The boring truth about email security

    David Sparks and John Gruber have said all that needs to be said about the revelation that was selling its users’ email data.

    It was easy for me to delete my account because I had really stopped looking at it already. Last year, I decided to just get out of the way of my email and just let Gmail’s stock filters for “social,” “promotions,” and “updates” channel 80% of my email into those non-action buckets.

    On the surface, it may seem odd that I would favor one ad company over another: dump but stay with Google’s Gmail. A lot of people have ostensibly moved away from Gmail for the same reason people were throwing up in their mouths over this week.

    But I have been using Gmail for a long time, and I have no plans to leave now. I understand that Google sees my email and pours it into its Alphabet soup, and I’m OK with that—not because I think Google is especially benevolent, but because I accept the truth about email data.

    I think a lot of people who leave Gmail because of privacy concerns are following the false hope that another company can magically “secure” their email. The truth is that your email will never be totally private. With the exception of email you send to yourself, email takes at least two servers to tango.

    Every copy of every email sent to/from you resides on some other email server. If you regularly email a specific person, there are probably thousands of your emails on their hard drive—perhaps the one in the old computer they just sold without wiping the hard drive.

    In other words, email is not the same as your note archive or your document repository. Email is necessarily out there. Everywhere.

    So in my mind, the solution to email privacy is email avoidance:

    • Take advantage of iMessage’s encryption for chats with friends and family
    • Move your project or work communication to an app like Basecamp

    That’s what I’ve done. Today, I see my email as a bloated version of Twitter: a constant inflow of chaff with the occasional strand of wheat, which mostly takes the form of customer email.

    I have no control over how many computers email me every day. But I can definitely control how much email I create myself.

    Be still my rolling Pencil

    If I’m using my iPad Pro, I’m almost always using my Apple Pencil, too. For me, the Pencil was a massive extension for the iPad and basically made it the go-to environment for reading, studying, and annotating PDFs.

    The Apple Pencil is great at many things. Staying still on a flat table is not one of them.

    I’ve tried several accessories and tricks for keeping the Pencil from racing away, but nothing works as well as the FRTMA Apple Pencil Magnetic Sleeve.

    • It makes the Pencil non-round, so it stays where you set it
    • It is extremely sleek, preserving the svelteness of the Pencil’s design, yet the sleeve adds a bit of tackiness that I actually prefer when writing
    • It’s magnetic, so it sticks to any iPad case

    The magnet is very strong. When attached to an iPad case, you can shake the case really hard, and it will not come off. It will, however, come off sometimes when it’s in my backpack, but in my experience, “losing” my Apple Pencil inside my backpack is the very best place to lose it—far better than seeing it race across a flat table and down the stairs of my favorite coffee shop.

    From clips to stories

    Renie Ritchie apparently wrote a treatise on Apple’s new Clips app, but don’t let that intimidate you. Clips is ridiculously easy to use, and most of its features are discoverable by just playing with it.

    The real brilliance of Clips is that you don’t even feel like you’re doing movie editing, but that’s exactly what you’re doing. Being able to shoot video is just one step of making a visual story. A movie obviously can’t exist without that step. But in my opinion, editing is way more important. Cutting, blending, and curating is what really makes something a story.

    I think the “cutting” step is what most iPhone-created movies need the most. I went a long way in solving this problem (accidentally) when I started using Snapchat about a year ago. Before Snapchat, I shot plenty of video with the iPhone, but I almost never did anything with it. The main problem was that my videos tended to be too long. This made them:

    1. Usually boring
    2. Longer than most people wanted to watch
    3. Too much of a hassle to upload due to their file size

    So on my phone they sat—unwatched.

    The more I used Snapchat for video, the more I realized the brilliance of its ten-second limitation. This constraint made it impossible to shoot long, boring videos and also forced me to throw away outtakes immediately. Before long, I wasn’t just using Snapchat to send video snaps, I was saving the videos to my phone.

