Chris Bailey

Benevolence →

Published August 22, 2024  ·  All posts on Aug 22  ·  

Benevolence and self-direction (described below) are usually near the top of the values we all share. Each of us also has an internal hierarchy of values, where we rank our values based on those we find extremely important to those that don’t really motivate us at all.

~ Chris Bailey, from There are just 10 basic values

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Benevolence—in my opinion—only pops up on our radar once we have enough time, energy and resources. Whether or not it’s clear in that moment, that’s because we, for the first time, manage an honest look back and actually realize all the places where we’ve received help from others. So that’s nice for ourselves, but also for the entire human race.

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Meh →

Published September 17, 2023  ·  All posts on Sep 17  ·  ,

In March of 2022 I returned to tracking my activity. For me, what gets tracked gets optimized. I created the simplest tracking worksheet that did what I wanted and I set about keeping track. There are things I loath about my current FitBit; I can’t quite entirely disable the notifications. And touch screens don’t work with sweaty fingers, which leads to frustration just when I’m exhausted. I’ve never had an Apple Watch, but maybe it was time?

When I bought the phone last year, I went all out. I got the 1 terabyte model (a ridiculous amount of storage space, in hindsight), because I expected to have the thing for a while. But I’ve come to resent this phone.

~ Chris Bailey from, Smartphones should not be this nice – Chris Bailey

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I went to the Apple Store to arrange for a battery replacement for my iPhone, and I intended to spend my waiting time examining watches. I spent an hour exploring and testing, and picked one out. I bought it, booted it up, synced it to my Apple ecosystem, and strapped it on. I went on my way with a new phone battery and $700 in conspicuous consumption on my wrist. Intending to lean into wearing and using the watch as much as possible.

And for the next two days I wanted to rip it off my wrist and smash it with a hammer. I spent endless hours trying to disable this, silence that, adjust this feature, avoid setting up that other feature… All because I wanted the Watch’s better GPS tracking of distance covered, and better biometric measurements. I struggled with trying to sleep with a digital screen strapped to my wrist—there is no digital screen that will ever exist, which is permitted in my sleep space. Alas, the Watch is the antithesis of calm technology and it was clear I was never going to change its DNA.

On the third day, I carefully put it all back in its packaging as best I could. I drove all the way back to the Apple Store. I knew Apple had a 7-day, no questions asked, full money back guarantee. I handed it back to a rep. They of course asked, “Was there a problem? Or something you didn’t like?” My reply—

“Meh.” And then I left.

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Calmness is needed →

Published August 27, 2023  ·  All posts on Aug 27  ·  , , ,

There is a time and place for maximum effort—yes, that’s a Deadpool reference—and there’s a time and place for stillness and calm. I’m fascinated by the relationship and interaction between physicality (as movement versus stillness) and mentality (as agitation versus calmness.) I’ve had transformational experiences at both extremes of physicality, with mental calmness. I do get mentally agitated. But I fear that too many people experience calmness far too rarely, possibly never.

This often means working more thoughtfully, and maybe even more slowly. Slow work is not unproductive work. What we lose in speed we more than make up for in deliberateness—as well as in undistracted attention, a critical factor of productivity.

~ Chris Bailey from, The productivity payoffs of a calm mind – Chris Bailey

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Sometimes people ask me about Stoicism, and I suck at explaining it. Thinking and writing about calmness today, I’m struck that I should probably mention eudaimonia (eu̯-dai̯-mon-ía). Eudaimonia is a key value Stoicism advocates striving for.

[…] is a state of being and consciousness that is consistent with the active, effective activity of ideal agency and in general is characterized by the calm (equanimity; tranquility) that comes from the absence of further moral struggle and the absence of retrospective regret or prospective alarm about things outside one’s control, together with the confidence that comes from the effortless persistence of moral purpose.

~ Lawrence Becker from, A New Stoicism p91

2.5 millenia later… calmness, equanimity, tranquility?

