How New Note-taking Apps Give You Information Management Superpowers

Master craftspeople don’t just work to make stuff; they also work on the work itself. A master carpenter will set up his shop for efficiency, develop deep relationships with his tools, and establish practices, habits, and mindsets that allow him to work in a state of flow.

Knowledge workers, too, must work on their work. As with craftspeople, this entails building empirical knowledge, developing generative mental models, and stewarding a toolset/environment that supports productive work.

Continue reading

Changes to Sketch’s Conceptual Model

A few days ago, I received an email from Sketch informing me (a customer) of upcoming changes to the app’s licensing model. They come as part of broader changes, which you can read about here.

I was thrilled when I discovered Sketch. For a long time, one of my primary tools was Macromedia Fireworks, a pioneering drawing and prototyping application that blended bitmaps and vectors and featured ‘symbols,’ reusable components that could take variables.

At the time, nothing matched Fireworks for UI work. The component-based paradigm allowed you to design a button and drop it into several screens using different labels. If you tweaked the original button, all instances would change. Amazing.

Continue reading

Digital Dependency

I’m old enough to remember knowing people’s phone numbers. Here’s how it worked: if I wanted to call a friend or family member, I’d pick up the phone and dialed. Their numbers were among the many pieces of information rattling around in my memory. Of course, I didn’t know everybody’s number; some I had written down in a paper-based address book. If the person I wanted to call wasn’t in my address book, I could look them up in the (also paper-based) phone directory. I could also ask someone else for their number.

It’s been a long time since I’ve had to go through this process. Here’s how I call someone these days: I search for the person’s name in my iPhone and tap their phone number. The marvelous pocket supercomputer takes it from there, initiating the call without me having to type (much less remember) the number. I don’t talk much on the phone anymore. Still, this new way of calling saves me lots of time. It’s also liberated me from having to remember lots of “useless” information. Why memorize frequently called numbers if I can just tap away at the person’s entry on my phone?

Continue reading

TAOI: Reimagining Email

The architecture of information:

The team at Basecamp has developed a new product, Hey. It seems like an interesting — and opinionated (I mean this in a good way) — reimagining of how email works. If you have some time, Basecamp CEO Jason Fried’s video introduction is worth your attention:

Hey was in the news yesterday because its mobile app is being pulled from Apple’s iOS App Store, and Basecamp’s management is vocally fighting the move. Much has been written about that situation already, and I won’t say more about it here. I say it “seems” interesting because I haven’t yet tried it firsthand; currently, access to the product is by-invitation. My thoughts below are based solely on the product’s website and the video above.

Continue reading

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.

Outlook Spaces

Last week I was reminiscing about Microsoft Entourage, an old (and discontinued) Mac groupware app:

Entourage was Microsoft’s answer for Mac users who wanted Outlook. Like Outlook, Entourage allowed you to manage your calendar, contacts, tasks, and notes, alongside email. But it also included an interesting feature that wasn’t available in Outlook: the Project Center.

The Project Center allowed you to create focused views of your emails, appointments, tasks, notes, and files. It narrowed down the information in Entourage according to project-specific filters that you’d configure. I was running a design consultancy at the time, and Project Center made it easier for me to keep track of several projects simultaneously.

Entourage was replaced by a “proper” Mac version of MS Outlook in 2010. Alas, the Project Center didn’t make the cut. At that point I moved to Mac OS’s built in calendar, contacts, and mail apps, and haven’t looked back.

I’m bringing this up because a recent post on The Verge highlights a leaked upcoming feature for Outlook:

Microsoft is working on a new organizational feature for Outlook, named Spaces. Twitter user WalkingCat revealed the new tool in a leaked video over the weekend, and Outlook Spaces looks like it’s designed to allow users to collate emails, notes, files, documents, calendar appointments, and to-do lists into online spaces. It looks like it will be useful for students or businesses that are planning projects.

I don’t usually point to posts about unreleased products, but am making an exception for this one because of two reasons. First, I have a soft spot for placemaking metaphors in software design. The name of this feature (“Spaces”) is clearly such a metaphor. Second, Outlook Spaces sounds a lot like Entourage’s Project Center — but smarter.

