Pretty Terrible: Archive

Published: April 6, 2017

I Read Cal Newport's Deep Work So You Don't Have To

Cal Newport’s Deep Work is both a useful and an incredibly infuriating work to read: there are a lot of really good productivity strategies but they're encased in a layer of academic tech-bro privilege of which he seems to be wholly unaware.

I also suspect you could glean most of Newport’s insights from his blog, upon which Deep Work seems to be based.

Newport draws a clear distinction between two types of work: deep work and shallow work.

Deep work is defined as:

Professional activities performed in a state of distraction-free concentration that push your cognitive capabilities to their limit. These efforts create new value, improve your skill, and are hard to replicate (page 3).

Shallow work is:

Non-cognitively demanding, logistical-style tasks, often performed while distracted. These efforts tend to not create much new value in the world and are easy to replicate (page 6).

Newport’s entire thesis is that deep work is, by its very definition, better than shallow work--because, in his opinion, this is the kind of work which is valuable. He never quite explains what he means by valuable, but it's clear that he does not find administrative work valuable--I wonder what his department's admins think of him? This stratification is consistent theme through the book.

The other consistent theme throughout the book is the use of successful white men as examples. There's no acknowledgement of the possible unfair advantages those individuals may have in their lives and Newport doesn't seem to realize that well-established thinkers and writers can make different decisions than those who are not so established. He also holds up CEOs as people who are highly skilled and who have earned their positions (pause for hysterical laughter) and, unfortunately, he’s uncritically bought into meritocracy ideal. As I said: academic tech-bro.

Newport puts forth four rules around developing a practice of working deeply and they form the meat of this book.

Rule 1: Work Deeply

This one seems to be pretty much a no-brainer, but there’s a fair bit of nuance in this section around evaluating your personal circumstances and determining which style of working best suits you: monastic, bimodal, rhythmic, or journalistic.

The monastic style requires you to essentially be able to ignore most or all aspects of day to day life in favor of your work. Bimodal requires the ability to be able to divide significant chunks of your time—weeks or months, not days or hours—to your work. For most people, neither of these styles are particularly realistic or attainable, which leaves rhythmic and journalistic. The rhythmic mode requires chunks of time and a “don’t break the chain” philosophy, where you do your work over consecutive days. Journalistic requires the ability to switch between modes of thought very quickly as you fit the work in where you can. I suspect that the rhythmic style is what works best for most people.

Once you’ve decided on your style, Newport recommends that you create rituals around your work and adhere to them as best you can. And while there is no one correct ritual, successful ones include clear starting and stopping times, locations, metrics for success, and what you’ll do in your life to support the work. Here’s an example: I’ve discovered that I am actually able to get writing done if I leave my house. So I have taken to blocking off chunks of time on my calendar for writing and going to the Starbucks that’s kind of near my house and writing for a few hours. What works for me, though, may not work for you and that’s fine.

Newport also recommends a process called 4DX: the four disciplines of execution, from the book of the same name. These principles are that you should focus on the “wildly important”, act on lead measures and not lag measures, keep a scoreboard, and create an accountability ritual, such as a weekly review. This is all based on the premise that execution is more difficult that strategy which I’ve found to be essentially true, except you don’t jump from strategy to execution without developing a plan. This read like a very high level summary of the 4DX principles and while Newport makes it clear that the philosophy isn't his own, he also never mentions that it's one created by FranklinCovey.

Other recommendations include making grand gestures—like checking into a hotel to finish a book—and not working in isolation, as contact with other people can feed serendipitous discovery. He also emphasizes the importance of downtime from work, which I was glad to see: working constantly with no breaks is not a way of working that is sustainable for pretty much anyone.

Rule 2: Embrace Boredom

Newport makes the observation that the ability to concentrate intensely is a skill that can be learned and one way to force yourself to learn it is to try to break your dependence on distractions--primarily the internet and social media. Newport relies heavily upon his anecdotal experiences to make sweeping statements about how and why people are distracted--he looks at his individual experience and assumes that his experience is universal.

I don’t disagree with his assertion that the internet and social media are tremendous distractions. They are. There’s a reason why programs like Anti-Social and Freedom exist and it’s because the internet is a great way to avoid doing work. But that doesn’t mean that it’s a universal bad thing or that there are no benefits. I do find it incredibly interesting that Newport makes no mention of this type of software, preferring instead to encourage the reader to just stay offline. (In my more uncharitable moments, I suspect Newport believes the use of these sorts of tools to manage time is weak.)

All that said, I find the idea of minimizing how often you switch between modes of thinking interesting and potentially helpful. I know that for myself, if I feel like I’m interrupted too often or if I have too many things to do all at once that I get overwhelmed and am unable to do any of them until I step back and evaluate the situation and put my tasks in order and only work on one thing at a time.

The whole point of embracing boredom is, essentially, to resist the urge to move to a new activity when you get bored or get stuck with your current one and that by leaning into the discomfort, you may gain some benefit from it.

Other things that are recommended in this section: creating false deadlines for yourself to trick yourself to work with greater intensity than you have in the past, using time that would otherwise be “wasted” while driving or walking to think in a structured way about your work (no suggestions on how to record those ideas while you’re otherwise occupied, though), and to memorize a deck of cards in order to practice a structured mode of thinking with unwavering attention. I find a lot of these suggestions interesting and mostly anecdotal in nature and probably not very useful for a lot of people out there. But if you're out there working on memorizing a deck of cards, do get in touch.

Rule 3: Quit Social Media

This is where the entire book goes off the rails and my notes from here on in shift from summarizing the information presented and into actual arguing with Cal Newport.

