Book Discussion: Deep Work, Part 4 – Embracing Boredom

Welcome to episode 144 of the Nerd Journey Podcast [@NerdJourney]! We’re John White (@vJourneyman) and Nick Korte (@NetworkNerd_), two Pre-Sales Technical Engineers who are hoping to bring you the IT career advice that we wish we’d been given earlier in our careers. In today’s episode we share part 4 of our book review on Deep Work by Cal Newport. We’ll talk through the book’s advice on embracing boredom, how it contributes to deep work, and share our reactions on practicality.

Original Recording Date: 10-14-2021

Topics – "Rule #2 – Embrace Boredom", Format Reminder, Taking Breaks from Focus, Work Like Teddy Roosevelt, Meditate Productively

00:57 – Part 4 of Our Discussion on Deep Work by Cal Newport

  • Check out Part 1, Episode 141, where we discussed the “Why?” of the book (why deep work). Part 2 (Episode 142) and Part 3 (Episode 143) were focused on the first rule of deep work, which was working deeply (the structure and the execution).
  • Format: We’ll do some summarization, then answer whether we believe the point, whether it applies to us, whether it makes us want to change, and what we anticipate changing, if anything.
  • One thing we realized is that we want to model how we’re going to try to read books that have a big impact on us from now on on by doing the following:
    • Summarize big points.
    • Take notes.
    • Record our reactions.
    • Record what we’re going to try to change.

5:03 Rule #2 – Embrace Boredom

The ability to perform cognitively demanding tasks with intense concentration is something that needs to be trained over time. It’s a skill, not a habit. People think they can lead highly distracted lives, then turn on concentration when they need it. Studies show that they’re wrong.

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

If you train your brain to be distracted and need the dopamine of changing tasks or seeking out digital distraction, you won’t be able to perform high level deep work. Don’t schedule deep work, assume everything is deep and schedule small times for shallow work.

Point #1: This strategy works even if your job requires lots of Internet use and/or prompt e-mail replies.

Schedule time for those tasks more frequently. Just keep to the discipline of scheduling.

Point #2: Regardless of how you schedule your Internet blocks, you must keep the time outside these blocks absolutely free from Internet use.

Resist the temptation to get connected during deep work. It’s too easy to get distracted while looking something up. If you’re blocked, then switch to a different offline activity.

Point #3: Scheduling Internet use at home as well as at work can further improve your concentration training.

You can’t just leave work and abandon your good behaviors, any more than a professional athlete can train all day then return home and ignore the diet they need to support their top performance. You can’t let your brain get wired for distraction during your time off.

8:48 Reactions

Do I believe this?

  • John: Yes. It makes sense that the brain circuits we train the most are the ones that we fall back on using. The idea that we’re training ourselves to need that jolt of dopamine that comes from indulging in social/news/doom scrolling is probably more destructive than I realized.

  • Nick: This is one is really interesting to me. I think we’re afraid of being bored in some ways like Tom Hollingsworth mentioned in Episode 127 (always feel we should be “doing something”). We have this need to fill the downtime. I completely buy into the need to train and get ourselves disciplined into new habits that don’t encourage seeking distraction. I think getting into a habit trains the skill of intense focus.

  • John: I think on the Deep Questions podcast Newport mentioned that at no other time in our history have we had devices in our hands that were built by social scientists to distract and endlessly grab our attention for monetization. When I was younger and had not yet been diagnosed with ADD, I always carried a paperback book around to distract me. I would read that whenever I wanted a distraction. Television is similar today with the ability to binge watch shows. I also remember playing solitaire on my mobile phone as a distraction while I was waiting for something. I would do that everywhere. Every time I would finish a game I would get that dopamine hit. I don’t have the app on my phone any longer. Now that I think about it, there are other behaviors like reading news feeds while waiting for a meeting to start. These are all specifically avoiding boredom. I am at times late for things so I won’t get there early and get bored. So many things for me are driven by this avoidance of boredom.

Does this apply to me?

  • John: Yes. I’ve already been talking about it.

  • Nick: I think it does. I think it applies more to checking e-mail followed by checking Twitter and LinkedIn. I might get up from my desk to get something to drink and end up checking LinkedIn / Twitter. I don’t find myself lingering there. I just feel this compulsive need to check it. I’m not present in the few minutes I take to be present doing something that isn’t work – complete irony.

