202306252017 Notes on "Deep Work"

Notes from a 2021 reading of this book. Contains a lot of advice on staying focused and productive in a world of distractions that I think will be always be useful.

Introduction

Definition: Deep work is work done in a distraction-free environment that pushes your cognitive ability to the limit. This kind of work generates value, and it also hard to replicate in other environments.

Its logical opposite — shallow work. Logistical tasks that are easy to replicate, and which usually don’t end up adding any value.

Why is Deep Work still relevant today? 2 reasons.

In an information economy, it’s an extremely valuable skill to be able to pick up complicated things quickly.
To succeed in a world of excess availability, where there are 10 different options for anything that you might want on the internet, the best (and only) way to distinguish yourself from the rest of the pack is to produce the absolute best work you can produce. This requires deep work.

Deep Work Hypothesis: The ability to do Deep Work is becoming rarer just as its becoming more valuable.

Part I

Deep Work is Valuable

Types of jobs that will be disproportionately valuable in the current economy:

High-Skilled Workers. “Are you good at working with intelligent machines or not?"
Superstars. People who’re the best at what they do. If other people want them, they can just hire them remotely.
Owners. People who have the capital to invest in the new technologies that are driving the restructuring.

Core Abilities for Thriving in the New Economy

Being able to quickly master hard things.
Being able to produce things at an elite level, both in terms of quality and speed. It’s not enough to just master things - you have to produce the corresponding tangible value.

These two core abilities depend on someone being able to do deep work.

Deep Work Helps You Quickly Learn Hard Things

Performance psychology from the 1970s found that deliberate practice was the answer for many performance differences between atheletes.

Components of deliberate practice:

Your attention is focused on whatever you’re trying to master
You receive feedback to correct your approach, allowing you to focus your attention on whatever would be most productive.

Deliberate practice has shown to be psychologically effective, but there’s a biological reason as well — the protein myelin, which surrounds neurons and makes them fire faster and cleaner, is put into place by oligodendrocytes, which are often triggered by repetitive behavior.

Deep Work Helps You Produce at an Elite Level

For Adam Grant, business professor at Wharton, splitting up his work in uninterrupted stretches has seemed to be crucial to his success. He does this “splitting up” in multiple ways:

Doing teaching in the fall, and research in the spring
Alternating between times when his door is open to students, and when he isolates and focuses on a single research task

A law of productivity: High-quality work produced = (time spent) x (intensity of focus)

Definition: Attention residue, when you switch from Task A to Task B but a residue of your attention remains thinking about the original task.

Exceptions

Jack Dorsey, chairman of Twitter and on the board for Square, seems like an exception (maybe he doesn't need deep work to be productive?)

In general, if deep work is so important, what about the distracted people that do well?

The point of good CEOs is that they’ve built up a treasure trove of experience that lets them make good decisions quickly.
In general, people who can afford to do this are very rare. It’s usually going to be to your advantage to strongly consider depth unless you’re a high level executive or something.

Deep Work is Rare

Three common modern trends:

Open offices
Instant communication (Slack, etc) in the office
Content producers need to have a social media presence

Obviously, these not only do not facilitate deep work, but are sometimes directly antithetical to deep work.

Definition: Metric black hole, the space into which depth-destroying behaviors fall into — resistant to easy measurement, but nevertheless decisively unproductive. Alternatively, practices that facilitate deep work are often hard to measure in terms of impact, so they also fall into this category.

If it was clear that certain practices were unproductive, they would’ve long been removed from the workspace, but because of the metric black hole, it is markedly unclear when certain practices are effective or not, which helps them continue even when they’re unproductive for employees.

Definition: Principle of Least Resistance: In the absence of other information, people in businesses (and in general) gravitate towards behaviors that are easiest in the moment.

Connectivity is easy in the moment — if you can always message someone on Slack, asking them for help, it’s a lot easier than having to wait a certain period of time and struggling to figure it out on your own.

Email is also something that’s easy to spend time on during the day, as opposed to having to thoughtfully think about how you actually want to allocate your time and energy during the day.

It’s also easy to forward emails to colleagues, with a one word missive like “Thoughts?”, but it causes a lot of pain and time on the colleagues’ part to come up with a good response.

Business as a Proxy for Productivity

For a lot of knowledge workers, it’s not exactly clear for them what it means to be successful and productive. Therefore, they’re turning to “visible busyness” because they don’t have a better way to demonstrate their value.

