I Just Followed You Again And I Promise I’m Not Crazy

If you’re a friend of mine you may think I’m a little crazy. If you get notifications when someone follows you on social media, particularly Twitter or Instagram, you may wonder if I’ve lost my marbles. Every couple of months you may notice that I’ve once again re-followed you for the second or fourth or tenth time (it depends how long we’ve known each other).

I’m not trying to get your attention or elicit a re-follow or send any message of any kind. What’s actually going on is that you just passed the relatively extreme filter I use when it comes to my social media lists.

Well, when I put it that way it makes it sound like I have some kind of sophisticated system or algorithm I run to create the most impactful, useful, and interesting social media feeds. That would be pretty far from the truth. What actually happens is that I generally start with a pretty small group of core people I enjoy or I think post interesting things that I like to follow (folks like yourself, obviously). However, over time I keep adding more and more folks to my lists. I follow a little bit more indiscriminately. I get an itchy follow finger, basically.

And then one day I wake up full of self-loathing for how little creative output I’ve had or how deep into a procrastination hole I’ve fallen and I look around for the quickest fix that will give me some immediate psychological relief. Given my minimalist tendencies and proclivity for extreme behavior in that direction, that often means wiping all my social media accounts clean. Back to zero. All gone.

And that feels good for a couple days or a couple weeks.

But then I realize that my lack of creative output or deep procrastination had very little to do with my social media accounts and I feel the void that they were filling in my life (social connection with real people, a steady stream of interesting and relevant content, the occasional easy, breezy entertainment, etc.) and I decide to start using them again. And then I start re-following folks.

And that’s how we get to where I feel the need to write an article about why I just re-followed you for the ninth time.

I try to write everyday. This is part of that. Have a thought? Tweet me, yo.

In Which I Have To Critique One Of My Intellectual Heroes: Or, Why Cal Newport Is Wrong

I’m a huge fan of Cal Newport’s writing. I read Deep Work the day it came out from cover to cover in less than a day. I read it four times in total in 2016. I’ve read So Good They Can’t Ignore You twice and have given it as gifts to multiple younger brothers and friends. I think his take on the deliberate cultivation of attention management skills is generally on point and a voice of reason in a very noisy world. I’m a huge fan of the digital minimalism idea he espouses and I think I would be a much more creative and productive individual if I could internalize more of his ideas.

However, I think I’m starting to see the limits of Cal’s experience as an academic in his writing about how work is done in the corporate world.

In his latest article, “An Early 20th Century Lesson on the Difference Between Convenience and Value” he shares a story about how the Pullman Company improved productivity by making it more difficult to communicate and coordinate across the organization. The ultimate “turns out” (“Everything you thought about a thing is actually wrong!”) story in a world that’s rife with email and Slack and instant messages, right?

It’s dangerous to take this story too literally or extrapolate it too far.

Much of the work I do at The Ready is helping organizations understand that they aren’t in the early 20th century anymore. The world in which the Pullman Company operated in the early 1900s is so radically different from today and extrapolating elements of their organizational operating system into our own organizations (organizations that probably aren’t manufacturing luxury train cars) should be taken with a huge grain of salt. Communication doesn’t need to be fluid in an organization where the economic forces aren’t as radical or rapidly changing as they are today (e.g. no Internet, less globally intertwined supply chains, less globalization, slower pace of business overall, etc.). The challenges organizations face today are often caused by broken communication. Departments that ought to be working together in tight cross-functional teams instead exist in functional silos that never talk to each other. Complex questions and conversations that many could value from are locked into individual’s inboxes — potentially useful information locked away in email purgatory.

In complex organizations its impossible to always know who specifically needs to know what piece of information so instead we push our clients to “default to open” and “work in public” and move their informational ecosystem to one where people can pull information as needed instead of being bombarded with an information avalanche. For all its faults, Slack and other tools like it can help enable these shifts in working that weren’t needed in the early 20th century but are allowing the firms of the 21st century to cope and thrive in a thoroughly VUCA world.

We should all continue taking Cal’s attention management advice on the individual level but we should also be wary about taking over simplistic views about what it means to work together in the 21st century. There’s a certain romance and elegance to looking at how things used to be done and applying those lessons to how we work today. And in some cases, there are valid ideas we should reinstate. But it’s important to remember that the business world of today looks very different from the business world of 100 years ago.

In many cases, the organizations who are upgrading their organizational operating systems are the ones navigating this uncertain and complex world better than those who are locked in the past.

Every day I try to come up with something insightful to say, write it, and publish it in less than 30 minutes. This was today’s effort. Have feedback? Leave a comment below or get at me on Twitter.

Is Your Organization Amazon-Proof?

If there’s one thing organizations need to take away from the recent Amazon acquisition of Whole Foods, it’s that everything can change in an industry in an instant. Last year’s strategic plan and budget can suddenly seem like relics of the past when something fundamentally shifts in a market and competitive landscape. All organizations need operating systems optimized for the kind of uncertain world where an online retailer/internet infrastructure provider/media company can buy one of the largest players in groceries. To live in a world where the unexpected becomes commonplace, organizations need operating systems where responsiveness, fluidity, and innovation are baked into just “how we do things around here.”

