CTO Compass

Discover the underrated skill to organise your thinking and boost your cognitive clarity

I've lost count of the number of times I've thought about something that seemed so clear in my head, only to write it down and find that it's just a jumbled mess that's unclear and confusing.

Fortunately, there’s a surprisingly simple method that helps you to think with more clarity and structure the chaos of your thoughts.

Outlines are everywhere

It turns out the secret lies in a simple, yet powerful technique we probably all learned in school but I believe is massively under-rated: outlining. It is a simple organisational technique with wide application.

When you look around, you’ll see them everywhere.

  • Projects, with their nested lists of tasks and subtasks.
  • The file system on your computer.
  • Mindmaps
  • Organisational charts

Structure, scaffolding and relationships

An outline is more than just a bullet list but the bullet format is important. It frees your mind from the tyranny of prose when the goal is to get the fleeting ideas from your brain as quickly as possible. Spelling, grammar and punctuation doesn’t matter to begin with.

Once you have your raw thoughts in front of you, then you can begin to tame them and refine them. There is an art to it. Outlining comes more naturally to some than others. When it’s done well;

  • It brings structure to your thoughts
  • It helps you to sequence them
  • It helps you to plan better
  • It helps you keep related ideas together and defines their relationships to one another.

With a little practice, anyone can do it and you’ll start to see how it improves the quality of your thinking.

Outliner software

You can use applications you’re probably familiar with like Microsoft Word and Google Docs with their nested bullets but they are not optimising for outlining.

Outliners, as they’re known, have been around as tools for thought on computers since at least the 1980s. One of the earliest originators of outliner software, Dave Winer, is still creating new versions today. You can use his basic web-based outliner Drummer for free. It’s great for getting started to learn and practice the techniques.

Dedicated outlining tools offer greater flexibility and features designed specifically for creating more complex outlines. My tool of choice is Roam Research. It is a new breed of note-taking application which takes outlining to a whole new level. It is easy to get started but has a lot of advanced functionality when you need it. As they like to say, it has a low floor but a high ceiling. In future emails, I’ll share more about this tool and how I use it. It is no exaggeration when I say that it has fundamentally helped me to improve my thinking skills and multiplied my productive output.

Outlines act as a framework for your thoughts, allowing for precise and clear development. They help you keep the overall picture in mind while ensuring each detail aligns with your overarching goal. I believe that mastering outlining is an essential skill for anyone who needs to organise complex ideas, whether that’s projects, writing a book or devising business strategies. It is the unseen force that helps you shape your abstract ideas into tangible outcomes.

Good outliners make it frictionless to move the units of information around quickly to rearrange, reorganise and rewrite them until they make logical sense.

Great outliners shrink the gap between your brain and your computer. They help create a flow state that extends your thinking capacity to bring greater clarity and insights to the problems that you need to solve.

Remember, like any skill, it requires deliberate practice and will likely be uncomfortable at first. There’s no time like the present. Why not try to draft an outline for your day, the next email you need to write, or reorganise a current project and start to see how you can quickly build a habit of clear thinking. Begin by outlining small, everyday things to develop the skill. Gradually, take on more complex challenges.

You will quickly see the improvement in your cognitive process as you break down, rearrange, and refocus on each component of your thoughts.It’s an iterative process—draft, review, rearrange, refine. As your outlines become more robust, you’ll find your work does too. You may be pleasantly surprised at how indispensable it becomes in managing your daily life and long-term goals.

⚡️ Thinking Time ⚡️

This week there’s no specific prompt, instead I suggest using your Thinking Time session to practice outlining in place of how you’d normally jot your thoughts down.

If you don’t have any outlining software, maybe give Drummer or Roam Research a try. It’s helpful to experience and practice how software tailored to the task can help you quickly and easily move your thoughts around, hiding information that’s not relevant so your brain can concentrate only on what matters at that moment.

Notice how outlining can enhance your focus and allow you to better visualise the steps needed to reach your objective.