The End of Private Libraries

There seem to be two kinds of people on this earth—those who love books and everyone else. The bookish have always been far outnumbered, and the gap must be widening in this age of endless digital entertainment. I count myself among the proud minority, but a book, of all things, has brought into question my lifelong practice of keeping a private library.

A recent acquisition illustrates the issue.

“Didn’t you just read this on your Kindle,” Lisa asks me as she flips through the book I’ve brought home.

I dislike direct questioning about my book-buying habits. It feels like the pointed inquiries on medical questionnaires about alcohol consumption.

“Yeah, but I liked it so much I wanted the hard copy,” I tell her.

The fact is, I will likely never read this book, even though I did enjoy it. I bought the book because I like having a visual, tangible record of the time this book and I spent together. I like scanning my shelves and seeing proof of a rich reading life. I like the way a roomful of books makes me feel about myself. Besides, I tell myself, there are worse ways to spend money.

Like most fixations, the origin can often be traced to our youngest days. Pine bookcases flanked the living room fireplace of my childhood home. I can picture the red and black spines of the encyclopedias that filled half those shelves. I spent hours poring over those portals of knowledge at an unnaturally young age. What an odd duck I must have been, this quiet young boy with his nose stuck in an encyclopedia.

A public library beckoned four blocks away, a magical place for a shy little kid. When a kind librarian led me to a shelf of thirty or forty Alfred Hitchcock and the Three Investigators mystery books, I kneeled in almost religious piety, awestruck.

I must have viewed that library as a refuge from the troubles my eight-year-old brain struggled to process at home. I felt safer exploring a haunted citadel in Istanbul with Jupiter Jones than I did around my own family. Later, when the divorce was final, and I moved with my mom and new stepdad to a trailer park in Forks, I dreamed of the calm order of that library — the hush and quiet — amidst the babble and grunge of a beaten-down logging town, our family the poorest in a landfill of white trash.

Living hand to mouth at a young age forever shaped my views on the importance of having enough money, but I’ve always spent freely on books. If I look up from where I write this, I can spot my earliest purchases. A Sentimental Education. Look Homeward, Angel. The Sun Also Rises. These old friends have stuck with me my entire life. Eight apartments and three houses, always near.

If I widen my gaze to take in the walls of shelves surrounding me — a collection of some two thousand volumes now — I can trace the outline of my life’s obsessions: boxing, gardening, philosophy, strategy, bird watching, statistics, history, poetry. Shelves and shelves of sailing and tall ships and the sea, books that even here in the desert can launch me miles and miles offshore. And so much great literature: the French, the Russians, the English, the Americans. These last shelved by era, early to late.

Each spine has meaning to me. I recall at a glance where and who I was when I read it. Pulling a book down from the shelves, I feel transported. The heft of the book in my hands, the smell, particularly from my oldest books, wafting up as I thumb through the pages, letting a random passage catch my eye. I read and remember.

In every other part of my life, I am downsizing, simplifying. Most unhappiness stems from a desire for material things. I fantasize about renting a flat in Madrid for three months with just a few clothes, a journal, and my Kindle. And yet, here I sit in this roomful of material things, these books of comfort and consolation, in complete denial of what I know to be true.

I admire those grand Country Manors with their massive libraries passed down for generations. Until recently, I imagined a distant future when my grandchildren and their grandchildren would cherish my library. Yet, times have changed. I have no Country Manor, and books, once the pinnacle of knowledge and wisdom, are no longer quite so prized.

Shaun Bythell, in his memoir, The Diary of a Bookseller, tells the awful truth. In his business, he buys personal libraries from estates. The heir, often the son or daughter of the deceased, shows little emotion toward the collection of dusty books they’ve inherited. “What would I want with all these?” They look around, bewildered. What must have cost a fortune and a lifetime to assemble is sold, gratefully, for $500. My shock when I read about this first encounter turned to numb despair as the situation repeated at various estates throughout the memoir. No one wants these books. No one.

I called my daughter in Los Angeles. She’s a reader like me but prefers a Kindle to physical books. Of course, she wants the books, she said, but without much enthusiasm.

The notion that this library and I might share the same dissolution took a while to accept, like a wild plot twist in a novel you didn’t see coming. Perhaps it never dawned on me how used bookstores acquire so many wonderful books in the first place. I pull down book after book for evidence. A set of Wallace Stegner books I purchased last year bears the previous owner’s carefully inscribed name and address. A Google search turns up the obituary: her death preceded my purchase by two short months.

