Writing

How A Hidden Feature in Bear Changed the Way I Review Notes

Tuesday, April 30, 2024 • 8 min read

This is the second of what might become a series of posts about how I use the Bear app to improve how I leverage notes in my reading and thinking. This is not a topic that will interest many, but writing a blog offers its indulgences. Unless your interests lie in the nerdier aspects of note-taking systems, you can safely skip this one.

If you told me a year ago that I’d write a blog post about the power of Apple widgets, I wouldn’t have believed you. But here I am—writing a blog post about Apple widgets.

You might be asking, what are you even talking about? What are widgets? Apple introduced these quirky appendages in 2020 as a way to present information from apps on the home screen of your iPhone, iPad, or Mac. The most popular widgets provide information about weather, stocks, and news. My reaction back then was decidedly ho-hum. Why would I want to clutter the precious real estate of my iPhone screen when I could just open the app?

A particular kind of widget in Bear 2 finally convinced me of their value.

In January, I switched from Craft to Bear 2 for my reading and knowledge notes. I shared why I chose Bear in this post. The switch went so well that I soon brought over my journal from Day One and my writing from Ulysses. For the past four months, almost everything I’ve written has started and ended in Bear.

I knew that Bear’s implementation of widgets was top-notch. Widgets are an afterthought in Craft, and Obsidian doesn’t offer them at all. What I didn’t understand was that a widget exists in Bear that does something you can’t even do in the app itself: the random note widget.

Before I dive into how important the random widget has become in my notes system, let me explain the problem it solves.

The Compounding Value of Review

When I first created my connected notes system, I clarified three vital parts of the process: capturing notes and quotes from my reading; curating what I’ve gathered into the system; and compounding the knowledge and insights I’ve gleaned with regular review.

I’ve earned high marks on capture and curation. I’ve had no problem marking passages I like on my Kindle in this digital age. My physical books are filled with margin notes. And I’ve done pretty well organizing all those notes and quotes into stand-alone documents for each book I’ve read. In the Zettelkasten way, I’ve written hundreds of “permanent notes,” which are ideas or knowledge areas I’ve encountered across my reading, linked and cross-linked with other related ideas and books.

But the compounding part of the system, which consists of reviewing my notes and looking for connections and insights I might have missed — arguably the most crucial phase — had lagged. I was reminded of this when I imported my notes from Craft to Bear. I needed to correct some formatting issues, which required inspecting each note individually. There were many notes — far too many — that I hadn’t touched since writing them. What’s the point of taking notes in the first place if you don’t review them?

If you just put notes in all the time and never review them, you’ll have a lot of garbage and hidden notes. You’ll look at your software and realize you don’t use it and abandon it. — Curtis McHale, PKM in Retrospect

An inspiration for a better review process came from my years of using ReadWise. For almost 1,000 mornings, I’ve reviewed a handful of randomly selected passages from the books and articles I’ve read using the ReadWise app on my iPhone or iPad. These bite-sized reviews are a terrific way to remember and connect with quotes that are meaningful to me.

On many mornings, I’ll have an aha! moment from reading a particular passage or the coincidental benefit of seeing these random quotes strung together.

When I discovered the existence of random note widgets, I had another one of those aha! moments. What if I expanded my morning ReadWise sessions to include random book and knowledge notes from Bear?

Review Your Notes with Random Widgets in Bear

This is easy to implement in Bear. Here’s a snapshot of my dedicated Bear home screen on my iPad. I have similar screens on my iPhone and Mac.

Bear Home Screen on iPad

The random widgets (circled in red) serve as my morning reminder to review one knowledge note, book note, journal entry, and vocabulary word. Each pulls from a specific tag in Bear. Here’s an example of how this works for a knowledge note in my system:

Knowledge Note Example

Notice the two tags at the bottom of the note. The knowledge tag organizes the note, and the review/wisdom tag serves as a status. I added this by dragging and dropping all my knowledge notes onto the review/wisdom tag in the sidebar. This instant drag-and-drop tag assignment is one of Bear’s superpowers. Any note with this tag will appear in my knowledge review widget.

Here’s the magic of using a separate status tag instead of the note’s organizational tag for the random widget. Once I review the note, I delete the review/wisdom tag to remove it from the pool. This way, I never review the same note twice.

I currently have three hundred knowledge notes and four hundred book notes. It should take a year — more or less — to review each one. This cadence feels right.

I’ve written thousands of journal entries over the past forty years. I use an Apple Shortcut to pull up those I’ve written on this day over my lifetime, an excellent review method I brought to Bear from Day One. Out of those thousands of entries, I’ve tagged about three hundred as particularly insightful. These are the ones I review with my random journal widget. I may decide after a year to revisit these, or I might switch to other journal tags I’ve used in the past: fatherhood, goals, philosophical musings, etc. Keeping the review tag separate from the journal entry’s organizational tag makes these thoughtful rotations possible.

My fourth widget is a flash-card-style vocabulary review for challenging words I’ve identified in my reading.¹ I’ve structured the layout of the note so the definition isn’t visible from my Home Screen. I’ve prepended the title with two colons so these notes don’t clutter up my quick-open note searches. While this works great for vocabulary, the idea could be applied to almost any study topic.

Vocabulary Review Notes in Bear

Eventually, the widgets on my home screen will appear blank, meaning I have completed a circuit through the pool of notes in that category. At this point, I’ll restart the process by dragging the current crop of notes to its appropriate review tag. Any new notes I’ve written will be added to the pool, and the virtuous cycle continues.

Make Review a Daily Habit

I’ve tried to inject substance into these morning review sessions beyond mere passive reading. I follow the outbound links. I review the incoming back-links. I prod myself with questions:

1. What else have I learned or considered since writing this note that I can add?
2. Are there other books or articles that I’ve read that relate? Or new knowledge notes I’ve created that I should link?
3. If it’s a knowledge note, is it still relevant? Alternatively, has it grown so large in links and backlinks that I should carve it into separate ideas?
4. Can anything in this note help me with what I’m working on right now?

Some reviews are quick. Others are more engaging, particularly when I come across a note from an important book I read a while ago but haven’t fully absorbed or implemented. This kind of review is one of the most valuable ways I learn to apply what I’ve read.

Setting up these widgets on my Mac and my devices took some time, but I have come to appreciate the visual reminder on my home screen. Unlike the myriad ways our devices can distract us, here’s an invitation to quietly reflect on the wisdom and lessons I’ve gathered from the writers and thinkers I admire most.

Best of all, I have a sustainable process that avoids the dreaded black hole syndrome that plagues so many well-intended note systems, and it ensures I’m getting the highest rate of return on my reading and thinking.

If you keep your notes in Bear and haven’t explored note reviews with a random widget, give it a try. If you’re not using Bear, what process do you have in place for review? Let me know in the comments below.

Bear 2 for Writing and Thinking

Friday, February 23, 2024 • 16 min read

For the past six weeks, I’ve been evaluating an app to replace Craft for my reading notes.  This post shares the reasons I’m moving away from Craft and why Bear 2 might be the best app around for writing and thinking on the Mac and iPad.

Craft and the Value of Connected Notes

I use Craft to capture the notes, quotes, and wisdom I’ve gleaned from reading and studying.  Before Craft, these notes languished in the margins of books or notecards stuffed in a file box.  In three years with Craft, I have written almost four hundred reading notes linked to several hundred dedicated theme notes, creating what is unfortunately called in personal knowledge management circles a “second brain.” 

The lofty promises of automatic insights from smart note-taking tools are mostly overblown.  I still resort to notecards or a paper notebook when I’m forced to really concentrate. A digital tool does solve the issue of near-instant retrieval, though, and there is goodness in gathering notes together in a trusted system. 

So, while Craft may not be self-aware (yet), it has helped me retain and apply more of what I read and let me inch further down the path to wisdom in the process. You can read this earlier post about how I use Craft to help me read better here.

All is not well with Craft, however. Development veered away from its original minimalist design 18 months ago to expand into the lucrative corporate note-taking market. The once pristine interface is now saddled with sharing and collaboration features that aren’t useful to me. With each update, the app gets more complicated to use. 

Meanwhile, important shortcomings still need to be addressed. Craft still doesn’t offer a way to use tags to organize notes. Its search function is too dumb to look across blocks of text in a document.  Note security lacks encryption or even two-factor authentication. The default font size can’t be increased, straining my tired eyes in the evening. There’s no way to create a backup of my notes database, which seems bonkers. Adding unnecessary insult, the annual subscription cost for Craft just doubled to $96 per year.

Perhaps my biggest issue with Craft is its lack of versatility. In addition to Craft, I keep my journal in Day One and write for others in Ulysses.  I tried Craft for all my writing two years ago, but I missed important features and capabilities of these two purpose-built apps, and Craft’s hobbled search function made it very difficult to find anything as the volume of notes increased. 

It troubles me to keep silos between my reading notes, my journal, and my public writing when there’s such potential for synergy. Many of the essays on this blog started as entries in my journal. Some were inspired by a book I had read. I am missing out on connections and insights that would be easier to grasp if my writing were centralized in one connected app.  

