Archive of posts with tag 'Productivity'

I have a bone to pick with recurring meetings. They’ve become a scourge that’s been amplified with fully distributed teams. What may start with clear intent as a space for a team to coordinate continuous work eventually devolves into a purely ceremonial affair. And they’ve gotten 10x worse since the pandemic turned every meeting into a remote one. This effect was visible long before COVID, but I think remoteness has magnified the negatives without adding any positives.

Since no one has to book a conference room, the bar to generating tons of ceremony “sync” sessions has dropped to the floor. Even worse, remoteness makes a bloated 15-person meeting not feel any bigger than the 4-person meeting it should’ve been. In person, the bloated attendee list would be an obviously bad idea — very few meetings should leave some attendees with standing-room-only.

These meetings show up on the calendar with positive intentions. A subset of folks from different teams might need to regularly stay in touch with one another on specific projects, or perhaps there’s always some active work to be coordinated. Maybe it’s a stand-up intended to be a high-signal-per-minute short session to sync team members as quickly as possible¹. There are good reasons the repeating function exists. But it’s overused. The decision to spawn a cross-functional recurring meeting isn’t considered deeply enough in terms of the cost, and the long-term purpose. Almost every time I’ve seen one appear on my calendar, there’s triggering project or event that compels someone to create it.

The “value per minute” of a recurring meeting might start high, but it decays over subsequent weeks. It’s like there’s a half-life on the value of a particular meeting, with its potency to get work done and problems solved waning substantially by month 3. But why does this happen so often?

For one, they’re too easy to create, and too hard to cancel. It requires the team as a whole to fundamentally not want to have the meeting, to be in favor of a meeting because it needs to happen. Gradually the utility : time ratio degrades, people get less and less out of their weekly session and are less engaged, just going through the motions. The whole group (especially meeting-originators) need to be on the lookout for ways to obsolete the need for having the meeting in the first place. I liked this from Aakash Gupta on Twitter, who says “meetings are like gravity”:

Meetings are like gravity.

You have to constantly be outrunning them.

Usually, formerly good meetings hit a point where either:
· too many people attend
· or, not enough progress is made

They lose their “value per minute.”

— Aakash Gupta 🚀 Product Growth Guy (@aakashg0) October 2, 2022

Different personalities and roles have differing preferences for what medium to use for each type of work. Some will always lean toward a meeting to communicate. Some want long-form writing. Some like incessant email chains. Choosing the right medium is Step One to escaping the recurrence gravity well. To quote myself from a previous post, meetings are just one medium for communicating and getting work done. A core contributor to “meeting fatigue” is when we’re choosing the wrong medium for work:

I know when I find myself in a useless meeting, its “meetingness” isn’t the issue; it’s that we could’ve accomplished the goal with a well-written document with inline comments, an internal blog post, an open-ended Slack chat, or a point-to-point phone call between two people. Or, alternately, it could be that a meeting is the optimal medium, but the problem lies elsewhere in planning, preparation, action-orientation, or the who’s who in attendance.

So what to do?

I recall this interview with Shopify founder and CEO Tobi Lutke. He mentions how they periodically mass-delete all recurring meetings from the corporate calendar:

That was a tangent, but to get back to the question you asked, we found that standing meetings were a real issue. They were extremely easy to create, and no one wanted to cancel them because someone was responsible for its creation. The person requesting to cancel would rather stick it out than have a very tough conversation saying, “Hey, this thing that you started is no longer valuable.” It’s just really difficult. So, we ran some analysis and we found out that half of all standing meetings were viewed as not valuable. It was an enormous amount of time being wasted. So we asked, “Why don’t we just delete all meetings?” And so we did. It was pretty rough, but we now operate on a schedule.

I don’t know if this is apocryphal or real, but it’s an interesting experiment in refocusing. Like a brush fire that clears the undergrowth for new life.

A few things we could do to minimize meetings, to force more thoughtful selection of medium for the message:

• Make fewer in the first place — Seems obvious. Can we just do 1? If one isn’t enough, can we just schedule 3 and go from there?
• Set end dates - 1 month, 3 months, whatever. This function exists, but I don’t think I’ve seen it used once in my career. The normal move is to say “we’ll cancel it later if we need to.”
• Don’t make anything? — Do we even need to meet? Could it have been an email? Do you need to write up thoughts/ideas? Maybe record a Loom? Make a Miro board?
• What if calendar tools let you see how many collective hours you’re scheduling? “For the next 1 month, this schedule will cost 60 hours of human time.” Not that this would stop some people, but may make you do a double-take to see the volume of time you’re about to commit.

Tyler Cowen says “context is that which is scarce”, meaning that we’re never lacking in information in our modern lives, but the means to make productive use of the information. Meetings often stem from people lacking context. The craving for context — to have a window into what’s going on, why it’s happening, and what to do next — generates temptations to “set up a quick meeting”. And if we know something is too big a topic for a single session, it’s too easy to say “let’s sync up weekly on this”.

A lot of coordination between people is about setting or sharing context. “Syncing up” is about sharing context. You can lean on recurring meetings to share context, which is occasionally okay if meeting trade-offs are worth it (in time required, efficiency). But sometimes we choose the wrong method for context-sharing between teams, and the need for too many meetings is merely a symptom of poorly-communicated context.

The latest episode of Notion’s Tools & Craft podcast features the excellent Andy Matuschak, talking about his research, productivity practices, and more.

Also check out Andy’s work on smoothly-ratcheting goal tracking and mastery learning.

When I read Cal Newport’s Deep Work a few years ago, one of my favorite ideas in the book that I keep coming back to in conversations is the idea of “busyness as a proxy for productivity”. Here’s how he puts it:

In the absence of clear indicators of what it means to be productive and valuable in their jobs, many knowledge workers turn back toward an industrial indicator of productivity: doing lots of stuff in a visible manner

We’ve all worked with violators of this. People that always have fully-booked calendars, can never find a time to get tasks done, and constantly talk about how busy they are. One of the reasons people do this, whether subconscious or not, is that in the world of knowledge work, it’s seen as a virtue to be busy. “Man, that guy is always in high demand, it’s impressive how many things he’s doing every day.”

But behind the scenes, the impact of each unit of time spent “being busy” is miniscule. It’s a classic mismanagement of time and attention, but one that has obvious roots given the incentives in business to be seen. And when a behavior is rewarded, in this case with attention and sometimes even respect, it perpetuates.

So let’s talk about motion. Busyness is a form of motion, usually described in an individual context. Motion and progress are terms that apply more at a team or organizational level. What is progress anyway? Clearly progress isn’t just “Stuff Happening.” There’s got to be an outcome for any of it to be worth it. There should be specific and consistent directionality to goals, and measurable steps to get there.

The motion of the team doesn’t necessarily tie back to an outcome anyone cares about, though.

One example where this happens in practice is the infamous Recurring Coordination Meeting — the Standup, the Check-In, the Sync Meeting. Someone sets up a weekly recurring meeting, often with few specifics as to the outcomes expected from each one. In subsequent weeks, the team now pulls itself away from other duties to distract itself with Another Meeting. Now I’ve rarely met anyone who enjoys these kinds of meetings in the absolute sense. At best we tolerate them, or see them as some form of ritual necessity. But so often some initial hangup or friction point triggers someone to decide “we need to stay in sync on this topic”, and they make the Check-In Meeting. In a snap we’ve committed several people to an unknown number of future hours for an often poorly-defined expectation. We’d have been better off with one-off meetings until we feel the team going wayward again, if we need to regroup.

An aside: I remember an anecdote about Tobi Lutke, CEO of Shopify periodically deleting all recurring meetings to reset commitments. Like a brushfire routinely clearing the corporate undergrowth of recurring time-sinks that may have long since outlived their usefulness.

But let’s get back to the “motion” piece of this. You’re now meeting once a week on a subject, and because the time since the last one is so short, you end up discussing the same topics again and again. You run through a loop with each meeting, repeatedly discussing the same things, with a tad more detail each time. Because we’re touching the topic regularly, sometimes beating the same topic to death in more than one of these meetings with different permutations of attendees, we feel like we’re “doing a lotta stuff”. We’re moving around, Trello cards are getting edited, Jira tickets are moved up and down the list, a few commits get made. But none of these motions are, necessarily, indicators of actual forward progress along the line we want. They might be, but they just as likely make us feel like we’re making progress when we’re really not.

I can get in the car and drive around the block over and over. Motion is happening, but am I getting anywhere?

Just measuring ticket throughput, or cycle time, or stories-per-sprint, or any other metric doesn’t mean you’re making progress in any meaningful sense. Those metrics might be directionally positive, but are they doing the thing you think they’re doing?

It’s imperative to have good yardsticks by which to measure progress, rather than motion.