Project Center had a lot of promise in theory. In practice, it was a slog. The problem was that the system required a lot of maintenance. The search filters for each project had to be adjusted often; if a team member joined or left the project, you had to re-configure the filters. You also had to manually tag emails, notes, tasks, and events. So while the system would indeed focus your information, it wasn’t very smart: you had to work at it, not just in it.

Outlook Spaces may solve this problem. The leaked description highlighted on The Verge suggests upcoming releases may use AI to automatically discover and group information. This would make using such a system much more practical, since it wouldn’t require as much maintenance. (Of course, this is assuming that the AI works properly.) The possibilities are exciting.

Still, such a system may not work for me in 2020. Twelve years ago, I communicated mostly through email, so Entourage was a nexus for my work life. These days, my communications are spread over a variety of systems: email, Slack,, Twitter, LinkedIn, etc. This makes it much more difficult to centralize communications, and a system like this one would have to include everything to be useful.

As a result, I suspect that Outlook Spaces would be most useful for organizations that are all-in on Microsoft’s ecosystem. That’s unlikely to be my case anytime soon. That said, I’m excited by the prospect of such at tool using modern technologies.

Leaked video reveals Microsoft’s new Outlook ‘Spaces’ feature

Alternatives to 32-bit Apps on macOS Catalina

When a new version of macOS comes out, I usually upgrade my computer relatively soon. I like having access to the latest features, and significant macOS release upgrades are generally trouble-free. That hasn’t been the case with the newest version, Catalina. The trouble stems from the fact that Catalina doesn’t run 32-bit applications. While most major software in the system is now 64-bits, there are still some stragglers — especially legacy apps and drivers that haven’t been (and likely won’t be) upgraded.

That’s why I waited longer than usual before upgrading to Catalina: there was one application in my system that was 32-bits, the driver for my Fujitsu ScanSnap S300M scanner. I knew this driver was incompatible because every time I launched it (under Mojave, the previous version of macOS), I’d get a warning saying that the app would not run in the future. (Here’s a way to learn which apps won’t work: under the Apple menu, go to About this Mac > System Report… > Legacy Software.)

Without this driver, the scanner is useless — even though the hardware is perfectly functional. This device is an important part of my workflow; I use it every other week to digitize most of my paper documents and correspondence. Fujitsu no longer sells this model and has no plans to release 64-bit drivers. So I was stuck. I had two choices: I could hold off on upgrading the operating system (for a while), or I could buy a new scanner. I didn’t like either option. Sooner or later, I’d have to upgrade the OS. And as I said, the scanner itself was in perfect condition; I didn’t need a new one. What to do?

It turns out there was a third option: look for an alternative driver. I found a third-party application called VueScan that works with a range of scanners, including the S300M. It’s been working well for me; the only downside is that it’s a bit slower than Fujitsu’s driver. But given my use of the scanner, it’s not slow enough to merit buying a new device.

Thus far, Catalina has been great. I’m especially enjoying the new Sidecar feature, which allows me to use my iPad as a second screen when I’m on the go. So far, everything is working for me — including my old scanner. The lesson: if you’re contemplating upgrading to Catalina, but are holding back because of legacy software on your system, consider looking for alternatives.

On Google Reader

Yesterday, I tweeted about missing Google Reader:

The tweet touched a nerve; lots of folks have chimed in, mostly agreeing with the sentiment or recommending substitutes.

To be clear, I still read RSS feeds every day. (I use Reeder on the Mac and iOS and synch my feeds using Feedly.) Although I’m open to exploring alternatives, I’m not unsatisfied with my current arrangement. (Ringing endorsement!) So I’m mostly not lamenting the loss of Google Reader’s functionality. Instead, I miss what Google Reader represented: a major technology company supporting a truly decentralized publishing platform.

