Tag: productivity

Goals for 2023

Photo by Engin Akyurt on Pexels.com

Over the years I have spent quite a bit of times on various experiments. In the 2010s, I considered the idea of the paperless office, embraced Evernote as a tool for paperless productivity, and wrote a popular series of posts on the subject. So far, in the early 2020s, my experimenting has shifted somewhat. I’ve re-embraced the idea of plain text files as my fundamental unit of work. A plain text file is both versatile and long-lasting. Text files created in the 1970s can still be read today. I found Obsidian, and took lessons from my Going Paperless experiment, to see what I “practically” paperless[1. As in “practical” uses, as opposed to absolute migration to a paper-free lifestyle.] lifestyle looked like using primarily plain text files.

In 2022, I’ve been pleased with how things are working out with Obsidian and plain text files, but there is room for improvement. I’ve identify three areas to experiment with throughout 2023. My hypothesis for this experiment is that improvements in these three areas will lead to more creative time in the years beyond. The three areas are: (1) Consolidation; (2) Simplification; (3) Automation.


When I look at my computer, I am often overwhelmed by all of the apps and tools I find on it, the vast majority of which I rarely use. It would be nice, I tell myself now and then, to get rid of those tools that I never use, but I am sometimes reluctant to do so, thinking that I might need the tool some day. To some extent, this is no different than trying to declutter at home.

While thinking about this recently, I realized that I made huge strides in consolidation over the last two years in terms of my work products, the vast majority of which are now plain text files. With a work product as simple and versatile as a plain text file, it should be much easier to give up apps I no longer need to manipulate those files.

The more I think about this, the more I believe I can get away with two primary work product formats: plain text files used in conjunction with Obsidian; and Wolfram Language notebooks (.nb files) used in conjunction with Wolfram Language and Mathematica.

Using text files as work products of Obsidian is pretty obvious and I’ve written extensively about my use of Obsidian. But Mathematica1?

I’ve been a very casual, hobbyist user of Mathematica for years now. But the more I play with it, and the more I learn about its symbolic and functional structure, the more impressed I am with the language. Moreover, the language now reaches into all aspects of computing so that it seems useful as a general purpose language. Finally, as a developer, I’ve already mastered more common languages like Python, JavaScript, C#, Perl, PHP, Ruby, etc., to my personal satisfaction. Becoming equally proficient in Wolfram Language would something new.

I am mentally dividing this consolidation into two parts:

  1. Plain text files as my primary work product: in the form of notes and writing.
  2. Wolfram Language scripts and notebooks as my primary tool for development and automation.

As I write this, there are about 100 applications in my Application folder on my laptop. That, of course, does not include the command line tools inherent in any Unix-based computer system. I’m using this number of 100 applications as a baseline to see how much I can consolidate over the course of 2023. Obviously, I need more than just Obsidian and Mathematica. For instance, I use Photoshop for photo editing. However, Mathematica has powerful photo- (and video- and sound-) editing tools that may be able to automate and supplant most of what I do in Photoshop. This is an example of the consolidation I am looking to do.

It will be interesting to see how well this consolidation works over the course of 2023.


As I worked through my Practically Paperless series, I noted that I was building up more and more complex structures for my notes, as well as relying increasingly on plug-ins, tags, etc.

In the months since finishing that series, I’ve been attempting to simply how I use Obsidian with plain text files. In the process of simplifying, I have the following things in mind to guide me:

  1. My primary work product is a text file. Whether a note, a blog post, a list, a trip summary, a reading note, the primary form in which the content appears is a plain text file.
  2. Using tools like Obsidian is a good for me, but I also keep in mind that these text files need to be useful in the absence of a tool like Obsidian. Keeping the work products themselves simple help in this regard. For example, the structure of markdown makes for simple way of parsing and interpreting these files outside of Obsidian.
  3. I’m trying to simplify my file structure, both within Obsidian and as a whole, including cloud platforms.

Over 2023, I’m looking to continue this simplification of my work products. With the following ideas in mind:

  1. My notes need to be usable outside Obsidian.
  2. My notes and files need to be easy to understand, not just for myself, but for others, especially Kelly and our kids.
  3. My notes and files need to be easy to find for me and for the family.


I spend a lot of time trying to automate processes. The idea here is to automate the stuff that is repeatable, so that I can spend more time on creative stuff. But often, the time it takes to implement such automation offsets the time it saves. Put another way, if it takes me 2 hours to write a script to automate a task that currently takes me 5 minutes per day, it will take 24 days once the automation is in place to pay back the time it it took to build the automation before it starts paying off.

In the past I’ve used all kinds of tools to implement automations: Python scripts, tools like Alfred or Keyboard Maestro, Apple Shortcuts, etc. In 2023, I am looking to use Wolfram Language as much as possible to automate things, in part because I’m fascinated to see the possibilities in the language, and in part as a way of becoming proficient in the language.

One simple example of this, which I will talk about in more detail in a subsequent post, is adding a list of files I created or updated on a given day to my Daily Notes. it is convenient for me to be able to see at a glance all of the files I worked on in a given day. The way I structure my daily notes makes the daily note the perfect place to store this information. But I don’t want to spend time searching my file system each day for all of the files I created or modified. So I’ve created a Wolfram Language script to do this automatically.

An example of my current Daily Note format, using today's note.
An example of my current Daily Note format, using today’s note.

Throughout 2023, I’ll be looking at how I work2 to identify inefficiencies, things that can be eliminated, and tasks and processes that can be automated, particular:

  1. Things I do frequently and are repeatable. In addition to the above, examples, might include: taking a blog post in note form and automatically publishing it to WordPress; or cropping and editing a photo in a repeatable way
  2. More complex tasks that I perform less frequently but at regular intervals, like archiving information.

Follow along on the journey

Because I know that other people are interesting in this sort of thing (a quick search of “productivity” gives an idea of just how much), I plan to write about this journey of mine throughout the year. As always, I am experimenting to see what works best for me. I know, for instance, that using Wolfram Language for a primary automation and scripting tool is probably outside the norm for many people. But I’m fascinated by the idea and that makes it fun for me. These will tend to be more technical posts, but they might be of interest to others, so, feel free to follow along, ask questions, and offer suggestions.

