How I Journal

March 15, 2020

This is part of a two post series on journaling. Part 1 discusses the benefits I have seen from journaling over the last decade, Part 2 discusses the process I have developed to reap those benefits._

In my last post, I described "why I journal", an expanded list of emotional and psychological benefits I have found in over a decade of consistent journaling.

When people ask "how I journal," they often begin by inquiring if it’s pen and paper or word documents on my computer. The answer is a bit more complicated than that. I would divide my system into A) processes I adhere to and B) tools and techniques. For me personally I’ve applied what I suspect is a reasonably modern take on this old craft, integrating media, keywords, hyperlinks, and digital process to make my journal work in the information age. Here are some aspects I optimized for as my journal grew into a larger part of my life, which may not be obvious in their importance from the outset:

Key Aspects for Process

Key Aspects for Tools

All of this is achieved primarily in Evernote, but you could use your own tools whether it’s OneNote, Bear, or Google Docs.

An Example: Putting It All Together

Before we get started, I thought I would give an example of how I generally go about constructing a journal entry. It’s a fairly loose process but involves leaving real-time, high-level markers for me to return to, where I then fill in what I hoped to capture from the memory.

Step 0: Start a new note in Evernote.

Step 1: Over the course of a new entry being open, I will add a few markers to my journal - I try for at least 3 inside each entry as it gives a pretty adequate snapshot of that point in time. “Markers” can be pretty broad

Step 2: Over the next few days, I will try to fill in a few paragraphs associated to the markers. Sometimes they are directly tied to the marker, like writing about my reactions to a specific place I visited on a trip. Other times they will be tangentially related to a marker, like writing about what was going on in the backdrop of my life during that same trip. As I get time at lunch, before I go to bed, over coffee in the morning, etc I will bang out a paragraph or two associated to each marker.

The whole time horizon for writing a single entry can be a single day or it can be a whole week. Total time for an entry is usually 15-60 minutes. Often times I have two or three journal entries in progress at any given time that I will return to markers and finish in a batch at a coffee shop or during a quiet, weekend morning. My best times to “close out” derelict journal entries is on planes and trains as I travel, which generally happens about once a month. Rather than play games on my phone, watch shows, or read - I prefer to write if I can.

With that high level picture described, here are the moving parts of the specific solution I have crafted for myself.

Process: My Rules for the Road

With regards to the actual content of the message, I have found three key actions on my part help me get the most out of my journal: templates, writing about positives, write about my feelings.

Use a Template

In my “marker” system above, I know generally what structure I am trying to achieve in each post - ideally three photos with three or more associated paragraphs. Anything more than that is icing on the cake; I have found such a system helps me achieve many of the benefits I am striving for. If you can’t decide on your own system, many different journaling systems have proliferated over the years. I recommend you pick one and use that as a starting point, slowly layering in your own requirements or sections as you need. Here are two systems I can recommend having used them before:

After using these two systems to help get my thoughts flowing over a few years, I have since transitioned to more free-form writing. Structure and “training wheels” are incredibly helpful to get started.

Lead with Positives, Then Layer on Negatives

The gratitude journal and the five minute journal both focus on positives, as I think any journal should. A journal can be a tome dedicated to a life lived intentionally with rich interactions and memories of those you love. I often get asked if I write about negatives, especially when I was using the gratitude or 5 minute formats. I initially focused on positives, and if my mind drifted to something darker I would then allow myself to write about negatives. But by forcing myself to first focus on positives, I was able to put the negatives in perspective before tackling them, rather than devolving into an angry rant (which can be good sometimes to get out of your system, but also destructive if it becomes habitual).

For example: if I had a long day of meetings with clients and the meetings went poorly, I may first write a gratitude about _getting through the day_ and showing some resilience despite a lackluster outcome. Perhaps some coworkers helped me along, perhaps I found some distractions to take the edge off the disappointment, perhaps I got a good workout in to release some tension afterward. Only after capturing this positive would I then jump into what had gone wrong, how that came about, what I or others had done to cause it, and more. By consistently leading with positives, I could feel my brain rewiring over time to scan my life for good outcomes worth being thankful for, as opposed to a default of focusing on bad outcomes.

