Deep Work – Book Review

What?: Book Review of Deep Work: Rules for Focused Success in a Distracted World.

Goal: Deep work (page 3 of book) = “Professional activities performed in a state of distraction-free concentration that push you cognitive capabilities to the limit. These efforts create new value, improve your skill, and are hard to replicate.”

Kryptonite: Shallow work (page 7 of book) = “Noncognitively demanding, logistical-style tasks, often performed while distracted. These efforts tend not to create much new value in the world and are easy to replicate.”

Why?: Must read book for knowledge workers seeking to reduce the distractions in their lives and reclaim the ability to do deep work. These notes are my own attempt at doing deep work on developing the process of deep work.

How?: My notes are below, hopefully will give sense of the structure/logic of the books arguments (in Part 1: The Idea) and process (in Part 2: The Rules). The book is highly recommended, link to purchase is above.

INTRODUCTION

Cal opens with the story of Carl Jung’ deep work sanctuary in the town of Bollingen. Taken from Mason Curry’ fantastic book Daily Rituals: How Artists Work.

The Daily Rituals book is a good companion piece to Deep Work and I highly recommend both since it demonstrates the actual thoughtfulness that went into the productive daily rituals of dozens of artists and creators. One can argue that “talent” and “genius” are an excuse that many of us use to let ourselves off the hook for not doing deep work. Swimming in the shallows is much easier.

Carl Jung needed his Bollingen sanctuary to do the consistent deep work necessary to counter the Freudian school in the 1920s and build the field of analytical psychology. Cal makes the argument that figures as diverse as J.K. Rowling and Bill Gates accomplished what they did due to a deep commitment to deep work – a rare and increasingly difficult skill in our hyperconnected/ distracted world.

Cal argues that unlike the folks mentioned above and many others, modern knowledge workers are losing the ability to do deep work – because of network tools (combination of social networking and infotainment sites optimized to keep you in the shallows: Facebook, Twitter, email, sms, Reddit, Buzzfeed etc.) that replace such deep work with connectivity and resultant shallow work. Network tools are ultimately responsible for fragmenting our discipline, days and schedules such that the unbroken chunks of time needed for deep work are not available.

For someone like me who has been working on developing deep work ability for sometime, these arguments are non-controversial. I believe whole sectors of the economy (e.g. advertising) are built around attention theft and distraction. The Internet just makes this worse since it enables jumping from one shallow to another painless and addictive.

However, this is not all bad. The very fact that you have read this review (hopefully without jumping to quickly check your Facebook, Twitter, email or text message feed) this far increases the odds that you agree with Cal’ core idea behind Deep Work (from page 8 of book):

“Our work culture’ shift towards the shallow (whether you think it is philosophically good or bad) is exposing a massive economic and personal opportunity for the few who recognize the potential of resisting this trend and prioritizing depth…”

Anecdote about Jason Benn’ learning programming…to highlight the contemporary benefit of deep work:

1. Deep work allows you to learn fast – an incredibly valuable skill at a time that our information economy is dependent on fast evolving and complex systems.
2. Deep work allows you to capitalize on the digital network revolution instead of getting drowned in its distracting shallows. By actually focusing on producing (instead of just consuming the latest distraction…) your best quality work, you can reach much larger audiences. A simple heuristic would be to not get stuck in the shallows of easy skills (from page 14 of book):

“The real rewards are reserved not for those who are comfortable using Facebook (a shallow task, easily replicated), but instead for those who are comfortable building the innovative distributed systems that run the service (a decidedly deep task, hard 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.

For those still not convinced, Part 1 argues more deeply about the importance of deep work.

PART 1: THE IDEA

For those on the fence, important to realize that deep work is increasingly THE differentiating factor for successful knowledge workers. In a world where most of your competitors are drowning in the shallows (social media, multi-tasking etc.), building your ability to do deep work is valuable, rare and meaningful – i.e., critical for a successful/ consequential life.