And Happy New Year, everyone.

Written on 29 December 2022.

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  1. There are other reasons for me to use this, but they are too technical to get into here.
  2. To be honest, I’m doing this constantly, but this year, I’ll be putting a special emphasis on it.

Keyboard Maestro: An Almost Invisible Superhero of Productivity

a person typing on a keyboard
Photo by Florenz Mendoza on Pexels.com

There are some tools that I use that are so seamlessly integrated with my workflow that they are almost invisible. They work so well that I simply don’t think about them. That really isn’t fair since tools like these do far more than they get credit for. And since I had a particular tool in mind today, for reasons I will explain, I thought I’d write about one such invisible superhero of productivity: Keyboard Maestro.

Keyboard Maestro is made by Stairways Software and it is Mac-only. If you are a Windows users, you can read with envy. If you are a Linux users, you probably don’t need a tool like Keyboard Maestro in the first place.

I have been using Keyboard Maestro for just over 8 years1 and I’m not sure I can quantify how much time it has saved me. Keyboard Maestro is an automation tool that combines three useful functions in one:

  1. Text expander
  2. Clipboard manager
  3. Automation engine

I think I first began using Keyboard Mastro as a substitute for TextExpander in order to get the expansions that I wanted. Keyboard Maestro can do text expanding, but even there it is powerful. It can take a simple expansion like ;;email and expand it to my email address. Honestly, I can’t remember the last time I had to type out my email address. Quite possibly it has been years. Like many text expanders you can set one phrase and have it expand to another.

But it can do more. It can perform transformations on the data. I wrote about a fairly simple version of this when I described how I used Keyboard Mastro to automatically add the next entry number to my journal in Obsidian. I have all kinds of useful text expansions and they have become so innate that I don’t even notice them. It would be fascinating to know just how much typing Keyboard Maestro has saved me over the years (and how many typos it has prevented).

Keyboard Maestro also serves as my clipboard manager. I am constantly copying things to the clipboard and pasting them other places. Keyboard Maestro keeps a history of my copies and allows me to access that history when I paste. Here is a glimpse of what that clipboard history looks like at the moment:

an image of my clipboard history in keyboard maestro, showing the last 5 copies I made, all ready for pasting

In addition to containing text, the clipboard can contain images. And when I paste something from the clipboard, I have the option of transforming it as I paste. Examples of this transformations include:

  • changing the capitalization of the text (all caps, all lowercase, title case, etc.)
  • manipulating an image by flipping it, rotating it, changing its size

This takes a lot of manual effort out of routine and reptitive tasks.

It was this clipboard history functionality that got me thinking about writing this post. I occasionally made use of PasteBot for this, but recently decided to consolidate this functionality into one app–much as I did with TextExpander. And since Keyboard Maestro does this so well, that was what I went with.

Keyboard Maestro can also do all kinds of automation, something I have only experimented with lightly over the years2, but something I am interested in making more use of.

As I said, Keyboard Maestro works so well, it is virtually invisible. I often forget I am even using it when I am typing. So I wanted to call attention to it, because it really is a powerful, useful, time-saving tool.

Written on March 11, 20223.

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  1. I just verified this, going back through my email to find the receipt from my first order, dated March 3, 2014.
  2. For an example, see how I used Keyboard Maestro, years ago, to automate pulling notes and highlights of my Kindle. I don’t use this automation anymore, but it is a good example of what is possible.
  3. Yes, even this dateline that you see at the end of each post is generated by a Keyboard Maestro macro that I created

The Irony of Four Thousand Weeks

Sometimes I don’t recognize the problem that is right in front of me. Take, for instance, the book I am currently reading, and nearly finished with, Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman. I started this book just after finishing The Big Roads by Earl Swift. Sometimes I finish a book in the middle of the day and immediately start the next one, but this was one of those times when I finished the book later in the day, and didn’t start Four Thousand Weeks until the following morning. I set out on my 6 am walk, and began listening to the audiobook edition.

Four Thousand Weeks is a book I needed to read. It has a lot to say about how we perceive time, how we perceive busyness, and the many, many traps that lie between the two. For instance, the more books I read, the more books I feel I need to read (butterfly effect of reading, folks). Knocking one book of my list adds three or four more to that list. It’s no different with tasks. The quicker you get through your to-do list, the more you find you have to add to it until you realize that you’ll never have an empty list and I’ll never read all of the books ever written.

So there I am on the bike path at 6:10 am listening to Four Thousand Weeks. For the last several years, I’ve tried to read at least 100 books each year. Audiobooks help greatly in this regard because I can multitask and I’ve gradually worked my way up to listening to most books at 1.8x. That’s the speed at which I’d listened to The Big Roads, and it was the speed I was listening to Four Thousand Weeks as I walked up the one steep hill on the bike path. At the top of the hill, I paused to jot down a note, and a few steps later, I paused again, and then again. And it was there, jotting down the third note that the irony of the situation dawned on me: here I was, multitasking, getting in my morning exercise while tearing my way through another book at 1.8x speed–a book that happened to be about how on average we live four thousand weeks, and maybe we should rethink the pace of our lives and all we are trying to accomplish in that time.

I slowed the speed of the audiobook down to 1.5x.

Often when I read nonfiction, I’ll have either a paper or e-book edition along with the audiobook so that I can more readily highlight passages or jot notes in the margins. Indeed, I have the e-book for Four Thousand Weeks in addition to the audiobook, and later that morning, using notes I’d jotted on my walk, I went back and highlighted passages. But circumstances were such that I mostly listened to the audiobook without following along in the e-book. And as I hit the last chapter, I realized that this book was too important, had too much good things to say, things I needed to hear, to rush through it.

So I am doing something I have done only once before1 since starting my list of books that I’ve read since 1996: I am re-reading Four Thousand Week immediately after I finish it. This second reading will be without the audiobook. It will be me sitting with the e-book, thinking carefully about what I am reading, and being more thoughtful about it. When I have finished it a second time, you can be sure I’ll share my thoughts with you. There are things that I have sensed in Four Thousand Weeks that warrant this closer reading.