My advice would be to first build the habit of recording positives, and use your journal as a sort of “rainy day fund” in which to deposit memories. I have found tremendous joy on my lowest days flipping through write-ups of meals shared with friends, time spent with family, trips to amazing places, or quiet, contemplative coffees. Also, by having a diversity of gratitudes that you contribute to over time, you’ll train yourself to be more in the moment and appreciate those times worth celebrating in your journal. I often find myself stopping and realizing I’m actively enjoying something so much that I’ll want to write about it later - a useful trigger to ensure I am purposefully savoring the here and now, rather than just letting it pass me by.

It was after I mastered this skill of seeking positivity that I began to allow myself to drift further into negatives. Though the above isn’t a hard and fast rule, I found it to be the best mechanism to ensure my journal didn’t become a graveyard of lamentable diatribes. My thoughts became more responsible.

Write about how you feel, not what happened

For me journaling is foremost a contemplative exercise in which I think about who I’ve been, who I am, and where I am going. Thus, simply “recording” events as they happened makes for poor introspection and even worse reading as time goes on. Consider these two entries and which you would rather tuck away for later.

The first reads like a grocery list, and frankly is how I used to write in my gratitude and 5 minute journals. Only after coming back a few years later did I realize how little this helped me understand who I was at the time and what was on my mind. It was simply an unimaginative sequence of happenings. To correct this, I tried to get a bit more in my head on any given event… what was the significance and why did I choose this, of all things, to write about? I found the results to be much more illuminating and help me actually process events with greater fidelity than I previously was capable of.

Writing about how I feel usually doubles as tracking “what happened." Often to describe my feelings I have to dive into the sights, sounds, quotes, and interactions that drove the memory, so simply changing the aperture of the writing lens was enough to derive a richer entry with about the same in-the-moment detail.

Tested Tools

To facilitate the above processes, I lean on a few critical tools. This is likely where my system diverges most from traditional journaling approaches because mine is highly digitized on purpose, affording me a great deal of benefits in accessing and finding memories. The core components are some form of cloud syncing, using images, and finding ways to link and search on entries.

Evernote for Ubiquitous Entry

I have been using Evernote daily for journaling and task management since 2012. It’s a service I happily pay for on a yearly basis because of the enormous value it affords me in keeping all my thought-work in one place. The ability to sync across multiple devices is a lynchpin of my system, because it allows me to jot down notes no matter where I am and refine them later on. I start most journal entries on my phone with a marker while I am out and about, and later I will return on my laptop to flesh out the thoughts. Once more, the fact I can sync between a personal and a work laptop, or access entries in the browser, means I am never more than an internet connection away from working on my journal. I also can dabble in local copies on my machines if I am flying or traveling internationally without consistent access to the web.

Evernote is the primary enabler of the “marker” templating system I described above. I will often add a marker while I am actively at an event with friends (say, a photo from my phone of us on a hike), sync it to my account, and then write in my journal that evening before I go to bed. If I have a good conversation with my parents, I’ll take a screen shot of my phone’s call summary with their name as a visual marker and later write about what we discussed and how it made me feel.

It’s a bit like leaving myself breadcrumbs to follow home, I drop these markers throughout the day. I am constantly in a dance of pushing markers into notes, syncing devices, filling out entries based on those markers later on, and syncing again. If I’m on the subway that will happen on my phone, if I’m eating lunch on a weekday that will happen in the browser of my work computer, if I’m on a plane home that will happen on my personal laptop. Evernote’s syncing feature allows for this type of ubiquitous, light-touch journaling system to work.

