Introduction

Defining the difference between Deep Work and Shallow Work, and why we should focus on the former.

Deep Work v.s. Shallow Work

  • Deep Work: 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.
  • Shallow Work: 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.

The Deep Work Hypothesis

The ability to perform deep work is becoming increasingly rare at exactly the same time it is becoming increasingly valuable in our economy. As a consequence, the few who cultivate this skill and then make it the core of their working life, will thrive.

Part I: Philosophies

“I will live the focused life, because it’s the best kind there is.” — Winifred Gallagher

The first two chapters of Part I were pragmatic. They argued that deep work is becoming increasingly valuable in our economy at the same time that it also is becoming increasingly rare. This represents a classic market mismatch: If you cultivate this skill, you’ll thrive professionally. The final chapter has little to add to this practical discussion. Instead, it moves beyond the well-reasoned and pragmatic to a more human level of resonance.

Deep Work Is Valuable

On Being Valuable: Two Core Abilities For Thriving In The New Economy

  1. The Ability To Quickly Master Hard Things: Deliberate practice
  2. The Ability To Produce At An Elite Level, In Terms Of Both Quality And Speed: High-quality work produced = time spent * intensity of focus

The two core abilities just described depend on your ability to perform deep work.

Deep Work Is Rare

Reasons Why Deep Work Is Rare:

  • Metric Black Hole: A lot of things are hard to measure, and therefore ignored.
  • The Principle Of Least Resistance: In a business setting, without clear feedback on the impact of various behaviors to the bottom line, we will tend toward behaviors that are easiest in the moment.
  • Busyness As A Proxy For Productivity: In the absence of clear indicators of what it means to be productive and valuable in their jobs, many knowledge workers turn back toward an industrial indicator of productivity: doing lots of stuff in a visible manner.

The principle of least resistance, protected from scrutiny by the metric black hole, supports work cultures that are shallow.

Deep Work Is Meaningful

  • A Neurological Argument For Depth: We tend to place a lot of emphasis on our circumstances, assuming that what (not) happens to us determines how we feel. However, decades of research suggests that our worldview is based on what we pay attention to, and the content of what we focus on matters. If we give rapt attention to important things, and therefore also ignore shallow negative things, we’ll experience our working life as more important and positive.
  • A Psychological Argument For Depth: Mihaly Csikszentmihalyi’s concept of flow — the best moments usually occur when a person’s body or mind is stretched to its limits in a voluntary effort to accomplish something difficult and worthwhile. The feeling of going deep is in itself very rewarding, our minds like this challenge, regardless of the subject or the content.
  • A Philosophical Argument For Depth: The idea of craftsmanship, is not to generate meaning, but rather to cultivate in himself the skill of discerning the meanings that are already there. There’s nothing intrinsic about the manual trades when it comes to generating meaning. Any pursuit — be it physical or cognitive — that supports a high level of skill can also generate a sense of sacredness. “We who cut mere stones must always be envisioning cathedrals”.

Part II: Strategies

We find ourselves in distracting open offices where inboxes cannot be neglected and meetings are incessant; we are disciples of depth in a shallow world. In part II, the book will show us how to use strategies to transform deep work from an aspiration into a regular and significant part of our daily schedule. One might ask: Why do we need such involved interventions?

What we know, is that people fight desires all day long, desire turned out to be the norm, not the exception. More importantly, we have a finite amount of willpower that becomes depleted as you use it. The key to developing a deep work habit is to move beyond good intentions and add routines and rituals to your working life designed to minimize the amount of your limited willpower necessary to transition into and maintain a state of unbroken concentration.

Work Deeply

Decide On Your Depth Philosophy

  • The Monastic Philosophy of Deep Work Scheduling: This philosophy attempts to maximize deep efforts by eliminating or radically minimizing shallow obligations. Practitioners of the monastic philosophy tend to have a well-defined and highly valued professional goal that they’re pursuing, and the bulk of their professional success comes from doing this one thing exceptionally well. This strategy works well for someone whose contribution to the world is discrete, clear, and individualized. Example: Donald Knuth.
  • The Bimodal Philosophy of Deep Work Scheduling: This philosophy asks that you divide your time, dedicating some clearly defined stretches to deep pursuits and leaving the rest open to everything else. During the deep time, the worker works monastically, with intense and uninterrupted concentration. During the shallow time, such focus is not prioritized. This division of time between deep and open can happen on multiple time scales. This philosophy is usually deployed by people who cannot succeed in the absence of substantial commitments to non-deep pursuits. Example: Carl Jung.
  • The Rhythmic Philosophy of Deep Work Scheduling: This philosophy argues that the easiest way to consistently start deep work sessions is to transform them into a simple regular habit. Generating a rhythm or chain for this work removes the need for you to invest energy in deciding if and when you’re going to go deep. Example: part of Cal Newport’s strategy.
  • The Journalistic Philosophy of Deep Work Scheduling: This philosophy envisions a world where individuals are trained to shift into a writing/deep mode on a moment’s notice, as is required by the deadline-driven nature of their profession. This approach relies on agility but is quite hard, and is not for deep work novices. Without practice, such switches can seriously deplete your finite willpower reserves. Example: Walter Isaacson. Part of Cal Newport’s strategy.