Google’s brand imparted some degree of credibility to an emergent ecosystem. I suspect a nontrivial number of people must’ve tried RSS feeds because Google provided a tool to read them. It’s great that tools like Feedly, Reeder, Feedbin, NetNewsWire, etc. exist, but none of them have the broad appeal or brand power that Google does.

I said I’m “mostly” not lamenting the loss of Google Reader’s functionality. This is because while current RSS readers offer the basics, Reader was a natural, cohesive component of my personal information ecosystem. Unsurprisingly, it looked and felt like (and integrated with) other Google tools like Gmail and Google Calendar, which I was using extensively at the time. As befit a Google product, Reader also offered excellent search capabilities. None of the RSS readers I’ve tried since offer the same level of coherence and integration that I experienced with Google Reader.

I sense Google Reader was a casualty of Google’s primary business model: selling its users’ attention to the highest bidder. I doubt RSS provided the scale or control required to run a mass advertising business. IMO it’s no coincidence that Google pulled the plug on Reader at a time when centralized social networks (Facebook, Twitter) were gaining traction in the mainstream. (Google+, which the company had launched a couple of years earlier, failed to take off. I wonder if they saw Reader as competition for G+?)

Six years after Google Reader’s disappearance, we’re wiser to the limits of centralized control over news aggregation. Subjectively, I sense many people are rediscovering the joys of blogging. (And, like me, using the social networks mostly as a way to publicize our blog posts.) Podcasts — which are based on syndicated feeds — seem to be more popular every year. While I miss Google Reader, I believe decentralized syndication is an essential part of the web’s future — not just its past. Is the time right for Google (or any of the other major tech platform companies) to embrace the platform again?

Desert Island Apps

I’m always looking for ways of optimizing my personal information ecosystem. By this, I mean focusing on the work rather than futzing with the environment where the work happens. Ideally, I’d log into my computer, do a bunch of work, and then log out without having to think too much about the tools I’m using or how I’m using them.

The challenge is that digital tools are constantly evolving. There may be a new app out there that eases a part of my workflow, or perhaps one of the tools I’m already using has a hidden feature I’m not using. Sometimes such innovations can lead to tremendous efficiency gains, so it’s important to step back and review the ecosystem every once in a while. It’s a tradeoff between spending time working on the work versus on the way we work. A subtle, but important distinction.

Earlier in my career, I devoted a higher percentage of my time to working on my ecosystem than I do now. My toolset has been relatively stable for a long time. In part, this is because I eventually realized that many “new and improved” digital tools are specialized adaptations of more general, deeper tools.

For example, when my family and I were preparing to move to the U.S., I bought an app that allowed me to catalog my book library. I spent quite a bit of time messing around with that app. Eventually, I realized it was actually a specialized spreadsheet — something that’s also true of many lightweight data management apps. Rather than spending time learning a new app that perhaps adds a couple of timesaving features (in the case of the library app, it was reading ISDN codes), I could devote the time instead to figuring out how to do what I needed with the tool I already had: Excel.

Excel is an example of what I call a “desert island” app. Like the concept of desert island books (i.e., the short list of books you’d like in your bag if you were to be stranded in a desert island), these are digital tools that I could use to get my work done even if I had access to nothing else. They tend to be deep and broad, have large and devoted communities of users, and have been around for a long time. Other tools that fall into that category for me are the Emacs text editor, the Unix shell (along with its suite of “small pieces loosely joined” mini-tools), OmniGraffle for diagramming, and Tinderbox for making sense of messes.

Editing my newsletter in Emacs.
Editing my newsletter in Emacs.

These are all tools I’ve used for over a decade. (In the case of Excel, Emacs, and the Unix shell, over two decades.) But even after all this time, I’m nowhere near mastering them. My relationship with these desert island apps is a lifelong journey in which I will continually become more proficient — which will, in turn, make me more efficient. I test drive new apps now and then, but I always return to these old standbys. The effort of learning to use them in new ways is often less than that required by integrating new tools into my workflow.

What about you? Do you have “desert island apps”? Please do let me know — I’m interested in learning about what makes digital systems stand the test of time.