This can entail quickly replying to emails, having a ton of meetings, meeting people in halls walking around, answering “Hall” or internal SO questions, etc.

This also becomes hard to disprove because of the metric black hole. Clearly, in the Information Age, busyness is at best tangentially related to busyness; sometimes it’s directly opposite to it.

The Cult of the Internet

It’s become increasingly easier to assume that any new hi-tech technology is for the good; we no longer consider the tradeoffs of the new efficiencies with the problems introduced.

Internet companies and internet products are seen as harbingers of a new technology and a new world, rather than what they actually are (companies, with investors, run by twenty-and-thirty-somethings looking to make a profit).

Deep Work struggles in the cult of the internet, because a lot of its core principles (quality, craftsmanship, mastery) are decidedly nontechnological, and just plain old unsexy compared to the new playthings of the Internet ideology.

Deep Work is Meaningful

For craftsmen, deep work and having a good life (enjoying the focus and concentration you need during your craftsmanship, and seeing the quality of the product you produce) are inextricably linked.

Argues that knowledge workers can extract the same level of satisfaction from deep work.

A Neurological Argument for Depth

Skillful management of attention is the sine qua non of the good life and the key to improving virtually every aspect of your experience.

Our brain constructs our worldview based on what we pay attention to.

If you spend enough time on deep work, which usually has a sense of gravitas associated with it, your mind will understand your world as rich in meaning and importance.

A Psychological Argument for Depth

Definition: Flow is a state in which the body or mind is stretched to its limits in pursuit of a difficult and worthwhile goal.

Deep Work produces a flow state, which produces happiness — deep work -> happiness.

A Philosophical Argument for Depth

After Descartes, and his focus on the individual, we’ve started tasking ourselves with creating meaning and finding meaningful things in our lives, which is difficult and can “induce a creeping nihilism”.

There’s nothing sacred in our lives anymore.

Going back to the example of the craftsman — the craftsman does not try to generate meaning, he just tries to discern existing meanings from things. That elevates his life from just the individual to something more.

Cool connection between good software engineering and good craftsmanship:

“Within the overall structure of a project there is always room for individuality and craftsmanship… One hundred years from now, our engineering may seem as archaic as the techniques used by medieval cathedral builders seem to today’s civil engineers, while our craftsmanship will still be honored.”

Even if the programming languages and techniques used in the future are way cleaner and more sophisticated than the code we write now, the code's quality/cleanliness/conciseness/clarity are all things that future generations will appreciate.

Your job doesn’t have to be glamorous for this to apply — it wasn’t ever glamorous to be a woodworker or a blacksmith. As long as you have a rarified approach to your work, you don’t need to have a rarified job.

Deep work can convert a task from a draining obligation to something that’s actively invigorating and satisfying.

Part II: The Rules

Rule 1. Work Deeply

The urge to turn your attention to superficial things is strong, which makes it hard to just decide to do deep work.

You have a finite amount of willpower, that becomes depleted as you use it.

Having a series of rituals and routines in place depletes a considerably less amount of your willpower, making it easy to keep going with good habits and deep work.

Examples of Deep Work Scheduling

Monastic Philosophy

Eliminating or radically minimizing shallow obligations

Bimodal Philosophy

Divide your time, dedicate specifically predefined stretches of time to deep work, and the rest of your time you can have free for everything else

For this specific approach, a day is the minimum amount of time you need for deep work (a few hours in the day is not enough, apparently)

Of course, the period of time could also be a specific season of the year, or a four-day-weekend as part of a week, and so on.

Rhythmic Philosophy

The easiest way to consistently start deep work sessions is to transform them into a regular habit.

This can also apply for a specific starting time that you start doing the work every day.

Make it so that just a little bit more gets done on a daily basis.

Journalistic Philosophy

Fit deep work wherever you can into your schedule.

Journalists are trained to shift into writing mode at a moment’s notice, because they always have to be ready to produce content by a specific deadline.

This approach is not for the deep work novice.

Context switching is hard.

Ritualize

Waiting for creative inspiration is usually not a good idea.

Most creatives have some sort of routine, or organization, that allows them to clear up their thoughts (thus freeing their brain for having more interesting thoughts).

Questions to Think About for Your Deep Work Ritual

Where will you work, and for how long? Be sure to provide a specific time frame.
How will you work, once you start to work? Banning internet use, maintaining a metric such as words produced per 20 minute interval, etc.
How will you support your work? Coffee, food, light exercise... As Nietzsche said: "It is only ideas gained from walking that have any worth."