Here’s Rich Hickey (creator of Clojure) on the benefits of stepping away from the computer, in his talk on “hammock-driven development”:

He differentiates what the “waking” mind and “background” mind are good at, which I’d interchangeably refer to as the “at the desk” mind and the “away from the computer” mind:

• Waking mind:
  • Good at critical thinking; analysis, tactics
  • Prone to finding local maxima
  • Can feed work to the background mind
• Background mind:
  • Good at making connections
  • Synthesis; strategy; abstractions and analogies
  • You can only feed it, not direct it

For anyone in a critical thinking-based market, I’m sure this rings accurate. Think about how we refer to eureka moments popping into our heads — ”shower thoughts”. This idea that we can “only feed it, not direct it” does feel true. For me the most interesting ideas don’t result from me saying “okay, it’s time to think about things” and writing down the result.

When I’m working on something, it’s challenging to get “unstuck” while sitting at my desk. Some days I can get in the zone, but most of the time the zone eludes me. It’s not even the active distractions of Slacks, meetings, and email (though those are never-ending), but temptation from the no-kidding thousands of individual little shiny threads to follow.

But then when I’m out for a walk, a run, or driving somewhere, thoughts and ideas abound. And of course I’m never in a good position to take notes or jump right into writing or doing anything about them at the time. My post from last year on Downtime Thinking looked at my experience with this phenomenon. I’ve experimented with techniques for bringing these modes closer together. Too many interesting ideas are lost in the transition between waking and background brain modes.

Hammock-driven creativity helps the mind jar loose from its normal working context. Environment is a strong contributor to controlling your behavior. For myself, my “normal” work environment — sitting at my desk, keyboard and mouse in hand, multiple monitors available — is associated in my brain with dozens of activities other than creative or critical thinking. I’ve experimented lately with “morning pages” as a mechanism working on the writing habit. Start a timer and do nothing but write free-form for 25 minutes. I’m having mixed success with it much of the time, but occasional sessions lead to solid ideas, and I’ll blow past my time commitment promise.

If I can combine the intentionality of morning pages with a minor change of scenery, the forces could combine into a productive combo.

In a recent interview, Jerry Seinfeld described his writing sessions, a brilliantly simple practice:

I still have a writing session every day. It’s another thing that organizes your mind. The coffee goes here. The pad goes here. The notes go here. My writing technique is just: You can’t do anything else. You don’t have to write, but you can’t do anything else. The writing is such an ordeal.

I love that: “You can’t do anything else. You don’t have to write, but you can’t do anything else.”

Setting the table for the writing session triggers the Pavlovian mode: “this is writing time.” Then you’ve got the intention, that you can’t do anything else. And I love how he gives himself the leeway to not even write! But in exchange for the freedom for work-avoidance, your only other option is staring at the wall.

For years Todoist was my tool of choice for task management. When Roam came on the scene for me earlier this year, I’d seen pretty compelling methods from the #roamcult for how to manage todos inside of Roam with its TODO feature. It was an intriguing idea: such a fast and simple way to capture things without leaving the current frame.

But it took me a while to go all-in on Roam for tasks. Todoist was so embedded in my muscle memory, especially with its accessible web and cross-platform mobile apps and its excellent quick-entry “Quick Add” flow from the desktop. It was going to require a lot to make the switch to a different system, and one that’s wildly different from the way any other task management app works.

I eventually took the plunge, moved all my pending tasks over to a Roam page from Todoist, and started to come up with a process. I was first just managing tasks from a giant temporary “Inbox” page, but over time I learned better how I wanted to fit them in with the advantages of a Roam-based daily workflow.

Though the switch to Roam for task management gives up some useful abilities with dedicated favorites like Todoist or Things, the gains with managing tasks alongside the rest of my knowledge graph are well worth the trade-offs. Most task management tools have way too many features for my needs, anyway. Here are just a few things I love about this process so far:

• You can insert todos in context — Being able to quickly slot todos anywhere is beautiful. As you’re writing other notes specific to projects, meetings, phone calls, articles, or anything else, you can Cmd-Enter and add something right as you’re thinking of it. This method ends up being a solid “ubiquitous capture” flow similar to what you’d do with Todoist or OmniFocus inboxes.
• The [[TODO]] page, pinned to the sidebar — This lets you quickly dredge up all of your todos regardless of where you scattered them. Use this plus filters to drill in to specific areas. A solid “inbox” equivalent to process your todos into other places.
• Add tags to filter for context — If you’re familiar with [GTD’s contexts](https://evomend.net/en/what-not-gtd-context/ “Contexts in), you’ll recognize this. I add tags to tasks so I can filter for all [[TODO]] tagged #Email, for example. Now let’s go over how I plan out my week with Roam.

My Weekly Process

At the beginning of each week, I start out by creating a new page for the week ahead, dated starting on Mondays. So this week’s page is [[📆 Weekly Plan: 2020/11/02]]. I just focus into the search bar and type it out.

For the page template I start out with sections for Weekly Goals and Daily Goals. The first I treat like a general holding area for tasks I want to work on in the upcoming week, and the latter I include a block for each day. Then I manually add in the dates for each day with Roam’s /date picker slash command (/today and /tomorrow can also be useful here, if relevant)¹. To make all of this faster, I use a TextExpander snippet to automatically insert the basics. Typing rcwp stamps in my basic template²:

- # Weekly Goals
    - 
- # Daily Goals
    - Monday: 
    - Tuesday:
    - Wednesday: 
    - Thursday: 
    - Friday:

When I started down this workflow path, I initially thought it’d be annoying to have to set up a new page each week. But so far it’s actually been valuable to force a start-of-week planning session to think through what I want to get done. Usually on Sunday nights I’ll go in and make the Weekly Plan page, then pull up my [[Projects]] page, [[Blog Ideas]], [[TODO]], or even my page from the previous week to look for all of the various tasks I might want to focus on.

Using the sidebar helps a lot here. I’ll pop open other pages with a Shift-click, then drag over todos I want to work on under the Weekly Goals section. If I want the todo to actually stay where it is and not move it to the Weekly Plan page, I use Roam’s Alt-click and drag to bring over a block reference instead of the entire block itself. This is a neat way to keep todos in the right place, but have a reference to them in your task plan. There’s an example of this in the video below, where I’ve got a trip planning project page with tasks on it that I want to stay there, but still see in my weekly view.

Once I’ve got a batch of tasks entered under the week, I’ll start queueing them up into their appropriate days. Some things have deadlines or due dates I’m trying to manage to, so need to get done at specific times. Others I’ll just leave in the Weekly section until I know when I plan to do it. Regularly on weekday mornings I’ll go to my plan and pull in what I want to get done that day. It’s a living document until the week is over, a part of my morning routine to go to this page.

My favorite thing about this process is how it manifests your tasks on the Daily Notes page. Because the Daily Note automatically displays references to any page that includes that day’s date, you get a slick little embedded list of the day’s tasks. The Daily Notes view is my default working mode during a typical work day, so this is an excellent place to have all of those queued up activities available on the same page where I’m taking meeting notes and the like.

Areas for Improvement

After about 2 months committed to this process, it’s pretty solid for me. I’m not missing as much from my old workflow as I thought I would, and I’m enjoying the benefits of Roam’s graph structure too much to reconsider now. Plus the potential is high that the lightning-fast Roam team will add improvements to all this.

Todoist’s Quick Add is something I’d love an equivalent for somehow in Roam. The Capture mobile entry web app that Roam has isn’t bad, but it’s not that fast for adding new items quickly while on the go. To fill in this gap now I’ll usually just throw things into a sheet in Drafts which gets processed later back at my desk.

Multiplayer abilities were something I never took advantage of in Todoist, but are a key piece of any work (or even family) project management usage. Roam’s recent additions in support of multiplayer look promising here, but that hasn’t been relevant to me just yet. Multiuser project management (that tools like Asana excel at) is a beast in itself to solve.

Managing dates isn’t as smooth as in most task management apps, but there are some advantages I really do like. For any task entered anywhere in your graph, you can add a future date to it and have it magically appear in Daily Notes references that day to jog your memory. A feature that no task management tool other than OmniFocus ever supported, but I’ve wanted ever since, is the idea of a Start Date. With that you could put in something you want to remember, but for later, put “in 90 days” next to it and it would disappear until resurfacing then. It was a great way to put in things you know you needed to remember, but don’t need to continue seeing in your list for weeks until it’s relevant. Dating your todos like the above is similar in concept: tagging them with a date 3 months out will make them pop back up when they need to be considered.

The Future

From what I’ve seen in Twitter discussions about the incoming Roam API, I’m hopeful that its hyperactive developer community will jump right into building applications on Roam for workflows like this. A dedicated, customizable app specifically for task management built on the “Roam platform” would be a phenomenal tool worthy of driving its own second-order revenue for a developer. Thinking about David Crandall’s piece on the prospects of Roam as a service layer, there’s so much potential for it to power its own developer marketplace.

In the next post I’ll go over my current workflow for using Daily Notes. It’s an interesting companion to this process of task management.

Earlier this month I passed the 2-year mark of writing on this site every day. If on that first day, deciding to embark on this streak, you’d told me that in October 2020 I’d still be going, 2018 me would’ve laughed it off. Doing it even for a few months sounded impossible.

What helped make it reality was converting writing into a continuous background activity, an ever-present filter for thoughts, ideas, and readings to pass through. Every time I read an article or have an idea, I filter it through the writing lens — Would this make a good article? Do I have a unique angle on this idea?