As I consider the likely future of this little library, I feel more reflective than anguished. After all, books are beacons of light for me, as for many wayward travelers. Let that be enough. My gaze slips along the spines, and I acknowledge each silently. How many thousands of hours have we spent together, ruminating, investigating? How many journeys? These books have shaped and reshaped me. How can you tell where the stories end and the man begins?

I imagine a time when these books take flight, like a great host of swallows, all chaos and boxes and pages aflutter, and in time settle on a thousand different shelves to inspire a thousand new owners.

Until then, let’s commiserate together, my friends, my shipmates. Let us sing on the deck of this foundering ship, our voices a cheer across the ages.

The End of Private Libraries Read More »

Bear 2 for Writing and Thinking

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

Features Craft Obsidian Bear
Intuitive Design 8 4 9
Note Linking 9 9 7
Mobile Experience 8 5 9
Performance/Stability 7 9 9
Search 5 10 10
Versatility 6 9 9
Future Proof 7 9 9
Security / Backups 3 8 9
Cost 6 8 10
Overall 6.6 7.9 9.0

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.

Bear 2 for Writing and Thinking Read More »

Reading The Story of Civilization

In the spring of last year, I started reading The Story of Civilization by Will and Ariel Durant. This is no quick undertaking. Spanning eleven volumes and 10,000 pages, it will take me the rest of this year to finish.

The first volume was published in 1935 when Durant had just turned 50. He published the final volume forty years later. Midway through these decades of writing, Will’s wife Ariel became a co-author and active collaborator in this epic undertaking. Together, they read an average of five hundred books as research for each published volume.

The Story of Civilization is regarded as one of the most compelling narratives of world history ever written. The tenth volume, Rousseau and Revolution, won the Pulitzer Prize for general non-fiction in 1968. Goodreads currently gives these books a 4.4 out of 5. Such a high rating is rare, which indicates how readers truly admire the series. Essayist Jamie Todd Rubin chose these as the sole books to take along to his proverbial desert island, which was all the prompting I needed to start this adventure.

While the books were best-sellers during their time, I do wonder how many people got around to reading them. Who has the time to read this much history? After all, this set collected dust on my bookshelves for twenty-five years before I picked up the first volume.

But the intrepid reader who perseveres is in for a telling of history unlike any other. Durant’s writing is clear, colorful, engaging, and occasionally laugh-out-loud funny. He’s good at digging into the philosophical and religious beliefs of these ancient civilizations to parse out what elements contribute to our present-day ideas and also what, if any, stand up to his skeptical intellect. He pokes fun at the war-mongering gods of Egypt and Persia but shows genuine reverence for the ancient Hindu Upanishads with their belief in impersonal immortality and the oneness we share with the universe. In Ancient Rome, we learn about Julius Caesar and Nero, yes, but also about thinkers like Cicero and Seneca, about the everyday lives of both emperors and peasants, how they cooked, celebrated, and prayed. I feel like I’m on a journey through time with Professor Durant, and he’s motioning for me to sit nearer to him while we take all this in together.

I have a personal reason for reading these books. I inherited the first six volumes from my grandmother, which were a Christmas gift to her from my grandfather in 1959. He died a few years later, before the seventh volume was published and before I had a chance to meet him. My grandmother became a widow at 57, two years younger than I am today. She was always a voracious reader, and I know I inherited my love of learning and books from her.

I have the benefit of my grandmother’s notes in the margins as she read these books some forty years ago. I recognize her cursive handwriting, her exclamation marks, her underlining. I am adding my notes to hers. It’s like we’re reading this grand history together. Maybe one day, my daughter will join us in this shared experience across time and generations.

I am nearing the end of the fifth volume, The Renaissance, which covers the history of Italy from the 14th to mid-16th centuries. My progress is slow but steady. I read an average of 30 pages a night in my little library, hot tea by my side, pen in hand. I’ve come to cherish this time with Professor Durant. There have been more than a few times when my jaw dropped open in sheer disbelief at what I’ve read. I am shocked both by the crazy shit that has happened during the darker periods of our history and that it took so many years for me to learn all of this.