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Mind your attention →

Published July 21, 2023  ·  All posts on Jul 21  ·  ,

I’m sold on the idea that mindfulness is the key which unlocks everything else. I get chuffed when something grabs my attention. I’m fine with noticing; It’s good that I notice emergency vehicles. But realizing I’ve blown the last 5 minutes doom-scrolling in Instagram? Not cool.

There’s a reason for this. Our experiences in the digital realm are usually very novel—and this novelty leads to the release of dopamine in our brain. Dopamine doesn’t lead us to feel happy and satisfied in and of itself—it leads us to feel as though pleasure is right around the corner, so it keeps us wanting more. The more novel an app, the more we get hooked—we feel a constant rush and keep using the app until we remember to stop. (Here’s looking at you, TikTok.)

~ Chris Bailey from, 5 lessons I learned switching to a flip phone for a month – Chris Bailey

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This is a longer than usual article from Bailey and it’s stuffed full of insight. One item of note is he frequently gets very intentional about testing things to their logical conclusion. This article comes from him trying to live his life without a smart phone. His conclusion (and I agree) is that smart phones are awesome. Unfortunately, there’s some bad opportunities mixed in too. (Ocean and surfing, yay! Sharks, not so much.) Want to see how addicted you are to your phone? Try this.

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Periscope depth →

Published March 5, 2023  ·  All posts on Mar 5  ·  

When we have a bit of time to relax, we tend to spend time on activities that provide us with a quick dopamine hit. This is especially the case when we spend our downtime in the digital world. The key to relaxation is to invest in strategies that make your mind less stimulated. Usually this means spending more time in the analog world.

~ Chris Bailey from, The Key to Relaxation

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That analog world can be outside moving or inside doing some yoga, sipping coffee, reading, or spending time with people physically present. The more time I can spend in the analog world, the better my life is.

I have a lot of hard-learned knowledge around what works for me in the morning, and I urge you to experiment to find out what works for you. For years I’ve been using the word “surfacing” to refer to that moment when I transition from simply being myself, to engaging with the world through technology. Surfacing is a submarine reference; Like a submarine, at some point each morning—sometimes after Noon—I sneak up to periscope depth and without making a ripple on the surface I peek to see what in the world might be close at hand. I know that once I break the surface, my life that day changes. One moment, I’m out of sight being self-directed (not necessarily selfish, but rather directing myself) and the next moment there’s an endless world vying for my attention.

My point is not that there’s something wrong with the world. (There is, but that’s not my point.) My point is that the world is simply present. It is ever-present. It’s not the world’s responsibility to not bother me. It is my responsibility to choose. I must choose when to engage and when to be the void. I must choose how to be present for those to whom I am beholden, and I must choose to not waste my energies on everything else. Because there is literally an infinite amount of everything else and chasing that is a fool’s errand.

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Basic values →

Published November 18, 2022  ·  All posts on Nov 18  ·  ,

There are some consistencies in what we all value. For example, most of us tend to prioritize caring for others more highly than dominating and controlling others—the latter two “are among the least important values to most people in most societies.”

~ Chris Bailey from, There are just 10 basic values

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I really enjoy sipping a cup of tea and taking a stroll through the gardens of others’ minds. Seeing the topiaries they’ve created never ceases to amaze me. Integration of knowledge is a hard problem (the hardest of all as a mere mortal?) Being able to see how someone has organized their thinking helps me examine how I’ve organized my thinking. Certainly, there are gardens I don’t bother visiting. But generally, being open and curious has led me to countless conversations of both the actual kind and the kind to which Niccolò Machiavelli refers.

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I’m triggered, now what? →

Published October 9, 2022  ·  All posts on Oct 9  ·  ,

The more fun your work, the less likely it is to set off these triggers. You won’t struggle to focus—tasks will attract your attention because they’ll be far less tedious, frustrating, challenging, and so on. There are a lot of strategies for overcoming procrastination. But making a project more fun disables a bunch of procrastination triggers at once, while also making your work more enjoyable. It’s a great strategy.