Does it make me want to change behavior?

  • John: Yes.

  • Nick: Yes.

What will I change to align myself with this idea?

John: I need to resist the news app. Maybe uninstall it or block it? That’s the thing I use on my phone the most to distract myself. And I’m not sure what the point of it is. In retrospect it’s to head off boredom and to distract myself from the deep work I actually need to accomplish. It’s very easy to jump through recommended videos for hours on YouTube. I need to work on tightly scheduling social media or YouTube with specific goals. I think I’ve turned off the majority of my e-mail notifications and don’t want to use it as my task list. I feel I have successfully moved away from e-mail as my task organization system.

  • Nick: I might need to logout of Twitter and LikedIn on my phone like I did with Facebook. Then there’s no way to check it when I take a break. But also maybe I should leave my phone at my desk when I take a break. I’m not so important that I can’t be away from my phone for 5 minutes. I need to work on the scheduling part across the board. I have done better about closing e-mail down to focus, but there’s a subconscious grinding away that is happening when I do it. Maybe that goes away?

  • John: John found he was depending on e-mail notifications to remind him to do things. The e-mails he had been sent that were not archived or deleted sitting in the Inbox were the reminders. Moving the task organization system to somewhere else (not your Inbox but to a Task). For John it was that feeling he was forgetting something. Now he creates a deadline on the calendar to ensure nothing is forgotten.

  • Nick: It’s more this need to be responsive than anything and a fear of not being responsive enough.

  • John: The way to reach me if you need me to be responsive faster is a text and then escalate to a call, so I wouldn’t leave my phone somewhere. I would never expect someone to respond in 2 minutes to an e-mail. Calling, leaving a voicemail, or war dialing would be more of an emergency. If I was in a meeting and saw someone had called me a few times in a row I would step away in answer, thinking it’s an emergency. Maybe I should publish that because probably not everyone knows it.

23:48 – Work Like Teddy Roosevelt

This is about short periods of intense concentration with no breaks and no distractions. But one should probably emphasize the intense concentration and not the short periods.

Meditate Productively

Meditate on a professional problem while you’re engaged in a mostly mindless physical task (going for a walk, for example). Continue the intense focus.

Suggestion #1: Be Wary of Distractions and Looping

If something else pops into your mind, redirect the mind back to the problem on which you’re focusing and the next step in the problem solving process.

Suggestion #2: Structure Your Deep Thinking

Review the variables of the problem, define the next step question you need to answer, and think about that. At the end of your time, consolidate your gains by making sure you know the answer you came to or the progress you made. (Unsaid – record this).

Memorize a Deck of Cards

Engaging in other cognitively demanding activities can help you in your deep work process. It acts as additional training. There was also a story from the book about a man who converted to orthodox Judaism who was engaged in a serious study of the Torah, which was extremely cognitively demanding. This boosted his professional abilities as well. See also Moonwalking with Einstein by Joshua Foer.

27:34 Reactions

Do I believe this?

  • John: Parts of it. I’m suspicious of the “Work Like Teddy Roosevelt” section because it feels like the Journalistic Philosophy of switching on intense work. Or the total blockout of all distractions seems like it’s not something one could just start out doing. Applying pressure on yourself and ramp up of anxiety to get yourself to work may for me allow more procrastination. I like the Meditation idea in conjunction with physical activity (maybe even taking a walk through nature and not being in front of a computer). I also like the idea of picking up some other cognitively demanding hobby which also trains your concentration. That would be almost any skilled hobby, actually. Swing dancing used to be a serious hobby of mine. Learning the moves was extremely cognitively demanding.

    • Listen to the cognitive boost a co-worker of John’s got from learning swing dancing.
  • Nick: I like the idea of giving yourself a short amount of time and putting some pressure on. I think I’ll have to see if the stress level going up a little in this experiment increases or decreases my ability to concentrate deeply. I like the structuring your deep thinking. I feel like the structuring deep thinking is the deep work session equivalent of the shutdown routine you’re supposed to implement at the end of each day.

  • John: This reminded me of a point made in Your Brain at Work by David Rock. The author talks about how your brain needs a balance of stress and reward hormones. Finding that balance of engagement and excitement (but not too much of either) seems to be the way to go.

