Re-thinking Digital Note-taking

Note-taking is central to my work. Every day I sketch ideas, capture meeting minutes, annotate bookmarks, draft new posts, etc. I’ve done this for a long time using both digital and analog notebooks. However, over the last couple of years, I’ve started feeling constrained by some of my tools. In particular, I’ve realized that I can create the most value when I can quickly spot patterns to generate insights, but the way I’ve been taking notes doesn’t lend itself to sparking new connections.

My primary note-taking tool over the last eight years has been OneNote. I started using OneNote because I wanted to hand-write my notes digitally, and Windows tablets were the only viable way to do so before the Apple Pencil came along. When the iPad Pro + Apple Pencil appeared, I left Windows tablets behind (one less OS to maintain!) but kept using OneNote. While the iPad app doesn’t have as many features as the Windows version, it’s close enough for my purposes.

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A New Normal

Tom Warren writing in The Verge:

Microsoft is revealing more about how people are using its Teams app, and it predicts the novel coronavirus pandemic will be a turning point that will change how we work and learn forever. Demand for Microsoft Teams surged worldwide last month, jumping from 32 million daily active users to 44 million in just a week. While usage continues to rise, Microsoft is releasing a new remote work trend report to highlight how work habits are changing.

The article offers some details about the increase in usage of Microsoft’s Teams and Stream remote collaboration tools during the pandemic. No surprise there; we’ve seen similar reports from Slack and Zoom. But more interestingly, the article also speculates about our technology landscape after the crisis has passed:

“It’s clear to me there will be a new normal,” explains [Microsoft 365 head Jared]Spataro. “If you look at what’s happening in China and what’s happening in Singapore, you essentially are in a time machine. We don’t see people going back to work and having it be all the same. There are different restrictions to society, there are new patterns in the way people work. There are societies that are thinking of A days and B days of who gets to go into the office and who works remote.”

As a result, widespread adoption of remote collaboration technologies will become a more permanent feature of the workplace, with less of the stigma they had before the pandemic:

Microsoft is also seeing cases where remote workers can no longer be an afterthought in meetings, and how chat can influence video calls. “The simplest example is how important chat becomes as part of a meeting,” says Spataro. “We’re not seeing it as being incidental anymore, we’re actually seeing it be a new modality for people to contribute to the meeting.” This could involve people chatting alongside video meetings, and coworkers upvoting suggestions and real-time feedback.

I don’t have firsthand experience with Teams. However, I’ve used competing systems — including Zoom, Webex, GoToMeeting, Slack, and Skype — for a long time. Many offer the ability to chat alongside video calls. Invariably, the chat feature feels tacked on, with little thought to the integration between it and the video stream.

Mixing synchronous and asynchronous communications is a tough challenge, but it also has lots of potentials. For example, I’ve been in remote meetings where team members collaborate to write meeting minutes using Google Docs in real-time. With enough people taking notes, the result is a powerful augmentation of everyone’s cognitive abilities. Still, the tool isn’t designed to do this. There is no connection between the words in the document and what’s said in the call.

Such new work modalities have been around for a while, but the pandemic is accelerating their adoption. We’re likely to see innovations that will be with us long after the crisis subsides.

Microsoft Thinks Coronavirus Will Forever Change the Way We Work and Learn

Reevaluating How We Use Social Networks

Home-bound for three weeks, I’ve come to rely on the internet for social interactions with anyone except my family. Now more than ever, I’m thinking about the role information environments play in my life. Some are helping make things better, and others, not so much.

Among the helpful ones, I count the information environments that are essential to my work: Zoom for synchronous communications and Slack for asynchronous ones. I’m a longtime user of Zoom, but the lockdown has nudged me to learn somewhat obscure features that make it more valuable to me. I have some concerns about Zoom’s privacy and security policies, but overall I’m satisfied with the system. Slack is something of a mess (I often have trouble finding older stuff or orienting myself within threads,) but the company is working to make it better. And in many ways, it’s an improvement over the most obvious alternative, email.