I’ve reached a point in life where I have the time to dedicate to personal projects. Early retirement has its thrills and challenges. Without direction or structure, I could see how I could squander these precious years. But this is something I’ve dreamed of doing since college. I always loved literature and philosophy, but I was too practical to consider a career in academia. Instead, I compromised. I majored in accounting with a personal vow to resume a scholar’s life as soon as financially possible. In hindsight, that is exactly what I have done.

I read a lot, but my knowledge of history is uneven. I’ve read many biographies and a few accounts of specific eras. I have a good grasp of the history of the British Navy during the Age of Sail, early American history, and World War II. I know a little about Ancient Greece and Rome from my readings of philosophy and Stoicism. But these pockets of knowledge feel like tiny stabs of light in an immense underground cavern. Reading Durant, I am slowly illuminating the darkness. I am renewing my education, my scholarship.

Rounding out my knowledge of history complements my other reading as well. How many books have you read that referenced a historical event or leader that you glossed over? If you’re like me, a lot. Having a broad sense of history has deepened my understanding of practically every book I’ve read since I started this adventure. I feel extra synapses firing when I understand a historical reference that would have flown over my head before this newfound knowledge. And with bi-directional links in Craft, my reading notes have exploded in value with the addition of this history overlay. I feel nearer to wisdom the more I read these books.

In the Dark Ages, owning a copy of the Bible was strongly discouraged by the Roman Catholic Church. It was believed that only the clergy could properly interpret the Scriptures. A driving force behind the Italian Renaissance was a loosening of these religious laws to permit a greater pursuit of knowledge, which in turn led to a rediscovery of the philosophy and wisdom of the ancient Greeks and Romans.

Today, we face a different obstacle. Our attention spans have shortened from the constant dopamine drip of social media and TikTok videos, the binge-worthy Netflix dramas, and the pressure to keep up with present events that wash over us like a river. We divide ourselves into polarizing groups, yet read the same books, the same news feeds, and the same websites, and thus end up thinking the same way. Our horizons are laughably short. Modern wisdom can sometimes feel like an oxymoron.

Perhaps, then, a study of history is the antidote we all need to make sense of this distracted and confusing world. Maybe the context of prior ages could help us better understand our current struggles. As they say, those who cannot remember the past are condemned to repeat it.

Reading The Story of Civilization Read More »

My Two Journals

I surprised myself a little over a year ago by writing in a paper journal every morning. The surprise wasn’t that I was keeping a journal but that I was doing it by hand. I had been using the Day One journaling app to record my private thoughts for over a decade. But this was no ordinary year. After suffering an immeasurable loss, I yearned for the comfort that sometimes only flows from pen and paper.

Yet what’s even more surprising is that this was no momentary whim. I’ve kept up this daily habit of scribbling in a notebook in the morning and typing in Day One at night for over a year now. And I think I’ve pieced together why, for me, the combination of analog and digital writing has developed into the best possible journaling experience.

The Benefits of Journaling

Keeping a journal promotes mindfulness, reduces stress and anxiety, improves memory, and can enhance creativity. Journaling can also help you heal from profound loss, providing solace, catharsis, and a means to explore feelings that might otherwise get suppressed. When my son was killed in a motorcycle accident a little over a year ago, I turned to my journal as a way to process my grief.

I am not new to journaling. I’ve kept a private journal for more than thirty years. I filled a dozen notebooks before switching over to Day One in 2012. My journal holds almost four thousand entries dating back as far as 1982.1 I haven’t missed a night of journaling in almost a thousand days.

The Lure of Paper

Despite my appreciation for digital efficiency, I’ve always carried a Field Notes notebook in the back pocket of my jeans or my bag. I like the feel of a pen in my hand when I’m thinking. When we moved to Arizona last year, I knew we wouldn’t be traveling as much as we did aboard our trawler. I decided to upgrade to a full-size desk journal for a change of pace. As one does, I scoured the internet for a suitable notebook.2

I chose the B5 Journal Pro from Scribbles That Matter, which is roughly the size of an iPad, though much thicker. The notebook paper is numbered, dotted, and thick enough to feel luxurious and sturdy with no bleed-through (the paper is rated at 120 gsm). There are two placeholder ribbons, several index pages, and a tucked-in folder in the back of the book for storing notecards or loose paper. When you open the notebook, you hear that satisfying crack of the binding. The book lays flat on a desk.3 The cover is made from vegan leather and feels terrific. This is undoubtedly the nicest journal I’ve ever owned.