Ritualize

  • Great creative minds think like artists but work like accountants: They ritualize their work and approach. To make the most out of your deep work sessions, build rituals of the same level of strictness and idiosyncrasy. Some questions to address when deciding how to ritualize:
    • Where you will work and for how long
    • How you will work once you start to work
    • How you will support your work

    Be willing to experiment and figure out the right rituals.

  • Make Grand Gestures
    • By leveraging a radical change to your normal environment, coupled perhaps with a significant investment of effort or money, all dedicated toward supporting a deep work task, you increase the perceived importance of the task. This boost in importance reduces your mind’s instinct to procrastinate and delivers an injection of motivation and energy.
    • Grand Gesture is not just about the switch of environment, it’s the psychology of committing so seriously to the task at hand — put yourself in an exotic location to focus, to take a week off from work just to think, or to lock yourself in a hotel room until you complete an important invention: these gestures push your deep goal to a level of mental priority that helps unlock the needed mental resources.
  • Don’t Work Alone: Space plays a big role here. Cal Newport discussed the origin of “the theory of serendipitous creativity”, and how MIT and Bell Labs leveraged this. He also argued that the current open office approach in technology companies doesn’t get it quite right.
    • Key is to maintain both in a hub-and-spoke-style arrangement: expose yourself to ideas in hubs on a regular basis, but maintain a spoke in which to work deeply on what you encounter.
    • Distraction remains a destroyer of depth. Separate your pursuit of serendipitous encounters from your efforts to think deeply and build on these inspirations. You should try to optimize each effort separately, as opposed to mixing them together into a sludge that impedes both goals.
    • Even when you retreat to a spoke to think deeply, when it’s reasonable to leverage the whiteboard effect, do so. By working side by side with someone on a problem, you can push each other toward deeper levels of depth.

  • Execute Like A Business

    The 4DX framework is based on the fundamental premise that execution is more difficult than strategizing. After hundreds of case studies, these 4 basic disciplines seem to work well in conquering that difficulty.

    • Focus on the wildly important: Identify a small number of ambitious outcomes to pursue with your deep work hours.
    • Act on the lead measures: Lag measures are things that you are trying to ultimately improve. Lead measures measure the new behaviors that will drive success on the lag measures. For individual deep work, it’s easy to identify the relevant lead measure: time spent in a state of deep work dedicated toward your wildly important goal.
    • Keep a compelling scoreboard: individual scoreboard should be a physical artifact in the workspace that displays the individual’s current deep work hour count.
    • Create a cadence of accountability: weekly review, make plan for workweek ahead, look over scoreboard to celebrate good weeks, help understand what led to bad weeks, and figure out how to ensure a good score for the days ahead.
  • Be Lazy: have good separation of deep work and rest, a shutting down routine, which is based on two premises:
    • You have a plan you trust for its completion
    • It’s captured in a place where it will be revisited when the time is right

    Reasons why shutting down is good:

    • Downtime aids insights
    • Downtime helps recharge the energy needed to work deeply
    • The work that evening downtime replaces is usually not that important

Embrace Boredom

Rule 1 above taught us how to integrate deep work into our daily schedule and support it with routines and rituals designed to help you reach the limit. This section will help you significantly improve your limit of concentration. The key idea is that getting the most out of your deep work habit requires training, specifically to improve your ability to concentrate intensely and overcoming desire for distraction.

Don’t Take Breaks From Distraction. Instead Take Breaks From Focus

To succeed with deep work you must rewire your brain to be comfortable resisting distracting stimuli. This doesn’t mean that you have to eliminate distracting behaviors; it’s sufficient that you instead eliminate the ability of such behaviors to hijack your attention. Internet blocks are one such tactic:

  • Schedule in advance when you’ll use the internet, and then avoid it altogether outside these times: it’s not about internet usage itself, but the constant switching that teaches your mind to never tolerate an absence of novelty. This weakens your concentration muscles.
  • This strategy works even if your job requires lots of internet use and/or prompt e-mail replies: the total number or duration of your internet blocks doesn’t matter nearly as much as making sure that the integrity of your offline blocks remains intact.
  • Regardless of how you schedule your internet blocks, you must keep the time outside these blocks absolutely free from internet use. (I still find this a bit questionable.)
  • Scheduling internet use at home as well as at work can further improve your concentration training

Work Like Teddy Roosevelt

  • Identify a deep task. Estimate how long you’d normally put aside for an obligation of this type, then give yourself a hard deadline that drastically reduces this time. This earlier deadline forces you to work with great intensity.
  • Don’t try this experiment more than once a week at first — giving your brain practice with intensity, but also giving it rest. Once you feel confident in your ability to trade concentration for completion time, increase the frequency.