Both Slack and Zoom are environments that enable private social networks. They make it possible for people to collaborate remotely in (relatively) small groups. These days, most of my interpersonal interactions happen in either of the two. But not all; I’m also spending more time on three big, public social networks: Twitter, LinkedIn, and Facebook. I’ve been using these places for a long time, but the lockdown is leading me to reevaluate how I use them.

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Honing Our Remote Collaboration Abilities

Most of my career, I’ve worked in a blend of physical and digital environments. While most of my “productive” time has been in front of screens — initially desktop computers, then laptops, and increasingly mobile devices — with few exceptions, I’ve worked with teams and clients I’ve met regularly in “real” spaces like offices and conference rooms.

My collaborators and I would check in on each other in these physical spaces every once in a while, and then go back online. Often, our bodies sat in the same building — which we’d spend much time moving to and from — even though most of our attention while there was focused on our individual computer screens.

That changed two weeks ago. Like many of you, I’m now entirely online — for work, at least. My schedule is still packed, but all meetings are now happening in screens. I only see my collaborators in grids of small rectangles arranged haphazardly in an application window. In one sense, we’re pros at it; we’ve been doing this for years, after all. But now that we have no choice, we’re becoming even more adept at new ways of collaborating remotely.

For example, this week, I learned that Zoom — the software I’ve been using for years for most of my remote meetings — offers breakout “rooms.” This feature allows participants in a conference call to break off from the main meeting into groups to have a smaller discussion or work out a gnarly problem. It’s a boon for remote workshop facilitation. How long has this feature been there? I don’t know, but I never needed to look for it. Now that circumstances have called for it, I’ve gained a new ability.

I expect to learn many other techniques to improve how I collaborate remotely before this unique period of working from home is over. I aim to emerge from this experience as an expert in remote facilitation and teaching. At first, I’ll be clumsy at it — but so is everyone else. I expect we’ll all be more patient with each other at this time, given we’re all trying to get over the awkwardness of being fully remote. But we’ve been granted the opportunity to practice remote collaboration intensely over the next few weeks, and our new abilities will expand the scope of who we can serve, and when.

The Dynamics of Remote All-hands Meetings

Over the last few weeks, COVID-19 went from being a news item to being the news. And this past week, those of us in the United States started feeling the impact of the disease firsthand. Fortunately, for most people, the impact isn’t health-related. Currently, many of us are more affected by measures to curb the pandemic than by the disease itself. For a privileged few — including myself — the primary impact in the near-term is a shift to working from home.

For software designers like myself, working primarily from home isn’t as much of a burden as it would be for people in many other industries. The stuff we work on is the same stuff that we communicate with, so moving work online is feasible. However, it still requires adjustments. Team dynamics are different when working remotely. If you’re used to working with others in physical environments, you’ve internalized ways of working and hierarchies that have emerged in (and made possible by) the environments you share. As you shift to new environments, these hierarchies become visible.

This week I participated in a recurring all-hands meeting. I’d been in these meetings many times before, always in all in the same physical space. The atmosphere had always been casual, but the structure of the room, and the way we arranged ourselves in the space, implied and reinforced a hierarchy. There was always a sense that someone was leading the meeting at any given time; the rest of us were more of an audience. Our shared attention was on a vertical surface at the “front” of the room: a whiteboard. The meeting “leader” usually stood near this whiteboard, sometimes holding a marker. Those of us in the “audience” faced this whiteboard so we could see it and the speaker.

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What Did I Learn?

Like many other people, I have a morning routine. Journaling is an important part of this routine. Every morning, at the start of my day, I set aside a few minutes to reflect on the previous day and what today holds.