    Now that Clips is here, I’m using the iPhone’s camera app for video more often, but I’m still shooting very short duration clips a la Snapchat. Clips makes it ridiculously easy to fuse some or all of any video into a series of clips. Being able to mix videos and pictures into a single clip creates the same effect of a Snapchat story, but it keeps everything on my phone so that I can share it in other ways—notably with people who don’t use Snapchat.

    It’s really the story you should be after.

    If you pay attention to almost any TV show, movie, or professionally-made internet video, the very longest shots last no more than than five to eight seconds. In action movies, shot length can average as little as two seconds! Some action movies have over 3,000 shots in them. Changing scenes and angles just makes the visual aspect more engaging.

    I used Clips to make a couple of short “movies,” each consisting of 5–10 short videos and photos I took last week on a family vacation. In a lot of cases, I only grabbed a few of the best seconds of each clip. Creating each “movie” took just minutes using only my iPhone. I’m 100% sure none of those individual videos would have gotten shared if I hadn’t used Clips to make them into a story.

    Thoughts on iOS automation

    It’s funny to hear so many people complain about the lack of automation in iOS. In reality, iOS automation has already happened. We were just looking the other way, and when we turned around, we couldn’t remember what was there before.

    I can’t think of a better measure of the success of automation than how quickly an automated process becomes forgotten. Automation’s role in the human experience, after all, is to make us forget. Automation frees us to work on new problems beyond the old problem horizon. Automation paves over cavernous ravines, replacing them with short, straight paths to the adjacent possible.

    There are countless examples of how iOS has done this. Take photography.

    Before the PC, the steps to share pictures usually spanned weeks:

    1. Remember to bring a camera with me
    2. Take pictures on film
    3. Physically deliver the film to a developer days later
    4. Wait more days for the film to be developed
    5. Physically pick up the developed photos
    6. Physically mail the photos to someone, who would receive them days later

    When digital photography and the PC arrived, the process shortened, and the output expanded:

    1. Remember to bring a camera with me
    2. Take a picture on a memory card
    3. Remove the memory card from the camera and insert it into a PC
    4. Upload to websites, instantly sharing with hundreds of people or more

    Once the iPhone camera fully came of age, the steps became:

    1. Pull out my phone and shoot
    2. Tap to share

    Weeks reduced to seconds. The need to bring a physical object with me: gone. The monetary cost of photography: eliminated. And in many cases, the quality of the final product: dramatically better.

    The hassles of pre-iPhone photography: forgotten.

    The adjacent possibilities unlocked by the confluence of the iPhone’s camera and mobile connectivity:

    • Shareable HD video from anyone’s pocket
    • FaceTime and other wireless video calling
    • Document scanning
    • Snapchat, or more generally, the concept of photo messaging
    • Augmented reality

    There are so many examples of other things iOS has automated that we never even thought needed automating. Just look at your home screen. The iPhone is essentially a universal remote for modern life.

    Traditional computer automation (scripting, better inter-app communication, etc.) is a pretty narrow frontier of iOS automation yet to be fully solved. I’m not convinced that it even needs to be solved as long as we have traditional computers with open file systems. But I believe it will either be solved, or the need for solving it will be obviated by other advances in iOS.

    For now, I will continue to enjoy using iOS and macOS, which are much greater together than they are apart. It is impossible to predict the future, but I’m pretty sure we can rule out a “single device for all uses” scenario.

    Computers will continue to automate things we never associated with computers. We will continue looking for new problems. And we will continue forgetting about the tedium of times gone by.

    And, not or

    During Sal Soghoian’s appearance on Mac Power Users, he talks about his philosophy on “and, not or”:

    A lot of people mistakenly embrace the concept of or when it’s not necessary. There really needs to be and. And and doesn’t necessarily cost more… it just offers more.

    Every minute of this show is worth listening to because Sal exudes genius every time he speaks, but his “and, not or” philosophy is a seriously great piece of wisdom, and I hope that now that Sal is outside of Apple he has more opportunity to speak and write about it.

    In my experience—observing both myself and others—the “or” mindset usually leads to paralysis or unneeded time spent rebuilding an entire workflow to fit perfectly in a new framework.

