Tackling New Challenges

When starting something new, you either know what steps are required to bring the undertaking to life, or you don’t. The former is the case when you’ve done something similar before. Let’s say you’re a designer who’s just started working on the design of a feature for a financial services system. If you’ve worked on a similar system in the past, you’ll have expectations about what you (and others) should do and in what sequence. You’ll mainly be looking for where your new project diverges from the patterns you’ve picked up from prior experience.

Other undertakings may be new to you but have been well-documented by others. Perhaps you’ve never worked on the design of the specific type of challenge this financial services system requires, but other people have. You can ask them, or read about it. It’ll take you a bit more time to get up to speed with such a project than if you have previous experience with something like it, but at least you have a framework to build on. Your challenge will be not just spotting instances where the project at hand varies from the pattern but also understanding what it is.

Still another class of undertaking is entirely new to you and to others. This is obviously a greater challenge than either of the two previous classes: You’ll be grappling with the content and context of the challenge and the frameworks that inform them. You may even have to invent frameworks and implement mechanisms to update them. This requires that you understand what goals they’re serving. But perhaps even the goals are unclear, and all you have is a hunch to go on. Scary stuff, especially if you’re committing resources to the project.

While this last class of challenges is rare, it can lead to breakthroughs. When facing such a challenge, I try to look for frameworks I can leverage from other fields. (Early in my career, I was using what I learned in architecture school in order to design websites.) The work will diverge fairly quickly as the specific character of the new challenge becomes evident, but starting with a dummy framework offers a point of departure and makes the undertaking less scary.

Intentional Computing

Thanks to the generosity of my friend Alex Baumgardt—who gifted me a functioning logic board—yesterday I brought my old Mac SE/30 back to life. My kids spent an hour or so exploring old games on its 9-inch monochrome screen while I reminisced about the days when that Mac was my primary computing experience. (My daughter Julia is smitten with Zork; I’m giddy.)

The kids had lots of questions.

“Does it have color?” No, it only has black and white.

“Does it have sound?” It used to. Gotta look into that.

“Does it play [current game]?” No, alas.

“Was it expensive?” In its day, it was very expensive.

“Does it ‘do’ the internet?” No, this one doesn’t.

An artifact from a different world.

I put my iPhone 8 Plus next to the SE/30. The phone’s screen lit up instantly, as it always does. It’s always on, and always on me. I’ve stopped thinking about using the iPhone as something I do. Instead, it’s become a natural extension of my day-to-day being. I simply take it out of my pocket, sometimes mindlessly.

Using the old Mac, on the other hand, is an intentional act. It’s off most of the time. To turn it on, you must flip a large mechanical switch on its back. It makes a loud, satisfying “thunk!” Various noises follow: a fan spinning up, the faint chirping of the disk drive. Then the “happy Mac” icon on the screen. A little world coming to life. Eventually, a folder appears showing the software available on the system. There’s not much there; a few games, a paint program, perhaps a text editor. No web browser, of course. (Although this particular Mac once had Netscape installed on it; I’d use it to browse the early web through a dial-up modem.)

“What do I want to do now?” isn’t a question I ever asked of this system. If I’d gone through the trouble of turning it on, it was because there was something I needed to do: work on a history paper, sequence some music, create an architectural model. (Yes, on the 9-inch screen! Good times.) A more intentional—a more mindful—way of computing. Closer to using a fine tool than a television.

I’m writing this in Ulysses’s “distraction-free” mode. Many text editors today have a similar feature: a way of forcing our always-on, always-connected, always-beckoning devices into something that works more like an SE/30. But what I’m talking about here is more than cutting out distractions; it’s about a different conception of the work and the tools used to do the work. It’s about computing as a discreet activity: something with a beginning, an end, a goal, with no possibility of meandering onto random destinations. As wonderful as the iPhone is (and it is a technological wonder), revisiting this 30-year-old computer made me think George R.R. Martin may be onto something.

Folder-centric to App-centric Workflows

Yesterday I had a busy day, that had me shuttling between Berkeley, Oakland, and San Francisco. In days like these, I prefer to work from my iPad (as opposed to a traditional laptop computer.) The iPad takes up less space, which makes it easier to use in cramped public transport. It also has an LTE modem, so I can remain connected to the internet when I’m out and about. Its smaller screen also encourages focus, which helps in distracting environments. I love it, and on days like these, I wonder when the day will come when I can do most of my work from an iPad.