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  1. I loved Bruce Springsteen’s memoir Born to Run so much that I started it over as soon as I finished it the first time.

Why To-Do Apps Don’t Work (For Me)

Back in June, I wrote about the project management paradox. In that piece, I tried to answer the question,

Why is it that I can manage large, complicated, technical projects at work, but be paralyzed with indecision when it comes to managing my own to-do list outside of work? What’s worse, I can’t even settle on a way to manage that to-do list.

Well, Clive Thompson1 may have the answer. In his recent article in the September issue of WIRED, Thompson asks the question: why don’t to-do apps help us get stuff done? It turns out, there are a lot of good reasons, and even the makers of the apps agree with them. He writes,

The creators of personal to-do apps–or task management software, as it’s sometimes called–generally agree that they haven’t cracked the nut.

The fact that to-do apps makes it easier for us to record what we have to do is part of the problem. We accumulate more stuff because it is easy to accumulate. The fact that there are market forces driving us to feel more productive also help to proliferate tasks. Then, too, we don’t often think of the accumulation of to-do items in a time-context: we only have so much time in our lives to get things done, so we need a better way of figuring out what matters and then actually doing that stuff.

It is a fascinating read, especially for someone (like me) who has tried and failed with so many to-do apps. And some of the conclusions drawn in the article vindicate my recent musings on the lure of paper. Thompson writes,

In this vein, a whole bench of task management philosophers believe that the best interface isn’t digital at all–it’s paper.

For anyone interested in the psychology of task management, to say nothing of the failure of to-do list apps to achieve their goals, this article is for you. I recommend checking it out.

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  1. If you haven’t read Thompson’s book, Coders, it too is a great read. It described the kinds of things I do in my day job more accurately than other things I’ve read about coding.

The Lure of Paper Systems

Not long ago, I came across Ryan Holiday’s notecard system for remembering, organizing, and using everything he reads. It was instantly appealing to me, the way that reading about John Gadd’s journals changed the way I did my own journals back in 2017. You can read about Ryan’s methods at length, but the gist of it is that he puts everything onto 4×6 index cards which he then categorizes, files, and then uses for whatever he needs. As soon as I finished reading his post (which was originally written in 2014) I bought myself 300 4×6 index cards with the idea of testing out the method with my own reading notes. (A few examples that I used for this post are below.)

I enjoy reading, but I also read to learn. I mark up books, both paper and digital, and then I take those notes and capture them in Obsidian. After that… not much happens. It took a fair amount of time for me to write the scripts that I used to capture those notes and link them the way I wanted in Obsidian. I like being able to see the web of relationships that form, but the return hasn’t been worth the investment.

This seems to be a theme with me when it comes to digital systems. I find very cool tools, and then decide that they aren’t quite cool enough, that they need more. I’ll then spend a ton of time writing my own code to integrate, automate, and manipulate the tools to do something very specific for me–in this case, take my Kindle highlights and notes and move them into Obsidian. I spent years doing this with Evernote, only to find my use of Evernote scale back to basic document capture. I’ve probably spent more hours writing scripts to automate tasks around my writing than I have actually writing fiction. And I can’t even begin to quantify the amount of time I have spent investigating tools, switching to them for a period of time, only to find something else later.

I find myself increasingly drawn back to paper systems. Recently, I tried switching to a digital journal as a mean to be more efficient, but ultimately switched back to paper. I’ve never found a notes app that works well for me for ephemeral notes. Instead, I’ve been incredibly happy using Field Notes notebooks to serve this purpose. And while I do have a digital version of my reading list, my master list is contained in the pages of a Leuchtterm 1917 notebook.

a recent page from my master reading list notebook
A recent page from my “master” reading list notebook.

Thinking about this, it seems that paper systems are more effective for me than digital ones. There are a number of reasons for this, but they boil down to four things: simplicity, ease-of-use, effectiveness, and longevity


  • If I need to make a quick note, I simply pull out my Field Notes notebook and jot it down. I have yet to find an app that works faster or more reliably than that.
  • When I want to write in my journal, I pull it off the shelf and start writing. There is no need to log into a computer, or open a document, no need to worry about formatting or data syncing.
  • For me, the thing I want to do needs to be really simple, otherwise, I’ll eventually give up on it.

Ease of use

  • You can’t get much simpler than scribbling in a notebook or on an index card. There are no keyboard commands to remember, commands that often vary from one app to another. There is nothing to “save” or “open.” I don’t have to worry about syncing with cloud services, or whether a password has expired.
  • If the power is out, or I don’t have Internet access, my notebooks and note cards are still accessible and usable.


These simple system work for me. I have little processes I’ve built up (how I number my journal entries for easy indexing) or how to Iabel post ideas in my Field Notes notebook so that I can easily identify them for later use.

But perhaps what makes these systems most effective is that I don’t get distracted writing code to try to improve them. Being on paper, they are already about as refined as they can get.


I still have notebooks from college, and diaries from 25 years ago. I have school papers going back to kindergarten. Yet I have only a small number of digital files from college: a few papers, a few stories I wrote. Most notes I took on the computer back then are gone. I can’t begin to imagine how much digital stuff I’ve created that has been lost over the years, not by accident, but because I simply didn’t care enough to keep it. For me, if I can touch it, it seems to matter more than if I can’t.

There is always the question of how long digital media will last. We’ve only had it in the modern sense for about fifty years. But there are countless diaries and journals that have survived hundreds of years. Famous examples include John Adams1 and John Quincy Adams, Henry David Thoreau, Samuel Pepys, and of course, Leonardo Da Vinci. As Walter Isaacson wrote in his biography of Da Vinci:

His mind, I think, is best revealed in the more than 7,200 pages of his notes and scribbles that, miraculously, survive to this day. Paper turns out to be a superb information-storage technology, still readable after 500 years, which our town tweets likely won’t be.