Chapter 1: Deep Work is Valuable

Stories about the value created by the deep work of Nate Silver, David H. Hansson and John Doerr. These three respectively belong to three separate categories of 21st century workers outlined in the book Race Against the Machine: How the Digital Revolution is Accelerating Innovation, Driving Productivity, and Irreversibly Transforming Employment and the Economy

1. The High-skilled workers: comfort with complex systems and intelligent machines.
2. The Superstars: With no/few substitutes in “winner-takes-all” markets.
3. The Owners: the capital providers who can leverage technology on a never before seen scale.

Cal argues that if you can join one of these three groups, you will do well. If you can’t, you might still do well (due to local factors like supply-demand in your region and/or industry) but your situation will be more precarious.

Two Core Abilities for Thriving in the New Economy:

1. The ability to quickly master hard things: The learning payoff from deep work. Anecdotes about Nate Silver, SQL databases and Stata (I was surprised to learn that Nate Silver doesn’t use R). Simply put, your ability to comprehend complex systems and learn the tools that make these systems understandable and actionable requires deep work and deliberate practice.

2. The ability to produce at an elite level, in terms of both quality and speed: Story of David Hansson’ reaching programming superstardom by creating Ruby on Rails. The work process of marketing professor Adam Grant was in a recent book excerpt.

Cal ends this chapter with a brief on Jack Dorsey (co-founder of Twitter & Square) as a person who thrives without depth. However, this was in my opinion one of the weaker sections of the book since Dorsey is now clearly more of a manager than a maker, a distinction wonderfully made by Paul Graham.

Chapter 2: Deep Work is Rare

Three trends in the workplace that damage your ability to do deep dives:

1. Open-offices: a complete shift towards collaborative work spaces at new tech companies such as Facebook. Microsoft in its heyday used to publicize getting your own office as key to doing valuable work
2. Instant messaging
3. Push for content producers to maintain social media presence

All three trends decrease one’s ability to do deep work due to attention fragmentation. Cal argues that the unquestioned support for these trends is a result of the difficulty of assigning credit to individuals for contributions (what economists call performance ambiguity). In the absence of clear metrics for deeper work, busyness becomes a proxy for productivity.

The Principle of Least Resistance (page 58 onwards): 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…[this principle} “protected from scrutiny by the metric black hole, supports work cultures that save us from the short-term discomfort of concentration and planning, at the expense of long-term satisfaction and the production of real value.”

Busyness as Proxy for Productivity (page 64): 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.

I especially liked this section since it gets to the core of why people waste time in impression management by doing busywork – the black hole of performance metrics makes the quick responder to emails/ messages appear to be a great producer in spite of their drowning in the shallows doing easily replicable work.

Chapter 3: Deep Work is Meaningful

Easily the most philosophical section of the book – Cal connects deep work with the sacred craftsmanship embodied in the work of Mathew Crawford Shop Class as Soulcraft: An Inquiry into the Value of Work.

The link between depth and meaningful work gets muddied as knowledge workers are encouraged to engage the “community” via social networking, i.e., stay in the shallows. Similar to the earlier connection between deliberate practice and deep work, in this section Cal connects depth to Mihaly Csikszentmihalyi’ notion of Flow and its link with happiness, Flow: The Psychology of Optimal Experience (Harper Perennial Modern Classics).

This section ends with what was the theme of Cal’s earlier book: So Good They Can’t Ignore You: Why Skills Trump Passion in the Quest for Work You Love:

Deep Work/Flow/ Deliberate Practice ⇒ Career Capital ⇒ Opportunities and Success.

Notice that “follow your passion” is not part of this equation. Instead, the key insight (page 91) is that:

“You don’t need a rarified job; you need instead a rarified approach to your work.”

If one is undisciplined and unfocused enough to be distracted by shallow work, the solution is not a “dream job” but developing a more craftsperson like approach to ones work and putting in the rituals and processes that allow deep work to happen, the point of the next section of the book.

PART 2: THE RULES

This is arguably the more important part of the book since it focuses on actual steps to take as you build your Deep Work processes. This part is split into four rules (chapters):

Rule #1: Work Deeply

Understand the importance of willpower as a finite resource (I no longer believe that willpower is a finite resource. People conflate ego depletion or finite willpower with decision fatigue. In addition, the idea of ego depletion or finite willpower has not been supported in replication studies) i.e., structure your life to limit its depletion. Routines and rituals protect you from letting your attention get hijacked by the superficial.