James Clear writes about how your environment is a strong contributor to effective habit-forming. One of the techniques he describes resonates with me and fits my behavior patterns nicely: staging your environment by putting enablers “in the flow”:

You can apply a similar strategy by designing an environment where good habits “get in the flow” of your normal behaviors. For example, if you want to practice a musical instrument, you could place it in the middle of your living room. Similarly, you are more likely to go to the gym if it is literally on the way home from work than if the gym is only five minutes away, but in the opposite direction of your commute. Whenever possible, design your habits so they fit in the flow of your current patterns.

My writing filter above is a version of this. It’s a context that keeps me accreting ideas together as fodder for writing topics. This perpetual context is one version of an environment that happens to work well for me. I have reminders in Roam, various “ideas” tags, tools to dictate quick thoughts to a scratchpad. And the goal commitment itself eventually builds up enough gravitational force to do its own pulling.

If you can create patterns of behavior to support the building of a habit, it’s amazing what kind of change you can engender in your behavior.

After 747 consecutive days of publishing, it’s a good time to reflect on what I want to do with the site outside of regular posting.

In his piece “Why Books Don’t Work,” Andy Matuschak made a strong case that books are a poor medium for knowledge transfer. Even with the most advanced book experiences today (like digital ebook downloads to a Kindle), if you took away the digital e-ink screen, a reader from the 16th century would still recognize books as no different than what they had. We’ve added digital on-demand access, dictionary lookups, and the ability to have a library in your pocket¹, but the fundamental model for conveying the knowledge is still what Gutenberg would recognize, based on the “transmissionism” mode of teaching.

Matuschak quotes this great passage from Carl Sagan in Cosmos:

What an astonishing thing a book is. It’s a flat object made from a tree with flexible parts on which are imprinted lots of funny dark squiggles. But one glance at it and you’re inside the mind of another person, maybe somebody dead for thousands of years. Across the millennia, an author is speaking clearly and silently inside your head, directly to you. Writing is perhaps the greatest of human inventions, binding together people who never knew each other, citizens of distant epochs. Books break the shackles of time. A book is proof that humans are capable of working magic.

Knowledge is transmitted, as if by magic, across the decades and centuries. This makes it all-the-more unfortunate how bad our brains are at retaining all that information. We have a mechanism for cheap, reliable knowledge transfer, yet are still bad at hanging onto that knowledge.

One can also be reading books for enjoyment. The act of reading itself can be fun, even if the signal strength of retention is less than perfect. Fiction is like this, of course, where the primary goal is entertainment, not education. Not that there’s no wisdom embedded in fiction — in fact, I would make a case that fiction offers deep insights worthy of remembering². But I even see nonfiction works on my shelf that I remember enjoying years ago that I’ve mostly forgotten about, certainly in any conscious way that’s useful to me.

The defining purpose of nonfiction, though, is to educate, to convey ideas in a way that disseminates them to a wide audience and allows wisdom to compound over years by connecting dots in readers’ minds. Writers spend hundreds of hours distilling their ideas into works of a few hundred pages that we blaze through in a couple of weeks, retaining little.

Spaced repetition

Purely linear transmission is not the best model for understanding, but it’s the best that we have available to us today, cheaply and readily accessible. People like Andy Matuschak and his collaborator Michael Nielsen are busy behind the scenes working on this problem of how to build tools for thought that can harness the novel advantages of today’s technology. They experimented with this idea in their quantum.country project, using the complex subject of quantum computing combined with a “mnemonic medium” that integrated spaced repetition testing. The results they’ve shown from this experiment are promising evidence for the technique to increase retention. It’s a simple approach — interspersing simple questions within the text — but the problem is one of medium. Our existing reading and teaching tools don’t have affordances for this today.

Until we make headway in those new areas, what can we do to get more out of reading? How can we extract and retain the right ideas from what we read without having to reinvent the nature of books themselves?

Enter Readwise

One of the most useful tools I’ve discovered in the past year is Readwise, a service that’s working to solve this problem and enhance reading retention through a simple workflow:

• Readwise syncs your highlighted passages from Kindle, web articles, and even tweets
• See a sampling of those highlights in your inbox each day for review, through email or their mobile app (what they call your “Daily Readwise”)
• Highlights are selected randomly from your archive, and can be resurfaced with whatever regularity you prefer

It’s such a simple idea that, like all great innovations, makes the most of the pre-existing infrastructure around it. The goal is to help readers retain what they read. I love it because of how simple it is. Readers like me aren’t looking for something scientific or complex; even an incremental improvement in reading comprehension and recall is enough to enhance the overall nonfiction reading experience.

Because I read so much and highlight copiously, my Readwise has over a hundred books, each with dozens (if not hundreds) of highlighted passages. At last check I have around 5,000 highlights in the archive. As they come through in each day’s review, I regularly get to see things I highlighted years ago from books I sometimes barely remember reading. There have been numerous times where a passage has spurred me to go and re-download the book on my Kindle and skim back through. This trigger is exactly what I want out of a service like this: a reason to be more diligent in reading practice, highlighting, and regular review. Just in the past year or so of using it, I’ve been able to dredge quite a bit of fleeting knowledge back up into memory. Without a service like Readwise (even with highlighting), it’s highly unlikely I’d ever remember much more than a two-sentence synopsis of most books in my library.

Readwise follows a spaced repetition model for increasing recall. True spaced repetition systems use specific algorithms to extend the time between recall tests (like the Leitner system). For example, you might first get quizzed on an item a day after first being shown it, and if your answer is correct, then you’ll be asked again in 5 days, 10 days, et cetera. The correct/incorrect answer provides a feedback loop to the algorithm to best estimate the spacing for resurfacing it again.

Tuning your reviews

Since not all the books in your archive are of equal importance to you, you can tweak the frequency that highlights are resurfaced on a per-book basis. I only have a couple in my library that I’ve turned down. Usually the quantity of highlights in a book is a good proxy for how interested I am in retaining info from it, so books with very few highlights are already less likely to appear in the daily batch. You can also dial in the preferences for new versus old books. You can have it favor more recent reads to review information while the reading is fresh, or favor pulling up more items from farther back in time.

Integrations

The most commonly used integration is probably their Kindle sync service. It’s certainly the most high-volume for me. But in addition Readwise can sync from iBooks, and even has a slick camera-based OCR tool for clipping sections from physical books³. You can also pull in highlights articles through Pocket and Instapaper, and even save tweets or threads to include in your reviews. They’ve also got a super slick integration with Notion, if that’s something you’re interested in.

Active recall

A key feature related to the native concept of spaced repetition is Mastery mode, which allows you to generate flashcard-like questions from specific highlights. On each highlight shown in review, you can add it to your Mastery catalog, either generating a question & answer flashcard or a fill-in-the-blank version of the quote (a technique known as cloze deletion). I only do this for concrete statistics and facts that I find notable enough to want to remember. Depending on the types of works you read most frequently, though, this could be incredibly helpful, especially for content like digital textbooks.

In my now-hundreds of Daily Readwise reviews, there have been countless times that a highlight pulled up from the archives has prompted a thought or idea that I jotted down in my notes. Occasionally they’ve even spurred such deep thinking (usually because I see it in a moment of already thinking about a similar idea) that I haul off and write a blog post from it. This for me is the one of Readwise’s core values. Since writing is a medium for learning, a tool in the belt that helps you synthesize ideas for writing is a powerful one.

Readwise has been in everyday usage around here. I recently had a 110 day streak that I broke a week ago, but still I make it a point to pop it open every day when I get the morning push alert and flip through the clips it assembles.

Future Ideas

One unsolved (and maybe unsolvable) area is a way to address audiobooks. Certainly the technologies exist to do playback, capture, and speech-to-text transcription, but it’s a question of integrating these all together in a system that would work. Audible is the largest player by far, but it generally has poor support for integrations of any type, and also generally innovates at a snail’s pace. I’m not familiar with other audiobook players, but maybe one day there’ll be a way for a new entrant to encroach on Amazon’s monopoly in this space.

For podcasts there’s a new player called Airr that’s doing something interesting with this, using a feature they call “AirrQuotes.” It allows you to clip a segment of audio from a podcast, along with the text transcript to send to another app. I could see a future integration here where you could have podcast clips automatically transcribed and added to your Readwise archive. (Update: Airr integration is now live within the Airr app, like they’re reading my mind)

I’ve added a post-processing step to my reading to collect the noteworthy ideas, forcing myself to write a concise summary and bulleted list of the salient takeaways that resonated. I’ve done this now with my last few books and it’s been a fantastic way to parse through the content a second time — sort of like the first “active recall” review. This extra passthrough to aggregate thoughts into a system helps drive compound interest on the ideas.

It’s rare for new productivity tools to stick with me this long. All of the tools in my daily routines are ones I’ve relied on regularly, and it takes a while for new ones to really click. Readwise clicked for me early and earned its staying power right away. If you’re an avid reader, you’ll love it.

Florent Crivello had a short thread on Twitter contrasting the effectiveness on systems between Goldratt’s The Goal and Bill Walsh’s The Score Takes Care of Itself. One of the replies linked to this piece from Scott Young I found interesting for a couple of points on measuring productivity of systems.