But it is not just the paper of famous people that lasts. Currently, I am reading The British Are Coming by Rick Atkinson. In it, he describes the early battles of the Revolutionary War in great detail, often relying on the diaries of average citizens and militia on both sides of the fight. I’ve made it through the first three chapters as of this writing, and along the way, encountered the following citations:

  • …Lieutenant Frederick Mackenzie told his diary.
  • A physician visiting from Virginia told his diary…
  • …recorded in his diary
  • …Lieutenant Barker of the King’s Own told his diary.
  • …a parson told his diary
  • …a deacon in Brighton noted in his diary.
  • …Reverend Ezra Stiles told his diary…
  • Horace Walpole, ever astringent, told his diary…

There are about half a dozen more and that’s in just the first three chapters. You get the idea. There is a level of confidence in the longevity of paper systems that just doesn’t isn’t there with digital systems. Paper can burn, of course, but I treat paper with more care than I do digital documents.

One of the reasons I’ve put a lot of effort into digital systems in the past is to leverage their ability to do things faster than I can do them myself. Searching for something is a great example of this. Having my journals in digital form means that I could easily search for stuff in them. But when I have kept them in digital form, I’ve found that I simply don’t search them enough to make it worthwhile. Instead, I’ve developed a simple way of indexing my journals (on paper) so that if I don’t know immediately where to go, I can use the index as a guide.

a recent journal "index" page
Sample index page for August 2021. Number in parentheses represent journal entries on the topic

My reasons for building the scripts that take my reading notes and import them into Obsidian was to leverage Obsidian’s ability to link notes together. I thought I’d gain new insights from this. But this wasn’t how things turned out. The notes go in automatically, and I never look at them again. It has been different with the notecards. After finishing a book, I’ll go through it and make notecards from things I’ve highlighted in the book. I’ll organize them by topic or theme and them file them away. I do the same thing for anything I read: magazine articles, blog posts, etc. That means that some themes (say “Paper v. digital” — see the images above) contain cards from many different sources. That is much more useful to me. And there is something about the tactile use of paper, whether notebooks or cards, that impresses them into my memory better than looking at the same information on a screen.

More than any of that, however, is the time saved by not writing code to build all kinds of integrations that I won’t end up using. Instead, I can just read, or write, or jot downs notes.

This is not to say that paper is always better. I use Obsidian, for instance, for all of my work-related notes. I used to keep my notes in those marble notebooks you find for 50-cents at Target during back-to-school sales. But I do search work notes frequently, and often refer back to them. It makes much more sense to me to have those notes in digital form. I use Obsidian because underneath, it is just plain text and compatible with everything.

Calendars work better for me in digital form than they do on paper.

I prefer paper books to digital versions and paper magazines to electronic ones, but the fact that the latter take up no physical space is a big plus. So I read books on a Kindle in lieu of paper when it is convenient, and I read magazines mostly on my phone, except for a handful that I get in the mail each month, also because it is convenient.

But isn’t digital easier? Maybe, but maybe easy is not the point. In his post on his card system, Ryan Holiday writes:

I don’t want this to be easy. Writing them down by hand forces me to take my time and go over everything again (taking notes on a Kindle is too easy and that’s the problem). Also being able to physically arrange stuff is crucial for gettin gate structure of your book or project right. I can move cards from one category to another. As I shuffle through the cards, I dumb into stuff I had forgotten about.

This resonated with me. The ability to collect random bits and shuffle them and reshuffle them, that tactile feeling of manipulating the information, is important to me, and it is something that is much more difficult to do in digital systems that exist today. If you think of each “note” in Evernote as a card, how do you “shuffle” the notes into some useful order? How do you reshuffle them when needed? How do you easily “flip” to a random card? Ditto notes in Obsidian.

Paper systems are also cheap compared to their digital counterparts. Even my more expensive Moleskine Art Collection notebooks (about $28/each) cost less than half of an annual subscription to Evernote. And for the price of an iPhone or a MacBook, how many good notebooks, index cards, fountain pens, etc. could I buy that would far outlast the need for me to upgrade said phone or laptop?

A few days ago, I sat in my office with a 1996 diary in my lap, flipping through the pages and stopping now and then to read a passage. I wasn’t looking for anything in particular, just doing a bit of time travel. I could have done the same thing in a different way if that diary had been in digital form, but it wouldn’t have been the same. I wouldn’t have seen my own handwriting, and the cross-outs I’d made here and there. I wouldn’t have seen the color of the ink change from one day to another, or how I wrote in cursive one day and printed the next. I would have missed the blood stain on one page from a cut, or the corner I’d torn off a page to jot something down.

The lure of paper systems is about more than simplicity, ease of use, effectiveness, and longevity. The lure of paper systems, for me, is about history. The paper contains history. It yellows with age. It carries stains. It shows wear. It has a feel and smell and even a sound: pages riffling; that tap of an index card on your fingers; the whisper of a fountain pen across the page. Digital systems have none of these things, at least not to the extent that paper has. I can take a Field Notes notebook into the woods on a hike with me and not feel connected to the world. I can’t say the same when I have my phone and note-taking apps in my pocket.

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  1. Yes, I recognize the irony of linking to a digital version of a paper diary that has been around for over 200 years.

Weekly Playbook #5: Handling Email

For an overview of this series, see the debut post on my morning routine.


I’ve been using email for more than half my life. While it was available to me in college, I didn’t begin to use it until I started at my job a few months after I graduated. That was 1994 and I was 22 years old at the time. Nearly 27 years later, I think I’ve done a pretty good job with handling email. My inbox rarely contains more than a dozen message at any given moment. I frequently hit “inbox zero.” I’ve been through a variety of models for managing my email over the years, from an elaborate folder structure to the minimalist structure I’ve used for the last fifteen years or so.

Until recently, I kept up with my email more or less in real time. I’d clear out messages as they came in, respond as they came in, prune and refile throughout the day. As I developed my morning routine, one of the things I wanted to try was to see if it was possible to handle my email once a day, in the mornings, after I’d finished my writing. This playbook is what has come out of that experimentation so far.


