On journaling for over a decade

Mar 25, 2017

* * *

I’ve written every day since the fifth grade. That’s about 12 years of daily writing (and counting). I’ve recently been experimenting with different ways to capture my thoughts, which made me think back to how this all got started in the first place and how my writing process has evolved. I’d like to share that retrospective with you! Now!


My mom bought me a notebook and encouraged me to write in it while I was still in elementary school.[1] As for myself, I would write for a day or two but would fall off quickly. I was a kid, so I had better things to do.

One day, however, I discovered Diary of a Wimpy Kid. This was way before it went into print and became a New York Times best seller and (probably lame) film franchise. In 2005, the only way to read Diary of a Wimpy Kid was to click page-by-page on FunBrain. And I loved it.

It was the first book I read that made me consistently laugh out loud. The story arcs and character interactions were so mundane yet ridiculous that I surmised they had to be based off the author’s actual childhood experiences. There’s no reliance on pop culture references to get a cheap laugh — just solid characterization and clear, relatable writing.

The author Jeff Kinney does a great job of creating a wide cast of realistic characters, from bizarre relatives to classmates you swear are based off people from your own junior high days. Since there’s no main story arc, Kinney is able to lay the seeds for future gags weeks or months in advance before diverting the reader’s attention to another plot point. The format kept me clicking through pages, and when a gag finally resurfaced, I was always surprised and satisfied.

Despite the art’s simplicity, the simple outlines clearly conveyed emotion. They were almost like hieroglyphs: stiff and awkward, but they suggested to me that it was okay to draw even if I wasn’t “good.” More importantly, just because they didn’t look “good” didn’t mean they weren’t funny. The consistently recurring body components became a form of shorthand. Try and tell me that the left guy’s hand isn’t hilarious:

page 7, cred to Jeff Kinney
page 7, cred to Jeff Kinney

With a picture on almost every page, the pages flew by.

Around the same time, the Dear Dumb Diary series began, and I happened to get the first few through Scholastic book orders.[2] Similar to Wimpy Kid, they consistently got me to burst out laughing. In contrast to Kinney’s art, which only had one line thickness and seemed vector-based, Jim Benton’s drawings were loose and expressive, obviously drawn by hand with a Wacom tablet. His stories didn’t try to stick too close to reality but hilarious metaphors and outlandish imagery carried them nonetheless.

Looking back, the main characters of these series are not great humans, which made them stand out from the typical do-gooders of children’s books. They’re self-centered, dodge work, and are obsessed about the pettiest things. Yet despite it all, they remain sympathetic and relatable characters.

So anyway, two book series were funny enough to inspire me to write daily for the rest of my life.


I began to write and draw in paper notebooks. Taking after Wimpy Kid, I didn’t want to write in a “diary” because those were for girls. I wrote in “journals” instead.

Wimpy Kid and Dear Dumb Diary set the precedent, so I knew it was okay to draw. They also taught me that it was okay if the drawings were loose and not too carefully rendered. It was about getting my message across and being funny.

I would also tape physical memorabilia into the pages, which usually just meant amusement park maps in those days. Once I even taped the popsicle stick that the lorikeets at an eco-park ate birdseed off of. That journal was pretty bulky.

At some point, I began ending each entry with a rating of how the day went. Smiley faces were the metric. Over the years, inflation grew rampant. It got to the point where it was too tedious to draw the sheer quantity of lines and curves, so I would just put a multiplier by a single face.


I first discovered TiddlyWiki through Lifehacker, which I used to browse daily back in the day[3]. My first post dates back to February 29, 2008. I was in eighth grade (and it was a leap year).

I called it my DreamSketcher, from a phrase used in The Boy Who Saved Baseball by John H. Ritter. It started off as a place to store some passwords and ideas for new films after my friend Max and I produced our YouTube viral sensation, Spy Nerds 3. I was still writing in physical notebooks until April 27, 2008. The first sentence of my first DreamSketcher journal entry reads as follows:

Well, I just finished my last journal. A real journal. Meatspace, lines and holes and smudges and my illegible handwriting. I’ll just write in here until I get off my bum and start another one. Hopefully that will be tomorrow.

The next day, I wrote:

Couldn’t find a journal and it’s 10:37.


Writing digitally proved to be easier than going to the effort of finding a new journal, but I was aware of the tradeoffs, even from the first day:

Man. I can’t doodle on Tiddlywiki…That kinda sucks. And I can’t really rate my day…Oh, wait. Yes I can.

:D 62

However, I could now link entries to each other, categorize posts with tags, and search my thoughts by date and keyword. With these new affordances, I began using DreamSketcher as additional memory for my brain. I made entries cataloging websites I discovered, bands I should listen to, and words I thought were cool, and on and on.