Journal Pro from Scribbles That Matter
Journal Pro from Scribbles That Matter

I didn’t know how I would use the notebook at first, but a pattern soon emerged. I reached for it as I sipped my first cup of coffee in the morning while my mind was fresh and any dreams still lingered. I would write a half page of fragments, lists, how I slept, and stray thoughts that were top of mind. Sometimes, my pen would linger over the page for minutes, my mind in a meditative trance. Other times, the words that escaped my pen surprised me, like a possessed Ouija board. Later in the day or evening, I might write a little more about the book I was reading or capture a quote I had heard, but most of the action this notebook saw was during that first cup of morning coffee.

I wrote more honestly and sincerely about the loss I had suffered than I did at the keyboard. Slowly, over days and weeks, the pages filled and overflowed with feelings my stoic heart couldn’t express in front of a blinking cursor.

After several months of morning writing, I marveled over how connected I had become to this notebook. Would-be journal keepers who give up too soon miss out on the magic of a journal filled with 50 or more pages of their musings. Flipping back through prior days and weeks of writing reveals the mosaic of meaning you missed because you were standing too near. These cryptic clues drawn from your subconscious remain invisible until you turn the pages just right and suddenly glimpse the pattern. The invitation to revisit what you wrote yesterday or last month prompts you to probe deeper into the crux of what’s troubling you.

Why Two Journals

And yet, as much as I enjoy this handwritten journal, I still use Day One in the evenings. The two journals flow from different parts of my brain, though they work together in an interesting way.

At a keyboard, I write in complete sentences in my practiced journal voice. I am articulate. I write to understand, yes, but also to communicate with some future version of myself, or potentially others. All my published essays began as one of these nightly journal entries. The handwritten notebook is focused squarely on the present moment; the writing in Day One leans back and tilts forward. One is meditation; the other is memoir.

During the time I’ve kept the handwritten journal, the quality of my writing in Day One feels richer. Fragmentary scribbles in the morning often blossom after a day of rumination, elongating into full sentences and paragraphs. A vague concept at daybreak might give birth to the start of an essay that night or maybe a few days or weeks later. There is a give-and-take between these two journals that I’ve come to appreciate.

And besides, Day One isn’t going anywhere. With thousands of entries spanning three decades of my life, the app holds tremendous value for me. I search it often to track down events, trips, critical milestones in my life. The memories I’ve captured of my son stand out like beacons of light on my darker days. Writing each night in Day One is a ritual that helps settle my mind and bring closure to the day.

A New Year, A New Journal

I completed the final page of my paper journal on the last day of 2023. I realized this potentiality in the middle of December and managed my writing output to coincide with this tidy conclusion. Filling one of these journals each calendar year feels right.

After so many years of digital journaling, I forgot what it felt like to retire one. I had grown quite attached to this old journal with its hundreds of pages of private thoughts. After a year of daily use, the book held up surprisingly well. No loose pages, and the binding is still tight. Before shelving it in its lovely slipcase alongside my other paper journals, I archived a PDF copy with the scanner app on my iPhone for safekeeping.

I am slowly breaking in the new notebook, an identical twin to its predecessor. I miss paging through past entries before I start to write in the morning. But, perhaps it’s a good reminder to celebrate new beginnings and the ever-changing nature of life, to close the book on a year of sorrow. I am not healed. There is no healing from some losses. But, at least I can measure the distance I have traveled through the pages of my two journals.

Do you keep a journal? Do you use an app, or do you write by hand? Or both? I’d love to hear about your experiences with journaling in the comments below.

  1. I liked Day One so much that I transcribed my old journals to have a complete digital archive.
  2. If you’re curious about the features and characteristics that make a great notebook, I highly recommend Mark Fig’s Hobbyist Hangout podcast on notebooks.
  3. I followed Ryder Carroll’s advice on how to break in a new notebook, which I’m sure helped the notebook lay flat and keep the spine from wearing.

