A recent post from Jamie got me thinking about our relationship to boredom and good deep thinking and progress on hard problems in our lives. I’ll start by highlighting a pertinent paragraph he writes as he wrestles with the choice to always have an audiobook around.

The walk got me thinking: there are probably a lot of reasons why I went through a serious, multi-year bout of writer’s block. But one of those reasons may have been that I gave myself no time to think and dream. I became increasingly obsessed with reading in every free moment I had, which meant there was no time for daydreaming, except maybe in the shower. And I’d sped up my showers so that they lasted just a couple of minutes. Upon returning from my walk this morning, I decided that, at least for a while, I’m going to take quite walks. I’m going to give up the guaranteed 45 minutes of audiobook listening in favor of 45 minutes of daydreaming. It may not solve all of my issues with with fiction writing I’ve had these last few years, but maybe it will help a little. Jamie Todd Rubin

I’ve been thinking about this and my tendency to always have a podcast playing in my ears when I’m out for a bike ride. Or how about YouTube playing to the side of the sink when I’m doing the evening clean-up. Am I limiting myself from boredom and good thinking time?

We Fear We Might Miss Something

I love podcasts. I’ve listened to MacBreak Weekly for at least 10 years, probably longer. I continually add podcasts to my list to listen to and only rarely catch up on them. I also rarely delete podcasts when I’ve got behind in part because I fear I may miss something that’s useful to me. It may be some macOS tip I didn’t know or some great iPad accessory that will…no it won’t revolutionize my life but how will I know if I don’t listen?

This is similar to the marketing coup that social media has accomplished1, we fear that if we don’t engage in the “conversation” we may miss out on something vital. In this case, both Jamie and I are worried that if we don’t listen to books/podcasts while doing other activities we may miss out on some crucial good and we’ll never be able to recoup that theoretical loss.

We’ve been trained over years to think that any unproductive hour is an hour wasted2. Merely walking the dog, or running and cycling, without something else being accomplished at the same time is one of those “unproductive” hours. Much weeping and gnashing of teeth should happen in our lives if we don’t make sure that time is productive.

Boredom Takes Training

Practices like this are hard habits to kick too. Who believes that you need to train yourself to be bored? According to Cal Newport though, this is exactly what is required of us3. If we want more focus, and more creativity we must wean ourselves off constant distractions and allow boredom and difficulty to happen so that we can understand what we think.

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If at the first sign of difficult tasks we switch to some high-stimuli/low-value task (say Instagram or email checking) we train ourselves to hate anything hard which will limit what we accomplish in our lives. It makes it easy to fall into the trap of believing that we should just follow our passion, instead of bringing our passion with us into everything that we do.

If you’re not uncomfortable in then you’re probably stuck at “barely acceptable” in whatever you’re pursuing4. While acceptable may be easy, it’s not going to help you build career capital so that you can have a long strong career that’s worth working.

Remember that not every moment must be free of boredom and you should stop looking for distractions that are going to short circuit your thinking process5. We should not be children that succumb to the need for immediate pleasure.

Allowing Default Processing

When we can start to embrace boredom we let our default mode network operate. This type of brain processing can let us “mull things over” in a way that’s unconscious but can bring solutions to problems or ideas out of nowhere. But as soon as we fill every idle minute with something, we override the default mode network with active thinking.

In this way, a good thing, reading books while walking, turns into an attention trap. It traps us into a middling priority or something that is a good goal, but not good enough to override the harm caused by stopping all mind wandering.

The devices we carry with us are great at ensuring we never have time to think.

Are Book Totals Feel Good Goals?

For me, I wonder if listening to enough podcasts is simply a feel-good goal. Getting through them all, and picking up a small tip here and there makes me feel good. It makes me feel like I’m getting more productive and learning stuff, but at what cost?

Is it costing me more in lost ideas for courses and writing? I remember riding my bike as a teenager and talking to myself about the problems I had in life. I remember coming come from rides feeling a lightness because I had worked out some things that felt like a huge intractable problem when I left the house.

What problem solving am I currently being robbed of?

Embrace Rare and Fleeting Stillness

When we put away the distractions we can recognize that while stillness feels rare and fleeting, it’s actually all around us if we take a minute to recognize it6. The look of the leaves as the sun passes dappled through the trees is something I love, but miss when I’m distracted by some point made in a podcast.

What else am I entirely missing in my life? What would I gain by shutting off the distractions sometimes and experiencing what is around me?

Jason Snell shared that Shortcuts on macOS has made his automation easily portable. I never even thought about this angle for Shortcuts being awesome on macOS. I have a bunch of terminal scripts that I save in iCloud already, but even more of my computer setup will be done for me as Shortcuts stops being so buggy on macOS and as developers embrace it as they have on mobile devices.

I also came across an interesting article by Mark Suster about networking. I admit I struggle with this, but we’re moving 8 hours away and I will need to build a new local network of people. I’ll need to make myself known to whatever tech community is in Prince George so I can take advantage of opportunities there like I have here. I’ve added this as a note for February 2022 in my Bullet Journal, because I figure the first month of living there will be full with simply getting settled.


  1. Deep Work 206 
  2. Four Thousand Weeks 134 
  3. Deep Work Loc 1705 
  4. Soo Good They Can’t Ignore You Loc 1169 
  5. Mastery Loc 1280 
  6. Stillness is the Key Page 131