Unfortunately, I don’t think that’s the reality for most.

How many orgs can absorb a shockwave like Amazon moving firmly into their market and feel confident that they have the processes, people, and policies that will allow them to do what needs to be done to adjust accordingly? Not many. Too many organizations are reliant on a single charismatic leader or a cabal of executives that are somehow supposed to guide the organization through tumult they never even saw coming and are left as surprised as everyone else. Does that fill you with confidence?

Great organizations have flexibility and resilience and responsiveness baked into every fiber of their being. Their hiring processes optimize for people with the right mindset. Their resource allocation processes remain flexible (i.e. not locked into annual cycles). They build teams that come together around solving real problems regardless of organizational hierarchy or politics. They push trust and autonomy to the edges of the organization so that decisions can be made quickly and those who are closest to the customers have the greatest ability to do what’s needed to be done to make or keep those customers happy.

It’s a fundamental shift from how most organizations think about themselves and how they show up in the world.

It’ll be interesting to watch as the volatility inevitably continues to increase. More Amazon/Whole Foods-scale acquisitions, more unpredictable sociopolitical events, and more, “What the hell is happening?” moments will start to separate the orgs who get it from the ones who don’t. The orgs who try to retrench and consolidate power will find themselves brittle and at risk. The orgs who embrace the unpredictable nature of the world and build the capabilities into their system, even if that looks messy or inefficient or unorganized — those are the orgs that will own the future.

I love that my job is helping organizations get ready for that future.

I try to write something (moderately insightful) every day in 30 minutes or less. Have a comment or question? Catch me on Twitter.

Making a Weekly Personal Metrics Spreadsheet

The times where I collected the most data about my life were not necessarily the times where I felt like I was making the most interesting insights about my life. Said another way, more data doesn’t always mean more better conclusions. Ahem. Something like that.

For the past year or so I’ve adhered to a pretty simple weekly habit that has made my efforts to quantify aspects of my life so much more useful. I call it my Weekly Personal Metrics spreadsheet.


The problem it’s trying to solve is — in a world of lots of data easily collected, how do you even remember what you’re tracking, let alone actually remember to go look at it and see if you can glean any insights? In a perfect world all of the interesting data I want to collect would be done so passively and a smart app or operating system would crunch it and feed me interesting tidbits (yes, I know Exist.io and Addapp exist but I have found them…. wanting).

The simple trick is to sit down once a week and collect all my various data points and manually add them to a simple spreadsheet. Then, I can look at them and compare them against the previous week (which is what I do most often and where the red/green cell colors come from). If I was more industrious I could make all sorts of visualizations to show how I’m doing on the various metrics I’m tracking (that might be an end of year project actually).

This simple little addition to my weekly routine has actually been pretty great. It helps me notice when I’m letting things spin out of control (I’m looking at you Sleep and Weight) and make changes before things get totally out of hand. It lets me really lean into as many passive sources of data collection as possible because instead of just letting them slip away into the ether I know I’m going to extract everything once a week.

I’ll go into more depth about why I track what I track in a future article. For now, you’ll just have to be happy with the nuts and bolts of setting up a Weekly Personal Metrics spreadsheet.

Making your own is as simple as figuring out a.) what’s important enough (or easy enough) to track? b.) when will you update it? That’s about it. Find important things that are easy to track (sleep is a good starting point if you have an Apple Watch and weight is kind of a no-brainer if you have a scale) and once a week pull the data into a spreadsheet. Do that every week for a long time and you’ll start to see the patterns emerge.

This is part of my semi-regular* series where I conceive of an article idea, write it, edit it, and publish it in 30 minutes or less. Have a thought? Leave a comment or follow me on Twitter.

*Where semi-regular means I sometimes go weeks without writing.

A Minimalist’s WWDC Desires

I’m a pretty unabashed Apple fan. I use almost exclusively Apple products in my personal and professional tech life and for the most part they have served me well. However, seeing as we’re just a day away from WWDC I figured I’d capture some quick thoughts about what I hope to see them do.

In general, I’m very much a minimalist which means I try to be very thoughtful about which tools I use — and how. I don’t really care about brand new pieces of hardware or amazing new apps. I own and copiously use a 12" iPad Pro and Pencil, iPhone 7 Plus, and MacBook in my personal and professional (management consultant) life. And yes, my definition of minimalism includes owning three different and very expensive pieces of technology. Then again, my phone’s home screen also looks like this:


Before I dive into the specifics, here are some things I’m always looking for from the tech tools I own and use regularly:

  1. Like I just said, great stock apps. I always default to using the stock apps until they can no longer get the job done.

  2. Storing data in the cloud as much as possible. I want as little of my data as possible to be tied to specific devices.

  3. Great syncing. I’m almost equally likely to work from my iPad, iPhone, and MacBook. I want to be able to pick up any of them and know everything is synced and ready to go.

  4. Reliability. I want to think about whether or not my tools are going to “work” as much as possible.

  5. Use all the information you have about me to be as useful as possible. This means using context to be helpful in surprising ways.