  1. Reply to email messages I flagged the previous day. Use canned replies, if possible.
  2. Move the replied-to message to my Archive folder.
  3. Scan my inbox for messages that can be deleted without being read. Update filters to weed these out in the future, if possible.
  4. Delete the unneeded messages.
  5. Read the remaining new messages
  6. Take action on the email if action is quick. If it takes more time, snooze the email for a later date/time.
  7. Move messages that don’t require a response to my Archive folder.
  8. Flag messages that require a response and leave in my Inbox. I use the Pin function in my mail client for this.
  9. Compose any new messages I need to send


Example: Handling this morning’s email

My basic philosophy here is to try to deal with email once per day. So far, this doesn’t work out quite this way in practice, but I’ve found that it means I am checking email much less frequently during the day. And it does help me to make sure I am replying to email only once each day. Here is what my inbox looked like as I composed this post:

My morning inbox, before running through my playbook.

The first thing I do is to reply to any email messages in my inbox that I flagged the previous day. If possible, I’ll use a canned reply. I have a few of these. One common example is when I get unsolicited requests to do a guest post on my blog. If I find that I am writing the same reply over and over, I will also use this time to compose a reply that I will turn into a canned reply that I can use in the future. Once I’ve replied to a message, I immediately move into my Archive folder. This morning was nice. I had no email that I flagged for reply.

Next, I look for email that can be deleted without being read. Often these are newsletters I didn’t subscribe to, or notifications from service I use that I don’t need to see. For the former, I’ll see if there is an easy way to unsubscribe. I’ll also use this opportunity to improve my inbox filters so that messages like these never make it to my inbox in the first place. The MetLife Dental Claim email is a good example of a message I can just delete as I know it contains no useful information (just a link to the site).

Next, I’ll read through what is left. I always enjoy Melanie Novak’s posts which is why I subscribed to her blog. No action other than to read. For blogs, I’ll use the email as a reminder to go to the blog itself to read so that the blogs get the views. Besides, I prefer reading on the blog than in email. It makes it easy to comment. Once I’ve opened the blog in a browser, I’ll delete the message from my inbox.

The Ring message requires an action on my part, but it is not something I want to do now, so I’ll snooze that for Friday when I know I will have time.

Dan Roberts is the CEO of Ouellette & Associates, a great company I’ve worked with in the past, and from which I have received some of the most practical project management training I’ve encountered, to say nothing of their outstanding customer support training, which focuses on moments of truth. I saw that Dan is starting a podcast, and the action here was to get more information about the podcast and when it drops.

The message from Capclave (my local science fiction convention) has been sitting in my inbox for almost a week now, which is rare for me. Since it is going to take more than a few minutes to handle this, I’ll snooze it until Friday.

The nice thing about this morning is that I have no email that requires a reply, so there is nothing to flag (so far). This is where I tend to dip into email throughout the day, checking to see if there is anything I need to reply to and flagging it so that I can reply tomorrow. I also don’t have any new mail to send out, so it was a quick and easy morning for me. At the end of the process, my inbox looked like this:

My morning inbox after running through my playbook: inbox zero achieved!

I don’t achieve inbox zero every morning, but as I said, I usually don’t have more than a dozen messages in my inbox at any one time. One nice side effect of this is that people can expect to get a reply from me first thing in the morning, the day after they’ve sent me a message. First thing in the morning is also when I sent out my new messages, if I have any.

Filing my email

When I began using email in 1994, I was using a Unix-based email system that allowed for the creation of folders in the same way you could create folders in a file system. I had a fairly elaborate scheme for organizing my email into folders. back then, but about fifteen years ago, I moved to a much simpler scheme, consisting of four active folders. The four folders are:

  • Inbox – where I process new email.
  • Archive – where I store all email that I want to keep
  • Sent – where I store copies of email that I sent, including replies
  • Upcoming Travel – where I store current messages related to upcoming travel (confirmations, tickets, etc.)

It occurred to me that the power of search made it simple to find pretty much anything I needed without spending a lot of time figuring out where to file a message. So if a message doesn’t go into the trash, it goes into the Archive folder. Travel-related messages take a detour to the Upcoming Travel folder until they are no longer needed, at which point they go into the archive folder as well.

If I need to find something, I just run a search and can usually find what I am looking for within a few seconds.

My mail apps

Currently, I am using the Spark mail app for handling mail on my computer. On my phone I use the Spark mail app for iOS. I just like the simplicity and functionality of Spark better than the native Mac mail app.

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The Weekly Playbook #3: My Evening Routine

For an overview of this series, see the debut post on my morning routine.


Recently, I wrote about how I form my habits. In light of that post, I thought I’d write about my evening routine since it helps to reinforce the habits that I have been working to form. I wrote about my morning routine in an earlier post. That routine covers the first two and a half hours of my day.


From start to finish, my evening routine covers the last two and half hours of my day. Bold items are ones that I try to do every day regardless of circumstance.

  • Blog edits (30 min)
  • Mind dump (10 min)
  • Prepare tomorrow’s to-do list (10 min)
  • Journal (10 min)
  • Workout (50 min)
  • Update habit journal (10 min)
  • Shower (10 min)
  • Meditate, unguided (10 min)


Like my morning routine, my evening playbook doesn’t have fixed clock times associated with it. I usually try to get started by around 7:30 or 8:00p, but that can vary. I’m more focused on how long it takes to do the things, than when I actually do them.

Blog edits allow me to re-read the posts that I have coming out the following day, make tweaks, add finishing touches, and try to catch typos that I am famous for making. This is relatively new. In the past, I was willing to trade accuracy for speed in my posts, typing fast, but occasionally making mistakes that I didn’t worry too much about. But I’m trying to do better here, and so this gives me the time to review. I’m usually two or three days ahead in what I’ve written so I focus on the post coming out the following day. If I have time after that, I will review other posts, or continue to write ones that I started in my morning writing session.

In looking for ways to improve my sleep, one of the things that I’ve been doing is attempting to clear my head of anything that will keep me awake. The mind dump, journaling, and meditation all work toward this end. The mind dump is a very GTD-esque task. I take a sheet of paper and jot down everything that I’ve got on my mind. At first, I left work-related tasks out of this, but I found that I think about work when falling asleep so I’ve started to really try to dump everything I can. This gets it out of my head and onto paper, my simple manifestation of David Allen’s inbox. I don’t spent more than 10 minutes on this. I avoid looking at my to-do list or email or other things when doing this because if something isn’t on my mind, I don’t want to put it there by mistake.