Here Cal introduces 4 philosophies of Deep Work:

1. The Monastic Philosophy of Deep Work: could be title the way of the reclusive genius, exemplified by Stanford’ Donald Knuth and Neal Stephenson This strategy works by eliminating or radically minimizing shallow obligations.

Key question: would you like to be known for creating iconoclastic works or for being responsive and approachable? Clearly, not a strategy for everyone.

2. The Bimodal Philosophy of Deep Work: A more reasonable work strategy, involves splitting your days between deep and shallow work. The former periods should allow for unbroken cognitive intensity, i.e., no open emails or Facebook newsfeeds. A very attractive idea from Cal (page 108): “dedicate a four-day weekend to depth and the rest to open time.”

Key question: is the value derived (serendipity, collaboration etc.) or need for (part of job etc.) shallow work great enough that the monastic style wouldn’t work.

3. The Rhythmic Philosophy of Deep Work: Transform deep work into regularly scheduled work and don’t break the chain.

Key question: Is your day-to-day life going to allow you to follow a bimodal (let alone monastic) process? If not, the rhythmic philosophy might be for you. It allows for daily scheduling and chipping away at building your deep work muscles instead of running the equivalent of a deep work marathon as a beginner.

4. The Journalistic Philosophy of Deep Work (115): In this section Cal uses Walter Issacson’ career as a prototype. Apparently, Issacson due to his training as a journalist (constant deadline driven writing habit) was trained to “shift into a writing mode on a moments notice.”

Key question: This philosophy depends heavily on your ability to do the instantaneous cognitive switches from shallow to deep work when time permits. Can you do that?

According to Cal, he follows the journalistic method although he organizes/schedules deep work.

Ritualizing and scheduling key elements (Where you’ll work? How long? How you’ll work? How you’ll support your work) will reduce your cognitive switching costs, decision fatigue and willpower depletion that can derail the best-laid plans.

The remainder of this chapter discusses the grand gesture (demonstrating commitment either in time and/or $ in doing the deep work), the hub-and-spoke architecture of innovation (switching between collaborative serendipity and isolated deep work), the whiteboard effect (collaboration as a way to add deadlines/ constraints to trigger deep work).

The Four Disciplines of Executing (since executing is more difficult than strategizing):

1. Focus on the wildly important: i.e. make the priority THE PRIORITY.
2. Act on lead measure: e.g. focus on inputs (hours spent/week in deep work) than distant outputs.
3. Keep a compelling scorecard: to tally and calibrate #2.
4. Create a cadence of accountability: use scheduled reviews to link your plans to execution.

Be Lazy: (page 143) “deep work – the serious efforts that produce things the world values…these efforts need the support of a mind regularly released to leisure.” Shutdown work thinking completely at the end of the day – avoid the pinprick onslaught of small obligations. Formalizing this process by actually having a shutdown ritual was my key takeaway from the end of this section.

Rule #2: Embrace Boredom

Ability to concentrate intensely is a skill that must be trained…simultaneously wean your mind from a dependence on distraction.

Most people take breaks from distractions (email, instant messaging, meetings, social networking etc.) to work. Cal recommends the opposite (161): “schedule the occasional break from focus to give in to distraction”. Here’s a challenge: schedule in advance when you will use the Internet, and then avoid it altogether outside these times.

Three points about Internet Scheduling:

1. This strategy works even if your job requires internet use and/or prompt email replies: you can schedule internet blocks frequently.
2. Keep the time outside internet blocks absolutely internet-free: self-explanatory, resist the temptation to give in.
3. Schedule the internet at home as well to improve concentration training: ignore texts, calls, internet outside of your scheduled blocks – even at home.

“to wait and be bored has become a novel experience in modern life, but from the perspective of concentration training, it’s incredibly valuable.” (page 165)

Productive Meditation (170): take a period in which you’re occupied physically but not mentally – walking, jogging, driving, showering, swimming (in my case) – to focus your attention on a single well-defined professional problem (writing a paper outline, preparing a talk, business strategy etc.).

Suggestion #1: Be wary of distraction & looping – i.e. avoiding going deeper/ next steps and instead attention just rehashing what you already know.