    The most agile, modular solution is usually some of this and that. “Or” breeds an “all or nothing” approach that usually just ends in nothing. “And” moves things forward

    What’s the best computer for productivity? A MacBook and an iPad Pro.

    Where should I store notes? DEVONthink and Apple Notes.

    Where should I write? Drafts and Ulysses and Sublime Text.

    What’s the best way to outline? Plain text and iThoughts and OmniOutliner.

    What camera should I use? A DSLR and my iPhone.

    What’s the best way to sketch a visual design concept? Real paper and an Apple Pencil / iPad.

    Where do tasks belong? OmniFocus and Reminders and TaskPaper.

    What PDF app should I use for mark up? PDF Expert and LiquidText and Notability.

    In each case, the “and” mindset lets my mind get out of the way of itself. “And” imposes less friction between ideas and actions.

    LaTeX comes to Pages

    As you may have heard, Pages now supports LaTeX equations in both iOS and macOS. Even though it’s not nearly as robust as writing and typesetting LaTeX using MacTeX, it’s extremely well implemented and will be a huge convenience, especially for one-off files and shorter documents.

    I like how the Equation editor in Pages provides a live preview of the equation as you type it:

    As an added bonus, even though Keynote does not have the same direct LaTeX support as Pages, I found that you can copy the equation in Pages as an image and simply paste it into Keynote. The image appears to be a vector graphic because it scales perfectly without any resolution loss.

    In a nutshell, this means you can also quickly add equations to Keynote via Pages on the fly.

    LiquidText 3.0 redefines what's possible with a PDF and an iPad once again

    MacStories has a nice review of the latest update to LiquidText. At last, it supports the Apple Pencil.

    Part of what makes this version of LiquidText so amazing to use is that your finger and the Pencil can do different things. It’s like having two tools in your hand.

    Finger selections can make excerpts even while the Pencil is in drawing or highlighting mode. The Pencil can draw anywhere—not just on the PDF like most PDF editors, but even in the LiquidText workspace, right alongside your excerpts and comments.

    You can even drawn a circle or box around anything in the PDF, and it extracts it as an image to the workspace. The image can be copied to your clipboard and even pasted into other apps. This is the first time I’ve ever been able to capture a portion of a PDF as an image without having to screenshot the whole screen and crop in Photos. This opens a lot of possibilities—like being able to capture a graphic and paste it into an app like Notability, to collect it with other visual notes.

    The makers of LiquidText are really redefining what you can do with an iPad. Bigger picture, the iPad Pro + Apple Pencil + software like LiquidText, DEVONthink, PDF Expert, and Notability make for an incredible PDF system—one that is way more powerful than a traditional desktop computer.

    Next fun

    If a project, task, or reminder is stalled, overly deferred, or procrastinated, the correct next action is always: Decide how to make this fun.

    The cost of monetization

    David Heinemeier Hansson going off on monetization schemes:

    Consumption of monetized apps should always be pondered with skepticism. The whole lot of them fall into what we should label “a family of products with known mental carcinogens; further study recommended”.

    Consume or be consumed.

    Regular expressions and Sublime Text

    Regular expressions seem very difficult to learn at first, but once you get the hang of them, they are powerful tools. I’m using them more and more in Python scripts and also find/replace workflows in Sublime Text.

    Since I have several regular expressions that I use over and over (and over) again, I decided to store them in TextExpander for quick reference. I prefix each snippet with rx, which lets me use the TextExpander global shortcut to bring up a TextExpander search box anywhere in macOS so I can just grab the one I need.

    Using regular expressions to find text in Sublime Text is easy, but remember to press the .* button on the far left of the find/replace form first.

    Regular expressions are even more powerful when you learn the “replace” syntax in Sublime Text. In the screenshot above, the regular expression ^.*\{frame\} is designed to find lines containing the LaTeX Beamer frame environment and match all text from the beginning of the line through the closing } to the right of frame.