TiddlyWiki is pure HTML and Javascript, so it can be used locally and offline. That also makes it quite future-proof; I still have a backup copy saved, and I’m looking at it right now.[4]

I ended up using TrueCrypt to protect my incredibly confidential thoughts on web comics and my teachers.


There’s a lost period of time between my last TiddlyWiki entry on May 11, 2011 and my first OneNote entry on June 29, 2011. I can’t recall why I stopped writing or if I used some other format temporarily. The closest proxy of a journal I have for that time period would be the my Gmail records. It’s crazy looking back at how my generation used email as a form of communication before the rise of smartphones, but that’s a post (or art piece) for another day.

I probably came across OneNote because of Lifehacker as well. I started using it as a journal the summer after junior year of high school, so the first month’s posts are all about LBW.

I carried on the TiddlyWiki tradition of using OneNote as an additional brain storage. I created a notebook specifically for school stuff (the most literal and obvious use of OneNote’s notebook UX metaphor), and I experimented with using it as a to-do list. However, even now, I have yet to come up with a to-do list system that I use for more than a few weeks.

One thing that OneNote could do that TiddlyWiki couldn’t was copy-and-paste images (in TiddlyWiki, you had to download them first), so I began to use it as a Courier, where I would curate art and inspiration.

I’ve been using OneNote for the last five years or so, but it’s been suffering from growing pains lately.

Growing pains

I used Windows computers up until my final HP ProBook died after freshman year at Stanford. I ended up buying a MacBook Air (that I still use to this day) because my dad had a hefty Apple gift card from a bank giveaway.

I used Parallels for a while in order to continue using OneNote, but a Mac version released about a year later.

Around September last year, OneNote kept crashing. It seemed to be having caching problems, and I realized that I had hit the 5 GB online size quota for cloud storage. I still wanted 5 years of my identity to be backed up, so I had to figure out what to cut.


At this point, I took stock of the different ways I used OneNote, and determined how I should separate these different goals. My OneNote is sprawling at this point. I went through and outlined its basic structure here.

I determined my main use cases:

  1. Daily journaling
  2. Curated collection of art that inspires me
  3. Ideas and images that make me laugh / cry
  4. Lists of things (films to watch, songs I can play, potential baby names, business ideas, etc)[5]
  5. Cached articles in case they disappear behind a paywall someday or I need offline entertainment
  6. Annotated collections of article links

Over the past few months, I’ve been experimenting with a variety of apps to fulfill these needs.


I discovered nvALT after my initial Google research to digital journaling and note taking. I took away three main principles:

  1. Portability
    • Plain text and Markdown are readable, universally importable, and relatively future-proof.
  2. Search over hierarchy
    • Instead of a nested jumble of directories, keep everything in one folder but maintain tags that you can easily search. Sometimes, I can distinctly remember snippets of what I wrote, so I can also search by a phrase and see the appropriate notes filter into the sidebar.
  3. Don’t leave the keyboard
    • This is related to #2. Instead of wasting time scrolling and clicking through different notebooks, tabs, and pages in OneNote, I can easily use keyboard shortcuts to search and select or create a new note entirely. This works especially well since my next step is to write, which means my fingers are already where they need to be.

nvALT is a great example of Doing One Thing Well. The keyboard shortcuts allow me to do what I need without the need to reach for a mouse or trackpad, and search is blazing fast. I know that it’s fulfilling my needs because I now get frustrated at how slow OneNote is for search and how I find it frustrating that I have to spatially remember which section a page is in and how far down I have to scroll to reach it.

Brett also introduced me to TextExpander, so now I have a lot of autocomplete macros for coding and oft-repeated phrases. Also I don’t manually date everything like I did with OneNote (I didn’t like the date formatting for its autocomplete). Searching by date used to be ambiguous because I didn’t use 2-digits (so month 10 showed up before month 9). Plus, I used American-style formatting, which is good for readability (everyone knows the year already), but bad for sorting. date format

Besides daily journaling, I also use it to take notes while I’m reading books, to write drafts for the blog, and to replace the lists that used to be in OneNote (Simpsons episodes to watch, songs that are stuck in my head, tech blogs that I should probably be reading, etc). I use Byword when I’m writing posts like these. I just hit 100 drafts at this point, so I’ve got a lot to share.


nvALT has trouble with large text files, so I get cursor lag when I update some of my heftier lists. There isn’t a real tag system, so I include tags as part of the filename (e.g. “dailyx”, “writingx”, “listx”). However, filtering by search will include any other files that include a link to a file with the word. An alternative would be to include tags at the beginning of each file, but I don’t like mixing metadata with content.

