they could not see the other side of the forest. This uncertainty lowered morale. Additionally the forest started to have a hallucinatory effect on the travelers, making them feel as though they were going in circles. Does this sound familiar to you? Personally, I have felt the same way when executing a long business plan.

At one point Bilbo climbed a tree to gage their progress. He was blinded by the light and could not see over the adjacent trees. If he was able to see, he would have seen that they were nearly at the edge of the forest. Instead he gave a false report that disparaged the rest of the group. This in turn made them diverge from the path landing them in trouble with a group of giant spiders. Typical.

So what is the lesson (other than don’t trust wizards)?

Plans need built in measurements and review periods that occur often. It is important to stick your head above the trees and make an accurate assessment so that you know how the plan is panning out. These measurements must return results that accurately gage progress toward the ultimate goal. Unfortunately for Bilbo and his companions, they were unable to determine that their plan was actually working. The one measurement they did take was inconclusive and only further frustrated the team.

Don't overestimate your understanding of the environment and your ability to predict future events. This kind of arrogance can be very damaging. More often than not, if the goal is a good one, the path will be unpredictable. Embrace the chaos! Gandalf exhibited this type of arrogance by dictating a simplistic plan, not taking into consideration the effect the forest would have on the travelers.

Don't wing it. People who get tired of plans that don't seem to bring results often go to the complete opposite side of the spectrum and stop planning altogether. Without a plan, it is difficult to measure progress, which is bad for morale. In Bilbo’s case, the team became frustrated and started to venture into the forest without much thought, leading them into the clutches of the spiders.

Create short term plans that have the goal of gaining more knowledge. If you are Bilbo and cannot see over the next tree or beyond a mountain because you are in a valley, then make the next plan to get to the top of a different tree or to get over the mountain. Maybe you will look over the trees and see that you need to turn south 10 degrees. That would be great. You would know where you are and that you should make a small change that will cause a huge difference.

Robert Burns wrote, “The best-laid plans of mice and men often go awry.” As humans, we like to think we are in complete control of our environment. However, as Burns suggests, maybe the control we have over our destiny is no more than that of a field mouse.

Thanks for reading! If you found value in this, I would really appreciate it if you scrolled a little further and hit the heart shaped Recommend button.

Life Hack: Your Story, Experience, etc

This is a collection for writers who share their life story and experience. This collection is managed by @tkwyoung and @aptnumber2.

Thanks to Eda Kaplan.

David Kaplan

Written by

Writer, software developer and all around thinker of wacky thoughts. Head of Software Engineering at Policygenius.

Life Hack: Your Story, Experience, etc

This is a collection for writers who share their life story and experience. This collection is managed by @tkwyoung and @aptnumber2.