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Published February 8, 2020 Updated July 24, 2021

Of the many techniques you’ll pick up over the course of your career, one worth investing in early is journaling. Journaling might not seem like a worthy endeavor at first. Capturing important moments of your life on a daily basis might even seem like extra work on top of everything else you are juggling in your life but, in time, journaling will pay dividends if you stay disciplined and detailed. As you grow older, the details of earlier experiences will grow foggy in your mind. Being able to reconstitute past experiences in order to apply to them to present situations will help you make more informed decisions.

Additionally, journaling serves a dual purpose as it makes you a better writer. This is a wonderful skill to have which shouldn’t be underestimated. In addition to technical expertise, being able to express your thoughts succinctly, supported with documented details, is a sought after skill. Inadvertently exercising this part of your mind, on a regular basis, will allow you to keep this skill sharp.


How you organize your journal entries is up to you. Everyone is different and there is no right or wrong way to do this as long as it makes sense, is easy to add new entries, and can be searched through quickly. To start with, journal entries are meant to be chronological, so it does help to use a date/time structure:

  • Format: <year>/<month>/<day>/<hour>/<minute>/<second>

  • Example: 2020/01/01/10/10/10

Use of categories (for high level organization) and tags (for associations across categories) can be helpful too. Useful categories to start with could include:

  • Work – Lessons learned from paid work. In addition to the benefits of helping you stay organized and not let important ideas slip through the cracks, this also serves as a way to measure the pulse on how you are feeling about the work you are doing and the progress being made. When you look back over time and see a rocky or downward curve, it might be time to move on to something new. On the other hand, the use of your journal might be motivational, can serve as a reminder to explore previous ideas in greater detail, and can even help solve current problems.

  • Side Projects – Lessons you want to capture related to open source software, hobbies, etc. that might be worth sharing in a public forum at some point but currently is raw material.

  • Personal - For private thoughts and ideas of use only to you. This might include your health, mood, personal reflections, relationships, etc.

As for tags, you might want to use a single tag or multiple tags in order break down journal entries beyond high level categories. Tags make it easier to search for entries faster when, for example, you have a Dotfiles project you’ve been working on and you have it tagged as dotfiles too. Using multiple tags helps connect related journal entries across categories which is another nice way to group related information.

It never hurts to have a few tools to ease this organization of your thoughts. Here are a some recommendations:

  • Obsidian - Supports macOS and iOS. Has great sync capability between desktop and mobile, Markdown support, and becomes a second brain for organizing, tagging, and backlinking information however you see fit. It’s free to get started and $4/month to add sync features.

  • Roam - Supports macOS and is a way to document notes, thoughts, articles, snippets, etc. Like Notion, you can link all of these thoughts together for easy access. Roam will set you back $15/month or $165/year, though.

  • Notion - Supports macOS and iOS and is an all-in-one workspace for capturing notes, tasks, images, etc. The interface is basically a thin veneer over a complex database that can capture all sorts of information you might want to throw at it. Notion is free to use but you can pay a monthly fee for collaboration/sharing features.

  • Notes - Native to macOS and iOS, provides a free solution for gettings started which sync capabilities.


Choose a schedule, for writing journal entries that you are comfortable with. I would recommend at a minimum, to journal daily, even if briefly. It’s up to you to be disciplined about this as as only you will benefit. You can schedule this as a recurring action in your task manager or as a calendar event. Use whatever best fits your workflow and be diligent about it.

In addition to scheduling, you can capture important events as they occur such as thoughts while in a meeting or when working on complex technical issues. Yes, a journal can also be a helpful scratch pad for further reflective and refined thought later. If real-time journaling isn’t sufficient, try scheduling an end-of-day reminder to reflect on the day’s experiences.

Automation, as mentioned earlier, is key to being successful so figure out what works best for your mind and mode of operation. Here are some tools worth adding to your toolbox:

  • OmniFocus - Based on David Allen’s Getting Things Done book. It can cost over $100 when you buy the macOS and iOS versions but syncing is free. It’s a powerful tool and worth the investment.

  • Reminders - Doesn’t have a lot of bells and whistles but will definitely help get you started until you outgrow it. Free for macOS and iOS.

  • Calendar - If task managers are not for you, consider investing in calendar software and setup recurring events/reminders that way. Free for macOS and iOS.


In order to learn from past mistakes, experiences, and build upon earlier lessons it is important to review and reflect on your progress. A good rule of thumb is to conduct this kind of "self retrospective" weekly, monthly, and yearly. This’ll help keep where you have been and where you are headed in perspective. Plus, it’s nice to see how far you’ve come or gone off the tracks in case you need to pivot and course correct.

Personal Results

Over the years, maintaining a Pensieve so-to-speak has made me:

  • A stronger writer – As mentioned earlier, since I’ve been journaling, I’ve found I’ve become a much stronger when writing Git commits, responding to group chat messages, creating pull requests, replying to emails, etc. I find my content is structured and well composed rather than short, terse, or staccato.

  • A stronger learner - When capturing and reflecting on the various experiences of your past life you can see connections that weren’t there before. It’s fascinating when I reflect on past work and realize I’ve forgotten a tool or technique that I didn’t fully understand at the time. Now I have much more knowledge and context for how to apply that to the current situation and thus have saved myself additional time.

  • A stronger mentor – When you accumulate a lot of experience and expertise, you can forget what was the source of your tacit knowledge. I’ve found being able to search for and share recorded knowledge so others may learn and grow in a similar manner helps make you a fount of information.

Closing Thoughts

Your future self will thank your past self for recording this history. Being able to understand the long tail of your work — and therefore your life — is valuable in making informed decisions on what actions you’ll take next. Mine this information often because your experiences are gold.