The idea in books like The Goal and its modern IT counterpart The Phoenix Project present the process management paradigm of the Theory of Constraints. The shortest possible version of the TOC says that the output of a process or system is limited to the volume permitted through its narrowest constraint — a chain is only as strong as its weakest link. You could increase the efficiency, quality, or speed of all the remaining steps and not increase overall output if you’ve got a bottleneck.

This post first debates whether you’re better off measuring inputs or outputs to determine a system’s effectiveness. Books like The Goal seem to state that it’s all about the output; outcome over everything else; ends versus means. But Young makes the point that measuring only outputs is often not granular enough in complex systems to tie the application of a new technique or system to the change in outcome:

I’ve met a few consultants that have the following business model: I help you implement some idea for your business. If profits go up, you pay me a percentage. If they don’t, you don’t owe me anything. Win-win, right?

The trick is that businesses with volatile income will have many ups and downs. Most of that is random noise. Now imagine a consultant shows up with worthless advice—pure placebo effect. Half the businesses he consults go up, and he gets a hefty cut of the upside. Half go down, and he gets nothing. He makes a fortune, even though the advice is worthless.

He also references the Hawthorne effect, a phenomenon in which individuals modify their behavior in reaction to awareness that they’re being observed. If a consultant comes in to implement a new process, or you make a new “expert” hire that starts changing things, and results get better, how do you know there’s a causal link? What if the act of bringing in the consultant or new hire was what spurred the uptick, not their “improvements”? (People start working harder when there’s a consultant coming around, or when there’s a new manager in their department)¹

Another dimension orthogonal to input-output is scale — big, long-term items, or the activities happening at the individual task list level:

Plotted on two axes like this, I’m reminded of the Eisenhower Matrix for thinking about task priority:

Just like how with time management we want to orient ourselves toward the “not urgent / important” quadrant, in the productivity matrix we want to do things that push us toward the right spot in “big picture / output” quadrant. Not everything worth doing to position correctly on the scale-to-throughput chart falls in the same place. Just like with the TOC, bottlenecks exist at various stages and differ in levels of effort to widen or correct them. The “ROI” on a process change could by high-R, low-I, or the reverse. The effectiveness with which you can widen the bottleneck is often (but not always) decoupled from how much effort it takes.

I like Young’s framing here on what to do and how to measure. If we’re seeking areas we can clearly measure, we know those are unlikely to be in the upper right quadrant. The lower left is great for aligning your measurements because of the clarity and speed possible at that scale. This is the best of the diagrams to explain a measurement strategy:

So as he says in the post: “pick a few metrics that will estimate what matters.” You want to figure out measurable items that directionally vector toward where you want to be — toward big outputs.

With a model like this, you can select tight, measurable metrics that aim the right direction, then make adjustments to course correct. Metrics that live in the lower left quadrants should have tight feedback loops, giving you signals on what adjustments are needed. Like all well-designed, robust systems, you want to build a productivity measurement model that’s adaptable, using trial and error to improve.

Check out Scott Young’s full post; it’s excellent.

🐉 Hic Sunt Dracones

Adam Elkus with a great essay on the current moment:

“Is this as bad as 1968?” is an utterly meaningless question precisely for this underlying reason. People do not invoke 1968 because of the objective similarities between 2020 and 1968. They do so because we have crossed a threshold at which basic foundations of social organization we take for granted now seem up for grabs. This is an inherently subjective determination, based on the circumstances of our present much as people in 1968 similarly judged the state of their worlds to be in flux. 1968 is an arbitrary signpost on an unfamiliar road we are driving down at breakneck speeds. You can blast “Gimme Shelter” on the car stereo for the aesthetic, but it’s not worth much more than that.

📆 Contemplating Calendars

Devon Zuegel with ideas on how to better utilize your calendar for things beyond appointments and meetings. A few ideas I’d like to commit to doing, especially with using the calendar as a recall tool for memory.

🔬 Science 2.0

Robin Hanson on experts, prestige, skepticism:

Just as our distant ancestors were too gullible (factually, if not strategically) about their sources of knowledge on the physical world around them, we today are too gullible on how much we can trust the many experts on which we rely. Oh we are quite capable of skepticism about our rivals, such as rival governments and their laws and officials. Or rival professions and their experts. Or rival suppliers within our profession. But without such rivalry, we revert to gullibility, at least regarding “our” prestigious experts who follow proper procedures.

🏛 The Individual, the State, and the Virus

I agree with most of Kling’s takes here on the role the state should play in the coronavirus crisis.

👩🏽‍💻 Mapping the Future of Work

A nice comprehensive list of SaaS products for the workplace, across a ton of different categories. Great work by Pietro Invernizzi putting this database together.

⌨️ Stephen Wolfram’s Personal Infrastructure

Mathematician and computer scientist Stephen Wolfram wrote this epic essay on his personal productivity infrastructure.

✍🏼 The Enemies of Writing

A great piece from the Atlantic’s George Packer, a transcript of his acceptance speech for the Hitchens Prize.

At a moment when democracy is under siege around the world, these scenes from our literary life sound pretty trivial. But if writers are afraid of the sound of their own voice, then honest, clear, original work is not going to flourish, and without it, the politicians and tech moguls and TV demagogues have less to worry about. It doesn’t matter if you hold impeccable views, or which side of the political divide you’re on: Fear breeds self-censorship, and self-censorship is more insidious than the state-imposed kind, because it’s a surer way of killing the impulse to think, which requires an unfettered mind. A writer can still write while hiding from the thought police. But a writer who carries the thought police around in his head, who always feels compelled to ask: Can I say this? Do I have a right? Is my terminology correct? Will my allies get angry? Will it help my enemies? Could it get me ratioed on Twitter?—that writer’s words will soon become lifeless. A writer who’s afraid to tell people what they don’t want to hear has chosen the wrong trade.

💵 Wealth Is What You Don’t Spend

Morgan Housel:

It might seem obvious that savings is your ability to reject what you could spend. But the majority of financial goals are about earning more – better investment returns and a higher-paying career. There’s nothing wrong with that. Earning more is wonderful, just like exercise. We just shouldn’t lose sight of the fact that earning more will do little for building wealth if every extra dollar is offset by a dollar of new spending.

The world is filled with the financial equivalent of athletes who finish every workout with four Big Macs. Wealth, at every income level, has less to do with your gains and more to do with your ability to leave gains alone without cashing them in.

📨 Superhuman and the Productivity Meta-Layer

An interesting response argument to Kevin Kwok’s post from a while back called the Arc of Collaboration. The meat of the argument is that corralling notifications from the dozens of input streams we all have is challenging, and that a “command line”-style interface like Superhuman’s could function as a filter point to visualize the input stream, but also engage with items in real time. A compelling case with mockups of how it could work (if service providers wanted to plug into this sort of “notification nexus”).

👏🏼 Applause Lights

This is from 2007, but is still a very astute observation in how politicians and activists use rhetoric to signal rather than recommend a real, actionable way forward on issues:

The substance of a democracy is the specific mechanism that resolves policy conflicts. If all groups had the same preferred policies, there would be no need for democracy—we would automatically cooperate. The resolution process can be a direct majority vote, or an elected legislature, or even a voter-sensitive behavior of an artificial intelligence, but it has to be something. What does it mean to call for a “democratic” solution if you don’t have a conflict-resolution mechanism in mind?

I think it means that you have said the word “democracy,” so the audience is supposed to cheer. It’s not so much a propositional statement or belief, as the equivalent of the “Applause” light that tells a studio audience when to clap.

📥 Busyness as a Proxy for Productivity

We’ve all seen this in the workplace — when email, chat, meetings, et cetera transform into signaling channels for looking busy. Cal Newport’s Deep Work (quoted in this post) has a fantastic section on this:

If you send and answer e-mails at all hours, if you schedule and attend meetings constantly, if you weigh in on instant message systems… all of these behaviors make you seem busy in a public manner. If you’re using busyness as a proxy for productivity, then these behaviors can seem crucial for convincing yourself and others that you’re doing your job well.

Knowledge work is not an assembly line, and extracting value from information is an activity that’s often at odds with busyness, not supported by it.

🖋 Magic Ink: Information Software and the Graphical User Interface

One of those fantastic online papers from Bret Victor.

Andy Grove is widely respected as an authority figure on business management. Best known for his work at Intel during the 1980s, his book High Output Management is regularly cited as one of the best in the genre of business books. After having it on my list for years and finally reading it earlier this year, I’d wholeheartedly agree. It’s the best book out there about business planning, management, and efficiency, still just as pertinent today as it was when it was first published in 1983.

Its relevance more than 30 years later attests to the universality of its value. I’ve mentioned before here my personal interest in understanding first principles approaches to thinking over derivative systems typically touted by the self-help and business publishing community. The book’s extreme practicality and information density falls in line with what you’d expect from an engineer like Grove — light on the fluff and “case study”-type stuff that permeates and inflates page counts of other business books.

