Regularly writing down both what I’m thinking and how I think about things has been the highest impact career tool I’ve learned to date (it’s up there with learning Vim). It helps me get ‘unstuck’ when I’m uncertain, understand my reactions to events, and teach and grow my colleagues. The what and how parts are distinctive, with how being the most important. I’ll explain this distinction using a common example of where I, and the folks I work with, get stuck: making a decision about something important. I’ll then explain why writing down how you think, and then deconstructing and improving that, is the key to rapid personal development.

The “What”⌗

Okay, so let’s talk about decision making as an example. Long ago, before I was enlightened, this is how I made decisions:

  1. Think hard about the decision in my own head.
  2. Constantly flip-flop over the decision choices.
  3. Ask someone for their opinion.
  4. Unconfidently make a choice.

Spending time deliberating this in my own head meant that I was limited to the memory capacity of my brain, constantly paging in and out options to evaluate. For complex decisions, this felt tiring, and inefficient. So I moved to lists, and a more structured way of ‘weighing up’ options (which really just looked like making odds on a horse race, and gambling on the option which gave me the best risk adjusted return):

This was better. I’m breaking down the decision making process into smaller chunks: list out the options and, for any given option, simulate the future, calculate the risks, etc. It felt easier, and the process seems more quantifiable, and perhaps even more rational. It was also significantly easier to communicate with others the current ‘state’ of the decision making process so that they could help.

This process is the writing down of my what for a given decision. And writing down the what is often where most people stop, having tasted the pure satisfaction of getting things out of their head, breaking them down, and putting them on paper.

The “How”⌗

Taking on bigger career challenges meant significantly more complex decisions, and I started getting stuck more often. Based on the advice of smart people who deal with lots of complexity, I started focusing on how I make decisions: writing down, deconstructing, and analyzing my how, which was vastly higher leverage and far more satisfying. This satisfaction comes in several ways, because once you’ve written down how you think, you can:

  • Look at your how objectively and identify gaps
  • Identify the steps where your brain can fool you (bias!)
  • Share your how with others
  • Improve it!

Sharing your how with people has two really awesome benefits: 1) they can give you feedback, and 2) it gives your colleagues the ability to anticipate and predict the what that the how generates.

When I write down the how for a given area, I follow a standard template:

  • Philosophy and Principles
  • The Model
  • Test Cases
  • Resources I used

This is best demonstrated with an example. Here’s a link to my Decision Making Mental Model[1], which describes how I think about making and executing decisions (single page version is here). The Philosophy and Principles section frames the how with context. The Model section is a step-by-step process, with extra reference details for things I often forget (like in this case, “how to measure uncertainty”). Test Cases are written down accounts of the how in real life action (usually the more crazy cases) – I use these to mentally test incremental improvements I make. The Resources section is all the books and papers I’ve consumed that influenced my how.

If you’ve read that completely, it should be obvious the monstrous gaps between deliberating in your head, to creating lists with probabilities, to the process outlined in my how. I’d now argue the most important parts to decision making are:

  • “am I being fooled?“
  • communication
  • checkpointing
  • postmortem

These are parts of the process that I barely even thought about before I embarked on improving my how. It’s a significant up-leveling.

Incorporating the “how”⌗

You might be thinking “shit, this looks like a lot of work, it’s probably not worth it”. Before you throw in the towel, do the following: identify an area where you feel uncertain about something, write down that topic, then write down how you currently think about it. Here are examples if you’re struggling to bootstrap:

  • Leadership
  • Holding people accountable
  • Building an effective plan for you or your team
  • Resolving conflict

Then write down how you think about that as a simple bullet point list. If you struggle a little, and think it’s a bit incomplete, then hopefully you’re self motivated to keep on writing, thinking, reading, sharing, and improving your how.

Once I have something that feels rigid and complete, I refer to and follow it constantly. I use it to generate my what, and I write down the results of that too – it’s a written record of my how in action, which I can review over time to continuously improve. I have hundreds of pages of hows, and loads of spreadsheets that track their output, and I’ve been incrementally improving them for years.

If you write down and improve your how, you get a significantly better what for free.