I use that list to put together my to-do list for the following day. I pick the three things I want to get done at home, and the three things I want to get done at work and write them on an index card, which I keep in the back of my current Field Notes notebook. This sets up the next day for me and I don’t need to fall asleep wondering what I need to do.

Journaling at the end of the day allows me to get other thoughts out and provides a context for my overall day. The last thing I do is 10 minutes of unguided meditation as a final way of clearing my head, or being okay with whatever I can’t clear. I started with 20 minutes of unguided meditation, but that was too long for me so I scaled back.

I give myself 50 minutes for a workout to allow for stretching before and after. As I write this, I am focused only on stretching so that as I work my way toward cardio and light strength training, I don’t end up hurting myself. I alternate between a 30 minute stretch session one evening and a 15 minute the next.

In my post on how I form my habits, I mentioned my habit journal. I try to keep this updated throughout the day, noting when I wake up, what I eat, mistakes I made along the way, my exercise. I go to bed making sure it is up-to-date.

These playbooks are designed to be living documents. I tweak them as I make adjustments, figuring out what works and what doesn’t. So far, the playbook for my evening routine is working out pretty well.

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The Weekly Playbook #2: Curating Photos

For an overview of this series, see the debut post on my morning routine.


I don’t know about you, but I’ve got too many photos in my photo library and I don’t know what to do with them all. They are all digital, of course, so they don’t take up space. But there are three problems that plague me:

  1. Duplication: because there is no limit to how many pictures I can take, I tend toward taking a lot of the same thing.
  2. Ephemera: there are pictures I take so that I can use for a specific purpose: like the brand of detergent I need to pick up at the grocery story. These could be thrown away after I use them, but they never are.
  3. Lack of curation. Almost none of my photos are tagged, labeled, or otherwise curated in any way.

Recently, I decided to tackle this problem, and I developed a playbook for curating my photos. Here is what I do.


  1. Open the Photos app on my Mac.
  2. Select the “Weekly Photo Curation” Smart Album
  3. For each photo in the album, so one of two things:
    • Delete the photo
    • Give the photo a title, and optionally, give it keywords
  4. Repeat step 3 until all the Smart Album is empty.


I use Apple photos for managing my photos. As of this writing I’ve got over 25,000 photos there, many of which are duplicates or ephemera, and most lack curation.

I decided to tackle this problem by stopping the bleeding first. Thus, this playbook.

Defining the Smart Album

The “Weekly Photo Curation” Smart Album is defined as follows:

I search for any photos in the last 7 days that do not yet have a title. Since a Smart Album is a “live” album of the photos that match the criteria, each time I either delete a photo, or add a title, the photo drops out of the album so that I know I am finished when the album is empty.

What goes into the decision to delete or save? Mostly experience. I usually ask myself a few questions that go beyond the usual keeping a photo out of sentimentality or personal documentation:

  • Is the photo a duplicate or close enough to be considered a duplicate?
  • Is the photo distorted (blurry, etc.)?
  • Is the photo unique enough to keep for use on the blog? (I prefer to use my own photos on the blog than ones that come from curated sources online.)
  • Do I need this photo to be available in my Photo library? (Is it available somewhere else?)
  • Have I needed to find similar photos to this one recently?

Selecting a title

If I choose to keep a photo, I try to give it a succinct title that is specific enough to be useful in future searches. For instance, this morning I took a picture of the sunrise coming up behind the 7-Eleven which marks the halfway point of my morning walk. In this case, I simply titled the photo “Sunrise over 7-Eleven.” I try to be conscious that Apple Photos, like Google Photos, uses AI to be able to identify things in photos. Sunrises are one example that Apple Photos is probably good at. But the 7-Eleven in the photo is from the back, so there is not much of a change for the AI to identify it as such so I throw it into the title.

sunrise over 7-Eleven
Sunrise over 7-Eleven

Tackling the entire album

At some point, I’d like to go back and clean up the entire album, but with more than 25,000 photos, that seems an almost impossible task. Maybe at some point, I’ll put together a playlist which would allow me to review a month of photos at a time, slowly working my way backward. But for now, I’ve got too much on my plate already so I am focusing on ensuring good meta-data quality on photos going forward.

Also, I am trying to be more present when doing things, and am less likely to take as many photos as I used to. Every little bit helps.

I try to do this on Sunday mornings, immediately after completing my morning routine. I guess you could say that this has become part of my Sunday morning routine. That allows me to get the past week’s photo’s curated just as the new week is beginning.

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One Important Feature that Evernote Still Needs

Evernote has made some significant improvements lately. They have completely reengineered the backend. They have refreshed and improved the user interface. And they recently introduced integrated task management–something users have been requesting for a long time.

There is one feature that I would find incredibly useful that Evernote still needs: a Last Viewed date for a note.

Currently, Evernote provides two dates for each note: a Created date and an Updated date:

An example of Evernote note information showing the created and updated date fields.

The Created date is the date on which the note was originally created. (I often change this to match the date of a document to make searching by date range more effective). The Updated date is the last time the note was modified. What’s missing in the “Last Viewed” date.

Why is a “Last Viewed” date important? Evernote is not just static storage for me. It is a living memory–a repository of digital documents and other notes that I have been collecting for more than ten years now. I call it a living memory because I am always looking for ways to improve the value I get from what I have stored in there. Currently, I have over 13,000 notes stored in Evernote. Despite the methods I have come up with for making searching as easy as possible, it can sometimes be hard to narrow things down when there is a lot of noise.

A screen capture showing Evernote's count of my notes, currently at 13,263.

This is where a “Last Viewed” date plays a crucial role. If I had to guess, I’d say that three quarters of the notes I have in Evernote have never been looked at after their initial scanning or input. The question I ask myself is: if I never have to look at note that I am storing, then why am I storing it?

Certainly some notes are worth keeping, even if I haven’t looked at them in months or years. But there are also things like phone bills and Amazon receipts, and countless other documents that I probably will never have a need to look at. I don’t know this for sure at the outset, so I put them into Evernote just in case. But I would love to do a yearly review, looking at how many notes I haven’t viewed in the last, say, five years. If I could get such a list, I might simply move all of those notes to an Archive notebook, export that notebook to a file, and then delete the notebook from Evernote. This would remove a lot of noise that comes up in searches. And it really is noise, since they are notes that I have not looked at in the last five years.

