I created the life I live today writing in journals from cafes around the world.

Since the age of 17, I have kept a journal. I continue to write more and more and fill up the pages of my journals faster and faster.

Recently, I was asked how exactly I journal, how I thought about it, and how I arrive at what I do through writing.

I challenge myself to stretch my thinking through writing. In that space, I see problems and opportunities through a different lens.

Until I was asked “how,” I had not thought about it. The question prompted me to break what I do on the page down into it’s parts.

And here they are:

1) The Context in which I’m writing

2) The Prompts of which I’m writing towards.

I will explain each in more detail and provide examples of them in use.


The first of the two elements, context, breaks down into two parts as well.

1) Environment

2) Purpose

Let’s begin with the environment.

An Atmosphere for Creative Thought

  • Time
  • Location
  • Tools
  • Fuel

Time —

I try to setup my journaling sessions with times of day where I am most creative.

For me, this is the mornings. I can find extra enthusiasm in the afternoon on occasion, but that’s a rarity.

I align my journaling sessions with what I’m discovering is my natural cadence of flow. Flow being an “optimal state of consciousness, a peak state where we both feel our best and perform our best.”

My favorite times of day for finding flow:

  • In the mornings, after I complete my routine
  • Open afternoons
  • Friday afternoons to conclude my weekly reviews
  • Weekend mid-mornings

The key components here being; high energy and little time constraint.

Location —

Next I consider where I’m to sit down.

I choose to find a space clear of normal distractions. I prefer to get out of the house. If I am at home, it must be the morning when my energy and focus is at it’s peak.

Otherwise, I head for a cafe. Surrounded by more liveliness and free of normal distractions (fridge, making my bed, anything around the house), I can lock into the thinking I want to do.

My all time favorite location for journaling is aboard a plane. A few hours with no where else to go…up over clouds…so good.    

Tools —

I prefer pen and paper. Especially if I’m free writing.

I often sketch, draw arrows, and cross things out so the flexibility of a pen and paper suits me.

Up to you though. I write faster on a computer, and there’s benefits to that too.

I also must have quick access to books. Keeping quotes, passages and important concepts from important books easily accessible is a definite need during my thinking sessions.

If I’m at home, a stack of books growing next to me on the table is not an uncommon sight.  If I’m out and about the Kindle app on my phone works great.


And then comes my favorite piece of my environment, the fuel.

I call “fuel” any sort of substance that helps induce a state of flow for you.

Some examples:

  • Caffeine (people like coffee)
  • Alcohol (glass of wine, beer, etc.)
  • Various “smart drugs”

I choose coffee most often. But I also enjoy experimenting with others, a glass of wine or different smart drugs that help promote focus.  

Others enjoy a beer or two. Or, nothing at all. I sometimes just need a hot tea or something. Whatever works for you.

Let’s move onto the second part; purpose.

What Are You Trying to Do?

The second element of context is purpose.

After my I have an environment set, I ask myself “what’s my goal here?”

I’ll often have a target in mind before sitting down.

The worst thing of it is, when I sit down to write and do not have desire to achieve anything in particular I get the best output.

The pressure of “solving” or “fixing” something closes me up. When the pressure is off I notice my thinking is more open.

Often times, I’ll sit down to address one question, which leads me to another more important one. Malleability is key.  

Exploring ideas for the sake of revealing more my thinking to myself reveals some cool things.

What’s most important for me in my process is doing the thinking, and doing it consistently. This is my work. And to be professional, I must do it daily and create inspiration. I must avoid waiting for it to arrive.

A closely related thread, is the second of the two prongs: prompts.

Orienting the Mind:

If context is set, next comes choosing what it is you are to think about.

As mentioned before, sometimes you sit down with a prompt already in mind. Other times, your mind is primed but you have no urgent thing to address.

The quality of my journaling sessions are only as good as the questions I ask myself.

I collect questions and prompts from books, interviews, blogs, other writers, thinkers, etc.

Below I’ve provided some of my favorite questions. I’ll do my best to cite where or who they come from. They vary on topic; business, relationships, fulfillment, etc.

  • How would you 2x your business if you could not get any new customers? (Noah Kagan: Okdork.com)
  • How could you 10x any area of your life [business, wealth, relationships, health] in 12 weeks? (Taylor Pearson)
  • What is it that you love to do? What do you do that doesn’t feel like work at all? (The Big Leap || Gay Hendricks)
  • What are the 3 most valuable things you are doing right now? (The Big Leap || Gay Hendricks)
  • What are the things you are doing right now that are giving you the most energy, fulfillment, peak states, results, etc.? (80/20 Principle || Richard Koch)
  • What are the things you are doing right now that are taking energy away from you? (80/20 Principle || Richard Koch)
  • What are you avoiding doing? Why? (Taylor Pearson)
  • If you were given a million dollars today, what would you do tomorrow? (Tim Ferriss)
  • How would you achieve your current targets/goals in 1/2 the time if you had to?
  • What do you want? How do you get there?
  • Where is there opportunity to solve a greater problem?
  • Tim Ferriss also has a really great list of questions he likes to ask himself here

Insights Come with Space

One thing I have struggle with in the past is prioritizing time to pause, review and reflect on my work and life.

Over the last few years I have become intentional about putting the time in to do so.

Through this exercise I started to liken my life to a chess match. I make much more conscious moves, decisions and actions based on the feedback of my daily life.

I hope a look into this integral habit of mine has been useful for you.

If you have any questions, comments or thoughts please share!