Meditate Productively

Take a period in which you’re occupied physically but not mentally — walking, jogging, driving, showering — and focus your attention on a single well-defined professional problem:

  • Be Wary Of Distractions And Looping:
    • When you notice your attention slipping away, gently remind yourself that you can return to that thought later, then redirect your attention back.
    • Looping: your mind will attempt to avoid excess expenditure of energy when possible. One way to do that is to avoid diving deeper into the problem by instead looping over and over again on what you already know.
  • Structure Your Deep Thinking
    • Start with a careful review of the relevant variables for solving the problems and store these in your working memory
    • Define the specific next-step question you need to answer using these variables
    • Consolidate your gain by reviewing clearly the answer you identified

Memorize A Deck Of Cards

Training using memory palace. The key to this strategy is not the specifics, but instead the motivating idea that your ability to concentrate is only as strong as your commitment to train it.

Quit Social Media

The distraction of social media and infotainment are serious. These tools fragment our time and reduce our ability to concentrate. The problem is dire if you’re attempting to improve your ability to work deeply, because willpower is limited, and therefore the more enticing tools you have pulling at your attention, the harder it’ll be to maintain focus on something important. To master the art of deep work, you must take back control of your time and attention from these sources of distraction.

Tool Selection Philosophy

Internet can provide enormous values, and it’s unrealistic to give up internet altogether just to avoid distraction, so how do we reconcile this? Cal argues that the crucial thing is our attitude to tool selection. Here are two tool selection philosophies:

  • The Any-Benefit Approach to Network Tool Selection: You’re justified in using a network tool if you can identify any possible benefit to its use, or anything you might possibly miss out on if you don’t use it.
  • The Craftsman Approach to Tool Selection: Identify the core factors that determine success and happiness in your professional and personal life. Adopt a tool only if its positive impacts on these factors substantially outweigh its negative impacts.

The problem with the any-benefit approach is that it ignores all the potential negatives that come along with the tools in question. The craftsman approach to tool selection, is a lot more selective in weighing the pros and cons of using that tool.

Apply the Law of the Vital Few to Your Internet Habits

Here is the process to apply the law of the vital few:

  • Identify the main high level goals in both your professional and your personal life
  • List out for each the two or three most important activities that help you to achieve the goals. They should be specific enough to allow you to clearly picture doing them, but not so specific that it ties to a one time outcome.
  • Next, consider the network tools you currently use. For each such tool, go through the key activities you identified and ask whether the use of the tool has a substantially positive impact, a substantially negative impact, or little impact on your regular and successful participation in the activity.
  • Now the important decision — keep using this tool only if you concluded that it has substantial positive impacts and that these outweigh the negative impacts.

All of this is motivated by The Law of the Vital Few, sometimes also called the 80/20 rule. In many settings, 80 percent of a given effect is due to just 20 percent of the possible causes. Mathematically, it says that things follow a power law distribution. And the lesson here is that contributions to an outcome are not evenly distributed.

All activities, regardless of their importance, consume your same limited store of time and attention. If you service low-impact activities, therefore, you’re taking away time you could be spending on higher-impact activities. It’s a zero-sum game. And because your time returns substantially more rewards when invested in high-impact activities than when invested in low-impact activities, the more of it you shift to the latter, the lower your overall benefit.

Quit Social Media Experiment

Here is how you can conduct the experiment:

  • Ban yourself from using internet services for thirty days
  • Then by the end of the 30 day experiment, ask yourself:
    • Would the last thirty days have been notably better if I had been able to use this service?
    • Did people care that I wasn’t using this service?
  • If both are yes, then perhaps this tool has significance to you. But even then you should follow the vital few principle to carefully decide if this tool is for you.

Don’t Use the Internet to Entertain Yourself

“Great and profound mistake which my typical man makes in regard to his day, is that even though he doesn’t particularly enjoy his work, he persists in looking upon those hours from ten to six as the day, to which the ten hours preceding them and six hours following them are nothing but a prologue and epilogue. This is utterly illogical and unhealthy.” — Arnold Bennett

Bennett advocate the idea of “day within a day” — a man should and can make deliberate use of your time outside work, and put more thoughts into your leisure time:

  • Plan in advance what you’re going to do with your evenings and weekends before they begin.
  • Structured hobbies provide good fodder for these hours, as they generate specific actions with specific goals to fill your time.