Suggestion #2: Structure your deep thinking – i.e. keep the relevant variables in your working memory to play around with. Define the next-step questions.

Rule #3: Quit Social Media

This will be hard for many. Having quit Facebook 6 months ago for good, I understand Cal’s point about people looking at social network avoidance as an eccentricity.

Social networks fragment our time and attention – I now think of them almost as junk food, cant be part of a healthy lifestyle (although Twitter addiction is still an issue for me – working on it).

Cal’s fundamental argument (page 184): “accepting that these tools are not inherently evil, they might even be useful…but at the same time also accepting that the threshold for allowing a site regular access to your time and attention (not to mention personal data) should be much more stringent.”

The problem is that most people fall for FOMO and use…

The Any-Benefit Approach to Network Tool Selection: You’re justified in using a network tool if you can identify any possible to its use, or anything you might possibly miss out on if you don’t use it.

Instead use a more thoughtful approach to curating the tools that consume your time and attention…

The Craftsman Approach to Tool Selection: (page 191) Identify the core factors that determine success and happiness in your professional and personal life. Adopt a tool only if its positive impact on these factors substantially outweigh its negative impact.

The key takeaway here is to actually thoughtfully identify your goals (both professional and personal) and then analyze the impact of network (substantially +, substantially – or 0) tools on them. The word substantially is key, if excluded you run the risk of invoking FOMO for every tool out there.

Cal outlines examples of both professional (page 196) and personal goals (page 198) that are really succinct and allow you have a laser focus on priorities and the key activities that support.

The personal goal (maintaining close and rewarding friendships with a group of people who are important to me) is reflected in the key activities (which are not supported by Facebook).

1. Regularly take the time for meaningful connections with those who are most important to me (e.g. a long talk, a meal, joint activity).
2. Give of myself to those who are most important to me (e.g. making nontrivial sacrifices that improve their lives)

“If you service low-impact activities, therefore, you’re taking away time you could be spending on high-impact activities.”

Leave social media (all) for 30 days, then ask yourself:

1. Would the last 30 days have been notably better if I had been able to use this service?
2. Did people care that I wasn’t using this service?

The second question gets to the common belief that “people care what I have to say” According to Cal the rise of social media is driven by the disconnect between the real hard work of producing real value and the positive reward of having people pay attention to you. (page 207)

Instead, what we have a low-value quid pro quo of you “like” my status update and I’ll “like” yours.

A corollary of the above insight (applies to both social media and infotainment) is the need to put more thought into your leisure time – not getting lost in fruitless rabbit holes of clickbait.

Rule #4: Drain the Shallows

The last chapter focuses on the reality that many people will identify with – most workdays are not filled with real deep work but instead swimming in the shallows. Using the example of 37signal’ cofounder Jason Fried’s experiments with reduced work days following the logic that “When you have fewer hours you usually spend them more wisely”…Cal recommends:

Ruthlessly identify the shallowness in your current schedule…treat shallow work with suspicion because its damage is vastly underestimated (page 221).

Schedule your days in 30-minute increments – DO NOT LIVE IN AUTOPILOT MODE

Much of this section is derived from Cal’ fantastic blog that I recommend you check out:

Scheduling isn’t about constraints – its about thoughtfulness.

“You must overcome this distrust of structure if you want to approach your true potential as someone who creates things that matter.” (page 227).

A great takeaway from this part is this simple question to quantify the depth of any task: 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?

Say NO to projects infused with shallowness…make NO the default answer.

Become Hard to Reach

1. Make people who send you email do more work – create sender filters.
2. Do more work when you send or reply to emails – i.e. close loops…
3. Don’t respond: avoid responses to emails that have one or more of the following: a) Ambiguous or hard to make reasonable response. b) Not a question or proposal that interests you. c) Nothing good would happen if you did respond and nothing bad would happen if you didn’t respond.

This connects with Tim Ferriss’ blog post on Letting Bad Things Happen.

CONCLUSION

I cannot recommend this book highly enough. As I mentioned in the opening, this review is really for my own use – to keep myself accountable to doing deep work. But I have no doubt that if you found my notes interesting enough to reach till this point, the book will be transformative.

Deep Work: Rules for Focused Success in a Distracted World