The problem is, of course, that Evernote does not have a “Last Viewed” date to query on. I suppose this would be the equivalent of the “Date Last Opened” on MacOS. It seems like it would be a simple matter to add the functionality for this information, although I suspect there would be no way of implementing it retroactively.

Still, I think this would be a useful feature, and one that corresponds to real memory, where things that we have no need of recalling are “erased” so that we can more readily remember other things.

Small Efficiencies in Workflow

With my recent plan to focus on my writing and improve my overall well-being (a.k.a. Project Sunrise), I have been hunting for small efficiencies in workflow that can have an outsized impact on my day. My morning routine takes about two and a half hours to complete. While developing the routine, I teased out actions or tasks that I could eliminate or improve upon to maximize the use of my time. Two examples come to mind.

Writing in my journal: content versus medium

Since 2017, I have been writing my journal longhand in large Moleskine notebooks. I’ve written about the advantages and disadvantages of having a paper journal versus a digital one in a piece called The Paradox of Journaling. I like the feeling of writing longhand, and I understand and believe in the durability of paper. But there are two tradeoffs to consider when time is limited and my goals depend on data:

  1. The speed and clarity with which I can write.
  2. The speed an accuracy with which I can find what I wrote about.

With limited time, I had to consider what is more valuable to me now, the content of my journaling or the medium in which it is stored. Today it is the content. Since I can type much faster than I can write longhand, since my typing is more clear than my handwriting, and since I express thoughts more clearly through a keyboard than a pen, it seemed prudent to switch my journaling to a digital form instead of a paper one. This is why for the last week, I have been composing it as a text file using Obsidian, despite what I wrote in February when I initially rejected the idea. The reasons I rejected it were valid then, but circumstances have changed, and I think this little efficiency will have long-term benefits.

One of those benefits is the speed with which I can find what I wrote about. It is much easier to search a text file than volumes of journals, even when they are roughly indexed. And time is the key. I want to spend as much of my time as possible on creative tasks. That said, to improve, I need to look back at the data I’ve collected so that I can apply it going forward. I can do this much more quickly searching a text file than books. Practical considerations–speed of input, clarity, and speed of retrieval–have overridden my desire to continue writing my journal longhand, at least for the duration.

Composing in WordPress

For a long time, I composed my blog posts in an external editor. That editor has changed over the years. I’ve written drafts in Scrivener, in Word, and most recently, in Obsidian, my current editor of choice. With my recent migration to WordPress hosting, and conversion to a modern WordPress theme, I have found WordPress’s native Gutenberg editor to be comfortable and easy to compose in directly. This saves a good deal of time. Prior to composing directly in WordPress my process looked like this:

  1. Write the post in Obsidian (or other editor)
  2. Copy the text out of Obsidian
  3. Paste it into a blank WordPress post
  4. Fix any formatting issues
  5. Publish.

For the last week I have been composing directly in WordPress which allows me to eliminate the administrative steps I was doing before. This shaves a little time spent on each post, which I get back for creative work, like writing the posts themselves.

These are small efficiencies. They don’t save huge chunks of time each, but the affect is cumulative. I journal in the morning and evening, so I am saving a little time each journaling session. I tend to write in the mornings, sometimes one post, sometimes more than one, and I save a little time with each draft. In a cumulative sense, over the long haul, I think small efficiencies like these have outsized results.

I am always looking for small efficiencies like these because of their magnified results over time. Do you have small efficiencies that you have discovered? If you feel like it, share them in the comments.

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The Weekly Playbook #1: My Morning Routine

Introduction: Playbooks are Practices

Welcome to the inaugural post of my new column, “The Weekly Playbook.” Each week I plan to feature a playbook that I use to help make my life a little easier. What is a playbook? A playbook is like an enhanced checklist that provides steps or outlines for a specific task that make it (a) repeatable, and (b) flexible. Playbooks help to save me time, build habits, and avoid making mistakes. Repeatability is key because it means I am not reinventing the wheel each time I am trying to perform some task. Flexibility means that playbook has built-in alternatives for when things go sideways. Over time, I kind of mentally absorb the playbook. In this sense, the playbook becomes the practice.

I first learned the value of a checklist when I was taking flying lessons in 1999-2000. Checklists are there to reinforce memory so that you avoid missing things. Back when I was flying, I learned to touch each item referred to on the checklist as a way of reinforcing that I was doing it. Playbooks came a bit later. I started to develop my own playbooks for work initially. After rolling out some big piece of software, I found that a standard manual or user guide wasn’t as effective as lots of short, focused lists on how to handle different situations. Over time, I began to create playbooks for myself in order to reduce the number of decision I had to make or the time I spent looking up information. They are also great at helping to form habits. In some ways, the Going Paperless series of posts that I wrote about Evernote where a set of playbooks in narrative form.

This series is different. First, the playlists that I’ll write about here are much wider in scope than the Going Paperless posts, which focused on the possibility of using digital tools like Evernote to replace the paper in my life. Second, the Going Paperless posts were more narrative in form. As you’ll see the playbooks I discuss have three parts:

  1. Background: Why I use the playbook or how it came to be.
  2. Playbook: The playbook itself which is often just a list and a set of alternatives.
  3. Commentary: Some words explaining the playbook in more detail.

I decided to post this series every Friday so that people had a chance to explore them over the weekend, when there tends to be more time. We’ll see how that works out. Given that I just began my creative new year with the goal of becoming a full-time writing in ten years, I thought I’d begin with the playbook that I worked up to help support his goal in the most generally way: my morning routine. Enjoy!


Project Sunrise is a codename I’ve given to my effort to improve my writing and writing opportunities over the next ten years so that when I retire from my day job (ten years hence) I can begin working as a full-time writer. The project involves more than just improving my writing, but also my overall health and well-being. Given that I still work full time and am raising three kids, I needed a way of ensuring I am getting time to write, analyzing and improve what I write, as well as improve my health and well-being into an already full day. This playbook outlines my newly revised morning routine. I’ve been beta-testing and tweaking this routine for a few weeks now, but began using it “in production” on July 1, 2021.


