Journaling as a Management Tool

I've been a developer — or a "software engineer" if I'm feeling lofty — since the beginning of my career, nearly 20 years ago. In my heart, a part of me will always be an engineer, but growth in a career often leads to change.

About four years ago, I was asked to join the leadership team at Blend as Director of Development. With the new title came many new responsibilities, not the least of which was management. I am not naturally gifted at management, and this was especially the case in that rocky first year. In management, your team depends on you to help follow up on solving pain points and barriers, and I don’t have the kind of memory — or effortless talent for organization — to manage the workload without help.

So I started journaling. And, I did what any good engineer would do: I supplemented my shortcomings with a blend of technology, process, and habit.

Journaling.

When I talk about journaling, I don’t mean in the "dear diary" sense. The journal is not about what I did that day — though you can often piece that together based on my entries — but rather about what I plan to do and am doing throughout the day.

My daily journal is built around a template that organizes the daily tasks I need to complete. This includes:

• Review Yesterday - This refreshes my memory on what was expected the day before, and also helps carry forward any incomplete threads. On Mondays, I review the previous week in full to restore context that may have been — and almost certainly was — lost over the weekend.
• A Day Plan - After reviewing the calendar and the full task list, I determine what can be done that day. I know it won’t all get done — I make this series of tasks in part so I don’t miss anything — but this mostly helps give me that little hit of satisfaction from checking a box once something is completed.
• A Decision Journal - A recent addition that has already been helpful. If I make any important decisions, I document the decision itself, the full details of that decision, and (perhaps most importantly) why the decision was made. I tag this as a “decision” to ease in documenting those times when we need context on why a change was made.
• A “ Wins” Journal - Did anything good happen today? Did we launch a site, or win an RFP? Make a new hire? I note it down here and tag the quarter so when our quarterly review comes around I can hopefully answer the question, "What wins did we have this quarter”?

Then, throughout the day, as I meet with people in formal meetings or check-ins, I note the meeting, tag their name, and take notes about what we talked about. That way, when we next meet, I can easily refer back to what we discussed, recapture context, and remember what I need to follow up on.

Technology.

There are plenty of options in the journaling and note-taking space, including Notion and Obsidian, but I use Logseq. Logseq requires a bit more “hands-on” effort to get synching across devices but has a focus on privacy and a level of control that I appreciate. And it’s open source!

I haven't used the other apps — and some folks may fight holy wars over which of these apps is the best — but ultimately it’s more about how you use the tool than the tool itself. Don’t sweat it — just pick something.

Here’s what’s behind Logseq, in a nutshell:

• A Daily Journal - Each time you open the app, you get a new journal entry for the day’s notes. Journal entries are, essentially, a collection of bullet points.
• Pages - You can also create pages just like journal entries, except specific to a topic rather than a date.
• Tags - You can tag things! This makes them easy to find and also facilitates connections.
• Tasks - By adding “TODO” or “LATER” at the start of a line, you can make any bullet point a task. The task system is less of a full-fledged task management tool, and more of a framework upon which you build a task management tool that works for you. (More on this later.)
• Templates - Need to fill something out more than once? Make it a template. Logseq will do the work of copying and pasting for you.

The thing that binds all this together is that every tag is actually a page. A journal entry is simply a page with a tag of a specific date. When you view a page or tag, you can see every time you’ve referenced that page or tag. All of these connections are tracked and visible.

For example, if you tag your journal entries with "Took #dog for a walk," and then went to your “dog” page, you’d see a list of all the entries where you took your dog for a walk, even though those are on different journal entries. Pretty slick!

Structure and pages.

Within my system, I use Logseq’s features and my own tags to keep things organized and structured.

Pages and tags.

As mentioned, pages are tags, and tags are pages. I have a bunch of tags that I keep information on:

• Each quarter gets a page. This page includes information such as our company’s goals, the general “theme” of the quarter, and any other information I need to keep top of mind. I also tag things with the quarter as I go so I can review at a glance the “quarterly review” level materials.
• Each recurring meeting gets a page. On daily journals I tag any topics I need to bring up in that meeting so, before the event, I can review them quickly and bring them forward.
• Each person gets a page. In addition to tagging items I need to bring for discussion with them, I also keep some general information about them on their respective pages. Things like their start date, current professional goals, and topics I need to follow up on or keep in mind for them.

On my people pages, I may even include some “not strictly work-related” information as a reminder to check in on things. Someone’s looking to buy a house? I may note that so later I can say, "Hey, did you ever get that house?”

At first this seemed a bit shrewd. You might argue that, if I truly cared, I wouldn’t need to write it down. I should just remember this stuff! But I’ve found that the correlation between how likely I am to forget something and how much I care about it is weak at best. I don’t care at all about Vanilla Ice’s 1990 hit “Ice, Ice, Baby,” but for some reason I can still rattle off the first verse from rote memory, without even thinking.

Memory is a strange and fragile thing. So I paper over my soft and squishy brain’s shortcomings with technology.

Tasks.

Making tasks is easy. Listing tasks you've made is surprisingly hard. There is no easily accessible way to just “show me all the incomplete tasks.”

But, tags can be easily listed. So every TODO I create gets tagged in one of a few ways:

• Tagged with a person - This will get checked off the next time I meet with that person.
• Tagged with a meeting - This will get checked off when I bring the topic up in the appropriate meeting.
• Tagged with a date - Tasks that have been tagged with a date will show up at the bottom of journal entries for a few days before being due. This is a nice way to disappear a task and have it reappear sometime in the future.
• Tagged with “soon” - This is the priority list that I review first when I have time to fill.
• Tagged with “eventually” - This list is aspirational. It’s the one I look at when I’m sitting in an airport, not necessarily expecting to work, but ending up with some time. It’s like a backlog of nice-to-have things.

Rituals.

Finally, “rituals” are just templates full of tasks. Each weekday has a separate template with all the tasks and sections I mentioned earlier. Each quarter has a template of tasks and reminders. I schedule quarterly reviews with a template that lists all the employees, their start dates, and other helpful information for scheduling.

I have templates with checklists for any relatively complex process I have to complete regularly, such as site deployments. The checklist has the bonus effect of helping confirm our process: "Hey, did I remember to do that one step I always forget?”

Bringing it all together.

So this is a lot. I get that.

I’ve been evolving this system for about a year and it’s grown into this rich system of journals, tags, tasks, and rituals. And, it will continue to evolve as I adjust my journaling habit.

Ultimately, the power of journaling in this way comes from the immediacy of the connections and the convenience of keeping all of my information in one cohesive place. I don’t have to rely on my own habits to go find a note in a paper bullet journal — with something like Logseq, I just glance at that page and all the connections swim to the top like magic, instantly, and effortlessly.

This is my system. It probably is different for you, but perhaps you'll consider a system like it. If you do, make sure you tag me on that first day.