At this point you might worry that adding such structure to your relaxation will defeat the purpose of relaxing, which many believe requires complete freedom from plans or obligations. Bennett, anticipated this complaint, and gave an elegant answer:

“What? You say that full energy given to those sixteen hours will lessen the value of the business eight? Not so. On the contrary, it will assuredly increase the value of the business eight. One of the chief things which my typical man has to learn is that the mental faculties are capable of a continuous hard activity; they do not tire like an arm or a leg. All they want is change, not rest, except in sleep.”

Drain the Shallows

The thesis of this chapter is that shallow work increasingly dominates the time and attention of knowledge workers. The problem with shallow work is that it takes up a lot of time, but if you eliminate it, the bottom line is barely affected. Therefore, it’s important to ruthlessly identify the shallowness in your current schedule, then cull it down to minimum levels — leaving more time for the deep efforts that ultimately matter most.

Schedule Every Minute Of Your Day

  • At the beginning of each day, plan your day. Divide the hours your workday into blocks and assign activities to the blocks. Every minute should be part of a block. As you go through the day, follow this schedule.
  • If your schedule is disrupted, you should, at the next available moment, take a few minutes to create a revised schedule. The goal is not to stick to a given schedule at all costs, it’s instead to maintain, at all times, a thoughtful say in what you’re doing with your time going forward.
  • If you find that schedule revisions become overwhelming in their frequency, recognize that you’re almost definitely underestimating how much time you’re going to need, do not fall into the trap of creating a base-case scenario wishful thinking schedule. If this does happen
    • Use the overflow conditional blocks — if you are not sure how much time a task will take, block additional time as buffer zone.
    • Be liberal with task blocks — have regularly occurring blocks of time to address surprises keeps things running smoothly.
  • In addition to regular schedules, you can adopt a rule that if you stumble onto an important insight, then this is a perfectly valid reason to ignore the rest of the schedule for the day. Stick with this unexpected insight until it loses steam. By then, step back and rebuild the schedule.

Quantify The Depth Of Every Activity

  • To quantify shallow work, use the following evaluation criterion: 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?. If a task requires many months of training to replicate a task, then this indicates that the task leverages hard-won expertise.
  • Once you know where your activities fall on the deep-to-shallow scale, bias your time toward the former.

Ask Your Boss for a Shallow Work Budget

  • Here is an important question that’s rarely asked: What percentage of my time should be spent on shallow work? Minimizing this percentage realistically will change your behaviors. You will be selective and say no to shallow projects, be more protective your time, and they force you to place a hard limit on the amount of less urgent obligation to creep your schedule.
  • The reason why these decisions should start with a conversation with your boss is that this agreement establishes implicit support from your workplace. This conversation will force the boss to give explicit approval for that ratio. Faced with these numbers, and the economic reality that it’s incredibly wasteful to pay a highly trained professional to send emails and attend meetings, a boss will be led to the natural conclusion that you need to say no to some shallow work to streamline for deeper work.

Finish Your Work By Five Thirty

  • Fixed Schedule Productivity: fix a firm goal of not working past a certain time, then work backward to find productivity strategies that allow you to satisfy this declaration.
    • Be very selective about saying yes to work that will yield shallow work
    • Be clear in the refusal but ambiguous in the explanation
    • Be incredible conscientious about managing time
  • This strategy frees up our time without diminishing the amount of new value we generate. It allows us to produce more than if we had defaulted to a more typical crowded schedule. The limits to our time necessitate more careful thinking about our organizational habits.

Become Hard to Reach

  • Make people who send you e-mail do more work
    • One approach is called sender filter — asking the correspondents to filter themselves before attempting to contact.
    • Cal even goes as far as “I will only respond to those proposals that are a good match for my schedule and interests”. The advantage is that it changes the expectation of whether the correspondent will receive a response, which frees you from the guilt of not replying.
  • Do more work when you send or reply to e-mails: Before sending a quick response, pause a moment before replying and take the time to answer the following key prompt:
    • What is the project represented by this message?
    • What is the most efficient (in terms of messages generated) process for bringing this project to a successful conclusion?

    He call this the process-centric approach to e-mails. The goal is to use this message to “close the loop”.

  • Do not Reply: Do not reply to an e-mail message if any of the following applies
    • It’s ambiguous or otherwise makes it hard for you to generate a reasonable response
    • It’s not a question or proposal that interests you
    • Nothing really good would happen if you did respond and nothing really bad would happen if you didn’t

    From Tim Ferriss: “Develop the habit of letting small bad things happen. If you don’t, you’ll never find time for the life-changing big things.”

Misc

  • Watch out for Attention residue: When switching from some task A to another task B, your attention doesn’t immediately follow. A residue of your attention remains stuck thinking about the original task.