  6. Thin, light, and well made.

  7. As simple as possible.

And now, on to some of my hopes for this year’s WWDC.

Better Siri

I would love a world where I could talk to my devices and trust they will do what I want them to do. Unfortunately, we are nowhere near that reality, yet. Siri needs to get more reliable and smarter about parsing my intention. The less “Siri syntax” I have to learn and the more I can talk like a normal human being, the better. Being able to successfully use my phone to do something other than starting or stopping a podcast without having to pull it out of my pocket would be great. #simplicity #reliability

Apple VPN

Somebody on some podcast I listen to suggested this as something that would be really interesting for Apple to offer and I’m on board. I’d pay a couple bucks a month for an Apple VPN (especially given our current political climate). I’ve used a standalone VPN off and on for the last couple years but having something built into the OS (both iOS and macOS) would really simplify things. #simplicity #reliability

Rumored “Siri Speaker”

I don’t have a huge desire for a new piece of hardware to manage, especially since I’ve been having more success using “Hey Siri” on my watch and phone recently (although, not enough success given wish list item #1). However, if Apple focused on making the speaker really good I might be interested if it could feasibly replace one or both of my SONOS speakers. I’ll trade my two SONOS speakers for a really high quality “Siri Speaker” (especially since they both sit on my desk and I live in a studio apartment — meaning I don’t need the separate rooms functionality). What would make this an instabuy for me is if it also contains wireless router functionality, thus replacing my Airport Express, too. #simplicity

Native Sleep Tracking with iPhone + Apple Watch

I’ve used AutoSleep and Sleep++ in the past but I’d love for Apple to just take this over and do it really, really well. AutoSleep is a design nightmare and Sleep++ is fine but has to be turned on manually. I’d really like to see what Apple could do with a native solution. #simplicity #stockapps

Natural Language Processing in Calendar.app

The default calendar app can handle basically everything I need but every time I move away from Fantastical 2 I miss how easy it is to create new events. I don’t want to spin dials or click through options. Let me just type (or say!) a sentence like a person and make my event from that. #simplicity #stockapps

Make Keychain a Legit Standalone Password Manager

I’ve become more interested in the past few weeks in seeing whether Keychain can truly replace 1Password. I’m not sure that it can at the moment… but it’s not too far away from being able to do so. Would love to see Apple lean into this. #simplicity #stockapps

Auto-Start Workouts on Watch

I always forget to start a running workout on my watch when I go for a run. But it knows my footfall cadence, heartrate, (and if I had a newer watch, my GPS location). Meaning, if you can tell I’m running just start a running workout! Or shoot me a push notification that says, “Yo, it looks like you’re running. Are you running?” I’ll bet it could figure out whether I’m swimming or cycling or anything else, too. Be smart about helping me capture these workouts! #simplicity #context

More Granular Notification Settings

I don’t let many notifications come through, but I would love to have control of my Do Not Disturb preferences on an app-by-app basis. Meaning, I’d love to have all my work related apps (a group that I could designate) not be allowed to send me any notifications after 6:00 PM but let my entertainment or messaging based apps keep notifying me until 10:00 PM or so. Even better granularity would be if my phone would shoot me notifications (or not) based on information from my calendar or location in the world, too. #simplicity #context

More Actions From Notifications

Again, I don’t have many notifications hitting my phone/watch… but the ones that do come through I’d love to be able to do more with. Give me more actions so that when I happen to get a notification that I can do something with I can take care of it instantly. #simplicity #context

Better Podcasts App

Every time I try to use the default podcasts app for any length of time I almost always end up reinstalling Overcast. I’m trying to figure out why since ideally a podcast app isn’t something you have to actively engage with very much. I think I just don’t like, or aren’t used to, how it’s laid out. I don’t need to be able to find new podcasts easily so I think the fact that Search, Featured, and Top Charts take up 3/5 of the menu bar real estate really throws it off. #stockapps

TV App

I appreciate the effort of centralizing my video watching experience into one app but if everything isn’t in there then it’s not really solving any problems. Make whatever deals you need to make to get everything in there… or just don’t do it. #stockapps

More Cross Platform Consistency

I don’t think macOS needs to become an iOS clone. I get that the two systems serve different purposes. But there is some really low hanging fruit that should be unified across them. Stuff like setting a timer with Siri on my MacBook. Why can’t I do that? Why is music, TV, movies, and apps all unified under iTunes on my Mac but broken into separate apps on my iOS devices. Let’s clean this up. #simplicity #reliability

iPad Hardware

I’m intrigued by the rumored new 10” iPad form factor that would exist between the original size and the honking 12” size. I think the 12” is slightly too big for me most of the time. I also think that future iPads should get some kind of super unobtrusive kickstand on the back so I can use it without a cover/case. Keep pushing thinness, too. #simplicity #thinandlight


I like the new butterfly switch keyboards… except for the fact that I’ve had to get a stuck key fixed three times. Keep the low key travel but make it more reliable. Also, no need to make this any thinner. Keep it the same size but cram some more batteries in there. More battery life is more important than lighter or thinner at this point. #reliability


I think AirPods in black would be delightful. I would also like them to be a touch more consistent when I tap to invoke Siri. #reliability

Apple Pencil

Make it so this bastard doesn’t roll away from me without me having to put a stupid third party clip on it. Put an on/off switch on it so the battery doesn’t die as much. And I’d be okay with making it a tiny bit thicker. #simplicity

What about you? What would make your computing life simpler and more enjoyable this year?