I’ve written here before about a couple of specific topics from the book — about Grove’s perspective on meetings, and on the concept of “modes of control” — but I wanted to give some more space to the book overall, as I believe it’s one of those rare pieces of core reading material on which hundred of other works are based.

The thesis he lays out is simple in principle: a business is a machine, the people and processes are its parts, with inputs (human effort, ideas, work) and outputs (its products and services). To develop a high output system, you have to peel apart its internal components, inspect how they interface with one another, and create a management infrastructure throughout that enables high leverage. Throughout the book’s chapters he touches on the stables of a manager’s workload: planning, meetings, making decisions, reporting, oversight, training, and more. What’s truly important isn’t any one of these particular components, though, it’s in the efficiency of the connections between them. In the analogy of the business to a machine, effective management is the design of the parts, the connections between them, and the lubrication to avoid slippage.

I’ll point out here that the book’s value is not limited to those that manage people. If you manage any system or procedure at all you’ll get value out of it. In fact, it’s useful to anyone that wants to understand what makes their organization tick and where they might fit into the machinery.

Creating Clarity from Abstraction

One of the driving factors that’s created a cottage industry around business processes, teamwork, and strategy (an industry that’s generated thousands of how-to books on the theme) is that the modern era of “knowledge work” requires working in so many abstractions. In the good old days of industrial production, the inputs, outputs, and stages in between were manifest in physical systems you could watch working together. Grove recognizes this point early¹ (emphasis mine):

Of course, the principle of work simplification is hardly new in the widget manufacturing arts. In fact, this is one of the things industrial engineers have been doing for a hundred years. But the application of the principle to improve the productivity of the “soft professions” — the administrative, professional, and managerial workplace — is new and slow to take hold. The major problem to be overcome is defining what the output of such work is or should be. As we will see, in the work of the soft professions, it becomes very difficult to distinguish between output and activity. And as noted, stressing output is the key to improving productivity, while looking to increase activity can result in just the opposite.

Too many businesses sit down and “strategize” by developing high-altitude mission statements, corporate principles, and annual goals. There’s nothing wrong with these things, but they ultimately aren’t granular enough to become actionable by individual team members. Aligning around a well-articulated output at each employee’s level is critical to avoiding the “busyness” syndrome that plagues so much of the modern workplace. What’s missing is a tool to bridge this gap between high-minded mission statements and employees, one that arms them with actionable targets they can point at and measure progress on — enter OKRs.

Objectives, Results, and Measurement

A key concept articulated in High Output Management, one that’s been adopted widely today, is the Objectives and Key Results (OKRs) framework. It’s clear from the way Grove articulates it that he didn’t see OKRs as some kind of brand-building opportunity with an intent to sell this idea to the business community; he merely saw it as a way to give the company a circulatory system throughout to keep its teams in alignment on output. Like many of the ideas in the book, he has a succinct style of communicating these ideas that make them seem patently obvious, with a clarity that’s easy for anyone to comprehend.

Anyone in the knowledge work space (which is most of us) has seen this all over our organizations. Without the focus around the outcome — What exactly are we making? What do we want that to do for us? Why? — any organization can dissipate much of its energy in simply performing activities, the way an inefficient machine gives off much of its energy as heat from friction. The mission then is to make sure any activity performed at any level is clearly tied to output that stacks up with the organization’s top-level expectations.

The venture investor John Doerr, most known for his work with Kleiner Perkins and investments in Amazon, Google, Netscape, and other early internet companies, was an employee and colleague of Grove in the Intel days. I recently read his Measure What Matters, a book on the concept of OKRs and how they’re employed in various modern businesses. My problem with that book was that it’s simply a retelling of the core principles laid out in High Output Management, with most of the pages devoted to the “see how it works for organization X?” type of commercial trying to sell you on the idea of OKRs. That might be a good communication style for a certain type of reader, but I’d rather have the core building blocks and let me do the imagining of how it might impact my own work and organization. There are tons of other books and blog posts out there about OKRs, but I’d point anyone looking into them to High Output Management as a resource.

At the core OKRs are a great system because of how little “system” there really is. They’re intended to get a bunch of diverse people in a hierarchy working as a well-oiled machine, with the strongest emphasis on keeping the machine and it’s components focus on shared, agreed-upon outcomes. It’s about having the diligence to create a stacked set of priorities and goals, mutually agreed on, that cascade from the top down into the ranks. A well-designed OKR process should create a universe where everyone in the organization can point directly to their objectives, and any colleague can see the wiring up and down from there to the OKRs of others.

Writing as Reporting (and Thinking)

It’s partially my personal style, but I’m a huge believer in the idea of writing as a tool for status reporting, intra-office communication, and teamwork. Not only does writing things down create a log of someone’s idea or design concept, it’s a fantastic medium for forcing critical thinking. Jeff Bezos has famously required agendas for meetings at Amazon to be written up as long form proposals. This forces rigor in having focused meetings with thought out discussion topics. No one will spend time writing up a document if they don’t truly believe in it or haven’t thought it through, which saves everyone the wasted time of discussing poorly-considered ideas. The act of writing something down also forces you as the generator of an idea to ruminate on its implications, think about how to articulate it, and to create an element of knowledge to leave as an institutional guidepost for future coworkers thinking about related ideas.

Grove approaches managerial reporting and planning from a similar angle. While he highly values passing informal conversation in maintaining time-sensitive communication, he respects writing as a tool for clear thinking²:

I have to confess that the information most useful to me, and I suspect most useful to all managers, comes from quick, often casual verbal exchanges. This usually reaches a manager much faster than anything written down. And usually the more timely the information, the more valuable it is.

So why are written reports necessary at all? They obviously can’t provide timely information. What they do is constitute an archive of data, help to validate ad hoc inputs, and catch, in safety-net fashion, anything you may have missed. But reports also have another totally different function. As they are formulated and written, the author is forced to be more precise than he might be verbally. Hence their value stems from the discipline and the thinking the writer is forced to impose upon himself as he identifies and deals with the trouble spots in his presentation. Reports are more a medium of self-discipline than a way to communicate information. Writing the report is important; reading it often is not.

This same logic applies to so many things in business — the final version of a report, design spec, marketing strategy, or budget isn’t where all the value lies; the final output document is what enforces the discipline of that business process. The requirement to come away with the “Budget 2020.xlsx” file forces us to run through the planning process thoroughly. If done well, we only need to look at the document as a quarterly gut check. The planning process itself makes us think through priorities, objectives, and where we want to focus.

Add It to the Library

There’s a lot more excellent material in the pages of High Output Management than I can cover in a single blog post. My paperback copy sits on my shelf in my office and is scribbled all over. I pull it out regularly to cite paragraphs or reference things for my own communication within the company. It’s one of my first recommendations to anyone looking for a book on business or productivity.

As I’ve written before on this topic, separating goal-setting from habit-forming is important to do if you want to have success at either. Often people set goals without defining the daily behaviors that will enable them to achieve said goals.

I felt the goals I set this year were firmly in the SMART category, but it’s required diligence not to fall off the wagon of the daily habits. I set some big numbers down (importantly, only in a few areas), so I needed to break down those into daily and weekly patterns to pace myself in getting there.

This Farnam Street post makes the distinction between the two, and how to think about habit-creation:

Stephen King writes 1000 words a day, 365 days a year (a habit he describes as “a sort of creative sleep”). Athlete Eliud Kipchoge makes notes after each training session to establish areas which can be improved. These habits, repeated hundreds of times over years, are not incidental. With consistency, the benefits of these non-negotiable actions compound and lead to extraordinary achievements.

While goals rely on extrinsic motivation, habits are automatic. They literally rewire our brains.

My recent interest in OKRs (both for personal and professional use) gets to the nuts and bolts of this issue. You define the “Objective” (the goal) and “Key Results” (measurable behaviors, or habits) that you believe will put you over the goal marker. Then at the day-level of granularity, you only have to worry about hitting your marks on the behaviors.

Since you can’t reach your overarching goal in a single day anyway, I find it unhelpful and deflating sometimes to think about the sum total of effort it’ll take to reach. If I took my 500 mile goal for running this year and looked at the remaining miles left, I might think “oh man, that’s huge”. But when broken down into small steps, everything looks much more attainable. With smaller parts, you can work on how to build those behaviors into a healthy habit.

I’ve written here before about my enjoyment of working on the iPad Pro. Even with the excitement around Apple’s launch of the new Mac Pro this week, my favorite announcement was their “specialization” of iOS in the new iPadOS.

Running down the best features:

• Denser screen real estate — Anyone that uses an iPad for work lots of different apps is familiar with this gripe. The giant screen with a sparse scattering of tiny icons looks sort of ridiculous. That plus the addition of the anchorable Today Widget view on the left will both be massive improvements in speed.
• Multitasking improvements — I haven’t been a huge user of the Slide Over app capability, but the extension of that to support multiple app switching with a swipe looks awesome. And Split View with multiple documents in a single app is something I’ve always wanted.
• Pencil — Reducing latency and adding a slick Markup toolset as part of PencilKit for other apps. I use the Pencil every day, so this is just icing.
• More keyboard shortcuts — I’m a keyboarder; I hunt down and get to know the shortcuts for any apps I use. Already on iPad I use cmd-tab to switch apps, cmd-space (Spotlight) to launch apps, cmd-tab and cmd-W to open and close browser tabs, and probably more I don’t even realize. I hope what they’ve added to Safari leads to more conventions being adopted across other apps.
• Mouse support? — This looks like it might be weird, but I’m real curious to try it out.