~ Chris Bailey from, How to stop procrastinating by making your work more fun – Chris Bailey

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Great little article from Bailey with great points about the really common things that trigger procrastination, and some ideas on how to beat each one. What’s been working for me for a while is something inspired by Yoda’s comment that, “named your fear must be, before banish it you can.” I can tell when I’m procrastinating; perhaps not always, but definitely often. At the point of realization, I play the name–game: “Craig, what exactly is it that you don’t want to do?” Then like the school guidance counselor always trying to talk me out of sabotaging myself into detention, “Are you sure that’s the thing? Be specific.” Upon realizing I’m still in their office, “I don’t think you’re as sure as you think you are. Can you explain it to me like I’m 5 years old?” Until eventually, it’s so blinding clear what I need to do (or skip, or change, or screw up 3 minutes of courage, or whatever) that I just freaking stomp that procrastination.

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Guiding principles →

Published June 15, 2022  ·  All posts on Jun 15  ·  

We rarely take the time to capture these guiding principles—even though recognizing them can help steer our actions, lead us to better decisions, and let us live more in alignment with who we are.

~ Chris Bailey from, My 6 guiding principles – Chris Bailey

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As with Bailey, I don’t think I have a clear set of guiding principles. I’m not sure if I’m okay with that. I am sure that I do not want to spiral off and spend my entire day—that’s what would surely happen to me if I begin—thinking about this. Instead, I read his list and spent some time letting my thinking happen spurred by his principles. Just as he described, I did have one principle spring immediately to mind: Curiosity. To be powered by curiosity. To be passionately curious. “Curioser and curioser”, said Alice.

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Surface area of concern →

Published June 6, 2022  ·  All posts on Jun 6

Our “surface area of concern”—the number of events we pay attention to on a regular basis—has expanded alongside technology. This is not an inherently negative thing, but becomes one when it adds chronic stress, leads us to burnout, and affects our mental health.

~ Chris Bailey from, Your surface area of concern

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This is a precise and powerful way to describe something which lies at the root of many other phrases: Information overload, multi-tasking (as a way to fail), and spreading our attention too thin (as another way to fail), are just three examples. I’ve long since decided that I do not need to have an opinion on most things, and that frees me from feeling I need to notice as many things as possible.

For many years—but explicitly I have 3 years of journal entries where this is glaring—I’ve lamented wanting to spend more time on some specific things. And yet my days slip past doing other things. I’m not talking about things which get planned—a day at the beach, dinner at someone’s house, or weekend work in the yard. No, I’m talking about that, “where the hell did today go?” stuff. If you like visuals: The glass jar that I filled slowly all day with the sand of small things, only to realize at day’s end that there’s no way to put these larger rocks in. Ever. Because every tomorrow is like today. Dammit.

About a week ago I decided—memento mori, ya’ know—it’s time to flip that shit over. For several years now, I’ve been starting with pretty consistent morning routine. After that, I have four things that I want to do, and I’ve been doing those next. Sometimes that means I don’t touch anything else—not my phone, not my email, not other people, not bills, not even voicemail from roofers—until 4 in the afternoon. It sounds crazy, I know. Guess what? Every day I look at those four things and go: Shazam! Progress! …and it turns out that I then go on to pour in a ton of sand too—return that call [from yesterday], mow the lawn, run an errand, interact with people, etc..

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12% battery remaining →

Published June 2, 2022  ·  All posts on Jun 2  ·  

Productivity hacks are fun, but they don’t always produce the greatest returns on your time. If you care about productivity, be sure to invest in your energy levels.

~ Chris Bailey from, Don’t forget the basics of productivity

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I don’t do productivity “hacks.” I do productivity. My aversion to “hacking” anything runs deep. All of my productivity comes from doing things which return, the way compound interest returns. Whenever I can, I try to do the hard work up front. I am literally trying to pass gifts, (of time, energy, money, sanity,) to my future self.

It’s wise to occasionally erase the whiteboard to see what something could be like if built from scratch. It never ceases to amaze me when absolutely nothing happens nor changes when I entirely stop doing things. I recently removed an entire project—no one has even noticed. I recently was completely unreachable, (by everyone other than my wife,) for four days—no one noticed. If you started from a clean slate today, what would you choose to do?

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