A Subtle Mental Shift Is Kind of Rocking My World Right Now

I’m a man who love(d) a good goal.

Goals are supposed to provide clarity and potentially motivation (if it’s a particularly well-crafted goal) on a quest of personal development. I know all about how good goals are supposed to be set and I can break down an audacious goal into bite-sized chunks with the best of them. Unfortunately, this torrid love affair with goals has remained largely unrequited. Goals just don’t love me as much as I love them.

My eyes have been wandering and I think I may have found my next personal development amour and this time it feels a little bit different…

A Practice-Based Approach to Personal Development

A practice is more than just a goal. It’s a mindset and lens on life that permeates everything you do and think. You don’t ever achieve a final end state in a practice. There’s no final goal, ultimate boss, or checkbox to tick when you’ve finished. It’s a commitment to taking constant yet small action that helps you develop skill. It’s a way of life. It’s just how you think and act.

My goals were always designed around aspirations like “being in good shape” or accomplishing some sort of impressive extracurricular activity like “write a book” or “start a company.” They were my best shot at articulating the end state that I thought would bring me happiness and/or meaning. I’ve finally realized, though, that trying to set goals kind of flies in the face of a lot of what I believe about the difficulty and impracticality of predicting the future in a complex world. Who am I to know what specifically might be the best thing for me to pursue?

Therefore, I’ve been experimenting with having a small handful of “practices” that I’m always thinking about and trying to challenge and push myself in at all times. They aren’t goals and they are very broad. They come out of the self-knowledge I’ve gained over the past 30 years about when, where, and how I feel like I’m at my best. As of this writing, they are:

  • Mindfulness

  • Strength

  • Cooking

  • Journaling/Writing

  • Minimalism/Essentialism

  • Deep Work

My hypothesis is that developing skills in these areas (which obviously aren’t mutually exclusive) will serve me much more than any set of discrete goals ever could. Each of these practices can be developed with deliberate effort and consist of actual skills that can be practiced and refined.

I’m still working on the supporting mechanisms that will help me bring these to life, but so far I’ve landed on a couple that have worked well.

1. Weekly Freewriting & Reflection

First, I’ve set aside some time every weekend to just do some free writing about how the previous week went in each of my practices. What did I do to become more skilled in this area? What didn’t I do? What should I consider doing next week? Taking some time to just reflect and set some basic intentions helps me stay on the proper track.

2. Tracking Meaningful Metrics

Another thing I’m still in the process of doing is figuring out which metrics actually help me see development in each practice. The obvious one is simply the number of sessions in which I deliberately engage in the practice (number of strength workouts, number of meals cooked at home or new recipes tried, number of meditation sessions, etc.) but I think there may be a few others that are worth tracking. I already have a pretty robust weekly metrics habit where I regularly track a few numbers that matter to me so this is simply a matter of updating those metrics to make sure they directly support my practices.

3. Capturing Potential Next Actions (in a Low Key Way)

Finally, I created a folder for each practice within OmniFocus where I capture discrete next actions I could partake in to help me further develop my practices. These ideas often fall out of the freewriting exercise I shared above. I often start the freewriting exercise by quickly reviewing and checking off the actions I know I took in the previous week. For example, right now in my Cooking Practice I have the actions, “sharpen my knife,” “find a recipe to cook this week,” and “read another section in The Food Lab.” In my Strength Practice I have “bail on a squat” (so I can get over my fear of failing a rep and learn how to do it in a safe way) and “finish reading chapter 3 of Starting Strength.” I treat these next actions lightly and none of them have a due date. They’re just placeholders to help me figure out what to do when I decide I want to do a session in any of my Practices.

I’ve only been doing this for a couple weeks but the difference in my mindset has been incredible. Thinking about the ways I want to be better as never ending practices instead of finite goals has somehow completely shifted what it means to get better at something. My actions are no longer a means to an end but an end within themselves. Maybe it’s possible to make that mental shape without all the rigamarole I described above but for whatever reason this is really working for me.

Expect more on this topic as I continue tweaking the basic approach and getting deeper into the practices themselves.

This article is part of my daily challenge to write and publish something in about 30 minutes. Please excuse the length — if I had more time I would’ve written something shorter. I like feedback in the comments below or Twitter (@samspurlin).

I Am What I Re-Read

Earlier I tweeted:

“You are what you (re)read.”

With that in mind, I figured I’d share a handful of the books I’ve re-read recently (or most frequently):

  • Getting Things Done by David Allen (read 5 times): I read this every year or so. Each time I read it I find some new angle or idea that didn’t resonate with me in any of my earlier readings. It’s a book I turn to when I’m making transitions — most commonly out of a period of extreme busyness and into one of more calm. It helps re-center me.

