Checklist Journaling to Maximize Daily Productivity

Submitted by jordan on Tue, 10/29/2019 - 07:37

Whereas the minimalism and empty space of a journal creates a canvas for expression, the structure and satisfaction of a checkbox completed creates a sense of accomplishment. 

We use different mediums for different outcomes in our daily lives and our work. Between the blank sheet of a notebook or journal, and a well-structured daily checklist — we somehow find balance between the organic, spontaneous, and oh-shit-that’s-due-today nature of our lives. 

Over the past few years I’ve been using a daily checklist journal in order to keep track of my routine, daily work or non-work activities, and even some goals and quotes to keep me motivated. 

My structure is pretty straightforward:

  • Inspirational Quotes. What I look to when I’m a little lost.
  • Monthly / Long-term Goals. What I’m trying to accomplish this month, quarter, and year.
  • Morning Routine. Vitamins, exercise, medicine, journal prompts.
  • Evening Routine. Vitamins, journal prompts, bad habits (alcohol/sugar).
  • Priorities Table. Sales, delivery / operations, management, and relationship priorities. 
  • Learning Tasks. Right now I’m learning Russian, and Serverless framework. (Don’t worry, they’re not related.)
  • Writing Tasks. A short list of my current writing assignments for myself. I try to do these in the morning before competing needs grab my attention.
  • Everything Else. The middle of my day. Typically this is where I detail my checklist based on the work schedule I’ve set out for myself on my calendar. Follow by…
    • … a loooong laundry list of things I probably won’t get to today, but haven’t moved into JIRA, Life Story Map, or another note system to do later.
  • Backlog Grooming. A list of great ideas I’ve had, which I acknowledge I won’t get to and likely needs to be entered into JIRA or elsewhere for consideration. 
  • Reading. What am I reading?
  • Watchlist. What am I watching?

Many do may have a daily journal, but what makes my approach unique is the nature of duplicating the entry from day-to-day. 

By copying the journal entry in Evernote, I have a ritual for unchecking the repeatable tasks from my morning and evening routines, and outlining my work tasks against my calendar schedule. 

Preparing the note for tomorrow gives you an opportunity to reflect, observe your thoughts and patterns—and incrementally change your checklist over time in a way that allows you to track your growth and experience.

It takes a bit of practice to see the value in it, but here is a short list of the benefits. 

Daily Checklist Journaling Benefits

  • Track morning/evening routines. My morning and evening routines are repeatable, but some tasks aren’t meant to be done everyday. Perhaps once a month, or once a week. Tasks like beard grooming can be weekly, but reminders for which vitamins I’m taking, and did I remember to take them, can be very helpful in the long-run. 
  • Monitor good habits. How often I have sugar, or alcohol, or remember to take time to go for a walk—these have an impact on my mental and physical health. We can’t be perfect every day, but if you track it you can improve it. 
  • Monitor bad habits. We don’t have checklists for these items, but I like to think that when I do something wrong or poorly, I take the time to reflect and say: “X isn’t going well”. We don’t need to be verbose unless you need an outlet, but if you’re going through a poor relationship personally or professionally, reflecting on the frequency of these interactions may give you the perspective you need to change something .
  • Practicing gratitude in review. In the day to day of a checklist journal, it’s easy to get caught up in the next item on the list. This productivity hack is definitely not a good idea for those who obsess, because you’ll spend enough days with a checklist too long to complete everything—and that may bring you some self-doubt and frustration. 
  • Pruning repeatedly incomplete tasks. Day after day, the list of incomplete tasks pile up as you copy your note and extend your list. Reviewing incomplete tasks—you know the ones that just tend to drag on and on—will enable you to consciously prune once in a while. You may just find some solace in confidently saying “I’ll never get to this, let’s let it go”. Cross it out (strikethrough formatting in Evernote), and let it go as a checkbox unchecked.  
  • Scrapbook your digital experiences. Having Evernote and Notion at my fingertips on my phone and while browsing the web make it infinitely easier to capture the ephemeral interactions I have while chatting with others. Sometimes these little screenshots give the best perspective on a heartwarming exchange with a friend or loved one. Don’t discount them. 

What does it look like?

Perhaps rather than all of this talk about what it is, you should just see the template:

To use this just copy it into your Evernote, or convert it to Notion.