The improvements to Safari and Files aren’t too exciting because I don’t use either right now, but it’s still positive to see Apple put energy into iPad as a platform for real work. MacStories has a good roundup of details with everything included in the first version.

Calling it a completely different OS is inappropriate, at least at this stage. I hope that it’s just the tip of the iceberg with desktop-class optimizations for the larger screen.

🧠 A Latticework of Mental Models

This is an excellent archive on Farnam Street with background on 109 different mental models — first principles, Occam’s Razor, probabalistic thinking, and many more. So much great reading material here to study different modes of thinking. Like writer Shane Parrish puts it, this latticework helps you “think better”:

The quality of our thinking is proportional to the models in our head and their usefulness in the situation at hand. The more models you have—the bigger your toolbox—the more likely you are to have the right models to see reality. It turns out that when it comes to improving your ability to make decisions. Variety matters.

Most of us, however, are specialists. Instead of a latticework of mental models, we have a few from our discipline. Each specialist sees something different. By default, a typical Engineer will think in systems. A psychologist will think in terms of incentives. A biologist will think in terms of evolution. By putting these disciplines together in our head, we can walk around a problem in a three dimensional way. If we’re only looking at the problem one way, we’ve got a blind spot. And blind spots can kill you.

💾 Git History

A neat tool for visually browsing git commit history. Scrolling through commits does a nice animation to show you graphically what’s changing from step to step. Here’s an example with browserify.

✏️ Notion Pages

Over the last week I’ve been messing around with Notion, a productivity app that seemingly can do everything — a combination personal database, word processor, spreadsheet, notes app, and todo list. I’m trying it out for note taking and writing (mostly), but it’s got some potential to be a personal wiki, an idea which has always intrigued me but never felt worthwhile to try to set up and maintain. This site has a bunch of templates for Notion to help get started for different use cases. Just browsing it shows the diversity of things you can use it for.

Once a year around this time I like to do some “winter cleaning” of my personal security footprint, mostly covering passwords and internet service accounts I have that may be out-of-date, unmaintained, or unneeded.

1Password is a dream for things like this. If you don’t maintain an account, it’s well worth setting one up for the family with their 1Password for Families product tier. Worth every penny¹.

Good hygiene with passwords has been a perennial problem in internet-land, and the security risk only goes up with seemingly-daily announcements of the next hack or data breach. While those risks are part of our current reality, it’s possible to lower your risk profile with some simple maintenance tasks with 1Password. Here are some general best practices and my personal annual review process.

Raise the complexity

There’s no excuse not to be using highly complex passwords these days. When creating new 1P entries, you can autogenerate complex passwords. Sometimes you’ll need to tweak the generation parameters to create passwords that are acceptable for certain sites², but it’s worth making sure you’re maximizing the complexity where you can. When I review my accounts, I look for any entries that have less than 1P’s “Fantastic” rating, and sign into those and update them.

Watchtower

1Password has a feature called Watchtower that helps you conduct targeted review to keep yourself secure. Things like compromised or vulnerable logins, reused or weak passwords, or where 2FA isn’t enabled. It’s nice because it checks against a couple of known databases to help keep you on guard. This is the go-to spot to look for areas of attention in the review. It’s worth setting yourself a reminder (quarterly or so) to check here for any changes. If services you rarely use have security incidents, you probably won’t know, so this helps.

Two-factor authentication

I wrote previously about 1Password’s native two-factor authentication. Wherever possible and recommended I go through my account entries and enable 2FA setups with the one-time passwords configured. Another tip for this is to use a password field type to store the “recovery codes” that most services will generate for two-factor, which allow you to recover your password if something gets hosed. Web services commonly generate these codes in a text file for safe storage, which you can do in 1Password if you want, but I’ve never been a huge fan of the way file storage and linking works in the app. I prefer to copy the codes directly into the 1P database entry anyway.

Purge unused services

Shutting down accounts for services you don’t use is another good practice to reduce your exposure to breaches. If you aren’t using or no longer need a service, might as well not have it hanging out there. Since you can sort entries by “date used”, it’s straightforward to comb through ones you haven’t used all year and assess. When I go through my annual review, I always find a couple not worth keeping, so I sign in and spin them down if possible. If they don’t have a public-facing way to delete my account, I usually reset the password to something huge and delete whatever unrequired personal info might be on file (like credit cards and the like).

Other scattered tips

A few other pointers that factor into my annual review:

• Change any duplicates — I don’t intentionally create dupes, but it happens occasionally, especially when creating accounts from my phone when I just want to type a password in signup
• Check for https — This isn’t a huge problem these days, but a nice recent addition to 1Password will alert you to entries with insecure URLs
• Assess shared accounts — Using the 1Password for Families account, we have a single shared vault for accounts we both need: bank accounts, credit cards, kid-related stuff, Netflix, Amazon
• Organize — I go through and change entry names, make things consistent, and just generally scan through for any junk to keep it all clean

With the review done, it feels good to have a renewed sense of security having checked your digital footprint. A well-organized, clean 1Password setup can also be a huge productivity boost. The more services you work within (and the more secure you want your behaviors to be), the more a clean, healthy passwords vault will help you.

For all of the todo list apps out there, I’ve only seriously tried a couple of them. After using OmniFocus since its first version, I switched over to Todoist a couple years ago. There are many I haven’t even tried, but I’ve always tried to stay focused on doing the tasks rather than fiddling with my system. It’s especially ironic with productivity apps to be constantly messing with the workflow in search of some kind of optimization. As Tom eloquently put it a few years ago: “todo lists don’t make you productive.”

While I’m fully aware of that fact, the main value of a todo system for me is to have a container for ubiquitous capture, in GTD parlance. All of the knobs and switches with various tools — projects, contexts, due dates, start dates, priorities — don’t help with the core initial problem of getting the things in a single place. The second need (again, a simple one), is a straightforward interface that simplifies continued review.

So it needs to be as easy as possible to:

1. Capture new things
2. Review said things regularly to slot them into my plan

It turns out that most apps are at least passable at item two; it’s the first that can cause problems depending on preferences, work style, and day-to-day activity. I love having a notepad and pen for writing and sketching as often as I can, but I just don’t reliably have it with me enough to use for collecting things that need doing.

The number one advantage I quickly discovered with Todoist over other options is its cross-platform simplicity. Because of it’s web-centric architecture, it has a wide array of integrations with other services. It also has native mobile apps for any platform, a web app, and a desktop client (wrapper around the web app). This kind of “available everywhere” foundation forms the first basis of a good productivity tool. As the saying goes about photography: “the best camera is the one you have.” I treat productivity apps the same.

I don’t have too fancy of a setup with projects or contexts. The main way I use the app is to get things into the inbox as quickly as possible, then review and sort things into their proper places as often as I can. Usually once per day I’ll run through the inbox and file things off where they belong, or delete them if I’m actually not going to commit to them.

On the capture side, items get into the inbox one of three ways:

• Cmd-Shift-A quick add shortcut on the Mac
• The Today widget on my iPhone
• A Today workflow from the Shortcuts app I called “Dictate to Inbox”

The dictation flow is one of my favorites. I’m not a fan of the full Siri integration since I have too much trouble invoking Siri and getting the initial command to go from speech-to-text correctly. The Shortcut method makes it one swipe and one tap to invoke, and still leverages the Siri dictation piece. The problem with the full integration is it misunderstands the initial directive that I’m trying to make a new todo for the inbox, and will mistakenly call someone or look something up on the web (the ultimate useless cop-out from Siri that no one ever wants).

Todoist has a “karma” gamification component that I wish I didn’t enjoy as much as I do. Being motivated by artificial points rather than the importance of the work itself isn’t really what you’re going for with a productivity tool. But it adds a psychological gratification element to checking things off the list. I’m an advocate of keeping the end in mind, so if the means (ticking boxes for points) keep me actually doing the work written down on the list, then it works.

I’d like to try the sharing elements, so far I’ve only used it solo. Todoist isn’t great for general list-making (though it can do it if needed). Colette and I still use Wunderlist for groceries and shopping. There’s still not a better simple replacement we’ve found yet. It’s possible that a shared project in Todoist could do the job and is something I’d like to try.

Most reading on my iPad happens in Reeder, Instapaper, or a browser. I wanted to come up with a way to save URLs in a text file for easy access for new link posts and archive purposes. This seems like a great candidate use case for trying out Workflow again which Apple has renamed Shortcuts.

I use Ulysses for most note-taking and writing purposes on the iPad. It syncs with iCloud between desktop and mobile, has good organization support, and is a good Markdown editor. it also is integrated with Shortcuts.

First I set up a sheet in Ulysses called “Link Queue” where I’d keep a running list of URLs to save for later. After that placeholder is there, I pulled up the Share view on that Sheet (by sliding left to see more options), then tapped the “Copy Callback Identifier” option to grab the Sheet ID. That’s what’s needed in the action used in the Shortcut.