That said, working from the iPad requires that I shift how I think about the structure of my work. I’ve written before about how I keep all my project materials organized using folders in the file system of my Mac. While iOS includes a Files app that allows interacting with such file structures, the system encourages app-centric (rather than project-centric) way of working. Rather than thinking “I’m now working on project x, and all the stuff for project x is in this folder,” context switching calls for remembering what app I was working in: “I was editing the document for project x in Google Docs; hence I must open Google Docs.”

Many of the productivity apps in iOS allow for arbitrary document groupings. Hence, I find myself replicating my file structure in the various apps. I end up with a project x folder in Google Drive, another in Pages, another in Keynotes, another in OneNote, etc. This adds to my workload and requires that I keep track of which app I used for what. I find it a less natural way of working than keeping everything grouped in a single folder. It’s one of the challenges of working in iOS that I’m continually looking to overcome.

Tracking Commitments

You’re making commitments all the time. Let’s say you and I agree to meet on Tuesday at 9 am. That’s a commitment. If I show up at our agreed meeting place on Tuesday at 9 am and you’re not there, you will have broken your commitment. I’ll be disappointed, and perhaps somewhat upset at having wasted my time. You may apologize, and we can agree on a new time to meet. When the time for the meeting comes, I’ll be wary. You now have a track record of having broken a commitment to me.

So keeping commitments to others is important. But so is keeping commitments to yourself. While breaking a commitment you’ve made to yourself may not carry the same social stigma than breaking a commitment to someone else does, the effects can be just as bad. You start letting things slip by. Eventually, you think of your commitments as fluid—you abide by some, and not others. You allow the more difficult ones to slip by, even though they may be important.

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Start With a Structure

Often, one of the biggest obstacles to getting started with something is your canvas’s initial blank state. It may be a white sheet of paper or a blinking cursor in the word processor. You stare at it, not knowing where to begin. When facing these conditions, I often find that adding a bit of structure does the trick. Having a framework frees you from having to pick a place to start. With a skeleton in place, your next step becomes clearer: all you must do is flesh it out.

Here’s an example. Many times in my life I tried to start a journal. Invariably, I’d sit down at the beginning of the day intent on writing a journal entry. Facing the blank document, I wouldn’t know where to start. What should I write about? The first few days (while still in the rush of having started a journal) I’d slog through the indecision. But eventually, something would happen—I’d wake up late, or go on a business trip—that would disrupt my routine. Under time pressure, the blank document became too hard an obstacle to overcome. I’d give up on journaling that one day, and it became a precedent. Soon I’d give up altogether.

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Managing Screen Time

One of the best features of the most recent version of iOS is called Screen Time. It allows you to monitor and control what you do with your mobile devices and when. For example, you can find out how much time you’re spending on social media apps and whether your usage is increasing or decreasing. You can also set limits for yourself on the device overall or on a per-app basis. And if you use multiple iOS devices (such as an iPad and an iPhone) you can configure Screen Time to show you your behavior across all of them.

To access Screen Time, you must open the device’s Settings app. (This feels a bit incongruous. Although I understand this is an OS-level feature, it feels like something that should be independent of Settings. Anyways, I digress.) In the Settings app you’ll see an option for Screen Time:

If you tap on this menu item, you’ll be shown a screen that looks like this:

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So Many Books

As an independent consultant, I spend a lot of time working in coffee shops and other venues near my house. One of these is my local public library. The library is a great place to work: it’s quiet, has comfortable furniture, good light, and (relatively) fast internet access. It’s my favorite place to work from—when I don’t have to be in meetings, of course. But there’s a downside to working in the library: it’s full of books.

I have a book problem. I love reading and find it difficult to visit the library without being drawn to the shelves. Last time I was there I checked out Ken Kocienda’s Creative Selection, an insider’s story about what it was like to be behind the scene’s at Apple during the heyday of the Steve Jobs era. In particular, it focuses on how the company makes software design decisions. Right up my alley! I’m enjoying it, but starting to read it means I’m spending less time with another book I’d started recently. (Robert Greene’s newest, The Laws of Human Nature.) Greene’s book, in turn, intruded into another book I was reading.