See, Cal Newport doesn’t use any social media networks and since he doesn’t use them and is successful, then clearly they are of no use to anyone. I feel like there should be a rule that if you have chosen not to use particular tools then you don’t get to make assumptions about how they work or the sorts of ways people use them or what kinds of relationships people form on them.

Newport does not believe that it’s possible to have a meaningful friendship with someone you only know online. He does not believe that social media can be used for marketing in a way that works (and isn’t gross and invasive). And he believes that the reason most people are on social media is because they’re attention seeking.

I feel like Newport has a personal axe to grind, as he compares how hard he had to work to get his blog readership numbers up and then social media came along and—I don’t know, maybe Twitter pissed in his Wheaties or something? He actually wrote this comparison of social media to blog posts: “It [social media] has replaced this timeless capitalistic exchange with a shallow collectivist alternative” (page 207). I am pretty sure he just called Twitter a commie pinko and the only explanation I can see is that he feels as if he worked really hard to earn his success and that all those people over on Twitter haven’t and how dare they get something that Cal Newport doesn't believe they earned.

Is social media an unalloyed good? No. Can it be a tremendous source of distraction? Yes. But like nearly everything else, it does have its benefits. I do agree with Newport’s assertion that if you are not getting a significant positive benefit from being on a service that you shouldn’t be on it. I also am a strong advocate for curating your social media experience pretty vigorously and limiting the amount of time you spend on it. I find his idea of a 30 day break (inspired by that of Baratunde Thurston) interesting and potentially a source of very good information.

But at the end of this chapter, I feel like I learned a lot more about Cal Newport than I did about how social media can be a detriment to working deeply. He’s basically the equivalent of someone who smugly proclaims that they don't watch television and that the only reason they own one is for the purpose of watching documentaries on PBS. That was an eye roll provoking sort of thing to say 20 years ago and saying the same about the social media now is also eye roll provoking.

Newport attempts to pre-empt criticism of his approach to social media but his efforts sound less like a rebuttal of criticism and more like a self-improvement seminar hard sell tactic (“if this were really important to you, you’d find the $500 to take this course”).

Rule 4: Drain the Shallows

This section talks about strategies you can employ to do more deep work in your professional life and the main tactic is to determine which of your tasks are shallow and which are deep.

Newport uses the example of a tech company that moved to a four day work week during the summer while not seeing a consequent hit in productivity as a revolutionary concept and an example of reducing shallow work. Summer work hours aren’t exactly a new concept: the first ad agency I worked for in the late 90s had half days on summer Fridays and it’s my understanding that this was not an uncommon practice in the industry.

Newport recommends that you schedule every minute of your work day and that you be conservative in your scheduling, as people tend to be terrible at estimating how much time tasks will take. The goal isn’t to stick to a rigid time table, but to increase mindfulness and to see how you actually are spending your time versus how you would like to spend it. This is something I’ve been doing the last few weeks and it’s been very helpful and it has helped to keep me on task.

This exercise isn’t intended to act as a constraint on your day—you should feel free to rearrange and reconfigure things as your day changes, but with a basic structure in place, you are treating your time with the respect it deserves. I feel like this was probably the most valuable insight in the book--that we should treat our time with respect.

There's also an exercise where Newport suggests that you quantify the depth of every activity. The measurement he uses is this:

How long would it take (in months) to train a smart recent college graduate with no specialized training in my field to complete this task? (page 229)

This sort of thinking devalues the administrative work that makes it possible for people like Cal Newport to lock themselves away in offices and think their important thoughts. It is also deeply disrespectful of people who work their hands in one way or another—I wonder what Newport thinks of the work that goes into keeping the bathrooms at his workplace clean, if he even thinks about it at all. Hey Cal: those toilets don't get clean all by themselves.

He then gives three examples and these examples are clearly intended to make his chosen profession look more important the sort of work most white collar professionals find themselves doing. The first example is that it would take 55 to 75 months to train a recent college graduate to edit an academic paper (not write, edit) for publication, while the second and third examples are significantly more common types of work: creating presentations and attending strategy meetings. Newport feels that it would only take two to three months for a recent college graduate to learn to do these tasks competently and thus, it's shallow work and not truly valuable.

This is also when I started wondering if Newport has ever held a non-academic job or if he's just using what he's read in Dilbert as his mental model.

The rest of this section is devoted to strategies you can use to manipulate your manager into letting you blow off work that you have decided is shallow and unimportant (thereby adding those tasks to someone else’s task list) and how to avoid answering emails or answering them in such a way that you make it clear the other person is going to have to do the bulk of the work they’re asking you to help with. This all strikes me as really bad advice, depending on your workplace's culture.


Did I learn anything from this book other than the fact that I would like to smack some sense into Cal Newport? Sure. I learned that building more structure into your days and then holding to that structure is one way to make sure that the work you wish to do gets done. That my current strategy of minimizing my distractions and to scheduling time for distraction is not a bad strategy. It also reminded me of how I used to work when I was in school--I would schedule the times I would do work and then once that was done, I was free to do pretty much whatever I wanted. What I guess I'm trying to say is that Newport doesn't have any genuinely new insights, he just happens to have a blog with a large audience and a number of posts on the subject that he worked up into a book. (Nice use of content marketing strategy.)

I also learned that it’s possible to write an entire book about productivity and lose sight of the fact that different people are going to have different circumstances, both at home and at work. I have also learned that there are entirely too many people out there getting book contracts who think that their personal experiences are universal and extrapolate that into systems and rules that may not actually work for everyone (I ran into this same problem with Gretchen Rubin’s book on habits).

My ultimate takeaway is that time management—both scheduling and respecting your time—is critical to productivity and pretty much everything else in life.