How-To: Journal the Journey

Formalize the feedback loop by keeping a journal of what you do every day.

By Jason Womack, MEd, MA, Founder and CEO, The Jason Womack Company

We love to read about life. We talk about what happened, who’s doing what, and where people are going. One look at the newsstand in a bookstore or airport and the headlines of what people did compete for your attention!

For the next five weeks, follow your own story. Make a point to acknowledge what you did, how things are going, and where you plan to focus your attention next. As they say, it’s not only reaching the destination, but the journey you can learn from, as well. Journaling the journey is one way to look at your best efforts, and make them even better.

There are three time zones I journal the journey in. I write something every day. Pausing toward the end of the day long enough to think, I write about 100 words in a small journal I keep on the nightstand. Each day, I write about the past, the present, and/or the future.

Of course, it’s often the easiest to look backward, and almost everything we write stems from the past. When I capture what happened, I look at: where I was, who I was with, even what I was thinking. I look for and recognize surprises, good things, or when I was discouraged. Finally, I spin out of the past with the question, “If I were in that circumstance again, what might I do differently?

Next, there’s the present. Right now. Looking at where I am (whether I’m writing at home, in a hotel, or before falling asleep on another transatlantic flight), I capture the thoughts, feelings, worries, or plans that are “right there” calling for my attention. Am I tired? Enthusiastic? Am I feeling hopeful? Or am I overwhelmed or stressed?

Capturing this moment in writing is a challenge. Literally, as I’m writing, my mind wanders or the ambient environment grabs my attention—a sound from outside, my dog’s tail tapping the floor, my wife saying “good night” one last time, the telltale red blinking light on my BlackBerry seemingly yelling, “You. Have. A. MESSAGE!”

And, of course, there’s the future. What’s coming my way? What is six or 12 or even 18 months out that, as I let the words land on the page, I can begin to picture it, feel it, or hear it coming true?

Now, formal structures aside—writing yearly goals, tracking progress on previously agreed-upon projects—this “in-the-moment” and “end-of-the-day” kind of thinking has, in fact, been responsible for some of the big thinking I’ve done over the last decade. It seems that by the end of a day, when I’m nearing that long block of rest I know I need for the next day, I put things together based on what I’m experiencing in that moment.

Over time, I’ve collected a short checklist of questions I can use to trigger my thinking, and journal the journey. Here are just a few of the ones I use, day to day:

What have I learned today?

I know that every day I will be given an opportunity to identify something new. One look at my “magazines to read” stack or glance through my e-mail inbox hour to hour, and I’ll see something I’ve never seen before. At the end of the day, I will note anything I saw or heard for the first time and indicate why I think it’s noteworthy.

What opportunity did I create?

You immediately will know—in life or at work—if this question is appropriate for you. For me, it definitely is. I search back and ask myself who I met, where I went, and what I saw that may have a future opportunity. I’m not making a to-do list (I surely captured any tasks earlier in the day). I’m practicing thinking bigger.

What questions were answered?

Did a project ship? Did a contract get signed? Did a mystery get solved? Here is a real opportunity to “close the day.” I have found there is something about acknowledging completion that is positive and it’s relaxing. It is a way to mentally “check things off” and tell yourself, “We’re done with that for now.”

What question came up?

Yes, I kept to one question. If I decide to ask and write about this, I only pick one. Then, while I’m writing, I avoid answering it. Instead, I further clarify the WHAT behind the question. Occasionally, the question will transform itself while I’m writing!

I’ve heard that Albert Einstein always had a notepad nearby—even on his nightstand while he was sleeping. I would love to know what he thought as he captured his own ideas, theories, and questions over time.

I remind my clients of the subjective/objective nature of this journaling process. Of course, it’s an object—these are your words in your handwriting based on your thoughts and your ideas. Simultaneously, it is subjective as the things you write are from your experience, perspective, and interpretation.

Objectively speaking, it is important to keep some kind of record you can look back on and review. Being able to see what you saw, hear what you heard, and feel what you felt is a significant part of the self-leadership and mastery process. For those of you who are managers, executives, and founders, you definitely want this objective, “Where was I then…” record.