    By enclosing this search term in parentheses, I’m telling Sublime Text that I want to use it as a variable in my replace term. The variable is called $1. (You can separate multiple search terms with commas, to get $1, $2, etc.)

    Therefore my replace term % $1 will effectively insert the % (LaTeX comment symbol) at the beginning of each matched line. This comments out all lines containing the frame environment so that LaTeX will ignore them—something that’s very useful in one of my LaTeX workflows.

    But anyway, if you use Sublime Text a lot and want to take your find/replace routine to the next level, regular expressions are your friend.

    RegExRX is a really handy Mac app for building and testing regular expressions.

    Use universal clipboard to alleviate iCloud password pain

    Amid the storm of negative narratives on the state of Apple—and more generally how horrible life is today in the First World with all the worry over our expensive computers—it’s easy to lose sight of the fact that some things really are more awesome today than they used to be. And there is still much delight to be found in the details.

    One dash of unicorn tears introduced by iOS 10, and then later brought to macOS in Sierra, is universal clipboard. When I first heard Apple announce it, I was skeptical, but I really wanted to believe it would work. I imagined being able to copy text on my iPhone and paste it on my Mac (and vice versa). As amazing as that idea sounded last summer, actually seeing it work is even more amazing. I’ve yet to see it not work.

    Very recently I came across a use case for it that I never envisioned before: copying my iCloud password from one device to another. Before universal clipboard, if I had to enter an Apple ID or iCloud password in a prompt on, say, an iPad screen, I had to close the prompt, find 1Password, copy the password, then return to the prompt.

    Now, if I encounter a password prompt on an iPad, I just pull out my phone, copy it from 1Password there, and bang: It pastes right into the field on the iPad—even from the initial “splash” iCloud screen you get after an iOS update. Magic meets practicality.

    I still think Apple could alleviate iCloud password pain by making Touch ID more available on general password prompts in the App Store and iTunes, but with universal clipboard, life is just a little less bad in the First World.

    Simple PDF saved search tip

    If you’ve been using a Mac for a while, you probably know about smart folders, which are essentially saved searches. I’ve known about them for a long time, but for some reason never used them much. I’ve started to realize this was a huge mistake.

    Smart folders can be very specific and complicated, but even a simple one that looks for all PDFs across the file system is an incredible time saver. Being able to see recently modified PDFs from different applications in a common “folder” so that I can combine them and use them in different ways is way easier than doing PDF-specific searches or having a bunch of Finder windows open at once.

    The core feature of the Mac that’s yet to be replicated by iOS is the file system. The ability to have files scattered across a file system that any installed app can access is a taken-for-granted aspect of computing that I hope we never lose. For now, we haven’t, and I plan to use the hell out of it.

    To don't streaks

    Being January, a lot of people have habit-forming on the brain. My favorite app for habit-forming is Streaks, which is designed to encourage you to complete tasks over consecutive days, X times per week, etc. It can even read health data from your iPhone and automatically check off health-related tasks.

    I think most people approach habit-forming in terms of “things I want to do,” and that was generally me before 2016. But in 2016, I started taking a more inverted approach and embraced the “to-don’t.” I’m willing to bet for most people in modern times, you’ll find more low hanging fruit in to-don’t lists, which are simply lists of things you do not want to do.

    Great examples of things to not do or just do less:

    1. Don’t check email in the morning
    2. Only check Twitter once per day
    3. Don’t eat dessert Monday through Friday
    4. Look at the stock market only once per week

    I have had a lot of success with the “only once per day” variety. It’s really amazing how easy the internet makes it to check in on useless information and how much attention that destroys. It only takes one or two well-designed to-don’ts to indirectly make way for a significantly more focused day.

    Building long streaks of to-don’ts with an app like Streaks is surprisingly easy, and it’s really empowering to see that you only did something once per day for the last, say, 45 days, that you used to do 100 times a day.

    Things I got better at in 2016: Part 2 -- Time and project management

    Also see part 1 on technology things.