As a result, I’ve been eyeing a new home for my reading notes that might stretch to include my journal and other longer forms of writing. One place for all my words.

A Summer with Obsidian

The obvious choice for most serious note-takers is Obsidian, an app that has exploded in popularity over the past three years. Obsidian is available on most platforms, stores everything in plain text files, takes linking and back-linking to new heights of efficiency and geekiness, and can be customized with a vast array of visual themes and function-adding plugins. Technology bloggers celebrate Obsidian’s ability to easily handle their notes, journaling, and writing. 

I spent two months trying out Obsidian as a replacement for Craft last summer. I found the learning curve treacherously steep. For Mac users, the Electron interface is a confusing jumble, reminiscent of my early days with WordPerfect. Persistence and grit are rewarded with a powerful, capable notes app that can do almost anything. Readwise integration works like magic. Obsidian easily handled my 4,000 journal entries from Day One and allowed me to create links between my reading notes and journal without hampering performance or search. Obsidian is continually updated with new features to improve its note-taking capabilities.  It truly is a fantastic tool led by a conscientious, values-first team.

I wanted to love Obsidian, and the nerdiest part of me still does.  But all that power and customization led to continual tinkering. I experimented endlessly with themes and plugins to perfect my system. I spent hours watching YouTube videos to figure out ways to automate more and more elements of my note-taking. I became proficient with the query programming language of the DataView plugin. Updates to the app and its plugins were frequent but rarely in sync, which resulted in crashes and performance problems that required my attention. The iPad and iPhone apps were slow to open, buggy, and sometimes unusable. Worst of all, I mistook futzing with the app for actual, productive work. I became bedazzled by the technology in the way the hammer shapes the hand.  I’m sure at one point or another, I referred to Obsidian as My Precious. In the words of Roland Deschain, I had forgotten the face of my father.

Obsidian may be the perfect app for many, or even most. Just not me.  I packed up my notes and returned to Craft.

What’s Important to Me

A weakness in people interested in note-taking apps is the shiny object syndrome. We’re always looking for the next app that will perfect our note-taking system, which is often just procrastination from doing the more challenging work of thinking and writing.  I don’t want to be that guy who keeps changing apps or, heaven forbid, only writes about changing apps.

To guide me, I needed to settle on the things that mattered most in a note-taking and writing app:

1. Intuitive design. I appreciate uncluttered apps that allow me to focus on my words rather than the tool. Minimalist designs appeal the most to me, particularly those that adhere to Apple’s interface rules for the Mac and iPad.
2. Note linking. The app must be able to link one note to another and show incoming links from other notes.
3. iPad and iPhone. The app must offer iPad and iPhone apps with feature parity to its desktop app. I do 90% of my writing on an iPad Pro. I review reading notes and drafts of blog posts on an iPad Mini. I frequently capture notes and ideas on my iPhone.  The app has got to support all this.
4. Fast. The app must open quickly, support markdown, and allow keyboard shortcuts to write and navigate my notes.
5. Search. It must be easy to find notes with simple but effective searching technology.
6. Versatility.  The ideal app handles note-taking, journaling, and longer-form writing without too much compromise of using dedicated (but siloed) apps.
7. Stability.  The last thing I need when I’m trying to capture a fleeting thought is a frozen screen, a crash, or having to update the app again before I can use it. Frequent interface changes for no good reason drive me up the wall.
8. Reasonable cost. Any monthly or annual subscription cost must match the value received.
9. Future proof. The tool stores my writing in plain markdown text files or has robust and trusted export capabilities that provide access to my content easily in the future, regardless of the app.

These criteria helped narrow my selection to just a handful of possibilities.  One familiar name kept popping up. 

Bear 2

The Bear app has been around for a long time.  Its first public beta appeared almost ten years ago, putting it into grandfather status compared to its peers. Bear is developed by Shiny Frog, an “artisanal” software firm that makes just this one app, and only for the Mac, iPad, and iPhone. 

The first version of Bear was released in 2016 and earned critical acclaim for its calming and quirky interface and ability to import and export practically any kind of notes file. I used it to tackle the chore of shuttling my notes between Craft and Obsidian.  

After a concerning lull in active development, a modernized version of Bear came out last year.  Bear 2 supports note linking, offline access to files, tables, tables of content, footnotes, powerful search, and note encryption.  I looked at it briefly when it was first released but moved on when I learned its organizational scheme doesn’t support folders.  No folders? What?

I decided I should have another look after reading 300 Times a Day, a gushing blog post about Bear written by a writer I admire. What I discovered surprised me. 

Designed for Mac

First, Bear is only available on Mac and iOS devices: no Windows, Android, or even a web client.  As a result, Bear is developed by Mac users who understand and leverage every aspect of the hardware and software to make it as intuitive and powerful as possible.  This shows itself in myriad ways: swiping gestures on the iPad do what you expect.  Intuitive keyboard commands exist for everything.  It works like a Mac app.

Bear lets you add widgets to your Home Screen for instant access to a favorite note or the last few notes you edited. Sharing notes between apps is seamless. Bear makes good use of Apple Shortcuts for automating note creation. 

Bear also supports the Apple Watch to capture thoughts on the go. I thought this might be a gimmick, but I have used it on walks to record notes on audiobooks that I doubtless would have forgotten otherwise.

Bear note capture on Apple Watch

Hidden Power

Beneath its calming interface lurks a set of power functions that rival and, in some cases, exceed those found in Obsidian.  You can search for notes by keyword, tag, special operators, and note creation or modification time. Search results extend to the contents of PDFs and images. On the Mac, you can search and replace text within a note (a feature lacking in Craft). 

Images in notes can be cropped, resized, and renamed. Any PDFs you insert show a nice preview (optional) and viewer when opened. On the iPad, annotations of PDFs with the Apple Pencil are easy to make.

Bear’s sync engine relies on Apple’s CloudKit technology. In my short time with Bear, syncing notes between my Mac, iPad, and iPhone has been fast and error-free. All notes are encrypted with Apple’s private keys, meaning Bear has no access to my data. The app can be password protected, and individual notes can be further secured with a password. In contrast, none of my notes in Craft were encrypted or even protected with two-factor authentication. A Craft employee or ambitious hacker could read all my notes.  In Obsidian, notes are stored as a simple folder of text files, available to anyone with physical access to my computer. To me, Bear feels like the most secure of the bunch. 

You can create a complete backup of your Bear notes. It might seem basic, but this was one of my sore spots with Craft that failed to offer any way to back my system other than a raw markdown export of notes. 

Import and export functions are truly world-class. Built-in importers exist for Day One, Obsidian, Evernote, TextBundle, and folders of Markdown files.  You can export to TextBundle and Markdown as well. If you have PDFs and images in an Obsidian vault, Bear is one of the only apps I know that can import these without breaking attachment links. Documents can be shared in PDF, HTML, RTF, DOCX, and ePub formats. 

I imported my Day One journal into Bear as a test of performance. Importing 4,000 journal entries and over 1,000 images and PDFs took under three minutes. Tags from Day One came over flawlessly.  Searching those journal entries was lightning fast, and I successfully retrieved entries where the search term was embedded inside a PDF. 

Each note has an information panel that displays writing statistics like word count and reading time, a table of contents, and back-links. Back-links are presented in alphabetical order and can optionally show unlinked mentions.  A keyboard shortcut toggles these screens on and off.  The Mac version allows you to drag the panel to the side so it stays open as you navigate your notes for reference. 

Bear has the most powerful web capture of any tool I’ve used, including DevonThink. Share a web page with Bear, and it will convert it to a very presentable note, images and all. I couldn’t do that with Craft or Obsidian. 

Exquisite Writing

What I like best about Bear is how it encourages thoughtful, distraction-free writing. The typography is exquisite. You can change the default font, font size, margins, line, and paragraph spacing. Pro customers can choose from 28 built-in themes, but the default, in my eyes, is perfect. With a keyboard shortcut or a quick swipe with your finger, everything disappears but your words. 

Markdown symbols are hidden (if you want), and keyboard commands produce all the formatting if you prefer to not type the symbols.  You can add footnotes, tables, images, external links, bullet and numbered lists, and quoted passages from a tool palette that pops up as you need it.

Tags

Bear’s organization scheme relies on tags, not folders.  This was initially difficult for me to wrap my brain around. I’ve been using folders to store computer stuff for decades.  Yet the implementation of tags in Bear is intuitive and powerful.  The tags from my Day One journal populated in Bear, and I could nest these under a parent tag called journal by just editing the tag name. Hundreds of notes were updated with the new nested tag name in a couple of keystrokes. In short order, I recreated my folder system from Craft as nested tags in Bear.  Tags offer the added benefit of allowing notes to appear in more than one place in your system simply by adding a tag.  Working with tags these last six weeks, I no longer see the need for folders, which I guess is what Bear is getting at with their tags-only organization. 

Here’s a high-level view of my tags in Bear. You can select custom icons for each, some of which are initially set based on the tag name. Check out what Bear suggested for my “drafts” tag nested under Writing. Only a Mac developer would pay this level of attention to detail and poke fun at the same time.