Make Grand Gestures

Radically changing your environment in some way, along with investing a significant amount of effort (or money), signals to your brain that the task is important, and makes it more likely that you’ll continue using it.

Don’t Work Alone

Long setup provided here, but the main idea being that an open-office style, hyper-collaborative environment is not necessarily (immediately) detrimental to deep work.

The strategy here is to have an environment for deep work, but also having a series of hubs where you can regularly share ideas and build on them.

This is also not the whole story — sometimes a more collaborative (yet focused) environment is/was necessary to produce the best output (for example, the transistor).

Whiteboard effect -- working with someone else at the proverbial whiteboard can push you further along than if you were just working by yourself.

Execute Like a Business

4DX framework (4 Disciplines of Execution), for when you know what you have to do but you don’t how exactly to execute it.

Discipline 1. Focus on the Wildly Important.

Identify a small amount of ambitious pursuits to focus on during your work hours.

Choose the activity that’s going to drive the rest of your distractions away, because you’ll want so much to keep working on it.

Discipline 2: Act on the Lead Measures

Lag measures are the metrics that you’re ultimately trying to improve, like your overall RescueTime productivity score, for example.

Lead measures measure the new behaviors that are likely to drive success on the lag measures.

For example, a lead measure could be waking up early/sleeping, or having a regular Complice schedule every day, or eating well, or anything else that makes it more likely to have a good, productive day in the future, rather than trying to measure something that’s already in the past.

Another lead measure could be the time spent working on the important goal.

Discipline 3: Keep a Compelling Scoreboard

A visible record of the time spent on deep work for each hour, with a visible marker of the hour when a specific task was completed, for motivational purposes.

This also helps to calibrate the expectations for how many hours of deep work were needed per result.

Discipline 4: Create a Cadence of Accountability

Some kind of weekly review, where you make a plan for the workweek ahead.

Look over your scoreboard to celebrate good weeks, and understand what led to bad weeks

Be Lazy

By injecting regular moments during the day where your brain is relaxed and at leisure, you’re more likely to have insights, creative moments, and time to squeeze in deep work than if you have a bunch of meetings and busy work scheduled during the day.

How to implement “being lazy” in the information industry — after the workday, just stop thinking about work! Hard stop.

Reason 1: Downtime Aids Insights

Letting your subconscious brain mull over insights can often be a better use of time than consciously spending time wracking your brains over something.

I’ve noticed this too — things that I’m stressed/thinking about, I often just let them come to me, make decisions when the moments come, and don’t overthink them.

Reason 2: Downtime Helps Recharge the Energy Needed to Work Deeply

Pretty self-explanatory.

Spending time in nature can improve your ability to concentrate, apparently.

Walking on the street requires directed attention (so you don’t get run over), vs walking in nature provides less attention-hogging stimuli, letting your brain wander more.

The stimuli are still fairly interesting, however, which lets keeps your brain occupied enough that it doesn’t go looking for something else to think about, and this lets your attention replenish.

Reason 3: The Work That Evening Downtime Replaces Is Usually Not That Important

Your capacity for deep, elite work is limited for each day.

If you are able to get this done during the day, you don’t have much scope for stuff outside the day.

Commit to a shutdown ritual, that ensures that you have a plan for every incomplete task or goal.

Rule 2. Embrace Boredom

Rabbinic Judaism has a strong mental deep work component. Daily mental practice has served these people better than even their Ivy League degrees

Can’t spend time on deep work if you don’t wean your mind from a dependence on distraction.

Can’t flee from boredom!

If you’re used to spending every block of five free minutes checking your smartphone, your brain might be rewired to the point where your brain isn’t ready for deep work anymore!

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

Internet Sabbath - taking a break from the internet for one day a week

Alternative — choose a certain time where you can use the internet/give in to distractions, and don’t let it happen any other time.

If you really want to be distracted, but you notice that you have 30 minutes left, those 30 minutes will basically serve as mental calisthenics, and help train yourself

How to put this into practice:

The strat works even if you need a lot of Internet use (with the Focus app)

Regardless of how you schedule the Internet blocks, in any time outside of those blocks, you should keep the these blocks free of use.