I’ve written before about the structure of this journal. Recently, I’ve added a new section: What did I learn? Specifically, what did I learn the day before? (And by implication: How do I need to change my behavior?) I sit with it for a little while, replaying the previous day. These are some other questions that help with this exploration:

  • What did I try that didn’t play out as I expected?
  • What expectations did I have that weren’t met?
  • What expectations were exceeded?
  • What information would help reduce the gap between these expectations and actual outcomes in the future?
  • How can I procure this information?
  • What patterns have I noticed?
  • What happened unexpectedly/serendipitously?
  • What resonances/synchronicities did I notice?

This last question may seem weird; it requires unpacking. Sometimes I’ll be thinking about something and the next day (or sometimes, the same day), I’ll come across the same idea in a podcast, book, article, etc. An echo of sorts. Sometimes these resonances are very peculiar ideas, to the point where I’m startled by the coincidence.

I don’t think there’s anything supernatural at work. The fact that the concept stood out merely suggests that I’m paying attention to it on some deep level. It’s like when you’re thinking of buying a particular model of car and suddenly you see the same model everywhere. Those cars were always out there, but now your mind is primed to pay attention. These could be important signals.

Note these are questions about things that are under my control: my attitudes, expectations, plans, etc. I don’t bother to document things I learned due to events happening in the outside world, out of my control. (E.g., stuff in the news.) Rather, I’m trying to establish a feedback loop that allows me to become more effective over time. Growth calls for introspection; What did I learn? is a useful trigger.

Mind Your Baobabs

Skillful information management requires continuous vigilance and effort. If you’re an active participant in today’s world, stuff is constantly coming in. If you don’t develop practices to keep information organized, you will soon find yourself hobbled.

I’m reminded of a powerful image from one of my favorite books, Antoine de Saint Exupéry’s The Little Prince. You’ve probably read it, but here’s a quick synopsis in case you haven’t: The book’s narrator, an aviator, crash-lands in the Sahara. Alone and running out of provisions, he desperately tries to repair his aircraft. A mysterious child appears. He keeps the aviator company, sometimes annoying him with naive/profound requests.

In the course of their conversation, the aviator realizes that the child — the titular little prince — has come from another planet. It’s a small planet, but it keeps him constantly busy:

“It’s a question of discipline,” the little prince told me later on. “When you’re finished washing and dressing each morning, you must tend your planet. You must be sure you pull up the baobabs regularly, as soon as you can tell them apart from the rosebushes, which they closely resemble when they’re very young. It’s very tedious work, but very easy.”

Why baobabs? The little prince goes on to explain:

“Sometimes there’s no harm in postponing your work until later. But with baobabs, it’s always a catastrophe. I knew one planet that was inhabited by a lazy man. He had neglected three bushes…”

The baobabs

I think of this story every morning as I work through my email inbox. There are two types of people in the world: those who let email pile up in their inbox, and those who adhere to the “inbox zero” approach. I’m in the latter camp. There’s no middle ground.

Once a day, I “tend my planet” by going through every message in my inbox. Some get archived or deleted. Some I skim and save for later reference. Some I must act on immediately. I note the rest in my to-do application for future action.

Among other things, I’m looking out for baobabs. Most emails are one-time engagements. But some hint at bigger projects. These require special care​ because there’s only so much time available for such things. Too many of thes​e and things spiral out of control.

In some ways,​ we have it harder than the little prince. Most of us have more than one inbox to tend. I deal with email, Slack, a physical inbox, two physical mailboxes, Facebook messages, LinkedIn messages, Twitter messages, and more. All require constant attention.

I know people with thousands (in some cases, tens of thousands) of emails in their inbox. I shudder when I look at their phones or computers. I wonder, how many baobab seeds are lurking in there? One or two baobabs aren’t bad. In fact, they’re what keep the machinery running. The problem is when you have too many. Sorting them out calls for constant, proactive vigilance.

You can take a vacation once in a while; get a break from the onslaught of information. But watch out! When you come back you must attend to the backlog. Diligence is the price for effectiveness and peace of mind. The alternative is always a catastrophe.