  • Deep Work by Cal Newport (read 4 times): It’s surprising how many times I’ve read this considering it’s only been out for a year or so. When I’m feeling frustrated with a lack of progress in big and important work I often turn to this book to help get me back on track.

  • Flow by Mihaly Csikszentmihalyi (read 3 times): This is the book that changed everything for me. After I read it for the first time in early 2011 I decided to apply to graduate school to study positive psychology with Dr. Csikszentmihalyi. That was the best decision I ever could’ve made and I’ve been on a track of meaningful work ever since.

  • Mindfulness in Plain English by Henepola Gunaratana (read 3 times): I think this was the first book I read about mindfulness and I still think it’s the most clearly written and accessible of anything I’ve read. I try to always be reading a book related to my meditation practice and I like coming back to this one (in fact, I think I’m due for another re-reading).

  • Essentialism by Greg McKeown (read 2 times): When life feels overwhelming I come back to Essentialism. I aspire to essentialism in all aspects of how I spend my attention and this book always helps me recalibrate when I feel out of balance.

There are other books I’ve read at least twice (the Lord of the Rings trilogy, The Hobbit, Autopilot: The Art and Science of Doing Nothing, Zen Mind, Beginner’s Mind, The Power of Less, Reinventing Organizations, and In Praise of Slowness all fit that criteria according to a quick perusal of Goodreads), but the five I’ve listed above are the ones that come to mind when I think about books I’ve read more than once in the past and will likely keep reading in the future.

Part of me thinks that needing or desiring to re-read books is a failure because I evidently failed to retain the important information within. However, I’ve come to accept that 100% information retention is an unrealistic goal for me to strive for when reading for leisure and that even if I did have the ability to fully retain everything I read a large part of what I find meaningful depends on my personal experiences or emotions at the moment of reading — both things that vary with time.

What are books that you return to over and over? Are there certain books you turn to when you’re feeling a certain way?

This article is part of my (somewhat neglected) series where I challenge myself to draft, edit, and publish something in roughly 30 minutes every day. If you’re interested in what I’m reading you can follow me on Goodreads.


It’s 9:52 PM and I just brewed a cup of Sleepytime tea (which I’m not convinced packs much of a sleepy punch). I was about to wrap myself in a blanket and flop onto the couch and read a book on my iPad for an hour or so until I go to bed. Then I remembered this stupid little experiment where I’m challenging myself to write and publish something (nearly) every day.

The “nearly” modifier creates some nice ambiguity that I can use in my favor but I’m not sure I can go more than a week without writing and say I’m nearly doing something. That seems more like an occasionally than a nearly. Or a once-in-a-while.

I don’t think anyone has ever become world class in a discipline by doing something occasionally.

I don’t even really want to be a world class caliber writer (hence my satisfaction with nearly) — I just want to become better than I am right now. Maybe write a book. Definitely write some articles that make some folks say, “Hm, that was pretty good.” Modest goals for a modest commitment to getting better at something.

It’s 9:57 PM now and I still want to read this book and I still want to drink this tea and I still want to go to bed at a reasonable hour so I’m going to say this article is nearly, nah — absolutely, long enough. Because it’s not about writing something awesome once in awhile.

It’s all about writing something, anything, every day.

Well, nearly every day.

This article is part of an experiment where I challenge myself to write and publish something in under 3o minutes every day — typos and run on sentences and abuse of italics be damned.

The Power Usage of Default Apps

Sometimes being a power user means using specialized apps that allow for greater customization than what default apps or services can provide. Power users need special tools so they can tweak and optimize their workflows to the n-th degree.

I think there can be another definition of power user.

I like to explore the idea of being a “power user” of default apps. I like the challenge of artificially restricting myself to only default apps on all my devices (at least in areas where it isn’t prohibitively detrimental to my productivity). Creating this restraint does two things — first, it forces me to really know how to use the default apps and second, it forces me to keep my workflows and systems simpler than I may otherwise be inclined. Both of these are positive outcomes.

The default apps are often surprisingly robust. There’s rarely something I can’t do that I need to do with a default app. At the same time, since they tend to be simpler than other options I could avail myself of I’m forced to be more mindful about what “job” I’m actually hiring a piece of software to do. For example, I recently switched back to the default Mail app across all my devices (away from the incredibly customizable Airmail) because I realized I was using almost none of the customization available in the more advanced app. I was hiring Airmail to do a job that the default Mail app could do just as well — and actually a little bit better (it tends to be stabler and loads faster than Airmail). What I sacrifice in theoretical flexibility I gain in practical usability.

Obviously, there are gaps in what default apps can do. I’m actually writing this right now in Day One, a non-default app for journaling. What Day One does for me is valuable enough to let it break through my non-default app embargo because while I could use something like Pages or TextEdit to keep my digital journal, it would be a vastly diminished experience. Part of what keeps me journaling regularly is how enjoyable it is to use this app and the features it has specifically related to journaling. Another non-default app that I absolutely must use copiously is Slack. There is no Apple-made Slack client. Slack is Slack. And Slack is where 98% of my work communication happens. Thus, Slack lives on all my devices.