Tags and screen layout on the Mac in Bear 2

Cost

The pricing for Bear 2 is simple and fair. $2.99 per month or $29.99 per year for all its Pro features. Bear offers a free seven-day free trial.

A Wish List

There are a few areas where Bear falls behind Craft and/or Obsidian that do matter to me.  

1. Better control over back-link presentation.  Bear’s back-links are shown in a separate window without any ability to change the sort order. This could be better. Even without unlinked mentions, Craft's in-note presentation of backlinks is better than Bear or Obsidian.
2. Templates. Bear doesn’t yet offer the ability to create a new note using a template like Obsidian and Craft. I miss this feature, though it’s not that difficult to copy and paste from a template note. I’ve created my most frequently used templates using Apple Shortcuts, but it would be nice if Bear had the function built in as a keyboard command.
3. Improved persistence in note links.  I experienced what must be a bug when I inadvertently created a note with a name that already existed in my system. Links to the existing note were redirected to the new note without any notice or warning message. If I deleted the new note, all links created for the original note were erased.  This could create some serious data loss issues if not corrected.  Until this is fixed, I am mindful of naming new notes in Bear.
4. Version history. With Craft and Obsidian (with its premium sync service), revisions to individual notes are tracked and can be restored from a prior version with just a few clicks. This does not exist in Bear.
5. Quick open gesture.  Bear’s quick open gesture on an iPhone or iPad requires a three finger swipe down from the top of the screen. It works but isn’t always easy to carry out, especially one-handed on an iPhone. I believe pulling down from the top of the screen, which now searches within the note, would be better for this frequently used function.

My list of desires for Bear will be shorter than others interested in document collaboration or using platforms other than Mac and iOS.  Bear is working on a web version, which might satisfy some, but honestly, if you’re looking for collaboration or different platforms, Craft is still a great choice. Obsidian is hard to beat if multiple platforms, automation, and customization are essential.

Craft, Obsidian, and Bear — My Scorecard

Scorecard notes:

1. Links and Back-Links: Obsidian has world-class back-link capabilities, including unlinked mentions, but loses a point on presentation. Back-links are littered with brackets and garish yellow highlights that are difficult to read and give me headaches.
2. Future Proof: Craft loses points because alias wiki links revert to the original note name when exported. This export error affected nearly 100 of my Craft notes and took time to track down and correct. Obsidian ought to get a perfect ten since it stores everything in plain text, but the app lacks a TextBundle export function to preserve file links when moving to any other notes app.

Is Bear the one?

I’ve put Bear through its paces these last six weeks. I wrote a half dozen literature notes, over forty journal entries, and four blog posts. I expected Bear’s charm to wear off a little, but the joy is real. I am a little startled at how taken I am with the app. 

Still, I understand Bear isn’t for everyone.  It’s only available within the Apple ecosystem, lacks collaboration or web access, and can’t be customized or extended with plug-ins. It doesn’t even offer a way to organize your notes with folders.  These are deal killers for most.  

Steve Jobs believed that “innovation is saying ‘no’ to 1,000 things,” so you can focus all your energy on doing one thing incredibly well.  The Bear team at Shiny Frog must subscribe to this view. They’ve brought a laser-like focus to making an elegant, powerful writing and notes app for the Mac, iPad, and iPhone. For some lucky minority, Bear represents note-taking nirvana, an app closer in spirit to old-school typewriters and handwritten journals than typical feature-bloated software. An app that disappears into the background, letting you zero in on the most essential thing: your words.

It’s clear that Bear can handily replace Craft as my note-taking app.  I didn’t expect that Bear could so easily supplant Day One for journaling and Ulysses for writing. These are amazing, purpose-built apps that I’ve enjoyed for years. There are features I’d miss: “On this Day” reflections, journal suggestions and prompts in Day One; WordPress publication and manual sheet reordering in Ulysses. Yet, the power of having all my writing in one connected and comfortable place feels tantalizingly near. 

Bear might just become my only digital tool for writing and thinking.

Questions or thoughts about Bear, Craft, or Obsidian? Leave a note in the comment section below.

A Writer’s Journal: Day One or Craft?

Saturday, February 26, 2022 • 12 min read

I’ve kept a journal for most of my adult life. I got started in my early twenties filling dozens of blank journal books. Ten years ago, I went digital with an app called Day One, and I have been using an iPad to journal since then. My journal holds thousands of entries — over a million words — spanning more than thirty years of private thoughts and memories.

Day One is my most consistently used app for the past decade. The app provides a calming, distraction-free writing interface and an end-to-end encrypted syncing service that keeps my writing secure but available on all my devices. It handles photos beautifully, accepts audio and video entries, automatically captures metadata about your writing environment like location and weather, and links automatically with Instagram. Journal templates, writing prompts, and the “On This Day” personal history review round out an incredible journaling experience. I enjoyed it so much that I even took the time a few years ago to type in my old paper journals to have a complete digital record of my life’s musings.

And yet, I’ve had this nagging idea that I should give up on Day One and start using Craft as my daily journal software.

Why would I leave Day One?

On the surface, I’ve wondered if I needed anything more than a basic writing app for my journal. After all, I wrote for years and years with just pen and paper. Did I need a dedicated app with another paid subscription?

Yet, my true interest is more profound than saving money or mere simplification. It’s widely known that to write well; you have to read. There’s no better on-the-job training for an aspiring author than to read the works of other writers. It’s less commonly understood how many writers keep a private journal and, more importantly, how they leverage their private missives as inspiration for their published works. Henry David Thoreau, Joan Didion, and Susan Sontag were avid journalers who attributed at least part of their success to keeping a diary. David Sedaris and Joyce Carol Oates both consider their private journals to be critical parts of their writing process. Ralph Waldo Emerson filled nearly two hundred journal volumes over his lifetime, which he frequently consulted as source material for his essays and speeches. He spent months cataloging his journals to make access easier.

A reason I’ve maintained a journal for so many years stems from a deeply-held desire to become a published author. My earliest journal entries make this point again and again. When I root out the source of my few published pieces, each can be traced back to its origin in my journal.

As much as I love Day One, Craft has stolen my heart as an innovative note-taking and writing app that I’ve used for a little over a year as my knowledge management system. Modeled after Professor Luhmann’s Zettelkasten system, I use Craft to house about a thousand interconnected notes and insights from books I’ve read. The power of connecting reading notes through a system of links and backlinks is truly astonishing once you open your mind to the possibilities. I’ve shared how I use Craft to leverage what I read, and it’s this versatile linking capability that has drawn me to use it for my private journal.

What if, like Emerson, I took steps to make my journals easier to access when I’m writing for others? What if I brought together my journal writing and reading notes into the same cross-linked system? Would the organic connections I’ve discovered from my reading grow deeper through close association with thirty years of journals? Could swirling together my journal writing and book notes in a system like Craft make me a better, more productive writer?

Might the convenience of having all my writing in one place, fueled by the connecting power of links and backlinks, outweigh the benefits of a dedicated journaling app?

To answer these questions, I launched an experiment: I kept my daily journal in Craft for an entire month to see whether or not these private musings would infuse greater insights into my Zettelkasten system and, ultimately, better writing.

As part of the experiment, I imported 3,200 journal entries into Craft to test its search and linking capabilities (see the end of this post if you’re interested in learning how to export Day One to Craft). I initially expected to use Craft’s Daily Notes function but soon decided against that. The implementation of daily notes in Craft felt half-baked and disconnected from the central note-taking system. Instead, I created a “Journal” folder in the main Craft notes area, alongside my reading and permanent notes.

A Month of Journaling in Craft

Here’s what I learned after thirty consecutive days of journal writing in Craft:

Performance

I was concerned that Craft might lose its pep with several thousand journal entries spanning more than a million words added to its data banks, yet performance remained snappy. Search results were near-instantaneous, and syncing updates between the Mac and iPad were as fast as ever.

Security

Craft’s syncing system does not provide end-to-end encryption like Day One. I wasn’t very concerned about security or encryption for my reading notes. But my private journal? That’s a different story. In the end, I decided to accept the security risk for the promise of new insights and writing productivity garnered by a connected journal.

Writing Experience

I found the writing experience in Craft to be mostly pleasing. I hid the navigation sidebar with a keyboard command (CMD-) to provide a clean, distraction-free writing environment. Numbered lists, bullet lists, pictures, and even Apple Pencil drawings were easy to add. I enjoyed moving entire paragraphs around in my entry with just my index finger. But, there were some annoyances. Craft doesn’t permit a change to its default font or font size. I usually write in my journal before bed. In Day One, I scale up the font to make it easier on my tired eyes. In Craft, I found myself straining a bit when I wrote at the end of the day, wishing I could make that font a little easier to see. And while I generally don’t spend too much time editing my journal writing, I found Craft’s Undo capability tedious. While Day One will quickly erase an entire sentence with just a couple of CTL-Z commands, Craft insists on undoing each character, one by one, even to the point of redoing and undoing typos. It’s a small thing, but enough to pull me out of the writing trance when it happened, and something that more mature writing apps handle better. But, these are minor complaints. The overall writing experience in Craft was positive.

