022: Deep Work Part 2

Deep Work Part 2

Color Commentary

Table of Contents

1. Why Deep Work
2. Steps to Deep Work
3. Lack of Focus is Not a Character Flaw
4. Attention Residue
5. Shutdown Complete
6. Let’s Get Practical

1. Why Deep Work?

Brad Feld, a great venture capital investor, has been saying for years that the machines have already taken over “I don’t think enough people have accepted that the machines have already taken over. They are patiently waiting for us to catch up with them. The next time you are in front of your computer, notice how much information you are entering into it. It’s unclear whether we will have a computer-enhanced human future or a human-enhanced computer future, but it doesn’t matter. Our world is now interdependent with the machines, and more entrepreneurs should be working on the symbiosis between the two entities.”

He said that in 2012. Brad had just invested in early-stage Fitbit and I remember hearing him talk about it (I knew him when I lived in Boulder, Colorado) and thinking – um, really?

Well, Brad Feld is really smart. And he was clearly right. So how do we, the humans, move forward in a world of machines?

That is the premise of the book Deep Work, by Cal Newport, a computer science professor at Georgetown. I gave a short introduction to this book in the last issue, and now we can delve into it.

According to Newport, we do Deep Work and Shallow Work. (One assumes there is also…Medium-Depth Work? He doesn’t get into that. I don’t think professors do Medium-Depth.) His definitions of both are:

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. Deep work is necessary to wring every last drop of value out of your current intellectual capacity.”

Shallow Work:  “Noncognitively 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 machines are good at a lot of tasks, including both kinds of work, actually, but shallow work is the kind they can do less expensively than a human. Therefore, to succeed in today’s world and especially in the world of 20-30 years from now, Newport believes we have to be able to quickly master complicated things and be creative – and the only way to do that, he says, is to cultivate the ability to do deep work.

His version of deep work is what many describe as focused creativity.

Creativity is what makes most of us feel like doing whatever it is we do. Investing is the most creatively exciting task I have ever done, and the creativity it requires of me is what I love about it. I think it’s going to be a long time before our human ingenuity is threatened by the machines, so I take his point that that’s our human differentiator. It’s also what makes me want to get up in the morning, so, you know…there’s that.

Newport talks about creativity over and over in his book, and particularly how it’s not magical. It’s not happenstance. It’s not due to being a genius. It’s due to work. “Three to four hours a day, five days a week, of uninterrupted and carefully directed concentration, it turns out, can produce a lot of valuable output.” He went on: “In a New York Times column on the topic, David Brooks summarizes this reality more bluntly: “’[Great creative minds] think like artists but work like accountants.’”

I LOVE THIS. Obsessively. Great creative minds think like artists but work like accountants. That’s US. That’s investors. We get to be so creative, but the only way we get to be creative is if we show up to investing practice, regularly, to do the work and understand the companies. It’s perfect.

2. Steps to Deep Work

  1. Work Deeply. Create routines and rituals to make sure it occurs.
  2. Embrace Boredom. Deep work is a skill, not a habit. It’s like playing guitar, not flossing your teeth. Need to train for it. Can’t expect you’ll just be able to do it.
  3. Quit Social Media. If you’re going to take your attention and focus seriously, you’ve got to clean house. For most professionals, that’s going to mean you quit things like Facebook.
  4. Drain the Shallows. How do you reduce and control what remains of the shallow obligations that permeates most of our life? Can’t get it rid of it, but how do you control and reduce it enough to make space for deep work?

I’m going to touch on three subtopics that really grabbed me, all of which come back to his second step: Embrace Boredom.

3. Lack of focus is not a character flaw

Distraction from deep work is not just due to pervasive emails and social media, though those are primary distractors (and Newport gives some extremely practical tips in the book on how to reduce email back-and-forths). It’s US. It’s humans. It turns out, it’s our nature to prefer mind candy over hard concentration.

Newport cites a 2012 study that asked its subjects to report on desires they felt every thirty minutes. They discovered that people fight desires constantly, all day long, without end. (Side note: I’m not alone! I love this study, and also hate it for confirming that we seem to be wired for inner conflict. So there’s no respite?)

The top five desires the study subjects fought against include, not surprisingly, eating, sleeping, and sex – but also taking a break from hard work by checking email, going online, or watching TV. The study defines self-regulation as resolving goal conflicts internally. People with many conflicting goals must regulate themselves more often and with more self-control than people with clear goals, and minimal goal conflicts.

Suddenly, the genius of the book The One Thing’s advice to clear your mind of anything except your one most important goal, to the exclusion of everything else, is backed up by research. Reduce goal conflicts, therefore reduce the need for self-regulation, and therefore free up energy for focus.

Furthermore, get bored. Newport’s second step to deep work is to allow yourself time and space to get bored, so that your mind can wander into new ideas. He thinks a wandering mind is actually key to effective deep work because the subconscious can work on the harder problems if it has the time and energy to do so. The problem is that most of the time, we don’t give our brains that break. I don’t know about you, but if I have to wait in a line, I pull out my phone pretty quickly and start scrolling. He suggests NOT doing that. Look around, instead. It’s boring, and that’s the point. We avoid boredom like the plague because our brains somehow fight against us, seeking the desires cited in that study for immediate relief and mind candy. Yet, boredom is one of the best things we can offer ourselves to create a deep well of creative energy.