3 photos per entry

I use my phone’s camera or laptop screen capture software to ensure I grab at least 3 photos per journal entry. This is helpful in two ways

I’m a tremendously visual thinker, so I often can remember a conversation or experience by thinking about the snapshot I took to remember that specific time. Therefore if I see a photo within a journal entry, I will remember generally what I wrote even without reading the one or two paragraphs of associated text. If I’m looking for something very specific, the associated mental “meta-data” images provide makes posts easily findable and skimmable.

An additional benefit, interestingly, is having photos entries tends to provide richer echos of long forgotten entries. I’ll see an apartment I used to live in, a person I used to hang out with, a meal I used to cook, or a place I have long since visited and I am immediately transported back to a very different time in my life. The words I wrote associated to these images take on new meaning because I feel like I’m poking into a portal, able to see the imagery alongside the words in my mind of a time since passed. The quality of the photos doesn’t matter, as long as they contain some key facets of that period in my life.

For example, I was looking for a conversation I knew I had written about on New Years Eve a few years back, but wasn’t quite sure which New Years Eve journal entry it was located in. Just by looking at the associated marker images of various New Years entries, I was able to quickly locate that memory by finding the one of a dinner party at my friend’s house, as opposed to other venues in years past. What could have been a twenty or thirty minute fact-finding mission took only two or three minutes of filtering by New Years journal entries and then looking at photos.

Perhaps for others photos aren’t a necessary part of their journals; I find it to be an enormously high value-add that takes very little time or effort on my part, making it a slam dunk of an addition.

Hyperlinking and searching

Probably the most technical aspect of my journal is the wiki-style linking of entries to one another. Evernote and other digital note-taking tools enable the creation of internal links to other posts, allowing you to cross-link from entry to entry. This, combined with the ability to search on keywords to whittle down certain entries, makes my journal a place where I can easily find and access parts of my past I have written about. As someone who once kept a pen and paper journal, it’s a world-class improvement over boxes of old journals that are for the most part inaccessible and at times undecipherable.

I hyperlink across notes on a few dimensions. Here are a few to give you an idea:

On top of these hyperlinks, the most important thing to do is to ensure I am descriptive enough in my wording to ensure when I search for a particular memory, there is enough meat to locate the entry - almost like “memory SEO.” For example, the Washington Nationals recently competed in the World Series and I went to a watch party outside the stadium. I ensured my entry about that memory included “baseball,” “party,” “Washington Nationals,” “World Series” and more - as any of those terms will trigger a match. A week later, when I went to the Nationals Victory Parade in downtown DC, I hyperlinked back to the watch party memory to more closely tie those entries together. The end goal is to create a web of memories that I can jump around easily and arrive at adjacent thoughts.

Tying it all together

At any given time, I’m using the above rules to juggle anywhere from 1 - 5 posts simultaneously. I'm adding markers as I can, syncing between my devices, filling in details when I get downtime to write, hyperlinking posts together, revising thoughts until I get a journal entry to “done.” Thus, my journal is very much a reflection of what I see as a natural thought process: ever in motion, evolving, and in flux.

There are a number of moving parts to this system; I have slowly added them over time and for the most part all of this is just habit that naturally occurs over the course of the week. For each concept I outlined here, I tried 4 or 5 alternatives to arrive at this as what works for me. For anyone trying to get into journaling, I’d recommend not putting too much judgement on yourself or your process, but instead see it as a laboratory for experimenting how you express yourself and refine the tool for the goals you have in mind. If you’re deliberate enough, you will begin to prune away behaviors that don’t work for you and replace them with hallmarks unique to your system.

In a world where so much of our personal lives are broadcast out through social media posts, group chats, and short pings on messenger apps; I’ve come to enjoy this internal thinking ecosystem I created. Rather than being a distraction of who I am, it helps me process events more clearly, live in the moment, and refine my thinking in a concerted manner. As I put it earlier, this is a modern take on an old craft. My hope in showing the messiness of the process is to possibly inspire others to embrace the messiness and jump in.

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Dan Hedcut
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