Possibilities of Daily Checklist Journaling

If I had the time, I’d like to get more statistical data and correlations out of my journal. The repeatable daily tasks over a macro view can be quite nice, but as things stand with my Evernote, I’d have to do a lot of text analysis with something like geeknote. I just don’t have the time for that.

However, here are some thoughts on what’s possible, if I could query my journal for all of its statistical secrets:  

  • What routines did I have the most happiness as noted by my daily Mood Journaling.
  • When was I fasting, and how did that compare to my productivity?
  • When did I weigh myself? What did I weigh over time?
  • What were the days of highest checklist productivity?
  • What were the days of lowest checklist productivity?
  • When did I write the most that was not in a checklist item, e.g. where are my real journal entries in long-form?
  • How often do I mention specific friends or loved ones?

Evernote vs. Notion

I’ve used Evernote for years, now, but Notion has quickly risen up in my life through work and I’m considering migrating soon. A few things hold me back, and perhaps knowing about the trade-offs help you decide to use the right tool for you.

Evernote Pros

  • Flat text history of your journal for that day. 
  • OCR search for your images and scans of important documents. 
    • This is often important for me when I switch to my moleskine, and later want to commit the work back to my daily journal. 
  • Great search features across all notes. 

Evernote Cons

  • The application on my Mac OS desktop is often unstable. 
  • Doesn’t support markdown.
  • Doesn’t support embedded pages or complex objects like Notion. 
  • Interlinking is just like an HTML page, which is to say it’s not the best.
  • Limited API. 

Notion Pros

  • Pages organizable like a database.
  • Lines are organizable like a database.
  • Pages can have embedded rich-objects such as tables which have their own properties. 
  • Structured Data is much easier to track in Notion.
  • Strong API so I can extend some programmatic actions.

Notion Cons

  • Image scanning from the iOS app isn’t the best.
  • You can’t search for text in images. No OCR support.

Daily Checklist Journaling in the Future

If I could purpose build an app, I would add quite a few features including:

  • Conditionally remind me for important tasks on a given day. I could see this being done in Notion, where Notion knew what my Journal note of the day was, but it would probably stray too far away from the product’s core purpose and feature-set. Embedded attributes for a specific line item—such as an alarm—only makes sense if you’re using this like I am.
  • Automatically embed content from third-parties via API. I would love it if I could regularly, programmatically take my conversations from iMessages, Facebook Messenger, WhatsApp, and roll them up. We lose so much to these interactions, and sure it might be too much in a single note—but at least I would have it 20 years from now when one or all of these messenger platforms are gone. 
  • Integrated actions to fire APIs and webhooks. Checkboxes represent work tasks most of the time. I’d like to be able to fire a command that Pushes note to JIRA ticket, Logs time to Harvest, Send via Email. Ideally a blended version of what is possible with slash commands, to grab notes, copy them up, and send them where they need to be. This would have to be configurable, and represents a prosumer level of skill to configure and use—but my, how useful it would be! Notes as your command center, much in the same way Slack has become.

Conclusion

Once upon a time, I obsessed about my daily productivity. A busy day full of completed tasks made for a complete and whole life, right?

No.

These days I spend more time cutting back. Striking things out that I don’t need from my daily checklist, and waiting some time to delete them from my routine. The strikethrough of an incomplete tasks gives me the perspective to say: this is low priority and I’m consistently not doing it everyday, or have pushed it off for so long—that I should just say I will never do it.

Which isn’t to say I might not pick it up again in the future when it serves me. Many of these habits are about serving myself. Often selfishly, as it’s the only reminder in my day of how to focus, care, and nurture the things that I’ve consciously laid out in a monthly planning session, or sometimes, inspiration I’ve tapped anxiously on my phone in the middle of the night, betwixt dreams.

Of all of the benefits of my daily checklist journaling, I think the part I cherish the most is the continuity. Paper checklists, journal entries, and post-its fade and pile up in landfills. My digital anthology of the drab and drivel gives me a long-term view of how I’m doing, what I’ve spent my life doing, and gives me an instantaneous recall of important events we all don’t want to forget. 

So, perhaps even if you don’t find yourself feeling the call of the pen or the typewriter—consider the checklist for your daily reflection of self, productivity, and everything in between.