Search

With my journal now part of Craft, I could finally sift through decades of personal writing for insights to link to my knowledge system. Yet, I soon discovered that searching Craft with all those journal entries had limitations. Before this, a CMD-O search in Craft usually produced interesting and relevant results. Now with thousands of rambling journal entries thrown in, a search wasn’t as reliable or valuable. For instance, a CMD-O search in Craft for the word fatherhood produced a list of 30 randomly ordered documents. The same search in Day One found 65 entries, ordered properly by date. I learned Craft enforces a hard limit of 30 documents using this on-the-fly search method, though it’s unclear how it decides which to present. Craft’s dedicated search pane found all 65 fatherhood journal entries, but reviewing the search results was cumbersome. The journal entries were again presented in a random order, and the scroll bar persistently leaped back to the top of the list when I clicked on an entry, losing my place. This made a review of a long list of search results very challenging.

Further, Craft’s search functionality is ham-stringed by its reliance on text blocks. For example, If you search for a journal entry with the words fatherhood and marriage, Craft will only find documents where the words appear in the same paragraph. If the search words appear in different paragraphs of the same document, Craft won’t find it. Day One had no such limitation.

Dates

Dates are the universal building blocks of every journal. Since Craft is primarily a note-taking app, it doesn’t provide much context on the date something is added to the system. This can make finding entries for a particular day, week, or month more challenging. I partially solved this by appending the date to the journal entry’s title, so I can at least view the date as I scroll through a list of entries. But, there’s no easy way to zoom to a particular time period in Craft like you can with Day One.

Linking Struggles

Connecting thoughts through the power of two-way links was one of the main reasons I wanted to try Craft as a journaling tool. Surprisingly, I struggled to apply links when I journaled, and when I did, they served as a work-around to apply a tag vs. a legitimate link. This troubled me since creating these links comes so easily when I’m writing and curating reading notes. It seems my mental mode when I write in my journal doesn’t lend itself to self-editing or analytical reasoning. I must journal from a whole different side of my brain, favoring feelings, vague intuitions and dreams over links and connections and knowledge building. The writing fizzled any time I stopped to scan for potential links as I journaled. This happened again and again.

The Return to Day One

After a month of journal writing in Craft, I realized the truth. My journal isn’t meant to be poked or prodded, linked, or back-linked. For me, the act of writing every day in a journal is therapy; writing how I feel in the moment keeps me healthy and balanced. My attempt to elevate the process in Craft only diminished the meditative value of the journal writing, while producing little in the way of new connected insights. Not only that, but my system of carefully curated wisdom in Craft felt swamped by a tidal wave of mostly unremarkable and repeated personal observations, which obscured much more than it uncovered.

Before importing my journals, everything in Craft had been vetted and polished to contribute to my understanding of the world and what it means to be human. The source of these insights was gleaned from other writers’ books, but each note was carefully distilled and refined in a personal way that is meaningful to me. While my journals are comprised of all my own words and heart-felt reflections, they’re raw and meandering and filled with empty calories, which simply aren’t suitable for the wisdom I collect inside Craft.

So, my journaling experiment ended with a return to Day One, keeping Craft apart and sanctified as my knowledge system.

Back in Day One, I felt a new appreciation for the soft, cozy feeling the app offers the constant journaler: the writing prompt that stirs your imagination as you open the app; the time travel of reading your past “On This Day” entries that transports you back ten, twenty, even thirty years ago; the comfort and security of end to end encryption of my most private thoughts; the easy swiping through the past week’s entries to connect you to the story arc of your life; and maybe most important: that precious altered state you enter as you write for just yourself without any expectations or demands … but honesty.

This experiment may not have resulted in any new Emersonian journal insights, but it did ultimately lead me to a better way to leverage my journal writing in Craft. As part of my weekly review, I now take some quiet time with the analytical side of my brain to reread the previous week’s journal entries for insights and ideas that add something meaningful to my knowledge system in Craft. It’s the perfect way to maintain the therapy of my journal process while leveraging the best of my thinking in Craft. And since my lifetime of journal writing resides digitally in Day One, I’m just a couple clicks away from discovering those lost insights lurking inside this vault of my life’s experiences and musings.

Afterward: How to Export Day One to Craft

Here are the steps I took to export over 3,200 Day One journal entries and 700 embedded photos to Craft. I used the Bear and Hazel apps to help me in the process.

1. In Day One, I used the “Export … JSON” function to export all journal entries.
2. In Bear, I deleted any notes in the library, emptied the trash, and restarted the app.
3. I imported the Day One JSON file into Bear.
4. In Bear, I used the “Export as Markdown” function with “export attachments” checked. Craft limits each import of markdown notes to 2,000. To get the linked images to come across, you need to make sure your Bear export falls below this limit. In Bear, I selected about 1,500 entries and saved the export into an empty folder on the desktop. I called it Bear 1.
5. I repeated the process for the next 1,500 entries and again for the remaining entries. Folders Bear 1, Bear 2, and Bear 3 were now populated with markdown text files and folders of images and PDFs.
6. If my original Day One entry didn’t have a title, it used the first paragraph of the entry as its title in Craft, which was too long. I wanted to shorten that to a consistently formatted date. If it did have a title, I wanted to append a consistently formatted date to that title. I created a few simple rules in the excellent Hazel app to remedy this.
7. In Craft, I imported the contents of the Bear 1 folder using the “Markdown files” option. This added the first batch of journal entries to a newly created folder called Bear 1 inside another newly created folder called Imported Notes. This is important: I waited until the process concluded, and Craft was done syncing. In my case, this took about 15 minutes with my slow internet connection. If you move the entries out of the import folder before the sync is completed, many of the images in your entries won’t sync.
8. I repeated step #7 for Bear 2 and Bear 3 folders (this only applies if you have more than 2,000 entries in Day One). Again, I waited for each to fully sync before proceeding. I tested the sync on an iPad to see all the entries (and images) to confirm everything was working.
9. I moved the entries out of the Bear 1-2-3 folders into a Journal folder at the highest level in Craft. To do this, I had to select all the entries and keep scrolling down to the bottom of the window repeatedly to make sure I got them all.
10. For new entries written in Craft, I used the “/Date Today” keyboard command to append the current date to the end of the title to match the format used in the above Hazel rules.

The Craft App —A Year of Magical Linking

Wednesday, December 15, 2021 • 10 min read

It’s been a year since I adopted Craft as my primary research and note-taking app. I shared my impressions of Craft early on, but I thought I would provide an update on how I’m using the software and why, with all the other choices available in the personal knowledge management (PKM) space, I’m still all-in with Craft.

I use Craft as a Zettelkasten-style note-taking system fed by a healthy reading habit. I take notes on things that interest me so that I might use this knowledge to make better decisions and inform my own writing. Before Craft, these notes were scattered across note cards, journals, and the margins of books — locked away and seldom consulted. I had this uneasy feeling that I was wasting my time taking notes at all. But no longer. Over the year, the notes I created inside Craft have taken on a life of their own, approaching that mythic “second brain” potential. It took a while to reach critical mass, but I find that the time I spend — writing notes, linking notes, and exploring connections — now yields some of my most thoughtful and creative work.

So, yeah: I love Craft. The designers have created and continue to evolve an iPad-first thinking tool that enables me to focus on my ideas and connected thoughts without unnecessary complexity or clutter. It matches my sense of design sensibilities and interface delight; it works the way I think. With the announcement of Craft 2.0 and Craft X, I am more excited than ever about the future of this fantastic app.

In part, my enthusiasm for Craft stems from a short dalliance with Obsidian, another popular PKM app. I spent a few weeks in this alternate note-taking universe when ReadWise released its official plug-in for Obsidian. ReadWise is a service that gathers and resurfaces highlights and annotations from books and periodicals, scratching a particular itch for serious readers. Obsidian has won over many fans with its powerful linking tools on top of plain text files, and this new superpower of syncing ReadWise highlights automatically was too tempting not to try out. I soon learned that Obsidian wouldn’t work for me, and despite the automation with ReadWise, I hurried back to my beloved Craft. But in the process, I learned what matters most to me in using these knowledge and thinking tools that I thought would be useful to share with others who might be thinking about diving into the PKM world.

Six Reasons I Love Craft

1. Design

Craft is beautiful, drawing praise from just about everyone who tries it. The text spacing, the font choice, the intuitive user interface, the colors, and even the app icon options point to a gifted visionary with an intense focus on a near-perfect balance of form and function. Craft reminds me of the best of Apple’s hardware and software designs. But this beauty goes beyond appearance. Dragging a block or a note somewhere in the app (or outside of it) does exactly what you expect it should. Markdown text commands fly from my fingers and transform before my eyes into perfectly formatted text — no arcane symbols or HTML code to disrupt my thinking, no toggle between edit and preview mode to confuse me. My notes appear consistently polished, not janky with placeholder brackets, caret symbols, or exclamation marks. Sync is flawless. Intuitive keyboard shortcuts and slash commands keep my hands on the keyboard and my thoughts flowing without having to think; now, how again do you link to a block in another note? With other apps and Obsidian, in particular, the design and user interface feel like glaring distractions that interrupt flow. With Craft, everything on screen is there for a good purpose, nothing more. The interface fades into the background as I work, precisely what I want in a thinking tool like this.