Default apps I’ve recently re-embraced, though, include Notes, Podcasts Numbers, iBooks, Twitter, Apple Music, and Apple Maps. There may be “better” versions of each of these apps made by a third party developer but I’ve realized that in almost every case the default version is more than suitable for what I truly need it for. The fact that the Twitter app is worse than Tweetbot is actually making me use Twitter less — which is probably a good thing. Same with the Podcast app. Using Overcast makes it so easy to find other episodes of shows I like I often ended up spending more time listening to podcasts than I actually wanted. The Podcasts app doesn’t have cool features like Overcast… but it does pull down the handful of podcasts I subscribe to and let me listen to them. Which is really all I need.

Challenge yourself to give the default apps on your devices a try for a week or two and you may surprise yourself in realizing what is and isn’t necessary for you to be productive and happy.

This article is part of an experiment where I try to write and publish an idea in 30 minutes or less (nearly) every day, typos and logical sloppiness be damned. Want to keep the discussion going? Leave a comment below or find me on Twitter.

Your Priorities Are Only as Good as What You De-Prioritize

A few days ago I shared a personal practice that has been really valuable — the even-over statement. If you missed that article, the basic idea is that nothing is truly a priority unless you’re willing to sacrifice something else in the name of it. Using an even-over statement forces you to articulate that tradeoff in a way that can really help put a fine point on what you’re trying to do.

My three even-over statements for the first part of 2017 are:

  1. Sincerity e/o Irony

  2. Good Weeks e/o Good Days

  3. Consistent e/o Stochastic

I took a first stab at articulating what these actually mean to me in the original article, but upon further re-reading I realized I didn’t go into much detail about the “even over” part of each statement. It’s important to remember that an even-over statement is only as powerful as the good thing that’s being de-prioritized in each statement. To that end, I wanted to describe the deliberate tradeoff I’m making by adhering to these statements.

Sincerity even over Irony

As I mentioned before, the impetus of this even over statement comes from this excellent video from Will Schoder. I think part of the reason that it resonates so much with me is because it helped me realize how much of my own conduct and sense of humor leans on the ironic. It’s easy for me to be self-deprecating or cynical (which I consider cousins of irony) when I’m trying to be funny. It’s a.) too easy b.) a way to avoid being vulnerable and c.) frankly, not that funny.

Defaulting to sincerity does not come easily to me and yet I really value the people in my life who seem to be able to do a good job of it. I want to be more like them. I suspect it will make me a more pleasant person to be around, make me more effective in my work, and probably just improve my quality of life.

Good Weeks even over Good Days

I’m a huge believer in being mindful about how I spend my time and attention. I try not to let distractions interfere when I’m doing meaningful work — I mean, I read Deep Work by Cal Newport three times last year. Doing the right stuff, whether that’s taking care of myself physically or making sure I’m moving forward important work is central to my identity and sense of well-being. Unfortunately, this has often manifested in being way too hard on myself on a daily basis. It’s pretty unreasonable to expect every day to be amazing.

Even though it feels wrong I’m going to experiment with broadening my self-reflective (self-critical) horizon out to a weekly basis. Tied to this experiment is the realization that I almost always feel like I never get enough done on a daily basis but often surprise myself with how much I’m able to accomplish in an entire week. With that in mind, this even over statement is designed to bring me into alignment with that realization.

Consistent even over Stochastic

When I think of being stochastic I think of two things that are pretty positive: spontaneity and high intensity intervals. Being spontaneous is fun. People like spontaneous people (for the most part). Working in high intensity intervals aligns with much of my philosophy about how people are able to focus and develop a deep work practice. But for the time being I need to set these positive elements of a more stochastic working or self-care style aside and focus on doing the small, boring, yet absolutely vital things more consistently.

Even over statements don’t work if the thing you’re giving up isn’t difficult or intrinsically “good” in some way. In some respects, I think the power of this exercise and practice doesn’t come from the front half of these statements (the thing you want more of) but from selecting the right attribute to disengage with.

Only then do these “priorities” actually begin to be actual Priorities.

This article is part of a personal experiment where I write and publish something in 30 minutes or less (nearly) every day. Find a typo? Have a question or comment? Leave a comment below or talk to me on Twitter.

Is It Possible to “Be Hungry” Without Working Insane Hours?

What does it mean to be hungry in the context of your work — if you take working insane hours off the table as an option?

This idea came up during our recent Ready Week (a trimesterly week where we don’t do any client work and instead focus internally while capping it off with an all-hands retreat). We didn’t really dive into it in much detail so I wanted to take a stab at articulating something.

This is particularly important to us because we are a self-managing organization. Each member at The Ready holds a portfolio of roles. Each role holder is expected to figure out the best ways to “energize” their roles and the limitations on what you can and cannot do are fairly non-existent. There aren’t any roles in our organization whose purpose is to manage any of the other roles. The end result is an incredible amount of freedom and autonomy to do what I think is best. At the same time, it truly is up to me to figure out how to raise the bar on each of my roles.

That’s where the idea of hunger comes in. A truly self-managed organization only thrives when everybody is pushing up against the limits of what they think they can do. Without that deliberate expansion and exploration of what each role could or should do the organization remains static. It’s only when the edges are explored and challenged that the organization continues to grow and evolve.