Day One

My friend Matt introduced me to Day One last year as his main journaling tool. I tested it in parallel with nvALT, but nvALT’s speed and simplicity won out. However, I still use Day One for unexpectedly useful feature.

I’ve set up Day One so that a little menu bar item pops up every hour and asks me what I’ve been doing for the past hour. I knew there was a risk I would fall into bad habits during my quarter off, so it was a way to consciously reduce procrastination. Even though no one else is seeing my progress, sheepishly writing out that I’ve wasted the past hour of my precious, limited time on Earth is a good way to keep procrastination in check.

If objective recollection was my goal, I could probably take it a step further and use a time tracking app to track all my computer activity in the background. The historical data could be a good way to determine trends in my browsing habits, work/goof-off ratio, etc, but I’d say the main goal of the hourly reminder is actually to force me to actively evaluate my trajectory for the day and make adjustments as necessary.

If you’re impressed by arbitrary numbers, I have over 1,000 hourly entries at this point.


The reminders can sometimes jolt me out of my concentration if I’m in flow state or working on something time-sensitive. For example, I’ve had to frantically close the popup during timed coding challenges. It’s also fairly slow to start up and load the main app when I want to browse through entries.


I’m currently experimenting with using TiddlyWiki again, which had evolve quite a bit since my junior high days. The idea of creating a network of atomic information chunks that can be re-used and linked still makes sense to me as a memory augmentation tool.

Currently, I use one specifically for job reflection. After every coding challenge, phone screen, and onsite, I reflect on what I did well and what I could improve on. I also optimize and annotate solutions I came up with as well as take notes on general CS algorithms, data structures, and topics that could come up.


TiddlyWiki has already proven its future-proof reliability, but I wish more had been done to improve its interface. The customization syntax is incredibly complex and documentation is sparse. I’m definitely only using a fraction of TiddlyWiki’s capabilities. It also has its own formatting language, but I prefer to use Markdown at this point across all platforms. I use a Markdown plugin, but it doesn’t have any of the neat autocomplete or spellcheck features that nvALT and Day One have. I also can’t use Tab to indent, so it’s a real pain to format code blocks for my coding reflections.


The aforementioned formatting struggles of TiddlyWiki led me to Quiver. Looking back, note taking with code has always been difficult. In OneNote or Google Docs, they were always auto-capitalized and drowning in red squiggly underlines.[6] I wish I had known about Quiver during undergrad because I have 4 years of poorly-formatted CS notes in OneNote that could really use an upgrade.

Quiver uses a cell-based interface and has five different cell formats: plain text, Markdown, code, LaTeX, and diagram. I alternate between Markdown and code. The code cell uses Ace editor, so I can also switch between programming languages and it knows how to format and auto-complete.

Whereas TiddlyWiki focuses more on technical interviews and conceptual notes, I use Quiver to follow along with web dev tutorials and record language-specific quirks or concepts.


The main tradeoff to the cell-based design is that it can be pretty slow to load up and render some of my notes. The keyboard shortcuts are clunky compared to nvALT’s, and I can’t figure out how to use Ace editor plugins (once again, documentation is limited).

Old-school geekery

Quiver allows for both Vim and Emacs key bindings in the code cells, so I’ve begun exploring those recently after only using Sublime throughout undergrad. They’re pretty neat, and there’s less pressure to use them now that I don’t have to worry about assignment deadlines as I learn. However, I can’t figure out how to customize those either through Quiver, and customization is a pretty big part of both of those programs.


My OneNote size quota filled up because of all the images I had accrued over the years (use cases 2 and 3 from the list). I haven’t found an ideal solution for this yet.

My online research brought me to Pixave, and I basically just manually transferred all my images to Pixave.


OneNote was good for image curation because I could annotate images and link sources, while Pixave is basically just a glorified folder. I can add additional metadata, but I don’t think it’s very portable if I ever decide to stop using the app. Pixave can filter images by color which is ostensibly really useful, but the swatch selector is really clunky (yet again, no documentation).

Pinterest is a potential alternative, but I’d prefer a local solution that allows me to easily access my data and metadata without having to wait for the next x number of images to load as I scroll. There are also no good export options for Pinterest, and if it isn’t clear by now, I’m pretty into future-proofing.

And now I’m blogging

You’d think that after a decade of writing, it’d be easier to write these blog posts. Turns out it’s an entirely different beast. Daily journal writing usually only gets one draft. I’m reflecting and ruminating, not trying to craft a cohesive message. It’s been a challenging experience, but I’m proud of what I’ve shared this quarter.

