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?​

Work Anywhere

I’ve never liked the phrase “work-life balance.” It’s a bad distinction: work is a part of life, and being alive is a prerequisite to getting work done. To think of the two as separate is to impoverish both, so I’m inclined to blur the lines. This is easier to do today than ever before. Many people see this as a negative, but not me.

By “work,” I mean creating value for others in exchange for some remuneration. There’s no reason why this should be constrained to a particular time or place. We’ve inherited our current work patterns from a previous era when work required expensive, fixed infrastructure. (Think industrial factories.) People agreed to be at this infrastructure at particular times of day, in shifts. This maximized efficiency for industrial work.

But this is not necessarily efficient for information work. If a client emails me to ask a question, a faster reply is often more valuable than one that takes longer. Using my little glass rectangle, I can get back to them from anywhere. I’ve generated lots of value while sitting in public transport, waiting for the teller at the bank, after finishing lunch, etc. These impromptu dips into “work” aren’t an intrusion into “life” — I see both as a continuous stream.

Independent consulting gives me great control over when and where I work. When I don’t have meetings, I like to work from my local public library, which is always quiet and pleasant. Or maybe I’ll walk to a coffee shop for a cup of tea. Whatever the case, changing my physical environment helps me get things done. I cordon off particular activities to one place or the other; the change of venue is a palette cleanser that allows me to shift my focus from one task to another.

This way of working is very effective for me. There were times in my career when I forced myself to sit at the same desk for eight-hour work days. Even though I was “working” more, I was much less productive. Tethering myself to the same place and forcing myself to produce “on command” was often a recipe for frustration. That’s not how the mind works — at least not mine. I need to shift modes, change the zoom on the lens, get my body moving.

I can engage more fluidly because my work doesn’t happen in physical environments; it happens in information environments. With small, powerful electronic devices, I can access those information environments from anywhere. This calls for discipline — the work needs to be done, after all — and organization. But the payoff is a release from the tension many of us feel between “work” and “life.” A well-ordered information ecosystem can simultaneously make us more effective and more engaged with the world beyond our desks.

My Digital Memory

I was an early user of Gmail. I don’t remember exactly when I signed up for the service, but I do know I was using it by September of 2005. It became my primary mail system in a relatively short span of time. There were four features that drew me into Gmail:

  • Its amazing anti-spam filters. Hooboy has this saved my sanity!
  • Its lightweight web-based UI.
  • Its large (for the time) storage allocations.
  • Its search functionality, which is (still) one of the best I’ve experienced in any system.

It’s the last two of these features that I want to delve into here.

Gmail isn’t just an email system; it’s a digital memory of my life. Shortly after I started using it, I imported the previous four years of mail into my account. As a result, I have a searchable email archive of the last eighteen years or so. This is an incredibly powerful thing to have at your disposal.

Email isn’t just about communicating with other people: We also receive confirmations for doctors appointments, bank statements, flight boarding passes, contracts, etc. Over time, these things add up to an important repository of information about your life. Something that may seem trivial now can be quite important in the future. Because you have so much space in Gmail, you don’t have to throw it out. And because Gmail’s search is so good, you don’t have to worry about categorizing it upfront.

Last night I was making a list of trips I’ve been on over the past few years. Compiling this list was relatively easy using Gmails advanced search: I used the before and after operators to define time windows​ and included the three-letter​ airport codes where I frequently fly from (SFO and OAK.) I completed what could’ve been a long, tedious task in a matter of minutes.

I particularly feel the power of my digital memory in its converse. Once I was trying to recall the exact date of an event that occurred prior to 2001. This proved surprisingly challenging. I’ve been paperless for the past decade or so (meaning I scan every important paper-based document that comes my way,) but I have few documents in my system from before this time. For stuff between 2001-2008, I can fall back on my Gmail archive. But I have scant information in my system before 2001. Searches return nothing. I looked for a long time among old paper-based archives for the date I needed, only to come up empty-handed.

Some people are very disciplined about keeping archives. I’ve gotten more so over the years, but have little to show for earlier parts of my life. For stuff in between, I can rely on Gmail as a digital memory; it seldom lets me down.

Marc Andreessen’s Guide to Personal Productivity

How we organize our personal information ecosystems impacts our productivity. Some patterns work better than others. (I’m always looking for ways of being more productive, which is why I started a podcast on this subject.) Although everyone does this a bit differently, not everyone gets the same results. I’m especially keen in finding out how very successful people organize themselves.

Few people have been as successful in the tech world as Marc Andreessen. He’s the co-founder of several influential companies, including Netscape — which helped usher the web revolution — and Andreessen Horowitz, one of the leading investment firms in Silicon Valley. Mr. Andreessen published a blog post twelve years ago that lays out his productivity principles. Given how successful he’s been, this post is worth studying.

Mr. Andreessen’s advice includes some counter-intuitive ideas. For example, he suggests not keeping a schedule. By this, he means not committing to appointments in advance. Instead, he proposes you focus your attention on whatever is most important or interesting at any given time. While he acknowledges that this may not work for everyone, it’s an intriguing notion. I live by my calendar, and this post has me wondering what it’d be like to just go with the flow. (My work doesn’t give me much leeway here. But it begs the question: what would I need to change to allow me to eschew my schedule?)

I also love the idea of managing just three to-do lists. (Mr. Andreessen suggests a Todo List, a Watch List, and a Later List.) I follow my own take on David Allen’s “Getting Things Done” approach, which means I have per-project lists; that’s too many at any given time. So I’m drawn to this idea of boiling it down to three. Also, he suggests writing down the 3-5 most important things you must do every day to keep your priorities straight. This is something I’ve been doing for a long time, to great results.

