Stop thinking with your brain. Start thinking with a pen.
Some of the most famous leaders in history were writers. People like Buffett, Churchill, and Carnegie are almost as famous for their writing as they are for their business and political achievements. Churchill published 10 million words during his career.
But professional writing isn’t just about publishing or building an audience. It’s about reflection. It’s a tool to clarify your thinking. If you want to improve your ability to make important business decisions, you might try an activity I call strategy journaling.
The power of strategy journaling is that it forces you to wrestle with ideas. Entrepreneurs write to set direction, adopt or eliminate particular habits, explore business ideas, investigate interests, set priorities, and understand their own biases or lazy thinking.
Writing is a tool for taking deliberate action. Here’s how to use it effectively.
Getting started: Notebook, pen, and a specific prompt
I find that writing freehand is more effective for clarifying my thinking than writing from a computer. Computer writing is fast. Tools like Google Docs and Word make it easy to delete (and forget) your mistakes.
Writing freehand slows down your thinking and forces you to acknowledge your mistakes, both of which are helpful for reflection and strategic thinking.
So, get yourself a notebook and pen. Find a quiet area that’s conducive to thinking. Maybe pour yourself a coffee or smooth bourbon.
The most important part of strategy journaling is this: Don’t begin from a blank page. Start with a specific business question or prompt.
How do I solve X?
Should I go with X or Y?
What does X mean?
What is the one big thing I want to accomplish this year?
What KPIs will our company prioritize this quarter?
The specific prompt is what separates strategy journaling from mere blog writing or Morning Pages. You’re not writing simply to write. You’re writing to think.
Clarify your thinking
Writing is the ultimate BS meter. It forces you to wrestle with ideas and acknowledge what you don’t understand.
You may be able to talk your way around a nuanced topic at a dinner party. But most people cannot write clearly and persuasively about a topic unless they know it well.
This is why strategy journaling is so effective. If you think you understand a certain principle or technical process, write it down. Put your ideas on the page so that you can poke holes in your own arguments.
Writing shines a bright yellow spotlight on your mind. Reading it back, you will immediately see the points that are truly strong. You will also face the reality of what you don’t yet understand.
Find the through-line
Sometimes you understand a lot about a subject but still can’t write simply about it. You can list hundreds of technical and nuanced facts about your topic but struggle to distill that topic down to its essence.
Writing is the ultimate clarifier. Here’s a trick to focus and simplify your thinking:
I’ve done a lot of technical writing over the years. Sometimes I get to the end of a paragraph and think: This is too jumbled. What am I really trying to say?
That question is a powerful prompt. If I know something I’ve written is too technical, I might start the next sentence with, “What I’m trying to say is…”
Often, whatever is on the other side of that sentence is exponentially clearer than the jumbled paragraph. Now all you have to do is cross out the jumbled paragraph. Keep the essence.
Consider the options
Sometimes the options in front of you seem infinite. How do you select the right one and give it your undivided focus?
Write all the options down in one place. Now, trim, edit, reflect, and cross out.
This form of strategy journaling carries the same effect as creating a comprehensive to-do list. Get the options out of your head and down on paper.
You can consider your options in a clearer, more objective light. You make them real by putting them on the page.
Armed with your list, write the real pros and cons of each option. Cross out the obvious losers. Write to compare the best options in front of you.
After some reflection, conclude your writing with an action step. “Now that I’ve chosen X, I will do Y.”
Expand your interests
Curiosity can be an effective motivating force. What you do with that force is important. Motivation can lead you to action or distraction.
The internet is a lousy place to explore your interests. Instead of taking action on an idea, it’s too easy to just click around and see how others have explored that same interest.
Why is that a problem?
Instead of kickstarting a house project, you watch videos of other people accomplishing house projects. Instead of writing a book, you read articles about how others wrote their books.
In the end, you get the satisfaction of exploring an idea without having made any progress.
Writing is different. You can explore an interest and have something on the other side of it. You have an idea to share, a better understanding of the topic, or next steps for how to bring that interest into your reality.
Notice trends in your thinking
We all tend to remember our reasoning through a generous lens. If I make a bad decision, I convince myself it wasn’t so bad or that I didn’t think it through. I give myself the benefit of the doubt. It’s human nature, a form of psychological protection.
Strategy journaling forces you to face the errors in your thinking. If you wrote the idea, reflected on the pros and cons, moved forward with the decision, and then it failed, you can return to the journal entry and read the details for yourself.
What did you miss?
This is the real power of strategy journaling: Returning to your old ideas.
One of the reasons I eventually took an extended break from social media is because I noticed I’d been writing about the idea for years. It took going back through old notebooks to realize how long this idea had been on the back of my mind.
After that discovery, it became easy to take a year-long break because I knew this wasn’t an experiment I was trying on a whim.
You’ll love returning to old strategy journal entries. It’s a time machine into your previous thinking. You can see what mattered to you at the time of your writing. You can remember how certain decisions panned out over time.
Publish your best ideas
Strategy journaling is a thinking tool. But that doesn’t mean you can’t publish your best ideas. Publishing has become a cornerstone of my career, helping me find clients, make friends, and explore stories and ideas in public.
Publishing can also help with the thinking process. Writing and publishing are two parts of the same smooth engine:
Write to explore ideas.
Publish to receive feedback on those ideas.
Apply that feedback to improve your writing and thinking.
Rinse, repeat.
Not to mention, publishing comes with side benefits. You can grow a following, connect with like-minded people, and hear stories and questions to inspire your future work.
The purpose of strategy journaling isn’t to publish. But for the right topic, clicking publish can take strategy journaling to the next level.