The easiest way to think about being hungry at work is simply putting in more hours than anyone else. This is far too simple and unsustainable to be the actual answer. While we all sometimes put in more than the standard 40 hour week, we try to make that the exception rather than the rule. In many cases, working extreme hours is what you do when you don’t actually know how to have an impact or are more interested in “hunger theatre” than actual hunger.

For me, I’ve been exploring the ideas of prioritization and focus as my way of operationalizing hunger.

The two books I come back to again and again as I think about how to up the hunger factor in the way I work is Deep Work by Cal Newport and Essentialism by Greg McKeown.

On the Deep Work side of things, being hungry means tackling everything I do at work (and elsewhere) with single-minded focus and determination. It’s about being able to concentrate on something beyond the first twinges of discomfort in order to get beyond the surface level observations and output that are relatively easy to gain and thus less valuable.

Having a deep work practice, and having that practice be my standard operating procedure for when I’m “at work” strikes me as being hungry. Deep work isn’t easy. It doesn’t necessarily feel good. But a company full of people dedicated to the practice of deep work is a company that’s inevitably creating something new and valuable.

Prioritization, on the other hand, is about knowing what to go deep on. It runs the gamut from developing and using even-over statements, to ruthlessly unsubscribing from unproductive email, saying “no” far more frequently than I’d prefer otherwise, streamlining low-impact but necessary activity, etc.

My favorite resource related to prioritization is Essentialism. Essentially (heh), being hungry is about eliminating the vast majority of the low impact activities, responsibilities, and requests on my time. It’s about forcing myself to get clear about where and how I have the largest impact and ignoring everything that’s not that. In my specific situation, that may mean skipping a “let’s get coffee and chat” request in order to work deep on a new theoretical contribution to our work or setting aside time to turn off all my devices, go somewhere quiet, and just think for a bit.

The nice thing about operationalizing hunger as focus and prioritization is that neither of these are contingent upon time. They aren’t antithetical to work life balance (actually, they are directly in support of it).

If your next performance review came down to hunger what would you do in the next 90 days to make that the cornerstone of how you work?

This article is part of a new experiment where I write and publish something in about 30 minutes (nearly) every day. Find a typo? Have a question? Leave a comment or follow me on Twitter to chat.

A Nifty Tool for Making “Priority” Mean Something Again

One of my favorite thought technologies is the “even over statement.” An even over statement is a declaration of priority. It’s you saying you’re going to emphasize GOOD THING even over OTHER GOOD THING. It puts a delightful point on something we all know but rarely enact— that priorities require sacrifice. If there’s one word in the English language that has been bastardized beyond recognition it’s “priority.”

Maybe a long, long time ago attaching the word “priority” to an intention or a goal was something laudable. Now? It’s just the price of entry for joining the list of 17 other “priorities.”

When we work with teams at The Ready we often run them through a Strategy Meeting where we force them to create even over statements for their priorities. There’s always much gnashing of teeth and furrowing of brows but the end result always feels good. You leave the room knowing what to focus on and even more important, what’s okay to let slide in the pursuit of the actual priorities.

ANYWAY, preamble over.

I like to do strategy statements for myself. Here’s what I came up with. I’m going to run with these for at least a couple months and will revisit them later to see if they’re still resonating with me. Other than that, I’m going to bake some time into my weekly review each Sunday to reflect on them a bit.

These statements are meant to help guide me personally over the next few months and they are born of my self-observations and self-reflection. They are designed to address some areas of concern that have come to my attention and to be general enough to impact many aspects of my life but specific enough that they actually mean something.

Sincerity even over Irony

I’m tempted to just share this YouTube link and tell you that it encapsulates everything I’m trying to do with this statement better than I could ever write about it. In a nutshell, I think irony (and it’s close cousin, cynicism) have weaseled their way into my daily interactions and thought patterns to an unhealthy extent. Hip irony, sarcasm, and copious self-effacement have become crutches that prevent me from actually having to be sincere. From actually caring deeply about things. And while that’s not entirely accurate (I care deeply about lots of things) I don’t know that I’ve let that care and sincerity out of the closely held place I tend to keep them.

Good Weeks even over Good Days

I’m really hard on myself. Really, really, hard. My horizon for self-criticism has gotten far too short, though. I know that it’s okay to have off days but my modus operandi is to get far too critical with myself at the first sign of mediocrity. It comes from a good place (wanting to be a better person than I am today, wanting to make the world a better place, wanting to make the people around me happier/better/etc.) but the sick twist is that my self-criticism often gets in the way of me actually being able to do any of that.

So, instead, I’m going to broaden my horizon of criticism and reflection beyond the standard 24 hours I’ve been operating under. Now, I’m going to try to spend less time stressing about whether or not I had a good day and instead focus on figuring out how to have good weeks. I can still have a good week even if I sprinkle in the occasional bad day.

Consistent even over Stochastic

I have a small handful of simple activities that I know make me feel SO GOOD when I do them consistently. They are incredibly boring. Things like going to bed on time. Waking up on time. Meditating every day. Not eating out all the goddamn time. Working out consistently. Writing. Really groundbreaking stuff.