I first started posting publicly because I noticed how often I found myself telling the story of how I switched majors. It was a story people were interested in hearing, and I assumed that a wider audience might also appreciate it. I assume the only audience I can meaningfully write for would be people younger than me (or around the same age as me…maybe) because I have thoughts on high school and college and applying for jobs, but I guess that generalizes for most writing — you want to learn about an experience that you’ve never personally experienced, so the author has probably spent more time living than you.[7]


I have been warned by adults that some of my thoughts are a little too public, specifically my jobs essay, and I understand where they’re coming from. At the same time, I value honesty and vulnerability, and I believe the rewards I receive from this authenticity justifies the perceived risk. I’ve gotten way more encouraging messages about that post than I ever expected, and in terms of employers viewing this, I don’t think I would last long at a workplace that didn’t appreciate my candor in the first place.

I know I sound a bit cocky about this, but Dave Kerpen has more thoughts about this in his book (chapter 18: “Who You Are Online Is Who You Are in Life”) and he seems like a pretty respectable guy.

The Ideal

My OneNote refactoring process is still ongoing, but there are still plenty of improvements to be made. I am now split across 7 separate apps:

I’d love to have at least some of those consolidated in some panacea app with nvALT’s search and general zippiness, OneNote’s image OCR, Quiver’s cell-based formatting, and Vim’s text manipulation capabilities.[8]

There are also new products that I would also love to incorporate into my conglomerate, such as Thinglist and a localized version of Milanote.


It’s funny how things always come back around. Similar to this site’s current iteration as static HTML files, I’ve gone back to a simpler foundation of pure text files.

Writing this post made me realize that just because I switched to a digital format for writing didn’t mean I had to stop drawing on paper. James Kochalka drew daily journal entries for 14 years.

At this point, journal writing is 100% a compulsive habit for me, like brushing and flossing. I can’t to go sleep if I don’t put some words down.

Memory and immortality

So this post obviously isn’t just about journaling in the traditional sense. The bigger picture is that of memory augmentation.

The brain’s memory is fragile and unreliable. My friend Will loves thinking about knowledge management and recall. He imagines a world where we are constantly recording ourselves, so you can scrub back in time to recall that article you read at lunch or where you left your car keys.

For me, objective recall is only part of memory augmentation because it is passive. Journaling is active, a form of reflection and contemplation. A way to vent without judgement. Journaling is archaeological, revealing what I found important at the time (and it’s surprising to rediscover what I found important in junior high and high school). It puts my current concerns in perspective and reminds me both of how much has changed and how much remains the same about myself.

Whenever I visit Facebook, the Newsfeed inevitably has a long life update or musings on a political/global event from an acquaintance.[9] That seems to be the main use of the status update these days since Twitter and Instagram have gobbled up “short updates” territory. I think there’s value in consolidating those life updates and musings to a platform you own and control. Who wants their wedding photos sandwiched between Worldstar and Buzzfeed cooking videos?

At the core of all this obsessive writing and documentation is the desire for immortal preservation. Mark Manson writes about “immortality projects” (as defined by Ernest Becker) in his most recent book. It is the basis of civilization. It’s why people put their names on buildings or graffiti on the side of a bridge. It’s why hip-hop artists want to be the greatest of all time and why parents raise their children. Everything we do is driven by the belief and hope that our conceptual selves will last beyond our physical bodies.

Even Wimpy Kid touches upon this mentality in the early pages. With all the new technology that surrounds us and captures our every movement, at the heart of it all, we just want to be remembered.

Maybe with all I’ve written and collected, maybe my grandchildren will be able to read my thoughts. Maybe I can be reassembled as a virtual replica. At least for now, I find it important to consider every day how I want to be remembered.

  1. As I discovered just this winter break, my mom had kept a journal herself. We were moving houses, and she was going through old photo albums when she came across a small journal around the time I was born. She wrote in Chinese, with tidy and confident penmanship, about the little “first”s I was having as a baby.  ↩

  2. ’Member those paper catalogs they passed out in class? ‘Member??  ↩

  3. Like way back, when Gina Trapani was still editor-in-chief and before it got bought by Gawker. Looking back, browsing the site also sparked my interest and confidence in just making things  ↩

  4. Looks like I’m not the only one who’s impressed by TiddlyWiki’s robustness.  ↩

  5. This is really more to assuage my hoarding compulsion. I’ll never get through all the media I could potentially watch, but I can at least store it somewhere “just in case.“  ↩

  6. As a rule-of-thumb, any time you notice or observe a hacky workaround, you’ve just identified a strong need with a potential market.  ↩

  7. On the other hand, truly living and age aren’t always tightly coupled.  ↩

  8. Some geekiness to explore in the future: Notational Vim, VimWiki, EmacsWiki  ↩

  9. Or someone traveling looking for restaurant recommendations or a place to crash  ↩

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