    Honing time management skills is a lifelong process that starts at an early age. I don’t think it’s something that is perfectible. Instead, it’s something that someone can simply get better at with maturity and awareness. I feel like 2016 was my best “time management year” ever because of what I accomplished and the efficiency I felt in the day-to-day moments of my work.

    Based on self observation, these are the aspects of time and project management that I think I improved on the most.

    Time management

    I dedicated mornings to deep reading and tasks that require the most mental energy. I’ve always known that I do my best work in mornings, but in 2016 I made my most concerted effort ever to guard mornings for specific kinds of work.

    It’s a nuanced thing I guess, but the biggest change I made was that I stopped working on projects as linearly as I used to. Rather than use any time available to work on the “next task in line,” so to speak, I began carving projects up into more specific task categories using OmniFocus contexts.

    I’ve never been a fan of contexts like “high energy” and “low energy,” but I’ve learned to associate specific stages of my typical projects with energy states, which are largely dependent on the time of day. In doing this, I made more progress over longer time periods because projects were less likely to stall on high energy tasks that I used to try to take on in afternoons. Once afternoon rolled around, if a high energy task was next in line, I learned to let it go until the next morning, and I looked for lower energy (e.g. administrative tasks) to tackle.

    It’s kind of like learning to knock down a huge brick wall by chipping away at different spots until the whole thing collapses under its own weight, rather than tearing it down brute force brick-by-brick from right to left. At first it feels like you’re making less short-term progress when you take a more energy-based approach to work, but over longer periods, I believe you begin accomplishing not only a greater quantity of work, but a higher quality of work because at each stage, you give the work the appropriate amount of attention.

    The other benefit I began to feel is that I started keeping my admin-oriented tasks to a manageable number. They stopped piling up because I was able to knock them out during times of day that my mind was useless to work on higher value work anyway.

    I’ve begun to understand that I’m essentially a collection of “selves” that change subtly throughout the day, and I’ve learned to manage these “selves” as different workers—or like a great football coach who knows how to get each player to play to his full potential.

    I also became much more aware of how important sleep is to getting more out of all these “workers.” The closer I can come to seven-ish hours of sleep a night—not just in a given night, but in consecutive nights consistently—the higher I perform at every stage of the day.

    Project management

    I finally bought OmniPlan in 2016, and within only a few days of using it, my biggest disappointment was that I hadn’t bought it sooner. I’m probably a very unusual user of OmniPlan because I’m not a “project manager” in the formal sense, and I’m not using it to manage projects with multiple people.

    For me, it’s just very useful to have a time forecast for projects so that I can set realistic expectations for myself and my customers. Knowing when a project will likely end also lets me do more macro-level project planning to understand what I can realistically accomplish in the coming months or year so that I’m less likely to over-promised my time. Gantt charts are definitely not unique to OmniPlan, but I really like how the OmniGroup has implemented them in OmniPlan and how easy it is to work with them.

    OmniPlan makes it very easy to create task dependencies and realistically budget for weekends, holidays, and other planned time off. There is nothing better than taking time off and knowing your work is still on schedule when you get back.

    I’m using OmniPlan exclusively in iOS. It’s really great on my big iPad Pro, but it’s also surprisingly well implemented on the iPhone. I may buy the Mac version at some point, but the iOS version is satisfying all my needs for now.

    For me, OmniPlan complements OmniFocus. I used OmniFocus more than ever in 2016. In 2015, I began a trend of creating more, smaller OmniFocus projects rather than fewer, larger projects. The longer-term, multi-week and multi-month projects I track in OmniPlan are usually organized within specific folders in OmniFocus. Very roughly speaking, each OmniFocus project is corresponds to one or two tasks in OmniPlan.

    In OmniPlan, my goal is to forecast time, and so the tasks I create in OmniPlan need only be granular enough for that purpose. OmniFocus actions are much more granular, representing the steps I need to execute in the day-to-day and moment-to-moment to moment work of the project.

