Planning to Improvise

Open notebook with handwriting on the pages and a fountain pen lying on top.

image credit: Pexels

Are you familiar with NaNoWriMo? That’s a funny name for a cool idea. It stands for “National Novel Writing Month,” something that takes place every November. A giant online community of people all try to write a 50,000-word novel in November (or at least the first 50,000 words of a longer novel).

This year will be the fourth time I have participated in this event. My word counts the previous times I have done this? 50,000, 33,000, and 7,500. Which means technically I “won” it once.

Having done it 3 times, can you guess how many novel drafts I have completed?

Yup: 0.

Why? Because every time I did it I banged out the words, and, regardless of whether I reached the word count goal, I eventually lost steam in the story. Why? Because in every instance I got to a part where I was a little (or a lot) confused about what came next, or where the story should go, and then the doubts creeped in, and so I slowly tapered off and stopped writing.

This year, at the time of this writing (about 2/3rds of the way through November) I have written 34,447 words and am on pace to hit 50k by the end of the month.

More importantly, this time I am much more confident that I will be able to finish the first draft of this novel.

Why? Because I spent waaaaay more time this year in the planning and preparation stage.

Based on what I teach with “yes, and,” improv, and creativity, writing should be right up my alley. In the past I have started with anything ranging from a mildly detailed outline to just a basic idea of the story, and then started writing. Invariably this would lead to confusion or uncertainty down the road and I would stop.

This year I spent a lot of time creating a detailed outline. I have a spreadsheet with a list of every scene in the story, along with character sketches and backstories, location descriptions, etc. On some days it is still hard to write thanks to procrastination and the “blank page effect” but I never struggle due to confusion.

What does this have to do with you?

As an improviser, people sometimes assume that I don’t prepare, or that I don’t need to. And while it is true that I can respond and shift in the moment, I have found a simple truth about improvising, both on-stage and off:

The better prepared you are, the easier it is to improvise.

I still get to use my creativity even though I am writing from a detailed outline. Fun new ideas pop into my head and sometimes I modify the outline.

But the preparation helps. A lot.

This is the difference between improvising and “winging it.”

Improvising is about being flexible, responding to changes in the moment, and giving your creativity direction.

Winging it is about being lackadaisical and jumping in with little thought.

The danger, of course, is that preparing can become an excuse to never start. To combat this, I find external deadlines and commitments immensely helpful (like knowing I wanted to be ready to write on November 1st). Perhaps having an internal deadline, or a specific dream you are trying to achieve, or a persistent problem you are trying to solve would be more helpful to you. Do whatever best leverages your personal motivational style.

Notably, I used quite a bit of creativity and the improv approach during my planning and preparation, so it is an iterative process.

As you prepare to navigate a change (whether as a leader or on your own) think about the level of preparation you need to be able to take action, improvise, and let your creativity flourish. Set a deadline, set your base level of preparation, and get started!


Want help working on your preparation, creativity, problem-solving, or goal-achieving? Contact me and let me know - we can have a short call or quick email exchange exploring how I can help you, your team, or your organization!

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