Discussion Questions: Deep Work by Cal Newport

Description of the Book (from Amazon):

One of the most valuable skills in our economy is becoming increasingly rare. If you master this skill, you’ll achieve extraordinary results.
Deep work is the ability to focus without distraction on a cognitively demanding task. It’s a skill that allows you to quickly master complicated information and produce better results in less time. Deep work will make you better at what you do and provide the sense of true fulfillment that comes from craftsmanship. In short, deep work is like a super power in our increasingly competitive twenty-first century economy. And yet, most people have lost the ability to go deep-spending their days instead in a frantic blur of e-mail and social media, not even realizing there’s a better way.

To discuss this book in a group setting, you can use the following questions that I developed on my own.

Introduction

1. What did Carl Jung do to advance in his profession?
2. Without looking, define deep work.
3. What are the benefits of deep work according to Newport?
4. Why do we struggle to do deep work? What aspects of “network tools” do you find most distracting?
5. Define shallow work. Give some examples from your work life.
6. On page 12, Newport gives two reasons why deep work is valuable. What are they?
7. What is the deep work hypothesis?
8. “3 to 4 hours a day, five days a week, of uninterrupted and carefully directed concentration, it turns out, can produce a lot of valuable output.” (16) Is this a reasonable expectation for your current job?

Chapter 1: Deep Work is Valuable
1. On page 22, what does Newport argue is the answer to why Silver, Hanson, and Doerr are so successful?
2. What does Newport mean, that the great restructuring is not driving down all jobs but dividing them? (p.23)
3. How does the observation that the peak of the market will thrive while the rest suffer affect ministry? (p. 25)
4. What are the two core abilities for thriving in the new economy? (p. 29)
5. Who do you know in your profession that produces at an elite level? What do you observe about how they work?
6. Define deliberate practice. (p. 34)
7. What kind of work, if you could do it really well, would really improve your work performance?
8. Do you think your work fits the Jack Dorsey category? In what ways?

Chapter 2 — Deep Work is Rare
1. What business trends are taking away from our ability to do deep work?
2. Do you feel encouraged by your employer to do deep work? Why or why not? What would that look like? (p.57 — unconnected day?)
3. What is the principle of least resistance (p.58)?
4. What behaviours in your job are easiest in the moment (for you)?
5. What is the problem with running your day from your inbox?
6. Why is busyness seen as a proxy for productivity?
7. How necessary is social media for your job? What aspects of it are valuable?
8. How online should your job be?

Chapter 3 — Deep Work is Meaningful
1. What does Newport highlight about Ric the Blacksmith’s work?
2. What changes between manual work to knowledge work? (Moves from simple to define but difficult to accomplish to the opposite)
3. What is the neurological argument for depth?
4. How does spending time in a state of flow relate to how we understand our lives?
5. What is the psychological argument for depth?
6. Why do we assume that relaxation makes us happy instead of taxing body/mind work?
7. What is the philosophical argument for depth?
8. What does Descartes have to do with meaningful work?
9. Does your current work automatically qualify for being philosophically meaningful? Why or why not?

Chapter 4 — Work Deeply
1. What is the Eudamonia machine? Can you draw it? What is its purpose?
2. If we accept that deep work is valuable why don’t we just start doing it?
3. Do you feel regularly bombarded with the desire to do anything but work during the workday? (p.99)
4. why do we need routines and rituals for our working life?
5. What is the monastic philosophy of deep work scheduling? (p.103) Is this a reasonable approach to your current job?
6. What does Neil Stevenson see as two mutually exclusive options in the monastic philosophy? (105)
7. What is the bimodal philosophy of deep work?
8. What is the rhythmic philosophy of deep work scheduling? Why is rhythmic philosophy most common among deep workers in standard office jobs?
9. What is the journalist philosophy of deep work? Why is this approach not for a deep work novice?
10. Why are rituals of deep work important? What sorts of questions need to be answered by ritual?
11. What is a grand gesture and how does it relate to deep work?

12. What is the theory of serendipitous creativity? How is hub and spoke architecture related to it?
13. What is the first discipline of execution? What is “wildly important” in your job right now?
14. What is the difference between a lagging measure and a leading measure? What are some lagging measures and leading measures in our world?
15. What is the third discipline?
16. What is the fourth discipline?
17. How does laziness relate to deep work?
18. What are some of the reasons that Newport recommends a shutdown each evening?
19. What is a shut down ritual and why is it important?

Rule #2 — Embrace Boredom
1. What does studying the Talmud have to do with Deep Work?
2. Why do we not commonly think of deep work as a skill that can be trained?
3. How does ‘on-demand distraction’ relate to boredom and deep work?
4. According to Newport, can an Internet Sabbath cure your distraction problems?
5. What is the difference between breaks from distraction vs. breaks from focusing?
6. What is an Internet Block and how does it work?
7. What is the problem with even taking a small break to use the internet during a Block?
8. How did Teddy Roosevelt work and why does it matter?
9. How do you meditate productively? Why do you need to be active physically but not mentally?
10. What do you need to be aware of while productively meditating?
11. What does memorizing a deck of cards have to do with deep work?

Rule #3 — Quit Social Media
1. What was Baratunde Thurston‘s experiment? What did he learn?
2. What three points does Cal Newport draw from Thurston’s experiment?
3. Do you remember the reasons you first joined different social media sites?
4. What is the any-benefit approach to network tool selection? What are the problems with this approach?
5. How does haymaking compare with the use of network tools?
6. What is the craftsman approach to tool selection?
7. Choose a social network and identify some of the benefits and drawbacks of it.
8. what is the law of the vital few? How does it relate to our Internet habits?
9. Which network tools best support some of your high-level goals, and activities?
10. what do you think of the Ryan Nicodemus box packing solution to social media?
11. Why does Newport argue that you shouldn’t use the Internet to entertain yourself? do you need to put more thought into your leisure time? Why or why not?

Rule #4 — Drain the Shallows
1. Do you agree with Jason Fried that fewer official working hours help squeeze the fat out of the typical workweek? (216) What happens when you have a shorter week?
2. Do you think that having a month off to work on your own project would be helpful?
3. One way to drain the shallows according to Newport is to “Schedule every minute of your day.” What does he actually mean by that?
4. What does he argue that scheduling every minute accomplishes?
5. For you, what is the biggest appeal and biggest drawback of scheduling every minute of your day?
6. A second strategy is to try and quantify the depth of every activity. What is the question he recommends asking to figure this out? (229)
7. Take a few tasks in your work life and apply Newport’s grid to them. What do you discover?
8. What is fixed schedule productivity? How does Newport practice it?
9. What are some things you normally say “yes” to that you should probably say “no” to more often?
10. What are some of the tips he gives about email?
11. What does he mean by a “process-centric approach” to email?

Conclusion
1. What are your biggest takeaways from this book?