Scheduling internet use blocks for at home as well as at work can improve your concentration training further

Something that’s crucial — in places where you’re forced to wait, and if you’re in an offline block, it’s very important to resist the temptation to check Reddit or something, to alleviate the temporary boredom. It’ll be a very valuable use of time to just be with your thoughts.

Work Like Teddy Roosevelt

Didn’t work long hours, but he scheduled any free blocks between the hours of 8:30am and 4:30pm for studying, and he worked on his studies with incredible intensity.

A couple ways to challenge yourself to achieve this intensity — set a much tighter deadline for this work than you usually would, or set some kind of countdown timer, and put it in a place such that you can’t avoid but look at it when you work.

Meditate Productively

Take a period of time in which you’re occupied physically but not mentally (walking, joggling, driving, showering), and focus your attention on a single, well-defined professional problem.

Be Wary of Distractions and Looping

When you find yourself thinking about something that can derail your current train of thought, resist the temptation to continue down that mental path, remind yourself that you can return to that thought later, then redirect your attention back.

You can also find yourself looping over and over information that you already know about a problem.

When you’re working on a proof, you can see yourself going through preliminary results again and again, instead of building on these results for the broader problem.

Structure Your Deep Thinking

“Thinking deeply” about a problem isn’t always self-evident; the next steps that you face upon thinking about a problem can be decidedly non-obvious.

Possible steps for structuring your deep thinking:

Take a mental note of all the variables you have — AKA information that you already have access to, and store them in your working memory. Example: Main points that you’re trying to make in a book chapter (if you’re trying to outline the chapter), actual variables if you’re working through a proof.
Think of the “next-step question” — The specific question that you need to answer using those variables. How am I going to effectively open this chapter (given all the points that I need to make)? What can go wrong assuming this property doesn’t hold?
Consolidate your gains, by reviewing clearly the answer that you’ve identified

Memorize a Deck of Cards

A difference that researchers found between normal people and world-champions at memory was attentional control — how effectively participants could maintain focus on essential information.

Memory control thus has a natural corollary/application towards deep work.

Professional memory athletes never attempt rote memorization (it never works!)

Card memorization technique:

Take a place that you’re familiar with, and you can visualize in your head.
Fix in your mind a collection of 10 items in each of these rooms (big items).
Choose a specific order that you’ll look at each of these items, in each room.
Need to do this for 5 rooms, with 2 additional ones, for 52 cards.
Come up with a memorable person or thing with each of the 52 cards.
One example is that Donald Trump could be associated with the King of Diamonds.
Once you see a deck of cards imagine the corresponding memorable person or thing doing something memorable near that item, in your tour of your house. For example, if the first item and location is that mat in your front yard, and the first card is the King of Diamonds, then you can picture Trump wiping mud off his shoes on the entrymat in the front hallway.

Skimmed this chapter, because I didn’t think that it had much to add for me. I’m just going to include a couple of key takeaways here, that I saw while skimming this chapter.

The Law of the Vital Few: In many settings, 80 percent of given effect is due to just 20 percent of the possible causes

The way social media works — it’s a way to short-circuit the connection between the hard work of producing real value and the positive reward of having people pay attention to you.

You can basically get attention for free, as long as you give that same free, shallow attention to other people.

Put more thought into your leisure time.

Rule 4: Drain the Shallows

Company implemented a 4 day workweek, people were stingy with their time and used it more effectively

Hard to just have deep work though, shallow work is still sometimes important, and deep work is hard to maintain.

Schedule Every Minute of Your Day

We spend most of our days on autopilot, and don’t give much thought to what we’re doing with our time.

Blocking tasks in a notebook, with a line for each half-hour, is an option for good timeblocking.

Estimates will be wrong, and things will appear on your plate.

If schedule is disrupted, when you get a chance, you should try to create a revised schedule for the day

To allow for unpredictability, you can have overflow blocks, that can have a dual purpose (without having to keep changing the schedule on paper).

Spontaneity is encouraged, especially if you have an interesting insight - just reschedule when you the chance.

Quantify the Depth of Every Activity

I think RescueTime is good for this!

How to categorize tasks in terms of shallowness/depth: 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?

Finish Your Work by Five Thirty

Fixed schedule productivity

Refuse things definitively, but provide ambiguous explanations. Eg, sounds interesting, but I can’t make it due to schedule conflicts.

In turning down obligations, also resist the urge to offer a consolation prize that ends up devouring just as much of your schedule. A clean break is much better.