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Quicken Classic for Mac – A Long-time User Review

I’ve used some version of Quicken for 35 years. That puts me in a stodgy demographic that manages money in a certain “this is how I’ve always done it” way. For the uninitiated, Quicken is a personal finance software program that helps manage your checkbook and credit cards, pay your bills, keep to a budget, and track investments. It’s available on Windows and Mac, though there are differences in capabilities between the two. There are companion apps for iPhone and iPad, but they feel like afterthoughts, lacking key functionality of the desktop software. Quicken Classic is sold as an annual subscription across three offerings: Deluxe, Premier, and the recently released Business and Personal edition.

Seven years ago, I switched from Quicken Premier for Windows to the less capable Mac version. I’ve written previous blog posts about using Quicken on the Mac: in early 2018 when I switched and follow-on updates in 2019 and 2020. In large part, I was critical of the Mac version of the software, particularly its inability to export investment data.

In the intervening four years since my last post, Quicken has improved in many ways, including the ability to export all its data, including investments, to Quicken for Windows. With this critical functionality in place, I thought it was time to provide an updated and favorable review of the Mac version of Quicken and how I rely on it to manage almost every aspect of my financial life.

Why Quicken

I began my career in public accounting and held a CPA license in Washington state for over thirty years. I spent most of my career as a finance executive with a large publicly traded company, which allowed me direct experience with stock options, restricted stock units, performance shares, deferred compensation plans, and various employee benefit programs that follow that kind of employment. I’ve always tried to be disciplined when it comes to money, and I’m comfortable managing my own finances. With this background and financial situation, I have had many opportunities to evaluate and push the boundaries of Quicken as a personal finance program.

It takes time and expense to maintain a system like Quicken. Many manage their money with simpler apps or just by scanning their accounts online. For me, the effort of a system is worth it. With Quicken, I know what’s going on with my spending and income in relation to expectations every week. Every expense has a monthly budget that fits within a long-range plan. The impact of gyrations in the stock market is personalized with a press of a button. My entire financial history is accessible from Quicken’s search bar. Bills always get paid on time. Checks never bounce. I am rarely surprised at the end of a month, quarter, or year. The peace of mind I get from using Quicken far outweighs the cost.

As a disclaimer, I don’t work for Quicken or have any financial interest in the software or related services. Quicken doesn’t offer a free trial to evaluate, so unbiased reviews from actual users are helpful. I read almost everything I could find before switching to the Mac in 2018. Consider this update an act of paying it forward.

Recent Improvements

Since 2020, there have been dozens of software updates to Quicken. Unlike those early years when I first moved to the Mac, Quicken has now become a pleasure to use, and I consider it a stable, trusted system. Here are a few of the improvements that made the most significant impact on my use:

Error-free Transaction Downloading. The team at Quicken has vastly improved the technology involved in downloading transactions from banks, credit card companies, and brokerage firms. When I first used the Mac version, download errors would pop up continuously. Those days are happily behind me. I’ll go weeks and months between download errors, which seem to resolve after a day. My experience is limited to just a few institutions, so your own mileage may vary.

Investment Analysis and Dashboards. The Mac software now provides overall investment allocation between stocks, bonds, and cash, even with mutual funds that own a blend of assets. This update essentially removed the need for me to separately analyze my investments in Excel. In addition, a new dashboard provides a valuable snapshot of investment performance and holdings that rivals and, in some ways, exceeds my brokerage tools. Quicken’s investment section has become quite good.

New Investment Dashboard (Source: Quicken)
New Investment Dashboard (Source: Quicken)

Bill Manager. Quicken has refined its bill tracking and payment capabilities in a big way. The Premier version of Quicken offers free bill paying, but I prefer to send these occasional checks directly from my bank. I use their bill manager service, though, which does some pretty innovative things. First, it can download PDF statements automatically without having to log in to the payee’s website each month and hunt around for the statement. It also automatically schedules the payment based on the due date and records in the payment register. You can make payments directly from Quicken, but my recurring bills are paid automatically, so recording the transaction is all I need. A couple of companies I pay aren’t included in Quicken’s Bill Manager service, but these can be added manually. Second, I get a nice cash balance forecast as these future bill payments are scheduled in the register, preventing possible overdrafts or shortfalls. Bill Manager solves a problem I didn’t know I had, and I’m glad I have it.

Snappy Performance. The software runs faster thanks to performance improvements, particularly with newer Silicon Macs. I use Quicken on an M1 MacBook Air and an M2 Mac Mini. Both perform exceptionally well.