  Most people make the mistake of thinking design is what it looks like. People think it’s this veneer — that the designers are handed this box and told, ‘make it look good!’ That’s not what we think design is. It’s not just what it looks like and feels like. Design is how it works.

— Steve Jobs ¹

2. iPad-first

Since I use an iPad Pro for almost all my work, I need a platform without mobile compromises. Craft was designed for iPad first, and it truly feels that way with no limits in functionality or power. It actually took longer for the Mac app to gain all the iPad features, which is backward from most developed software (Craft’s Mac app just won Apple’s 2021 software of the year award, so I guess it caught up!).

In contrast, Obsidian’s mobile offerings launched late and are still hobbled by functionality gaps and far too many compromises for power use. During my time with Obsidian, I frequently pulled out my old MacBook Pro to do things, which felt jarring in my iPad-centric world.

3. Sharing and collaboration

Craft includes excellent sharing options to other formats: a nicely formatted email, PDF, Microsoft Word, Markdown, and Textbundle, which allows a complete export of your database to other apps like Bear or Obsidian. In addition, notes can be shared between apps like Ulysses, Day One, DevonThink, and Things. Craft allows seamless drag and drop between apps. On the iPad, I often have Ulysses and Craft open in split-screen mode to review my notes and drag over blocks of text to incorporate as I write. Inserting an image into a note from Photos or the web works equally well. It interacts with these other apps in a consistent, predictable way, allowing me to focus on the content. I can share notes with colleagues through a secret link or even publish whole sections of my notes to the web, rendered with all the style and interactivity of the app itself.

4. Innovation

In the past six months, Craft released an astounding 25 updates to the app. New features include a calendar function, integrated daily notes, tables, inline equations, local file storage, expanded app customization preferences, image and PDF annotation, Shortcuts functionality, Markdown export improvements, and significant app performance boosts. Perhaps the most exciting innovation is still to come with Craft X, an open-source plug-in platform that developers can use to create custom functionality within Craft. A ReadWise plug-in is already in testing, and the roadmap suggests we might see features like WordPress publishing, automated templates, and other workflow automation soon. The pace of innovation at Craft is astonishing.

5. Platform confidence

Company stability and sustainability are factors to consider before investing time and money in a product or service. Craft and Obsidian are roughly the same age, so comparing their business strategy for growth is instructive. Craft avoided the freemium model and enforced a subscription fee from the beginning, followed by a sizable round of venture capital to expand the team and fund product development. Between this recurring subscription revenue and the capital raise, cash flow should not be a top concern at Craft. In contrast, Obsidian relies on its two founders for software development and capital. The vast majority of users pay nothing for Obsidian, which puts pressure on the long-term sustainability of the business. Obsidian recently doubled the rates for their optional syncing and publishing services to improve cash flow. Everything else being equal, I would bet on the company with a sustainable business model, capital, and that financial metric that eludes so many startups: positive cash flow.

6. Future proof

One of the raps against Craft is its proprietary database, where it stores your notes. This database structure enables all of the amazing functionality and power of the app, but should Craft go out of business, all your information could technically vanish. In contrast, Obsidian stores your notes locally in plain text, which should always be accessible in the future. I’ve lost access to my share of old word-processing documents due to unsupported file formats, so I had a chance to test Craft’s export capabilities when I moved my notes to Obsidian and back again. The results surprised me.

Craft to Obsidian. The steps to export your Craft data really couldn’t be more straightforward. Select all your notes and use the export to Markdown function. This creates a nested folder of all your notes in Markdown text format alongside images, PDFs, or other files stored in Craft. Next, open the folder as a vault in Obsidian. That’s it. Your folder structure from Craft carries over to Obsidian. The links between documents, even links to specific blocks within a document, come through perfectly. The export of 2,000 notes took under a minute.

Obsidian to Craft. The process of getting my notes back out of Obsidian was surprisingly tricky. While notes in Obsidian are simple Markdown text files, maintaining the critical links between note files, images, and other embedded files is complicated without a proper export function (which Obsidian lacks). Thanks to a tip from Curtis McHale, I used Bear, a competing notes app, to import my notes from Obsidian. Since Bear doesn’t recognize folders, I had to consolidate all my notes from a dozen folders in Obsidian to one catch-all folder to avoid losing links. Bear was able to import all my notes, complete with links between notes, images, and PDFs, and then export them in a format that worked fine for Craft. Once in Craft, I had to refile all my notes back into my folder scheme, which took some time. For software that touts itself as the ultimate in future-proofing, I honestly didn’t expect it would be such a hassle to move my information back to Craft. Bear gets high marks here for serving as the go-between, but it seems like a pretty big gap for Obsidian not to have a proper export function.

Despite the time it took to retrieve my files from Obsidian, I discovered how easy it was to export my information from Craft, which isn’t something you usually figure out until it becomes a critical necessity. I now have very little hesitation with trusting my notes to the Craft with its top-notch export capabilities.

Is Craft for You?

I am sold on Craft as my knowledge tool, but that doesn’t mean it’s perfect or necessarily suitable for everyone. Obsidian is popular for good reason. It’s free for most users and available on more platforms, like Windows and Android. Secure encryption of your notes is possible with its optional sync service. It provides more powerful back-link capabilities and unlinked mentions, and a graph view of your linked notes that doesn’t exist in Craft. While the Obsidian interface doesn’t appeal to me, direct manipulation of Markdown and HTML code is the preferred way to write and think for many, particularly programmers. And, because it’s so easy to export my Craft data, I’m keeping Obsidian around for times when I want to dig deeper into unlinked mentions or mine insights from the notes graph.

In Atomic Habits, James Clear cautions about confusing motion with action when getting things done. Motion represents all those things we do before getting down to work. Thinking about it, planning, organizing your desk, making lists, selecting tools, etc. Action is doing the work itself. Since the work is often difficult and draining, it’s tempting to slip into the trap of motion, and switching software tools, like my two-week foray with Obsidian, is the very epitome of motion.

So, my advice is to pick a tool that feels right to you and stick with it. After all, the real value of these tools stems from the thoughts and connections you bring to it, which takes time and critical mass to yield any lasting benefits. After my year with Craft, it feels like we’re both just getting started.

Questions about Craft? Leave a note in the comment section below.

1. Quoted by Ken Kocienda in his book Creative Selection. Page 187. ↩

Grammarly, Ulysses and Lost Links

Saturday, October 23, 2021 • 3 min read

I’m a long-time subscriber of Grammarly, the subscription-based grammar checking and proofreading service. I’m the kind of writer that needs grammar and style checking. No matter how many times I review a draft, the round trip through Grammarly finds some sort of error. It’s tough to proofread your own writing, and incorporating this final check in my process has saved me from some otherwise mortifying bloopers. The cost of a premium Grammarly subscription feels low when compared to publishing articles with these dumb writing errors.

I use the writing app Ulysses for all my published writing. I love its distraction-free environment and its ability to publish directly to WordPress. Last year, Ulysses introduced a solid grammar and style checking tool of its own called Revision Mode. It’s a powerful proofreading tool, and I appreciate how convenient it is to check my text without leaving the app. But, at least for me, it’s not as comprehensive in its error-checking capabilities as Grammarly. When it was first released, I corrected drafts of my writing first in Ulysses with a follow-up check in Grammarly. Grammarly would always find additional mistakes that Ulysses missed. In addition, Grammarly points out wordy or unclear sentences and offers up alternative wording suggestions that are usually pretty good.

Grammarly doesn’t support the Markdown file format that Ulysses uses, so checking the text of a Ulysses document is done by copying and pasting between the apps. The problem with this approach is that any links to external sites get lost in this round-trip process.

I encountered this glitch recently after I publishing a blog post with a bunch of links to other websites. The links in the post-Grammarly document retained the appearance of a proper link with its blue underlined font, but clicking on any of them in the published article took you nowhere. The embedded link instructions were wiped clean. I had to hastily edit and republish the post once I discovered the error.

After this snafu, I contacted the support team at Ulysses and received the following guidance on how to send drafts to Grammarly and back without losing any data. I’m sharing here in case others might benefit from these instructions:

How to Preserve Links in the Round Trip between Ulysses and Grammarly:

When you copy text from Ulysses to Grammarly, perform a right-click › Copy as › Markdown. When you are done in Grammarly, copy the text there as would normally do, but then in Ulysses, right-click again › Paste from › Markdown (not Paste as...). Doing so will preserve any Markdown links in your Ulysses document.

I’ve tested this on both the Mac and iPad versions of Ulysses, and it works perfectly.