    At first I was worried I was just duplicating administrative work in OmniPlan by doing what can feel like recreating tasks there. But the return on this additional time investment has been huge. OmniPlan essentially gives me an additional time-oriented perspective of my projects that I don’t have in OmniFocus (or any other task management tool). For longer projects, it’s also very motivating on a daily basis to see how staying on a preset schedule today translates to time savings weeks in the future. It also helps avoid the natural tendency to waste time until a fast approaching deadline forces urgency.

    Bigger picture

    For most knowledge work, “project management” reduces to simply time management. Good planning is about turning each day into an urgent, but achievable deadline.

    Things I got better at in 2016: Part 1 – Technology

    This is a miscellaneous list of things I feel like I got better at in 2016 and hope to build on even more next year. Also see part 2 on time and project management.

    Regulator expressions

    Maybe just through sheer resolve, I finally got better at writing regulator expressions in 2016. If you work with text files in any capacity, learning regular expressions is well worth your time. They are so much more efficient than writing loops in scripts to clean up text files, and they really take ad hoc “find/replace” fixes to the next level in text editors like Sublime Text.

    There are infinite practical use cases for regular expressions if you can punch through their opaque syntax. For example, I can search for all hyphens that occur at the beginning of a line if I want to manipulate the indentation of a Markdown list.


    I continued to increase my time investment in Python, which has become my all-purpose programming language for manipulating large numbers of text files and even leveraging Terminal commands. There is something that’s just very friendly and universal about Python, and it’s cross-platform support makes me believe that the time I put into it today will continue to payoff for a very long time—even in a possible future where macOS and its Apple-centric scripting languages fade away.


    2016 was the year I finally parted with Evernote, and I couldn’t be happier with my decision to go all-in on DEVONthink Pro Office. I’ve been able to bring all of my content management under a single roof and enjoy the unrivaled organization tools, search operators, OCR, and security that DEVONthink offers. If you are a macOS/iOS person, I can’t recommend DEVONthink products enough.

    As 2016 draws to a close, and I begin organizing tax season information, it’s hard to believe I used to manage tax docs offline because I didn’t trust Evernote’s cloud storage. Now everything is securely accessible on my Mac, iPhone, and iPad.

    Static blogging

    I left SquareSpace for Jekyll in 2016. Eight months later, I still love the concept of a static website and the flexibility it’s given to my writing workflow on both the Mac and iOS. I also learned so much in the process of converting my blogging setup to Jekyll—Python tricks, etc. It was a great move, and I love the independence of having my own site, even if it’s just a small flicker of light compared to the social/aggregator sites that many think “killed” blogging. They haven’t killed this one.

    Long live the GIF!

    This year, I realized that the latest version of ScreenFlow lets you make GIFs. It’s simply another export option. GIFs take almost no time to create and are so much better for showing someone how to do something when you want an animated image but don’t need audio. If a screenshot is worth a thousand words, a good GIF is worth a thousand follow-up questions that don’t have to be asked.

    Miscellaneous Mac tips

    Sometimes the small, barely noteworthy adjustments to workflows make the biggest cumulative difference.

    • I learned that I can change the default folder for screenshots from the Desktop folder to Downloads (or any folder). My Downloads folder is an all purpose inbox that gets regularly cleaned by Hazel. It’s also easier to drag temporary files from the fan view of my Downloads folder in my dock than it is to show the Desktop.
    • I started using “All my files” in the Finder to quickly locate recently modified files for uploading in web forms, or to locate a file I accidentally saved in the wrong place on my Mac. The “All my files” search folder has been there forever. For some reason, I started taking advantage of it just a few months ago. It’s also a simple reminder of just how powerful the Mac filesystem itself is as a content management system.
    • I (surprisingly) embraced Siri on the Mac: “Show me keynote files I had open yesterday” and similar commands work flawlessly. Speaking really specific commands like that is much more efficient than doing custom Spotlight searches.
    • I moved to PDF Expert for almost all PDF editing and annotation tasks for two main reasons: 1) PDF Expert has gotten really good at the things I do to/with PDFs on a regular basis and 2) in macOS Sierra can no longer be trusted not to break PDFs.