Getting Rid of Ghosting in Notebook Scans

Much of my thinking happens with paper and pen. My notebook is an extension of my cognitive apparatus; I’ve become adept at externalizing my thoughts visually, which allows me to think more clearly. Scanning my notes — making them digital — is an essential part of this system. In this post I’ll share with you a simple hack that allows me to do this quickly and neatly using my iPhone.

I do most of my “pen and paper” thinking using a Leuchtturm 1917 notebook and various pens, all of which lay down stark black lines. Every other week or so, I scan my notes using Microsoft’s OfficeLens app, which sends them to OneNote. This has two advantages:

  1. it allows me to carry around all of my notes everywhere in my digital devices, and
  2. it OCRs my notes, so I can search my handwritten notes.

I can’t overstate how useful this is. I can access in my pocket many years’ worth of handwritten notes, which I can search like I do any other digital document. (I’ve written more about my process here.)

OfficeLens is a very powerful app. Among its many features, it has a “document” scanning mode that looks for the bounding rectangle of the thing you’re scanning, and when you take the photo it adjusts its perspective so the scan appears as a flat page. Then it adjusts the contrast of the image to make it as close as possible to black ink on white paper, which makes the scan clearer and more legible. (These features are not unique to OfficeLens; there are other mobile scanning apps that do this as well. I haven’t found any others that OCR my handwriting, though.)

As cool as this process is, it’s not without hiccups. Two issues in particular affect each of these features:

  1. Finding the bounds of the rectangle is dependent on the contrast between the border of the page you’re trying to scan and the surface the notebook is resting on. The feature works best if you’re taking the shot with the notebook resting on a very dark surface. Often, this isn’t the case. (For example, I’ve found most coffee shop tables aren’t dark enough under daylight conditions.)
  2. When you draw or write using dark pens, marks on the previous page often show through on the page you’re currently scanning. This is known as ghosting, and the effect is made worse by the algorithms used to turn up the contrast on the “document” scanning mode in apps such as OfficeLens. (Ghosting is what led me to adopt Leuchtturm notebooks over brands that use cheaper paper, such as Moleskine. Alas, Leuchtturm’s paper quality has become unreliable over time.)

The first problem slows down the process considerably, since you must adjust the bounding rectangle manually for each shot. The second problem can make the resulting scans harder to read.

I struggled for a long time with these issues. Eventually, I found a cheap and easy hack that solves both of them: I keep a piece of black construction paper folded in the notebook’s back pocket. When I’m going to scan my notes, I take out the black paper and put it immediately behind the page I’m scanning:

A notebook with black construction paper in the background

This has the effect of crisply defining the boundaries of the page and of rendering the ghosted marks invisible. (Notice in the shot above that I also cut a notch in the construction paper to the exact width of the notebook. Doing this increased the reliability of the rectangle-detection algorithm even more.)

I’ve become adept at putting the construction paper behind the page, flattening the notebook, and taking the shot. While the maneuver introduces a bit of friction into the scanning process, it’s become second nature. The bit of extra time it takes to move the construction paper between shots is well worth it. If you use your phone to scan your notebooks, and have found ghosting to be a problem, try this technique. You may be surprised at the results.

“Build More Roads” is Often the Wrong Answer

The Power Broker, Robert Caro’s masterful biography of Robert Moses, tells the story of how modern New York City came to be. Moses and his team were responsible for some of the most important public infrastructure interventions in and around New York City during a span of four decades starting in the mid-1920s. Under Moses’s leadership, the city gained new parks, playgrounds, bridges, and especially roads — sometimes at the expense of beloved neighborhoods and the disruption of countless lives. An unelected official, Moses became incredibly powerful; you can see his influence in New York even today.