Writing Things Down in a Paperless World

Friday, September 24, 2021 • 5 min read

For the past ten years, I have been on a mission to eradicate paper from my work and home life. I can now access information more quickly and from anywhere, whether at sea or at the Apple Store where I need to produce the invoice for a dead MacBook Pro. And yet, one hold-out refuses to go gently into that dark night of paper annihilation: my Field Notes notebooks. These pint-sized memo books with their quirky designs and durable paper still travel with me just about everywhere. I sometimes wonder at the irony of using a $1,000 iPad Pro as a lap desk to scribble in a $4 notebook.

With everything else in my life so digitally focused, why do I still fill one of these 48-page Field Notes every three or four weeks?

This morning, I pulled out a year’s worth of tattered notebooks to see if I could solve this mystery. To be honest, I was apprehensive at looking too closely. Part of me wanted to leave well enough alone and not probe, perhaps fearing that I would find a bunch of meaningless jibber-jabber and force myself to give up these little books that I love so much. With some trepidation then, I skimmed the scribbles, diagrams, lists, weird dreams, single underlined words, whole paragraphs of intense, slanted scrawl, arrows, and lots of scratched-out words. Each notebook told a confused story about my state of mind at the time: hopes and worries, looming decisions, crazy, half-baked ideas, and incomplete solutions to problems that troubled me. As I flipped the pages, I watched meandering thoughts morph and solidify under the pressure of continued probing and analysis.

Give me a small canvas of blank paper and a pen, and I can slip into a deeper mental state than I seem to achieve in front of a blinking cursor. After a few minutes of doodles, I may even open a tiny crack into my subconscious. The physical act of handwriting may provide a familiar comfort that allows my mind to settle and focus. Perhaps it’s the simplicity of the interface: no buttons, no battery to charge, just me and my ill-formed thoughts. Maybe the old leather cover I use to carry the notebook and pen, scuffed and softened over many years of use, sends a chemical signal through my fingertips to open, to relent.

Psychologists have shown that writing things down on paper helps you remember better. The folks at Field Notes understand this:

Jamie Rubin, a writer and technology enthusiast, recently returned to notecards for his reading notes after struggling to reap the benefits he expected from keeping these inside Obsidian. I store my reading notes in Craft but have encountered few of the promised eureka moments since adopting this Zettelkasten technique of hyper-linked notes. While I appreciate the ability to retrieve and update these notes quickly, I don’t seem to be able to think as clearly (or as abstractly) within an app like Craft as I do on paper.

In one of Nabokov’s lectures on literature ¹, he defines memory as one of the four key attributes of a good reader (or thinker). Whether you remember things by writing them down or searching your Obsidian vault might be a wash. He calls having a nearby dictionary the second important attribute. Here, I tip my hat to the internet. How satisfying it is to tap an unknown word on the screen of a Kindle with my finger, and as if by magic, a well-crafted definition (or translation, or Wikipedia page) appears without leaving my place in the text. But, it’s his final two attributes of a good reader, that of having an active imagination and some artistic sense, that strike me as the hardest to achieve digitally. Artistry and imagination are still the dominion of pad and paper.

When I’m stuck on something, I instinctively reach for my little notebook — not my iPad. And while what I capture is often raw and disjointed, I review these notes every morning over coffee, checking in with my subconscious, allowing fragments to inch together as if by magnetic pull. It might take days or even weeks of scribbles and circled words to reach true clarity of thought.

When Jimmy Buffett has an idea for a song — sometimes just a phrase — he writes it down on any available scrap of paper and stuffs it into an old sea chest. When he’s ready to write some new music, he sits down and pulls out all those scribbles, which I imagine must be torn off bar napkins and beer coasters, and sorts through them, one by one. He says many of his most popular songs marinated in his sea chest before emerging as lyrics.

I do something similar in Field Notes. I reserve the last page of every notebook for my “Compost Heap,” a technique I borrowed from Neil Gaiman’s wonderful MasterClass on storytelling. Here, I write down bizarre images from dreams, lines from songs, evocative phrases, short descriptions of people I’ve met, places I’ve visited — really anything. Over a few weeks, the list grows to a page or two of disconnected images and ideas, and often, I discover a larger mosaic than my conscious mind could articulate on its own.

The whimsy of Field Notes encourages this kind of abstraction. These little books would be plenty happy to record Scrabble scores or grocery lists or meeting notes. I’ve used beautiful leather-bound journals in the past and felt that unease at despoiling that first cream-colored, thick-stock blank page. Something fancy like that would freeze me in my tracks. But a wee Field Notes notebook urges me to scribble thoughts that haven’t left that gauzy symbolic state in my mind or bump together two very different lines of thinking whose offspring becomes a new insight.

Don’t get me wrong: a computer is terrific for capturing, storing and retrieving transactional or reference information. I would never go back to the stacks of files and paper that once littered my office. And while I love the promise of technology helping me uncover new insights and connections, I have come to accept — and celebrate — that my best thinking still takes place within the humble confines of a pen and a Field Notes notebook.

1. Vladimir Nabokov, Lectures on Literature (A Harvest Book, 1980), 32. ↩

Want to Keep a Journal? Go Digital

Thursday, January 21, 2021 • 6 min read

I’ve kept a personal journal for most of my adult life. These journals have helped me wrestle with every significant decision and manage through the many stresses of everyday life. Last month, I put down my millionth word in over 40 years of self-reflection.

I’ve written about the reasons to keep a journal, and by far the most frequent question I receive from readers is how to establish a regular habit of journaling. Many find it easy to start a journal but much more challenging to keep it up.

For years, I purchased attractive leather-bound journals to collect my thoughts, but some of these books took years to fill with my slanted, left-handed scrawl. There were a couple tumultuous years in my twenties when all I could muster was a single angst-ridden entry. It wasn’t until I moved to a remote island where I was forced to take a solitary ferry ride to work each morning and night before my journaling habit took hold. Watching a storm-tossed sea out the cabin windows of a ferry boat put me often in the mood to write.

Now, I realize that taking a ferry boat to establish a journaling habit isn’t practical for many people. However, I did learn something else about my journal keeping that might be more useful.

Eight years ago, I tried the Day One app to see if a digital approach might replace my cherished leather-bound books. Day One was one of the first journaling apps to come out for both the Mac and iPhone/iPad. My first entry wasn’t particularly optimistic about this new technology:

I think writing here in this way will have me more focused on the device than the words. Hard to imagine myself getting into the writing zone like this, always worrying about hitting the right keys ... Still, it is convenient, tapping away as I am now from my easy chair, writing this entry on my iPad instead of surfing web sites.

Journal entry: December 12, 2012

Despite my initial uncertainty, I adapted quickly to a digital process. Since 2013, Day One has been my sole journal writing tool, and I would never go back to hand writing my journals. A few years ago, I transcribed my old paper journals into Day One for digital safekeeping and to revisit my youthful writing. With all my journals reduced to ones and zeros, I recently measured my productivity before and after switching from paper. Here’s a chart of my journal entries over a long span of writing (eight years on paper, eight years using Day One):

In my final year of paper-based journaling, I wrote 33 entries. That’s a little under once a week. My journal output shot up five-fold in my first year of using Day One. Comparing eight-year time spans on both systems, I wrote four times more entries in Day One than on paper. Over the past couple of years, I’ve written just about every day in Day One. On top of this, I share more each time I write in Day One. My typical paper entry ran 300 words. In Day One, that has increased by 20 percent, now 365 words.

After all those years of writing on paper, how did Day One make me a more prolific journal writer?

I think the most significant breakthrough for me was ubiquitous access on mobile devices. I usually kept my paper journal in the glovebox of my truck, where I wrote during ferry crossings across Puget Sound. As a result, I seldom wrote at home, or at work, or on weekends. With Day One available on the Mac, iPhone and iPad, I could capture thoughts in many more places and times. I grew especially fond of writing on the iPad with its compact size, always-connected cellular radio, and comfortable keyboard. Last year, nearly 100% of my entries were written on the iPad.

Unlike a paper journal, Day One allows practically every form of digital communication to become part of a journal entry. Emails to friends and family, Facebook posts, and blog posts are just a copy and paste away from my journal. And of course, I can add photos. I have over 500 photos, videos and sound clips in my journal that bring a whole new level of intimacy that simply wasn’t possible in my old paper journals.

After I transcribed my old journals into Day One, I realized I had the ultimate personal knowledge system. Almost everything important that happened to me in the past 40 years is accessible with a quick search. What did my doctor tell me at that visit back in 2005? I can easily retrieve it. What were my daughter’s first words? I wrote about it (today, I would have recorded it!). I apply tags to my entries, which makes it incredibly powerful to review my personal musings on themes like fatherhood, marriage, spirituality, travel, etc. All of these thoughts were buried and locked away in my paper journals but are blissfully free in Day One. It’s become an incredible resource of information and insight about myself, which in turn has become a positive reinforcement loop to keep recording my thoughts.