From start to finish, this playbook takes 2 hours and 35 minutes to complete each morning. Bold items are the ones I try to do every day regardless of circumstances.

  • Walk (45 min)
  • Meditate, guided (10 min)
  • Shower (10 min)
  • Write (1 hr)
  • Journal, email, blog comments, etc. (30 min)


  • Bad weather? Replace walk with elliptical (45 min)
  • Short of time in the morning? Move writing to evening routine (1hr)


I have my morning routine list posted in a few places so that I can reference it at a glance. It is posted in my office above my screens so that I can see it when I am sitting at my desk. A copy of it is also taped into the back of the current Field Notes notebook that I carry around.


Note that there are no clock times associated with the playbook? To be as flexible as possible, my playbooks focus on duration, but not start or end times. As I’ve worked out this new routine, I try to get started at 5:50 am. But this list works just as well if I start at 7 am or 9 am. Everything just shifts relative to the time it takes. I’ve tested out each of the times listed to make sure they are reasonable. That way I know how long it will take to get through the routine.

It is important to me to have alternatives readily available. Nothing throws off a habit as much as an unexpected situation? What do I do if I am traveling? What do I do if the weather is bad? What if I have an early work meeting? Have a pre-defined set of alternatives means I don’t have to think about the answer in most situations.

Order matters to me on these playbooks. I walk first thing because it wake me up. I gave up caffeine 74 days ago (as I write this) so I no longer have that as an aid to alertness. The walk gets me fresh air and some immediate exercise and I come back to the house alert and ready for the day.

I use the Calm app for meditation. My preferred guided meditation is Jeff Warren’s “The Daily Trip” series. These last anywhere from 9-12 minutes and allow me to clear my head before getting started.

A shower after meditating helps wash away any residual sleepiness. Even though my showers are quick, it is also where my mind wanders and I try to guide it toward what I plan to write that day.

After the shower, I write. For instance, I am writing this post after my shower on July 1. On my walk and in the shower I was able to frame how I wanted to present these playbook posts (context, playbook, and commentary). I give myself an hour to write. Maybe I can write only one post, maybe more than one. Maybe I’m not in the mood to write. That’s okay, but I don’t allow myself to do anything else in that hour.

Finally, I give myself 30 minutes for journaling, handling any personal email, and reviewing any blog comments that I need to reply to.

Playbooks are designed to be living documents. I adjust them as needed as I learn better ways of doing things.

I also have a playbook for an evening routine, but I’ll save that one for another time.

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The Project Management Paradox

Why is it that I can manage large, complicated, technical projects at work, but be paralyzed with indecision when it comes to managing my own to-do list outside of work? What’s worse, I can’t even settle on a way to manage that to-do list.

I find myself thinking about this because I was revisiting an old favorite, Gina Trapani’s todo.txt system. Seven years ago, I wrote about my requirements for a to-do list app. There are five of them:

  1. The list be stored in an open format
  2. Priority is by list order
  3. One list to rule them all
  4. Easy archiving
  5. Accessible anywhere

I think these requirements still apply for the most part.

The paradox of all of this is that I am spending time trying to figure out how to manage my to-do list when I should be doing the things on that list. Over the years I have tried many task management systems and tools: David Allen’s Getting Things Done; Evernote; todotxt, todoist, bullet journals, and on and on. None of them have stuck permanently. The two best in terms of effectiveness and longevity were todoist and todotxt, and I think that is because they are relatively simple systems.

I am looking for a way out of this paradox. More and more it seems to me that to-do apps are a case study in great technology which can make us (well, make me at least) less efficient. I think about all of the time I have spent studying, testing, trying, and writing about to-do systems, and wonder how many practical items I could have slashed off my lists in that time.

Simplest is best. I find that I can too easily get bogged down in “features” and comparing and system to another, when I really need to be focusing on a system that is virtually invisible. I recently heard a podcast in which Jim Collins spoke about his own to-do list: he uses the Apple Notes program with a single note for his to-do items. What he does is lists the top three things to get done on a given day, and then separates the rest of his list by enough carriage returns so that when he looks at his phone, all he sees are those three things–but he can scroll down to see more. That is relatively simple, but not simple enough for me.

Last night, when I couldn’t sleep, I took to heart another piece of advice from Jim Collins: I applied the 20-minute rule. The rule states that if you can’t get back to sleep in 20 minutes, you should get up and do something. He says this is a great time for him to figure out what he needs to prepare for. I did that. I thought about how to tackle this problem once and for all. I’ve decided to go as simple as I possibly can.

First, I attempted to clear my head by dumping everything to a file in Obsidian. Call it my master list. This is everything. Well, almost everything. There are still things in my head that I haven’t gotten out yet, but I’m working on it.

Second, I picked three things I wanted to get done today. There is a stack of 200 index cards that have been sitting unused on my desk for months. I took one of those cards scribbled the date on the back, and then jotted down the three things I wanted to do in “next action” form. I included all of the information I needed to get those things done.

Third, I stuck the card in the back of my current Field Notes notebook. I always have the notebook with me so I always have the card with me.

Now I have a simple system for focusing on what I want to get done on a given day without it being difficult to maintain or overwhelming. On the back of the card I jotted an item from my master list that would be “nice to do” if I happen to have the time after getting the other items done.

At the end of the day, I remove the completed items from my master list, drop the old card in a box, and start a new card for the next day. Simple!

Someone is bound to ask why not just make the list in my Field Notes notebook. There are two reasons. First, I use my Field Notes to capture notes, observations, ideas, etc., but it is not meant to be for taking actions. I think of it more as a creative notebook, a creative record for my day. Second, I don’t want to begin associating mundane tasks with my notebook. I think it is better to have the card; the card represents the stuff I need to do. It’s the work. The notebook is the joy and fun.

I don’t know if this will work or not. Only time will tell. But it will be time I am not spending trying out this app and wondering if the features in that one aren’t better; or how I could automate my to-do list to show up in my Daily Notes in Obsidian each day; or any of a dozen other things that distract me from actually getting my tasks done. The index card also meets all of my to-do list app requirements.

I’ll let you know how it goes.