How I Manage ‘Thinking’ Time

Earlier this year, I asked what you’d like to know about how I get things done. I received many interesting requests, more than fit in a single post. So, I’m covering aspects of my setup in separate entries. This is the first of the series.

Rather than start with a tool or method, I’ll address a question asked by Andrea Tanzi:

Why start here? Tools come and go, but time is a constant. It underlies everything else. ‘Thinking time,’ as Andrea put it, is an especially limited resource. There are so many demands on our attention!

By ‘thinking time’ I mean focused time — i.e., moments when I can advance my work, learn, and write without distraction. The aspiration: to move things along by entering a state of flow. (A good book on this is Cal Newport’s Deep Work.)

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My Personal Information Ecosystem

I love learning about how other people get things done. (It’s one of the motivations for my podcast.) In that spirit, I’ve decided to share how I work. It may come across as self-indulgent, but perhaps it can also give you ideas.

In February, I mentioned on Twitter that I was working on a post about my ‘production function.’ (Tyler Cowen’s wonderful phrase.) I asked what you’d like to know about my setup, and several folks replied with angles I hadn’t considered.

As I outlined what I wanted to cover, I realized there’s too much for a single entry. So, I’m breaking it down into several shorter posts, which I’m also planning to post as tweetstorms.

This is the first of these posts, which will serve as an index. As I write more, I’ll add them here, calling out emerging patterns. (And integrating your feedback, so please let me know what you’d like to learn about.)

Here’s what I plan to cover:

  • Tools and techniques for personal information management
  • Software and hardware for better thinking
  • Frameworks and approaches for better time management
  • Whatever you’d like me to explore (let me know!)

My personal information ecosystem is constantly evolving, so I expect this to be a ‘living’ post. I’ll edit it to reflect how things change. For now, stay tuned.

Cover image: Detail from one of Benjamin Franklin’s virtue charts. Credit: Franklin’s Way.

A Year of This

It’s been a year since my family and I started ‘sheltering in-place’ — i.e., staying home to help curtail the spread of COVID-19. I’m still finding ways to adapt to this ‘new’ way of working.

A post I published on March 14, 2020 covered changes I observed in my first post-lockdown all-hands meeting. In particular, I noted our physical office had offered implicit structures that now had to be made explicit. Among other things, the new medium flattened hierarchies and didn’t provide a focus point in lieu of a whiteboard.

A year on, we’ve mostly normalized this way of working. After an awkward initial period (day-long Zoom marathons!), many of us have found ways to be productive. I was about to write ‘productive and engaged,’ but in my case, that wouldn’t be entirely true.

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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.