One of that study’s authors wrote a book called Willpower that I’ve put on my reading list. Newport sums it up thusly, in italics: “You have a finite amount of willpower that becomes depleted as you use it.” It’s not a character flaw to get tired and start to lose the ability to push yourself. It’s more like a muscle that gets tired. Isn’t that nice to know?

Therefore, setting up structures and rituals that reduce the amount of willpower needed to stay concentrated, as well as to allow your mind to relax and get bored, is absolutely key to being able to focus for long periods of time.

4. Attention Residue

There’s scientific evidence that if you are working deeply and switch your task, your attention doesn’t 100% move to that new task. There is residue of the previous task. It makes you perform more poorly on the new task. This concept of “attention residue” helps explain why deep work for several hours is so effective. Without the attention loss from switching tasks, the brain is more effective.

All of which tells me that my habit of keeping my phone next to me while I practice investing and checking it every time I get bored is NO BUENO. It’s creating attention residue. And it’s keeping me from my mind wandering through boredom.

And science is backing up the results. Neuroscientists believe that brain circuits get faster and more effective the more fatty tissue grows around each circuit, because it allows the cells to fire more effectively and faster. As you get better at a task, the science appears to show that more fatty tissue grows around the relevant neurons, and the corresponding brain circuit fires more effortlessly. It takes that circuit firing over and over again in succession to trigger the fatty tissue to grow.

It shows that deliberate, targeted practice works, on a neural level, to develop skill. Transferring your attention means switching neural pathways, which means the fatty tissue trigger might not fire.

How to reduce attention residue? I think it depends on what sort of deep worker you are. Newport says to create routines and rituals to make sure the deep work time occurs. Remember: think like artists but work like accountants. All great creators have routines such that it consistently opens the mind to deep work. I listed these methods in the last issue and am putting them here again because they are so helpful for modeling investing practice structure.

1. Monastery approach: This one is the most extreme. Think of a monk who detaches himself from the matrix. Not online, full hermit mode. Probably not realistic for any of us, but kind of nice to think about.

2. Bimodal approach: This is monk mode plus normal life, by dividing your time. For example, get away from everything for one week per month, then go back and do your normal job for three weeks. Or take an entire summer just to think. This professor wrote a really fun article, well worth a read, about her choice to do just that by taking one month in the summer, and also to limit her obligations to make sure she had the time to do deep work – and most of all, be happy.

3. Rhythmic approach: Like Jerry Seinfeld’s “write a joke every day.” Don’t break the streak! Maybe it’s 3 hours of deep work every day, no more, no less.

4. Journalistic approach: This one is probably what most of us do, right now. It’s certainly what I’ve done with my investing practice. Delve into deep work when you have the time and the inclination, like a journalist who needs to write on deadline. The challenge is to have a brain that’s ready to dive in on cue, and to keep diving in regularly and not letting it slip.

5. Shutdown Complete

Turn it OFF. Newport says he doesn’t work past 5pm. He calls it “digital sunset”: when the sun goes down, turn it off, it’s DONE. Yet, somehow he is way more productive than his peers.

He ends at 5 or 5:30. Checks his email to make sure nothing urgent (addresses urgent stuff), looks at what he can push into tomorrow, and then shuts down his computer and says to himself out loud: “Shutdown complete.” It’s very ritualistic. He then gives himself the rest he needs to create productively the next day.

Newport interviewed two people for the book about being “in flow,” feeling creative and energetic and like it’s all coming easily. Even in flow, it’s hard work on the brain to perform at a high level. The only way to do that sustainable is to shut down and rest. Just like an athlete, it’s training recovery so you’re consistently able to get up the next day and perform well. Athletes are sometimes called professional nappers, because their physical recovery is vital to their job. Whether brain or body, if you go hard, you need to recover. Newport says you can’t do deep work really more than 3-4 hours per day.

I am obsessed with this concept that taking a brain break all evening actually helps deep work the next day. It completely matches my own anecdotal experience. The takeaway from the science on taking a break actually is not only that taking a break is beneficial. We all knew that. It’s that NOT taking a break actually harms my ability to work well the next day. The harmful nature of constant busyness, constant brain work – whether deep or shallow – is my big takeaway from this book.

I’m going to be making some changes based on this research. It’s not the kind of change that is made overnight, and I’m not actually sure exactly what the change fully looks like yet. Still, here’s what I’m going to do:

  • Notice, and maybe track, the amount of time I spend per week in deep investing practice.
  • Notice, and maybe track, the amount of time I spend per week getting bored. (Curious about: is there a possible positive correlation between deep work time and getting bored time?)
  • Implement shutdown time. Accept that it may not happen every night, but if it happens more nights than not, that’s better than how it is now.
  • Create a shutdown ritual individual to me. Definitely make sure it includes loudly announcing to the entire room, however empty: “Shutdown Complete.”


Here’s a lovely little visual summary of Deep Work.

Does the concept of deep work appeal to you as an investor?

What type of deep worker do you think you are, according to Newport’s four styles?

It’s one thing to say “hey quit distracting yourself!” but that’s not very useful in real life. So, think about makes you feel fired up. What goal could you achieve in the next 6-12 months that will have a huge positive impact in your investing practice? Remember, we’re here for the long-term. Ten, twenty, thirty years of investing. Then, let practical limitations be crowded out by your passion for doing something great.

Great article on how one busy professor made her life work (also cited above)

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