You can see how this would be a problem. If I keep going this way, I won’t finish any of them. So I’m starting to develop more stringent criteria about what I let through my reading queue:

  • It must be relevant to my work
  • It must be authoritative
  • It must be something I’ve not read before (i.e., a subject I’m unfamiliar with)
  • It must be engaging (I won’t waste with poor writing, no matter how fascinating the subject)
  • Bonus points: it’s over twenty years old and still considered the go-to for its subject

Many books don’t pass this test; those go into a “for later” tab in OneNote. But will later ever come? At this pace, it won’t. (Several lifetimes aren’t enough for all the interesting books out there!) But that’s OK as long as the books that I do give my attention to are highly relevant and informative, and my filter list helps with that.

Project Focus Mode

For most of my career, I’ve worked on several projects simultaneously at any given time. This means lots of information coming and going from and to different people, keeping track of documents and commitments, scheduling meetings, etc. Most of it happens on my computer, which for almost twenty years has been a laptop. (Meaning: it comes with me.) In the past few years, more mobile devices (e.g., iPhone, iPad) have also joined my toolkit. There’s a lot of things going on in these information environments. Keeping everything organized impacts my effectiveness; the time I spend looking for stuff isn’t valuable to my clients. Early on I realized that the only way I’d be able to do this would be if I developed organization systems, and stuck to them over time.

For example, I always have a “projects” folder on my computer. Each project I take on gets an individual subfolder in there. These folders use consistent naming schemes. These days it’s usually the client name, followed by a dash, followed by a (brief!) unique project name. Why not per-client folders? At one point I realized I had to strike a balance between depth and breadth. Going n-folders deep often meant not locating things as quickly. Of course, over time this folder can get crowded. Eventually, I determined the projects folder only needed to contain active projects; I set up a separate “archive” folder where I moved completed project folders.

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A Strong Body for Strong Workshops

I’m in the midst of an intense week that has me facilitating co-creation workshops for six days back-to-back. Every day starts around 7:00 and usually wraps with dinner around 9pm. In the middle, there’s a lot of standing around putting stickies on walls, coordinating sketching exercises, and leading folks through various other activities. Facilitating workshops is hard work. Doing so day after day for more than a couple of days is very intense. It’s cognitively and physically exhausting, and only works if the facilitator takes care of his or her body. For me, this means:

  • Eating healthy foods in small amounts. Many workshops treat meal times as work/social activities, and many of the “social” foods in our culture (such as pizza and sandwiches) can be carbohydrate- and fat-rich. Eating lots of carb-rich foods in the middle of the day can lead to reduced performance in the afternoon; you don’t want to be crashing at a time when you’re supposed to be helping energize others. Also be wary of snack foods meant to keep team energy and morale up. (Our workshop features a big tub of animal crackers.) I keep healthy snacks in my backpack; it helps me resist the temptation of indulging in sweets.
  • Not drinking too much. There’s an important social component to working successfully with the same group of people over several days. Workshop participants often decompress by sharing a few drinks at the end of the day. A glass or two of wine or a cocktail may be ok, but be mindful of not over-indulging; you don’t want to try to lead a workshop while fighting a hangover.
  • Getting lots of sleep. Your body needs to recuperate after long days of work. Especially when drinks are involved, you may be tempted to hang out until the wee hours. Not getting enough sleep can seriously impair your effectiveness as a facilitator.
  • Meditating. I often start the day by sitting silently for 15-20 minutes, observing my breath. Doing so clears my mind and helps me prepare for the intense day ahead. Meditation requires no equipment; it’s an easy practice you can do anywhere at any time.
  • Working out. This is often harder to fit into workshop days, especially if schedules start early and end with dinner/drinks. However, it’s important to move your body—especially if you’ll be spending the rest of the day in a conference room. During workshops, I prefer to exercise by going for a run outdoors, even if it’s cold outside; I’ll be spending most of my time during the day inside an office or hotel and this is a good opportunity to get some fresh air.

Workshop facilitation is an intense cognitive activity; you must head into the day with a good idea of what you will be doing and what you expect to get out of it. But it also has an important physical component. The mind won’t be as effective if not supported by the body. When I’m leading workshops, I think of myself as a kind of athlete; as with other athletic endeavors, training, preparation, and discipline lead to better results. Taking care of your body is paramount if you aspire to lead workshops successfully.