Ulysses Share Sheet

In Shortcuts you only need a couple of steps. I set the shortcut to accept Text or URLs (in case I also want to append selected text blocks to the same file) and pass that to the “Add to Ulysses Sheet” action. This is where the ID copied above is entered. That’s all — link appended to the end, with a new line after, ready for the next in the queue.

This has already been a handy, quick way to keep URLs saved in a place where I can get them later.

Every time I mess around with Shortcuts I feel like I’m missing out on some handy automations. I need to keep it in mind when working to think through other repeated activities to streamline.

I write a ton on the computer, whether it’s for our product blog, internal documents, product help guides, this blog (rarely), or many other things, I tend to stick to the same set of tools for different pieces of my writing workflow.

Everything I write, even things like meeting notes only for myself, I write in Markdown. It’s essentially muscle memory at this point. I write for Jekyll-based websites quite a bit, I write issues and wiki pages on GitHub, I keep my personal journal in Day One, and several other places. All of them accept Markdown as input, so I’ve just formed a habit over the years where I write everything that way. So when I paste an unordered list from a note I made somewhere into a web document, it’s already formatted. If the destination for a block of content I wrote doesn’t work with Markdown, most tools have a “copy plain text” option that I’ll use if I want the raw words to format inside of another application (*cough* Microsoft Word *cough*).

Anyway, onto the geeky stuff…

Tools, we all love tools

I try tons of new tools all the time, and I’ve converted through different tools over the years. About 90% of writing is thinking, so being able to flexibly organize thoughts without fighting with tools is paramount to productive writing. Remember that the tools don’t make you write. I try to prevent myself from getting distracted with whatever the new “app of the week” is for text editing, and while having the proper tools is important, if your process ain’t broke, don’t fix it. Just like with todo lists, code editors, and online courses, another tool in the belt doesn’t make you a better producer… producing makes you a better producer¹. If you’re like me, it’s worth posting that above your desk to keep from fiddling with tools and systems and get to work. If you’re doing anything other than typing the words on the page, the tool isn’t going to help you make more letters appear! (I write that as a reminder to myself as much as anyone else.)

Now, with that said, here’s the short list of apps I use for writing, and for what purpose I use each depending on context:

• nvALT: This is the everyday workhorse. Since I write everything in plain text files, this editor from Brett Terpstra is my go-to for fast access to making new files. It’s typically the initial scratch pad while I’m on my Mac. If I jump on a phone call, I pop open nvALT and create a new text file to log notes. With quick keyboard shortcuts, every time I make a file it just appears in my txt directory in Dropbox, which other apps (including mobile ones) can have access to. It’s an unfancy writing tool for longform stuff, but the key is that there’s minimal friction between thought or idea and it being instantly captured in a reliable place.
• Byword: Used for longer-form editing, basically once something reaches the stage of an official piece of content like an article or guide, more than lists or scratch notes. It’s got a great interface for writing in Markdown, and a built-in preview mode for seeing the content rendered as HTML. Stuff that will end up on the web as articles usually happens here.
• Atom: I use Atom for editing things that involve code, or are typically intertwined with code like HTML or CSS. When I’m writing documentation for Fulcrum or contributing to other projects on GitHub, I use Atom.
• Paper, the IRL kind: If I don’t have access to my computer, I don’t feel like typing, or I want to make sketches, I keep field notes around for pen and paper notes.

iOS apps, where writing is typically harder

Longform content doesn’t usually happen much on iOS for me, unless the motivation strikes me to get my thoughts on paper and I’m not at my computer. Mostly from iOS I’m keeping notes or jotting things down.

• Drafts: What nvALT does on my desktop, Drafts does on my phone. Since most of the time from mobile I’m starting with a new file versus editing something in progress, Drafts is super fast for jumping right into a text edit mode to type out some quick notes. Where Drafts really comes into its own, though, are in its Actions capabilities. The idea is that anything starting as a piece of text can be fed into an Action within Drafts to pipe it into any of dozens of other places. Getting to know what’s possible in Drafts is a separate post in and of itself, but needless to say, it’s where I do probably 90% of my text typing on iOS.
• Editorial: I’ve just discovered this app recently after reading Federico Viticci’s stunningly in-depth review, and so far it’s a promising addition to the writing process from iOS. I’ve never been a heavy iPad user, but I’ve been debating jumping back into the iPad world again, particularly for working on something at home on the weekend, traveling, or otherwise mobile without my laptop. This app is ridiculously complex and powerful, and I’ve only started to scratch the surface.

Many people like Evernote and other cloud-based services for dealing with notes, but I like the idea of the archive of text I’ve produced since about 2009 all lives in plain files in a folder — completely portable, easy to back up, and generally friendly to copy or import into other places for publishing. I don’t need separate notebooks or embedded attachments or tagging on my files to get in the way, I just want an editor and the canvas for text. All of the tools I mentioned above have excellent full text searching capabilities, and after 6 years of managing all of my notes this way, search has never failed me for finding what I need.

One thing that my personal workflow doesn’t support directly (or at least I haven’t found a way) is on-the-fly collaborative editing. Most of the content I write is for myself, or at least doesn’t need to have other editors for most of its existence until it’s ready, but maybe there are tools out there I’ve not yet discovered. Currently for anything that needs to be collaborative from the get go I would use Google Docs, since it’s unmatched when it comes to real-time simultaneous multiuser editing. Other than that, anything that happens for publishing via GitHub already can be collaborated on asynchronously using pull requests and commit references, which our team uses constantly.

If readers have any suggestions of other methods for augmenting things, particularly collaborative editing a la Google Docs, ping me on Twitter, I’d love to find more options to make my flow even better.

I’ve talked before about the concept of “ubiquitous capture” and how achieving a system where you never lose an item is an ideal for a seamless GTD setup. No matter what task management tool you use of the hundreds of options, both automatic or analog, there are still moments when a fleeting piece of info we want to remember — either something new to do or an idea or breakthrough on an existing project task — slips through the cracks. The best system for managing all of your collective “stuff” is any that you trust to be the go-to place for all the things that require your attention.

In any GTD-esque system, the two core concepts are capture and review:

1. Capture anything on your mind so it lives in a system, not in your head.
2. Review your “inbox” on some repeated schedule to process things into the right place, grouping things by project, adding deadlines, or filing into contexts.

When I got started building my personal workflow, I found the biggest initial hurdle was a reliable mechanism for getting things into my inbox as quickly and readily as possible. I’ve tried notebooks, cards, text files, and most digital task apps to try and find a single tool that works, but there was always friction and things would get forgotten. My short term memory is horrendous, and most things needing to find their way into my inbox would occur to me while getting ready in the morning or while driving or biking to work.

Enter Siri

True ubiquitous capture is achieved by using whatever tools are most reliably available to you, and for me that’s OmniFocus and my iPhone. OmniFocus 2 for iOS added a built-in Reminders capture feature to pull things added to a specific list over into the OF inbox. Then using the “Siri, add this to my list…” command when dictating gives you hands-free, fast access to append items to the inbox. I say things like:

• “Add assemble new furniture to my inbox list”
• “Add get flu shot to my inbox list”
• “Remind me to take out the trash when I get home” (using location-aware contexts in OF)

With Siri set up this way, I now have a wider funnel for capturing anything I’m thinking about anywhere I’ve got my phone. So even when I’m in the car or working in the garage and some random item pops into my head, I can make sure it doesn’t slip through. It’ll be there waiting in my inbox for the next review when I’m processing my workload.

I’m an OmniFocus-flavored GTD adherent, or try to be. The iOS apps for OmniFocus were huge contributors to my mental adoption of my own GTD system. When OmniFocus 2 dropped a few weeks back for iPhone, I picked it up right away.

The new design lines up with the iOS 7 look. I really dig the flat UI style in utility apps like OmniFocus, or any app where function truly overrides form in importance—typically anything I open dozens of times of day as part of my routine. The new layout gives weight and screen real estate to the things you access more frequently, like the Inbox, Forecast, and Perspectives views. I’m really liking the inclusion of the Forecast view as a first-class citizen, with the top row devoted to giving you context on the next week out for tasks with deadlines.

As before, there’s a fast “Add to Inbox” button for quick capture. But rather than a button positioned somewhat arbitarily in a bottom navigation menu, it’s now an ever-present floating button, always in the bottom right for rapid inbox capture. Upcoming and overdue tasks are now symbolized with colored dots when in sub-views, and with colorized checkboxes in list views. The color highlights fit the iOS 7 aesthetic nicely, and give subtle indications of importance.

Like any effective design, the right balance of positioning and subtlety actually makes it clear how a feature should be used, and makes it simpler for you to integrate with your workflow. In past OmniFocus versions, I had a hard time figuring out how to make use of due dates (and start dates) properly, so I leaned away from using them.

With the latest iOS update, OmniFocus is now not only a tool that follows a GTD workflow, but one that actually leads you into better GTD practice.