Does this apply to me? / Does it make me want to change behavior?

  • John: Yes. I don’t think I do enough of the meditation. If at all. I don’t have a cognitively demanding hobby right now. I have not been swing dancing for some time. Maybe my approach to reading this book and others is a start.

  • Nick: I like to take walks most days of the week, and I find that I’ll either listen to an audiobook or just let my mind wander. Sometimes it will center / focus on a situation / problem on its own, but sometimes it’s a continuous stream of things that bounce around without any focus. I don’t know that I have tried to focus / hold my brain on a specific thing. We know that exercise can stimulate the brain.

What will I change to align myself with this idea?

  • John: I need to start adding meditative walks. There are some green spaces around where I live, and being able to schedule some deep work time away from the computer makes a lot of sense. As for adding a cognitively demanding hobby, I think it’s worth doing. Maybe I can pursue my reading in a more structured manner (i.e. a certain amount per night).

  • Nick: I feel like my subconscious is already grinding away on problems whether I want it to or not. I’ve been doing some meditation using Calm (follow the link for a 30-day guest pass) to quiet the mind and relieve anxiety. They have some great instrumental music to help you focus while you work. When you do a meditation with the app you are encouraged to focus on your breathing and to try to stay present, which I believe is the same focus you’re after when trying to solve a problem. Sometimes I will listen to one of these while I walk. Part of this is being present so you can focus. Meditation teaches you to learn to be present, to focus on the now. They even tell you to redirect your thoughts if they get sidetracked. I plan to keep doing it.

  • John: I like that idea. I think I have a similar app with some be present meditations. My team recently did one, and I found it really helpful and energizing. It cleared my mind from a lot of clutter. I was surprised that this actually worked, but it definitely did for me.

  • Nick: People could do this as part of a work shutdown routine or even before bedtime to keep your mind from racing. It takes practice to master, and you won’t always be able to keep it from happening. But it is the practice that is important.

  • John: This goes back to that idea of recognizing you are distracted and trying to get back to being present. The app I use is headspace.

  • Nick: If your workplace has a health and wellness benefit, ask about it before you pay for it yourself!

  • John: If you don’t have the benefit, ask your boss if you can expense the app.

40:07 – Summary thoughts on Rule #2: Embrace Boredom

  • John: The idea that we need to restructure our lives around avoiding distraction is compelling. I liked the on point advice. Maybe because it’s asking a lot to exercise the resistance against distraction, which seems to be the key to making something seem worthwhile. It’s quite reasonable to not check e-mail or something else when you have a couple of spare minutes, but it feels unreasonable at first.

  • Nick: The introduction of structure at this level sounds incredibly overwhelming. Don Jones mentioned in Episode 138 that he blocks a specific amount of time to answer online forum questions. I think when I was more active in the Spiceworks Community, that was my doomscroll addiction whenever I had a minute and even when I was trying to find answers. I never put limits on that time. I imagine the meta level structure is one of those things that takes a lot of work on the front end to get gains on the back end in efficiency. For example, not checking e-mail except during scheduled times is tough to do.

    • I feel like this period of deep work is exactly what Tom Limoncelli encouraged us to protect in Time Management for Systems Administrators. That time spent on finishing your most important priority is the deep work. It took reading Newport’s book to make that connection. I couldn’t do it well then. Maybe I can do better now.
  • John: You need different coaches to say things in a different way until it lands. And then you get the benefit of all that coaching all at once. Some of the advice from Getting Things Done, Your Brain at Work, and a number of others landed as a result of reading Deep Work.

    • In Newport’s Deep Questions Podcast, he encourages us to NOT time block family time. I can understand time blocking for online forums. But don’t time block weekends or family time.
    • Getting off the e-mail addiction felt like removing any other distraction (Facebook, Google News, forums). I feel like I have gone through that process. It involved going through a bunch of e-mail filtering to bubble up important messages. Think about what to delete, archive, and file. I automated a lot of this because I took advice of someone who had a talk on this when I joined Google (i.e. auto-filter for mailing lists).
  • Nick: I’m still in the detox process when it comes to e-mail.

Contact us if you’ve read Deep Work and have reactions you think we missed. We’d love to hear from you. If you have other books you’d recommend or if you need help on the journey, don’t hesitate to reach out.

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