Investment Data Export. Until late last year, Quicken for Mac’s export capabilities excluded investment data. This meant I could not move back to Quicken for Windows or any other competing personal finance apps without losing all my investment history. I hated having to rely on this one particular version of software for all my precious financial data. Luckily, Quicken has now fixed this shortcoming, and Mac users of the software can breathe a collective sigh of relief.

Mac Version Still Lags Windows

Despite the many improvements to the Mac version of Quicken, it still lags behind the Windows version in a few key areas:

  • Reporting in the Windows version is more robust, customizable, and allows comparisons to budget.
  • Windows Investment analysis is more in-depth with Morningstar Portfolio X-Ray and performance benchmarking.
  • Tax Center in Windows makes income tax planning easier by calculating estimated taxes using actual tax brackets on recorded income.

Other planning tools like Lifetime Planner, Debt Reduction, and Savings Goals haven’t made it to the Mac yet, but these tools always felt a little gimmicky. I didn’t use them on Windows, so I don’t miss them on Mac.

Quicken Risks and Alternatives

This is an interesting time for legacy software companies like Quicken. I suspect their loyal customers look a lot like me: retired or near retirement, comfortable with desktop apps, lugging along a decade or more of historical data within their app, and resistant to change.

Most new entrants into the personal finance technology space are mobile app-centric. Some don’t even offer desktop apps. Quicken has recently entered this space with its Simplify mobile app and likely believes it represents most of its future growth, which explains why it recently rebranded its desktop software to Quicken Classic.

Intuit, the former parent company of Quicken, recently announced the shutdown of its personal finance app, Mint. Mint is one of the most popular and longest-running app-based finance tools, so its demise sent shockwaves through its customer base. Indeed, this announcement caused me to look more carefully at my use of Quicken and think through what steps I would need to take if the service were similarly shuttered.

I think that the risk is relatively low. Aquiline Capital Partners acquired Quicken in 2021. Typically, private equity firms maintain ownership from five to seven years, so Quicken is in the sweet spot of ownership. Aquiline will be focused on investment and growth vs. the cost-cutting and profit harvesting that comes near the end of the investment horizon as they look to sell their asset. This is good news for Quicken’s current customers.

And yet, I can’t help but feel that users of Quicken software are on borrowed time. Highly regarded mobile apps like Monarch Money and Copilot will continue to improve and introduce more and more capabilities. Eventually, Quicken will be forced to mothball its desktop software as everything moves to the cloud and apps. This is one of the reasons I’m happy that Quicken for Mac’s export function now includes investment data. I might not need this now, but someday I will.

As a safeguard, I create and archive two export files from Quicken every quarter. One is simply the Quicken Transfer File (QFX) you can export from the file menu. I also download a CSV file of all my Quicken transactions by selecting All Transactions from the sidebar and choosing Export Register Transactions to CSV from the File menu. This yields a 60,000-row text file I can access with Excel to search and sort every transaction stored in Quicken for the past 30 years. Between these files, I’m confident I could move my history to a new finance app without too much trouble, even if Quicken stopped working altogether.

Recommendations

Quicken Classic for Mac has a lot going for it in 2024. The software is intuitive, stable, and a pleasure to use. I am pleased with Quicken’s decision to allow a complete export of my data, including investments, should I ever need it. As a Mac user, I have no desire to revert to the more capable Windows version through Parallels or some other clunky virtualization process.

Quicken’s subscription cost is fair for the value I receive, and the frequent updates are delivered almost monthly (as I write this, Quicken released Version 7.5.0, which introduced more new enhancements). Almost all personal finance apps use a subscription business model, and many are more expensive than Quicken. Buying an annual license during Black Friday sales in November can save 30-40% off the regular subscription rate.

For someone with 30 years of history with Quicken, I’m in no mood to switch platforms, given the state of the app today.

And yet, if I were just starting out, would I choose Quicken? I doubt it. From a clean slate, I would probably choose one of the more innovative mobile apps that deliver the power of personal financial management to your pocket or tablet. I plan to test drive a few of these over the coming year to better understand these next-generation tools.

Until then, Quicken for Mac will remain my everyday companion and financial advisor. If you’re a long-time Quicken for Windows user considering switching to the Mac, it’s an excellent time to make the leap.

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