Journaling – How to get started?

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Journaling – How to get started?

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If you’ve attended any of my leadership talks or workshops, you’ve heard me espouse the value of journaling as a leadership skills growth exercise.  

In my Certified Agile Leadership classes, I even give out a copy of my (current) favorite journal by Dingbats. It’s really an outstanding daily journal AND I encourage you to read the backstory about the company as well.

Since I talk about journaling so much, I’ve inspired a recent CAL class attendee to try it. But recently he sent me the following –

I’ve never been very good at journaling consistently and reading generic blog posts haven’t really motivated me. I was wondering if you’d be willing to share the types of things that you journal and the benefits that you find from the practice? 

Which I journaled about and then it inspired me to write this post 😉

  1. Find a quiet and regular time–It helps if you get into a rhythm in your journaling. So, given you schedule, try to find a quiet time each day where you can spend some time thinking and reflecting. Call it your journaling time and stick to it for a few weeks. Remember, it takes time to make it a habit, so force yourself to do it for a few weeks until it becomes more natural for you.

  2. It doesn’t have to take a long time—I usually spend about 15-20 minutes journaling each morning. But it could be as little as 5-minutes. Don’t get hung up on the amount of time. Instead focus on the quality of your reflection/thinking, and capturing a few relevant ideas for later consideration. In other words, start small but keep doing it.

  3. Use a physical journal—I realize that I’m sort of a dinosaur and everyone today writes on their laptops, phones, or tablets, but I want you to start out your journaling efforts on good, old-fashioned paper. I think the exercise of writing helps our thinking process and our retention. And don’t get hung up on perfect writing. There will be pages in your journal with just words or indecipherable pictures. That’s ok.

  4. Commit to doing it—Like anything worthwhile, for example losing weight, journaling success is tied to the commitment you give it. If you really focus on it and leverage the opportunity for reflection, introspection, idea/concept capture, connecting thoughts, etc. you’ll soon make it a regular part of your day.

  5. Expect to be amazed—I want you to enter each journaling session with the expectation of an explorer. Expecting that you will uncover things that you normally don’t take the time to think about. Some will be subtle and small things. Points for ongoing consideration. Others will be massive Aha’s that you will be surprised you have discovered sooner. And still others will be things that you’ve ignored or hidden away for so long that you never imagined them as important to your journey.

  • Personal Goals, Team Goals, Organizational Goals? And how to measure them?

  • Strategy development; problem solving ideas 

  • My strengths are? And how to increase them?

  • Appreciations – Family, Team, Organization, others?

  • Challenges – Largest? Top 10?

  • Things I need to face…Head on!

  • Ideas, brainstorming, lists, possibilities

  • What if…; what’s the worst that can happen?

  • Problem clarification; asking 5-why’s personally

  • Crucial Conversations I need to have; I need to receive

  • Learnings (what have I learned…to do, not to do?)

  • Planning learnings (what do I need to learn?)

  • Vision – Business or Personal

  • Where do I want to be in a month, quarter, year…specifically?

  • I am grateful for…

  • If today is my last day, what do I want to accomplish?

  • I received this feedback today, how to digest it? Look for the “truth” in it?

  • I get excited by? I feel sad when?

  • Remember to do this! Actions items

  • Note to self…

  • I failed today, I made a huge mistake today, how do I prevent them in the future?

  • I saw a team astound me today, by…

  • What made me smile today? What brought me joy?

  • I need to read this book…; put it on my reading list!

  • Wow, that was an interesting approach to…

And that’s just a quick list. I’m sure you can think of many more!

There’s this notion nowadays in the agile community of a concept called sense-making. I believe the genesis of it comes from Cynefin and Dave Snowden. But it might also predate his references.

Sense-making is also a useful notion from a journaling perspective.

So much occurs each day in our lives. If we’re not capturing it, it leaves us behind. Not only in our environment, but in our business culture, organizational dynamics, and teams. But also, within us. Within our own heads. Our journals, and our reflections during and after, can be of enormous help in our making sense of things.

Here are some follow-on references that compliment this post—


  2. HBR article that focuse on journaling and sensemaking –

  3. Here’s another guide with a solid list of things to journal about –



Hopefully, I’ve inspired you to begin journaling. Or to, at the very least, run a journaling experiment for 30-45 days and see what happens. You just might learn a new (and valuable) habit. 

Stay agile my friends,


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