Subjectively speaking, it is a roller-coaster ride. You’ll see the ups and downs, the days when you were “on” and the ones where you got beat up. When you go back and see these highs and lows, you’ll do so with the gift of hindsight. What seemed like a big deal (or, what seemed like just a little something) may wind up being different now than what you initially imagined.

Rarely to be shared, there’s going to be a natural cycle of review for you. Whether it is monthly, quarterly, or annually, there are benefits to seeing what you’ve captured over time:

  1. You’ll see where you were.
  2. You’ll build toward where you’re going.

Where were you?

Now that I have almost two decades’ worth of this daily journaling (some days I wrote no more than three lines, other days a hundred or more words), I can see what used to be a big deal. What was I worried about? What caused stress? What opportunities was I creating?

When I look over these pages, I’m catapulted in to the future—that is, I begin feeling the exhilaration of: “WOW, look how far I’ve come! I wonder what’s next.” It is that wonder that acts as an impulse to want to capture something with my pen—so that later on, again, I can say, “Oh, look at that small thing I used to think about that I considered a ‘big deal.’”

Next Steps

If you’re ready to make this learning commitment, I’ll guarantee you’ll like and learn from the results. Start today, and complete a five-week experiment. Who knows, in just a month from now, you may find your past, present, and future means while lot more. Here are the next steps to take:

Buy a nice journal and a couple of pens.

Gear…it makes a difference. Next time you’re out and about, stop by a stationery shop or a bookstore and handle a few different sized and colored journals. Pick one you’re going to use for just the next five weeks. Buy it, along with a few pens. (Whenever I pick up a new journal, I do purchase a half a dozen new pens—the same ones—because I know that over a period of time I will misplace that pen from time to time.) The fact that you have tools you like to use, tools that are standardized and always available, will make it easier to keep up with this habit. Because I travel so much (about 200 nights per year, over the last decade), I had to find a journal that was small enough to go where I go, and big enough to be able to capture my end-of-the-day thinking. I’ve experimented with different sized journals from different manufacturers and have found that some do, indeed, work better than others.

Put your journal where you can see it at the end of the day.

At home, in a hotel, even when I was riding my bike for 14 days throughout the Rocky Mountains of Colorado, I kept my journal where I knew I would see it at the end of the day. At home, it’s easy: on the nightstand. It’s right there, and before I fall asleep I reach over, take a few minutes, and fill a page.

If you travel, find a journal you can go everywhere with.

Not just the size, but the construction, as well. I have found that for my travel lifestyle, a hard-bound journal is sturdier and stands up to time better than a paper cover. I pack my journal on top of everything else in my suitcase, and it’s the first thing I unpack when I check into a hotel.

Set an alarm.

Of course, you want to think you’ll remember to do this every day, but I have found that to this day it helps if, from time to time (or, especially during really busy weeks) I set an alarm/calendar reminder to write in my journal. Usually I do remember to do this, but…I have been “saved by the bell” on more than a few occasions!

Start small.

You can begin by only writing a little bit each day. For the first few days, don’t worry so much about structure or scope or even format. Just get in the practice of putting pen to paper at the end of the day.

Review it at the end of five weeks.

This is how you’ll know whether or not it was worth it. Did what you write over the last 35 days show you anything, make you think anything, or prove you did anything differently? On your own path in life and at work, one way to make continual change and improvement is to start observing where you are, what you’re doing, and how you perceive it’s working for you.

Magazines, newspapers and tabloids are rife with stories and exposés of people’s lives. The popularity of these publications, and the widespread consumption of them only proves how focused we are on “story.” Hopefully, by capturing some more of your own story, you can begin to engage at a new level of professional development and focus on your most important things.

Jason Womack is the founder and CEO of The Jason Womack Company, which helps individual contributors, entrepreneurs, and executives work effectively and efficiently so they have the time, energy, and focus to achieve more in work and in life. He is also the author of “Your Best Just Got Better.” For more information, visit and or e-mail

Lorri Freifeld
Lorri Freifeld is the editor/publisher of Training magazine. She writes on a number of topics, including talent management, training technology, and leadership development. She spearheads two awards programs: the Training APEX Awards and Emerging Training Leaders. A writer/editor for the last 30 years, she has held editing positions at a variety of publications and holds a Master’s degree in journalism from New York University.