I use Dropbox as the nerve center for all of my digital goods, keeping data, configurations, histories, log files, and anything else I need access to centralized and available from my Mac or iOS devices.

Here are a few of my daily tools or information trails I want to keep synced up, so anything here can be a few clicks or a search away:

• Instant message chat history
• iTunes library
• Histories + log files
• OmniFocus backups

Chat Archiving

I use Messages on the desktop for all chat conversations with my Jabber and Google accounts. I access the transcript history daily to find things I told people in chat conversations, look up links I sent, and other things. So much of my communication happens via instant messaging that I rely on it to keep logs of interactions (albeit securely).

Backing up chat transcripts is simple with symlinks. For me, I want all chat logs to be archived into a Dropbox directory continuously, so I don’t have to remember to back them up. Messages stores its transcript files here:

~/Library/Messages/Archive/

Since I want my chats to all be instantly backed up to Dropbox, I symlink the directory into a ~/Dropbox/backups directory, like this:

ln -s ~/Library/Messages/Archive ~/Dropbox/backups/chats/

Linking those files to a Dropbox directory will automatically sync them to your account in real time, if you have syncing enabled. These files are then backed up for good, in case I need to search later. A downside with Messages is the transcript files are .ichat files, not plain text. So they can’t be searched from the Dropbox iOS app or mobile text readers. The in-app search works okay, but hopefully we’ll see some performance improvement there in the upcoming OS X Mavericks release. This piece from Glenn Fleishman has some other good tips on instant messaging with Messages.

iTunes

My iTunes media is mostly secure at this point, with iTunes Match and iCloud, but I still like to keep a backup of the raw XML library data. This contains a ton of stuff I don’t want to lose, like playlists, ratings, and other metadata. ID3 tags and album art are safe with the MP3 files. A couple of symlinks make it so every time I close iTunes, the latest changes to my library get backed up. The .itl file is the primary iTunes database, and the XML file adds a software compatibility layer for other apps that read from your library (like Garage Band and others):

ln -s ~/Music/iTunes/iTunes\ Library.itl \
  ~/Dropbox/backups/iTunes/iTunes\ Library.itl

ln -s ~/Music/iTunes/iTunes\ Music\ Library.xml \
  ~/Dropbox/backups/iTunes/iTunes\ Music\ Library.xml

History + Logs

On a daily basis, I’m all over the place with my machine — working with data in Postgres or SQLite, writing Ruby scripts, and just generally working on the shell doing tons of different things. I love having my command history for anything that has a CLI archived somewhere, so when I need to pull up some command or see how I had built a package from source, it’s as simple as searching a history file. Many Linux & Mac applications keep themselves a history file inside your home directory, typically hidden, like .bash_history for the bash shell environment. I use zsh, with the awesome oh-my-zsh environment framework, highly recommended. Here’s a few I keep around for posterity and convenience, in a “histories” backup¹ directory:

• ~/.zsh_history
• ~/.irb-history
• ~/.psql_history

With those backed up, I can always search the logs for when I installed something with Homebrew:

history | grep "brew install mapnik"

As for OmniFocus, backups are cake. Just check the preferences for the database backup location and frequency settings, and change it to somewhere within your Dropbox folder.

In addition to the convenience of keeping this stuff linked into a secure, synced place like Dropbox, using an online backup service (like the fantastic Backblaze) is a no-brainer for keeping your stuff safe. You should be using one. Even though Time Machine is super simple to get going to an external HDD, I don’t trust the hardware enough to rely solely on that.

Through a number of recommendations around the web, I’ve started using Drafts, an iOS app with an interesting workflow model that’s helping me replace a number of input channels for capturing different pieces of information while on-the-go.

It’s positioned primarily as a text editor or note-taking app for iOS, but it introduces a fundamentally different approach to the capture → process flow than most other solutions I’ve tried, even ones that I like. Like most heavy mobile users, I have a suite of apps I use constantly to capture different inputs: OmniFocus for task management, Mail for email, Byword for notes and Markdown content, Fantastical for calendar items, and others. I love each of these apps for what they do, but speed is paramount for capture to be truly ubiquitous, at least for me. And I sometimes find myself swiping around looking for the right app to put something.

The way Drafts handles input is novel because it puts the content first, and the action second. You can jot something down, then decide how to process it. Sometimes it’s a to-do, sometimes a draft of an email, and sometimes just a quick note. I love the idea of starting with a bit of text, then picking the chute down which to send it in step two. Open the app and its ready for some text; no need to add titles to text files, create a new document, or any other hurdle, just start typing. It’s my new method for throwing things in the OmniFocus inbox¹.

Depending on the exact wording of the quick note, it could end up as a to-do in my OF inbox:

• Set up phone call with John → Add to OmniFocus

Then later become an appointment for the calendar:

• Conference call with John 4/16 at 2pm → Parse in Fantastical²

One of my favorite features is the ability to write emails in Markdown. For quick replies I still use Mail (and most replies are quick from my iPhone, anyway), but for longer-form messages, I’ll open Drafts where I can include inline links and formatting using Markdown, then use the “Markdown: Email” feature to convert it and send as HTML email.

There are tons of actions supported for processing your input once you’ve entered it — Sending the text to email, Reminders, Messages, clipboard, printing, Dropbox — as well as the third-party app support. Things get really geeky once you dig into the customizable URL and Email actions.

This app is changing how I capture information from my iPhone, helping me strike a better balance between ubiquity of capture and the all-important correctness of processing. Highly recommended.

For the last month or so, I’ve been readopting the GTD methodology for organizing my work, personal and business. I read David Allen’s book back in 2007, and attempted to adopt the workflow. This was before having any sort of smart device, so workflow systems were much different back then. My system when I initially jumped in involved pens and pads, inboxes, folders — most of the recommended elements from the book. I didn’t last long, and since then I’ve only dabbled around really getting back into it. Merlin Mann and Dan Benjamin’s recent podcast series on the subject spurred me back into giving it another serious go.

Without getting into the weeds of the system, I’ve always seen three pillars to GTD that are critical to reaping benefit:

• Ubiquitous capture
• Breakdown your work into discrete, actionable tasks (processing)
• Weekly review of projects and actions

There are more elements to the total system, but these are the core functional components of GTD that I’ve adopted, eschewing the parts about the 43 folders and some of the other fiddly things like labelmakers and lettered reference file cabinets. I think a contributor to my initial dropoff with the system was not appreciating that you can adopt only some elements of the total system, as long as you’re closing all the loops.

Here’s a snapshot of how I’m reintegrating GTD into my daily flow:

Capture

I’m a heavy user of OmniFocus for everything task-related. The notion of “ubiquitous capture” is the first step to getting the thoughts, ideas, and tasks out of your brain and into the flow. For me, ubiquity means it needs to enter the river of material to be processed either through my Mac or my iPhone, one of which I’ll have at fingertips at all times. I love the tangibility of pen and paper, but I’m not trustworthy enough to have that at all times. There are OmniFocus versions for Mac and iOS, so that gets that piece out of the way. Plus they stay in sync over the air. If something you need to do something about enters your mind, there needs to be a frictionless way for it to enter the pipeline.

Processing

This is probably what I struggle with the most. This is where the majority of the thinking comes into play; What project is this action part of? Should I just do it right now? How many smaller actions does it need to be broken into?

Effective processing requires regular attention. If you just load up the inbox for weeks on end without sorting through each item and determining the next action (which could be deleting it), you end up working through tasks right out of the inbox. I can sort through the cruft in my inbox with vigilance and a heavy delete-key finger, but where I tend to fall off the wagon is with keeping the processing frequent enough not to get behind. I’ll find myself after a few consecutive hectic days cherry-picking actions to tackle right in the inbox, instead of hitting things from a higher level based on project importance or context. This can lead to wheel-spinning and procrastination, and put you right back to thrashing around with all that data in your head.

This time around, I’m putting more energy into the processing steps. Failure there is a large part of why I fell out with GTD some time back.

Reviewing

The weekly review is processing’s older brother, meant to walk you through each of the projects on your plate, reorganize them, enter any missing actions, and just generally get a “control tower” snapshot of all the runways in front of you. OmniFocus has an awesome “review” mode designed to handhold you through looking at each and every project in your OmniFocus database one by one. With a full force inbox dump, plus effective processing, it’s insane how many projects end up in the system. A good, regular review is a healthy way to clear the decks and make way for the projects that you’re actually going to do. This is another area I’ve struggled with in the past, it’s one of the last steps in truly closing loops and making sure your task database isn’t filled with garbage to fight with.

The unspoken “fourth pillar” in all of this is, naturally, doing. Inboxes, apps, text files, and folders aren’t going to actually accomplish those next actions for you. Many blog posts out there neglect to mention this most-critical piece of the flow (it seems obvious, right?), but it’s important. Making sure that the actions are as mindlessly straightforward as possible in the processing phase is critical to making the actions so easy, you hardly have to think while you’re cranking. GTD mostly serves as a method to create order from chaos. My personal objective is to get comfortable enough to make the system second-nature. I don’t want to think while I’m doing, at least not very much.

Related links:

• David Allen’s talk at Google, 2007
• Getting started with GTD