However, my favorite of Mr. Andreessen’s nuggets of advice is this: Only agree to new commitments when both your head and your heart say yes. I’ve been guilty of taking on too many things because I’m excited by the possibilities or interested in the subject (the heart saying “yes!”), only to find out later that I’m overcommitted and en route to disappointing myself and others. Giving the head a veto would’ve solved many difficulties for me.

It’s not a long post, and it’s aged well. (Just replace “iPod” with “iPhone”.) Well worth your attention.

Pmarca Guide to Personal Productivity

A Space for Collaboration

Yesterday I spent most of the afternoon working with a friend and colleague. We were synthesizing the results of a workshop we co-facilitated earlier in the week. It was fun, but I often felt constrained by the limitations of the space we were in and the technology we had available.

This type of work usually requires reviewing lots of photos from sketches and stickies posted on walls. My friend and I bounced ideas and memories from the workshop off of each other; we spotted patterns in these materials and captured them in a presentation deck. It’s easier to do this sort of work if we can both see the photos and files we’re editing. We took over the living room in my house, where we had access to ample wall space and projector. We projected photos from the workshop on one of the walls in the space, while we sat on the couch discussing their implications.

While this sounds like the ideal setup, soon it became apparent that there were limitations. For example, we were constrained to a single rectangular window of information on the wall. We could show photos and the document we were editing, but only if we split this rectangle, reducing our ability to see what we were doing. This was workable but not ideal.

A bigger issue was that only one of us could control what was being projected. For example, I was examining the photos from my laptop and my friend was editing the presentation deck. If I was sharing the pictures on the wall, we couldn’t see changes to the presentation deck and vice-versa. Yes, there are workarounds to this problem. For example, we could’ve used Google Docs (or something equivalent), which would’ve allowed us to edit the deck jointly. But this wasn’t ideal either. We spent more time than I would’ve liked trying to figure out how to best collaborate in this setup.

What I wanted was for all of the walls in my living room to be “digitally active” — to allow us to arbitrarily distribute our work around the room and jointly control it. Current computer display technologies are based on a one user/one computer/one display paradigm; projectors are treated as a display that is expected to be displaying the information of one computer at a time.

Instead, I’d like to place various photos on the walls around the room — perhaps recreating the space of the workshop. My friend would put his presentation on another wall. Both of us could then annotate and edit these digital objects arbitrarily. We’d be inhabiting a physical space that was also digitally active, a shared computing environment that we could inhabit and manipulate together.

Something like this is already being built at Dynamicland. That project features a space that allows users to manipulate digital information with physical artifacts. The digital information is projected onto the environment, with cameras detecting the positions of objects in physical space. As you manipulate these objects, the information projected on them changes. It’s a fascinating environment, one pregnant with potential. However, Dynamicland’s objective isn’t to extend our current collaboration paradigms but to reinvent them.

What I’m describing here is conceptually different: I want the sort of stuff we’re used to moving around in computer windows in our laptops and desktop computers up on the walls, while transcending the current single-user paradigm. (It’s a much more conservative vision than Dynamicland’s.) Does such a thing exist? (Perhaps using augmented reality instead of projectors?) It seems like it should be feasible.

Buffers: A Key to Working at Your Most Effective

I’m on an ongoing quest to be more effective with my time. This means — among other things — doing more with less: finding ways of being more productive in less time.

One of the most important principles I’ve learned is that my cognitive abilities vary throughout the day: Some times my mind feels fast and sharp while at others it feels slow and dull. Effectiveness requires the ​presence of mind to recognize when I’m in one state versus the other. Trying to get things done when I’m feeling dazed will lead to either taking longer, being frustrated, producing poor wor​k or — more often — a combination of all of them.

Knowing I’m not always available to do my best work, I batch tasks to focus on the ones I’m ready to work on at any given time. This requires creating buffers: parts of my information ecosystem I’ve set aside for “parking” things I’m not ready to deal with yet. Some of my buffers include:

Once every week or two I’ll go through each of these and “process” it — go through items in the inbox and do something with them, one at a time.

For example, I use one of my DevonThink inboxes to keep links I may share in my newsletter. I capture these throughout the day; perhaps I’ve read something in my RSS reader or through Twitter that may be of interest to my subscribers. I send that link to DevonThink, where it will wait until I start building my next newsletter.

I edit the newsletter every other Saturday. I’ve blocked time to sit at my computer and review all of the stories I’ve collected over the past two weeks. I decide which will make it into the next newsletter, and create short summaries that give readers the gist of the story. I’ll also write short posts, often inspired by what I’ve learned from reviewing the things that are going into the newsletter.

The process of editing the newsletter takes anywhere between two and four hours every two weeks. I consider it an effective use of my time. But this only works because I have a buffer; it’d take much longer if I had to deal with the materials I’m sharing at the moment I’ve found them — often with varying degrees of cognitive ability. Saturday mornings are less hectic for me than at other times of the week. I’m also usually rested. This gives me the necessary cognitive bandwidth to deal with this task.

The old Delphic maxim to “know thyself” is even more relevant today when we have so many sources of distraction. Knowing when you perform your best — and setting up places to park work until you’re able to deal with it at your most productive — is essential if you want to maximize your effectiveness. Setting aside buffers is a key component in an information ecosystem that’s structured to let you do your best work.​​