The core of Moses’s power lay in the Triborough Bridge Commission, which controlled the flow of traffic between Manhattan, The Bronx, and Queens. Tolls from vehicles driving across the Commission’s bridges generated immense revenues that paid for other projects, which in turn generated more revenues. For Moses, vehicular flow in New York City’s streets translated directly to more power. Thus, when considering means for transporting the city’s inhabitants, Moses’s team would gravitate towards more roads — even when it’d become clear that building more roads only increased congestion. The result was the defacement of major parts of the city with highways and roads that were constantly jammed with traffic.

You gotta watch incentives.

This comes to mind because of something that Jessica Ivins said on her interview for The Informed Life podcast:

So not everybody has the detail-oriented mind that I do, or not everybody works the same way I do. And because we’re small and I’ve been working here for almost 5 years, I have a sense of what works well for my co-workers. So for example, my coworker Thomas, I will assign him a to-do in Basecamp and he’ll get an email notification, but I’ll also send him a notice on Slack. And I’ll say, “Hey Thomas, I signed you this to-do on Basecamp, please review it by this date and see the to-do for details.” And that Slack message really helps him because he… I guess some people are really good at wrangling their inbox, other people really struggle with it. And I think that’s really typical.

It is typical. I’ve faced similar situations in other projects: Someone new joins the team, and you don’t yet know their communications preferences. Are they an email person? Do they prefer Slack? Or maybe iMessage? It’s not unusual to get a message in Slack followed by an email asking, “Did you see the message I put in Slack?” And of course, people’s preferences vary depending on other factors. For example, perhaps they only use Slack on their computers and find it easier to respond via SMS when they’re on the road.

Proprietary communications systems like Slack and Basecamp set out to solve the problems with older systems like email (and there are many!), but like Moses’s roads they can end up creating other problems. Now instead of one or two places to check your communications, you have five. You get reminders on one system (e.g., email) to check messages sent to you on another (e.g., Basecamp.) I’ve gotten messages on Slack to check something that was posted in Basecamp; later that evening I’ll also get an email reminder from Basecamp of all the things that were posted there during the day. The signal-to-noise ratio goes through the floor. And of course, now you have to keep track of where you saw the message or file if you ever need to get back to it. (“Did you send that document over email, or was it in Slack?”) As far as I know, it isn’t possible to search across all of these systems; it’s up to you to keep track of where things are. This is difficult, given the challenge I mentioned above. (I.e., different people have different communications preferences.)

The added complexity would be worthwhile if these systems enabled amazing new ways of working, but these proprietary communications systems bring little new to the table; most of the functionality they enable has been around for a while. Check out Jon Udell’s book Practical Internet Groupware for the state of the art twenty years ago; you’ll find lots that is familiar. It’s worth noting that that book advocated for building these communications systems atop existing open standard technologies. In this sense at least, the current state represents a regression from where things were in the late 90s.

I’m cranky about this stuff because in the past month I’ve joined three new Slacks and one Basecamp project. This is part of the job when you’re an independent consultant who works on several projects with different teams throughout the year. But I don’t enter these spaces casually. As someone who thinks about the longevity and resilience of information ecosystems, I’m concerned about my ability to find and keep track of stuff — especially in the long term. I dislike the proliferation of disconnected, single-purpose silos of information. While the discussions that happen in these places can be rich, vibrant, and productive (that is, when they’re not generating more noise in other channels), they’re locked away, inaccessible for future (even near-future) reference.

In the long term, building more roads isn’t the solution to the challenge of moving lots of people from one point to another. Past a certain volume, individual vehicles are inherently inefficient; one needs to re-think the structure of the transportation system from the ground up. This is more challenging if the people charged with the stewardship of these systems are incentivized to get more cars on the road. I sense similar problems with the communications challenges we face in organizations. When what you’re selling is access to Slack, your incentive​ is to get more people using Slack. That’s a different goal than getting people to communicate effectively. Yes, there is some overlap there — up to a point. How does the system scale?​