Some other reasons that drew me a digital tool like Day One:

• Data encryption and on-device security makes my electronic journal much, much more secure than a book I carry around. I once left my journal in a hotel room in Atlanta. It took a half dozen calls and six weeks to recover it. Needless to say, I was mortified at having my private thoughts pass through a stranger's hands.
• Day One offers daily journaling prompts, which help you if you’re unsure what to write. A few of these took me to unexpected places and developed into some of the most memorable entries.
• I’m able to time travel each morning as I read my “On This Day” entries. Day One pulls together every entry across all years from the current day into a special layout for review. Reading about my life in my own words from 25 years ago to the present day is incredible and frequently humbling.
• Day One adds meta-data to each entry behind the scenes like location, weather, and even what music you were listening to while you wrote. The world map of all the places I’ve journaled is fun to review.
• And finally, my journal entries can be exported into various formats as a backup in case Day One ever goes out of business. For example, I opened my lifetime of journal entries in Microsoft Word to calculate the writing statistics I cited previously.

If you keep buying attractive blank journals, but struggle to fill them, you should give a digital option like Day One a try. Set a daily reminder and take the few minutes you might otherwise spend on social media to write to yourself. Write about the big things in your life, but also the small, precious things. Or answer the day’s writing prompt. You might be surprised at what you share. And trust me: your future self will thank you.

The New Craft App Does More Than Keep Notes

Thursday, January 7, 2021 • 6 min read

About a month ago, I started using a new Mac/iOS app called Craft to help me make sense of books I read and organize ideas and content for my own writing. I was intrigued by the potential of bringing all my disparate notes into one friction-free digital home, enabling new connections and insights from all these books and ideas. The inspiration for this came from reading Sönke Ahrens’ book How to Take Smart Notes, which introduced me to Professor Luhmann’s famed Zettelkasten system.

Before discovering Craft, I used an assortment of tools that never really meshed with how I liked to work. I did my writing in Ulysses. I housed some frequently accessed PDFs in Apple Notes. I kept stacks of orphaned index cards with book notes and insights in a card box. I stored book notes and research references in DevonThink, along with lists of books I’ve read and others I wanted to read. While I enjoyed the retrieval power of DevonThink, its obtuse editing function frustrated me (why must I click into a different mode to edit a note?). Its inefficient sync process frequently had me exasperated, waiting for my notes to appear on whatever device I was using. There’s nothing that kills creativity faster than having to fiddle with technology before you can capture your thoughts. Or forgetting where you stored that quote you need for an essay you’re writing.

I was stumbling along unhappily with this setup when I heard about a new note-taking app that MacStories named their app of the year. That’s high praise for software released in November. So, what is Craft?

Craft shares note-taking functionality with apps like Evernote, Bear, Notion, or even Apple’s built-in Notes program. It works equally well on Mac, iPad and iPhone (no Android or Windows support at present). Its unique page and page-block system can include rich text, Markdown text, images, scans, Apple Pencil jottings, PDFs, and external links beautifully rendered on the same nicely formatted page. “Cards” of information and additional full pages can be inserted within a single page. With links and back-links between documents and even specific paragraphs on a page, It checks all the boxes for a proper Zettelkasten tool. Syncing is fast, sharing with others is simple and elegant, export options are robust, and real-time Google-like collaboration is built in. Ryan Christoffel’s in-depth review of Craft does a great job of showcasing the full functionality of the app.

The most important things to me were the ability to combine Markdown text and any kind of media on the same page, Zettelkasten-style links and back-links, and a native iPad app experience where I do most of my writing. I decided to give Craft a try over the holidays.

It took an evening to copy over decades worth of book notes and commonplace quotes from their various cubbyholes to Craft. I spent some extra time to drag book cover pictures my reviews and utilize the page styles that make this program so attractive.

Works great on Mac, iPhone and iPad

I began taking notes in Craft on the books I was reading. Gone were the editing frustrations and sync problems I’d faced with DevonThink. I found myself in the app a lot on whatever device I had near me — adding links to other books I’d already read with similar themes, more thinking, less fiddling. I felt drawn to the app, almost like the pull of social media apps like Facebook or Instagram, yet here, the content was my own creation.

It took another week to realize Craft is a writing tool that capably handles note storage and retrieval. To think of this as a mere note-taking app is missing the real power of the software.

The user interface is simply beautiful. Text and images are centered in the page with wide margins and plenty of white space. It reminds me of the Things task management app, which is high praise.

The beauty here is more than skin deep.

Hidden functionality awaits that is intuitive and powerful. Rearrange entire paragraphs or reorder lists by simply dragging with your finger. Pull a quote into an essay from your book review (also in Craft) using split-screen. Drag in a picture from a website or your photo album, and it appears just like you would expect. Performance is fast and stable.

Keyboard commands exist for practically everything. Markdown commands that my fingertips have long memorized transform into properly formatted text on the screen, so I don’t need to translate mentally. Links and style formatting are simple to apply, letting my mind stay focused on the content. The best way I can describe it is this: when I’m writing, I get exactly what I want without thinking about the technology. No friction. It just works. This is amazing for such a young app.

I came to Craft thinking it might replace DevonThink as my notes archive. Craft won that battle easily, at least for my needs. What I didn’t expect was a more fundamental shift in my workflow: that Craft might become my primary writing tool, replacing Ulysses.

With Craft, I seem to write better and with more focus. I’m not writing novels or a dissertation, so I don’t need most of the powerful features that come with a professional writing tool. Even so, immersed in my own curated knowledge sphere within Craft’s elegant writing interface, my elusive muse shows up and stays present much more often.

Could a beautiful, friction-free interface inspire better writing?

I have a few months before my Ulysses subscription renews. I’ll give this some time, but I do feel that Craft’s seamless, integrated writing experience could quite easily replace Ulysses as my primary writing tool. I don’t think early reviewers of Craft fully grasp the potential of this platform for writers. The tag line on Craft’s website provides a clue of their vision: “Craft brings back the joy to writing.”

My wish list for the app is surprisingly short. It needs end-to-end data encryption and better overall security. Capturing text from articles on the web with the iOS Share Sheet needs work. You can’t search inside PDFs like you can with DevonThink. Multiple windows on the Mac are a little hard to figure out. I wish TextExpander worked on iPad. But, honestly, these are minor complaints in what has quickly become an indispensable piece of software.

One thing I won’t bicker about is the subscription price. At $45 per year, it’s expensive when compared to note-taking options like Bear. But an app that handles note-taking and writing and Zettelkasten-style linking … for me, the value I’m getting matches the price. Rumor has it that a one-time purchase option may soon be available, hosted on your cloud platform of choice (iCloud, Dropbox, etc.) and without real-time collaboration, that may take away the sting of the high subscription price.

Most of all, I want to support the team that created this excellent new app to see what more they can bring to this emerging thinking and writing tool.

Give Craft a try. You might be very pleasantly surprised at what you find.

For the most recent update, see  The Craft App —A Year of Magical Linking.

One Simple Tip to Improve your Day One Journal

Wednesday, September 25, 2019 • 4 min read

Want to establish a consistent journaling habit and record your most important life events? Let me give you some simple advice from a long-time journal writer: scan your previous half dozen entries before you start to write. This two-minute drill will help you fight writer’s block and improve the overall content of your journals.

Let me explain.

Keeping a journal has many benefits. Looking back on thirty years of continuous journaling, I am grateful I took the time to capture my innermost thoughts on the big decisions I faced, the gains and the losses I experienced, and the otherwise-forgotten anecdotes of everyday life. I didn’t realize how much I would come to value the record I’ve created of my life.

The vast majority of my life’s journal is analog: my unflattering scrawl in small leather-bound books. I carried one in my battered briefcase and wrote most often while sailing on a ferry boat between my office and home.

Before sitting down to write in my journal, I would flip back through the preceding ten or twenty pages to remind myself where I left off and to help get the juices flowing for that day’s journal entry. This pre-writing review became almost an unconscious act after a time, feeling the ink with my fingertips as I scanned the pages, establishing a neural link between the present moment and the most recent past through my own words.

My journals teem with thoughts about the future: decisions I needed to make, thorny issues that were nagging me, and uncertain outcomes that hung in the balance. Scanning these recent pages before I began writing helped me address the resolution of some of those questions and improve the overall context of my journal entry as I picked up the pen and began to write.

I gave up paper journals about eight years ago and turned to Day One, a fantastic digital journaling platform. While I occasionally tap an entry from my iPhone or write a more extended entry on my office iMac, I vastly prefer the iPad for journal keeping. My entries typically run from 300 to 500 words, so I need a comfortable keyboard, and I prefer to write where I am - a wing chair in my library, a coffee shop, an airplane seat, or the cab of my truck while I’m waiting for the next ferry boat.

While digital journaling has many advantages over old-style paper, I’ve encountered two pitfalls which can diminish the quality and narrative of your journal writing “story,” or worse: stop you from writing altogether, frozen by writer’s block.

As I reviewed my earliest digital journal entries, I discovered that I was writing a lot less often than I had on paper. And I frequently repeated myself, forgetting what I had written in the previous days or weeks. I also failed to address some critical open questions I had posed during the last days or weeks. How could I leave myself hanging like this? Rereading these now, I am dismayed by the journaling amnesia of my younger self.

Why did this happen?

Every Day One entry starts with a blank screen and a flashing cursor; the proverbial blank page that can strike fear in even the most hardened writer. I have spent many wasted writing sessions entranced by that hypnotic blinking line, frozen in some meditative state, and unable to type even a single sentence.

Hemingway ended each writing session in mid-sentence, knowing exactly how he planned to finish it. This technique helped him jump-start the new day’s writing and avoid writer’s block. It’s so much easier to write after that first sentence is on the page.

Also, you’re more apt to write down independent and isolated thoughts when faced with a blank screen, disconnected from the storyline of yesterday or last week. The resulting journal over time will be more disjointed and lack continuity.

I’ve discovered that the solution to these digital journal obstacles is simple: scan your previous half dozen entries before you write.

Day One provides an easy way to flip through previous entries. On an iPad, swiping to the left lets you move to the next entry in a seamless, elegant way. I’ve trained myself to carry out this review every time I sit down to write. I almost always find one or two things I can clarify or resolve in that day’s entry. I find that these pre-writing reviews keep me from repeating myself too much, or rehashing already well-trodden topics. And I take Hemingway’s advice to start each journal entry where I last left off. No more writer’s block.

I’ve been doing these journal reviews before I write for about five years and can attest to the higher quality of the writing and the completeness of the story I am capturing in my journal.

If you’re trying to establish a journaling habit with a digital tool like Day One, consider practicing these journal reviews before you write. Take it from a 30+year constant journal keeper: your future self will thank you.

Book or Computer? The Best Place to Keep your Journal

Friday, January 26, 2018 • 9 min read

This is the second installment of a multi-part series on journal writing. The first post described the benefits of keeping a journal. Here, I’ll share thoughts on where to keep your journal: paper or digital.

For most of my adult life, I’ve kept a journal. I’ve always felt a calling to record my life, perhaps some homage to my love of books and reading. My earliest journals were blank hardback books, the first of which took nearly a decade of sporadic writing to fill. After I became more convinced of my journal keeping ability, I bought lovely leather-bound books with acid-free paper and a silk ribbon to mark my place. I figured I could splurge on a book that I might carry around with me daily for a year or more. I now have a shelf full of these beautiful books after two decades of near-daily writing.

How I Started Keeping a Journal

My journaling habit really took hold when I moved to Vashon 20 years ago. Vashon is an island in the middle of Puget Sound in Washington State, accessible only by ferry, so my daily commute to work each way involved thirty minutes of driving on back country roads and thirty minutes of combined waiting and sailing on a ferry boat to the mainland.

Vashon is known for many odd things, but one demographical fact is that a significant proportion of island inhabitants spend more than an hour each way in commuting to work. According to the 2000 census, only eight other zip codes in the nation have longer commuting times. Vashon shares its unique status with other towns in upstate New York and Connecticut, well known for long train rides into New York City. But Vashon? Weird fact.

With a two-hour daily commute, I had time each day to read and write. I listened to audiobooks during the driving part and turned to journal writing for the rest. With aspirations to be a writer, I figured keeping a journal would be a safe way to practice my craft. Plus, I felt compelled to record what was going on in my life, having just started a young family, moving from Seattle to a somewhat odd island, and scheming someday to leave my corporate job for a life aboard a sailboat with my family bound for unknown shores.

So I took pen to paper and kept a regular journal during this daily commute. Very soon after, my dreams of writing a great novel were dashed, having to accept that just about everything I wrote in my journal was awful. No one would want to read any part of it. After picking myself up and dusting myself off, I discovered something wonderful: it didn’t matter. The process of writing down my thoughts was helping me in other more important ways. I was soon hooked on daily journal writing.

The Delight of Paper Journals

Keeping a paper journal has its charm in today’s digital world. The feel of a real book in my hands as I prepared to write seemed to elevate my thinking, knowing whatever I wrote down would be permanent, everlasting. Before beginning to write, I would scan back over the prior entries, reacquainting myself with the recent past. This review promoted more continuity in my journal writing. My handwriting is not great, but my personality comes across better in cursive, from the emphasis I add or the hurriedness of my strokes, a sign that the words are racing out of me. I also enjoy deciphering the scratched out sections (what was I hiding from myself?) and my quirky little drawings and illustrations.

Paper journals do have their downsides. Once you fill one, access to those words is locked away. I have a dozen of these volumes stored in a box somewhere, collecting dust (more on how I solved this in a future post). Security is also lacking unless you’re careful to protect your journal from prying eyes. I once came home to my upset spouse after she found an old journal of mine which described an event which occurred long, long before we were married. She was too mad to be embarrassed at reading someone else’s journal and we quickly made up. The lesson remains. Finally, the types of things you can put in a journal are pretty limited: your handwriting, perhaps a drawing, a taped in picture or memento. It’s not practical to transcribe special emails, social media posts, or all the photos we now take with the ubiquitous smartphone cameras in our pockets.

As a technology fan, I always felt that a computer-based journal would make sense for me. I tried many different solutions over the past 15 years, from simple word processing tools to dedicated journaling software. None of these stuck for two main reasons: first, these solutions required a computer for the writing, and even a smallish laptop is still a lot less portable and convenient than a small journal. Paper and pen are hard to beat as a proven technology. And second, I found my writing style at a keyboard was too business-like from years of professional writing, and I got stymied by a blank screen and blinking cursor. None could replace my precious journal, trusted blue pen and the lap desk that I stowed away in my truck during my ferry commute.

The iPhone, the iPad, and one beautifully designed writing app changed all that.

Day One Journal Software

About six years ago, I switched over to a digital journaling platform called Day One. I started with this app on the Mac, but my electronic journaling flourished once I began using iPad. Here was a device that I carried with me everywhere, and when paired with a keyboard, was a terrific writing tool, small yet powerful, and for me, omnipresent. Day One deserves a dedicated post, but I’ll summarize why this app is so fabulous here:

1. Pervasive Input. It’s so easy to get words into my journal. I can write, dictate, copy and paste from an email or the web, from my iPhone, my iPad, or my Mac. Wherever I am, I have one of these devices at hand. Great quotes from books I’ve highlighted in my Kindle can be inserted without laborious rescribing. I can even automate journal entries from social media posts.
2. Access and Security. I have thousands of journal entries stored in Day One; some transcribed from paper journals going back over thirty years, all tagged and searchable. These journals are encrypted and secured by passwords.
3. Photos. Photos are easily added to a journal entry, either as a standalone entry or to augment a longer one. About half of my writing in the past year has an accompanying photo. A picture tells a thousand words, literally.
4. Tagging. Every entry is tagged with meta-data: location, weather, what music I was listening to when I was writing, where I was in the world, and keyword tags I’ve defined to help search and group entries.
5. Syncing. Day One uses a proprietary and encrypted sync service that lets me start an entry on my iPhone, say with a photo, and update it on the iPad or Mac. It also means my entire journal history is available on every device.
6. This Day in your History. Day One has a unique feature which shows me what I wrote on this day over my entire journal history. I’ve been keeping a journal a long time, and its such fun to revisit entries from years past.
7. Export Tools. I can export my journal to lots of different formats, including plain text, so I don’t have to worry about losing my writing if this software ever goes away.
8. Design. The app itself is stunning. You can tell a lot of time was spent thinking about how to bring the focus of the application to your writing, and doing away with the fluff and gunk of typical mobile apps.

There are a few drawbacks with Day One. First, it’s only available on the Mac, though both iOS and Android app are available on mobile devices. Second, an annual subscription is required to take advantage of its power and functionality. A lot of folks grumbled about this, but I was delighted when Day One made the switch to a subscription platform. I will gladly pay the $35 per year for software I use every day, knowing the company is now on solid financial footing in the crazy and non-sustainable app development world. Third, with all my journals in the cloud, there is a chance someone could hack into my account and gain access, despite the fancy encryption and passwords, to every personal word I’ve ever written. This is the new world we live in, and I grudgingly accept this risk.

I can share now after five full years of daily journal writing in Day One that I am a complete convert. I think better now at a keyboard and write without hesitation, even with a blinking cursor to taunt me. I believe my writing quality has increased without losing the intimacy and honesty of my pen and paper journal writing. I’ve lost the rhythm and practice of writing by hand, though I’ll admit I sometimes miss the tangible benefits of writing in a real book - the heft of the book, the personality of the pen strokes, the perceived longevity of text on paper.

With three decades of constant journaling behind me, I relish the ability to look back on private musings I wrote so many years ago, all from my iPhone. In fact, one of my morning rituals is to open Day One and read over the half-dozen or more entries I wrote on that day over the past decades. What an incredible gift it is to re-ignite those memories each morning. I can’t think of a better way to reflect on this amazing journey we’re all taking.

So Which Is Better?

The answer depends on which format best supports your writing habit. For me, the transition from keeping a paper journal to typing on a keyboard took years before it finally clicked. It was definitely a journey. Now I can’t imagine going back to a paper journal. But the best journal format is the one that keeps you writing, or at the very minimum, doesn’t stop you from writing. Find one you feel comfortable confiding in and write. And write again. Simple advice, maybe hard to implement.

If you’ve found your journal muse, what do you use, book or digital? I would love to read your feedback in the comment section below.