While these activities are certainly simple it hasn’t necessarily been easy to do them consistently. I go through short bursts where I nail them everyday. But then I’ll go through a burst where I do a few of them while letting the others fall to the wayside. Or I’ll do none of them for weeks. And then all of them for a week.

Considering how simple these things are and how I know how they have a huge impact on how I feel about myself (and thus how effective I am at work and how pleasant I am to be around and my general outlook on the world) there’s really no excuse for being so haphazard about them anymore. So, consistent even over stochastic I must be. I’m going to wrap these boring routines around me and wear them like a fucking blanket. It’s going to be so boring. And awesome.

Three statements. Three very clear strategies to help me navigate through an uncertain world. Here’s to a 2017 of sincerity, good weeks, and mind numbing consistency.

This is the first article in a new experiment where I write and publish something in about 30 minutes (nearly) every day. Find a typo? Have a question? Leave a comment or follow me on Twitter to chat.

2016 in Review: Podcasts

I’m a huge fan of podcasts but am fairly selective with what I add to my regular listening rotation because if I subscribe to something it means I listen to every episode (and have either been listening to it since day one or I worked my way through the entire back catalog). Most of these podcasts I’ve been listening to for years.

Looking at my list of podcasts I’m struck by how I listen to most of them because of the personalities of the hosts and not the topic of the show. You’ll see a lot of the same names in the descriptions below.

I also noticed that I really don’t enjoy interview podcasts. I know some of the most popular podcasts in the world follow this format (and some of my friends create podcasts in this style) but I just haven’t been able to get into that genre. Given the importance of personality to my podcast listening experience it’s not too surprising that I seem to prefer shows where the hosts are always the same people and therefore build up a rich history of subtext, inside jokes, and running bits that rewards the long time listener.

  • Above Avalon: This is the only podcast I listen to where it’s just one person talking the whole time. Neil Cybart consistently provides Apple analysis that’s refreshingly different from most of the other Apple pundits I follow.

  • Accidental Tech Podcast: Marco Arment, John Siracusa, and Casey Liss talking about Apple and other technology. I’ve been listening to Marco and John for years (back during the Hypercritical and Build and Analyze days) and have been listening to ATP since it was just a joke section during Neutral. A great example of three hosts with chemistry who all bring something different and valuable to the table.

  • Back to Work: Merlin Mann and Dan Benjamin talk about work, productivity, and anything else that comes across their radar on a weekly basis. This has been a staple of my podcast lineup for years.

  • Canvas: Federico Viticci and Fraser Speirs combine for the most delightfully accented podcast I listen to regularly. This is all about using iOS and as I’ve explored using iOS more on a day-to-day basis I’ve learned a ton from this podcast. I’ll probably be going back and listening to specific episodes again as I dive deeper into the iOS-centric lifestyle.

  • Connected: Myke Hurley, Federico Viticci, and Stephen Hackett combine for a weekly technology news show that always seems to find its way back into my lineup even if it does get occasionally lost during my regular podcast purges.

  • Cortex: Myke Hurley and CGP Grey host my favorite productivity podcast. Grey is a complete weirdo (in a good way) and Myke does a great job at bringing out the quirkiness. I get more ideas for my own productivity workflows from this podcast than anywhere else.

  • Do By Friday: Merlin Mann, Max Temkin, and Alex Cox host a weekly “challenge show” that is ostensibly centered on a weekly challenge. The challenge is mostly a McGuffin for a humorous conversation among three very funny people.

  • Exponent: This is one of the few podcasts I listen to that actually makes me feel better at my day job after listening to it (along with Above Avalon). Ben Thompson and James Allworth always have great conversations that range widely in topic. If you’re interested in technology this is definitely worth listening to.

  • The Flop House: Working through the entire back catalog of The Flop House was one of my crowning achievements in 2016. I’ve seen almost none of the movies they talk about and that never prevents me from enjoying every episode.

  • Hello Internet: Brady Haran and CGP Grey are professional YouTubers who started this podcast to talk about YouTube and have since created a podcast universe unto themselves. Brady and Grey are polar magnetic opposites which makes for great listening.

  • Living Zen Podcast: I think I caught this podcast at a weird time. The first episode I listened to was this incredibly personal and difficult sounding talk about how the center might not be able to continue because of a lack of funds. I don’t know what this means for the longevity of this podcast but so far it has been one of the more accessible zen podcasts I’ve found.

  • Ordinary Mind Zendo: This is the podcast of the zendo I joined in October. Good, short, talks.

  • Presidents Are People Too!: Elliott Kalan from The Flop House and historian Alexis Coe dive deep into the life of one former president in each episode. I became a huge fan of Elliott during my The Flop House obsession and resolved to listen to anything he was part of. A couple weeks ago my wishes were granted with this podcast. If you’re an Audible customer, you can listen to the episodes earlier than iTunes customers by checking out Channels.

  • Reconcilable Differences: Merlin Mann and John Siracusa have finally come together for the podcast we’ve been waiting forever for. John and Merlin have awesome chemistry.

  • Road Work: I was going to try to write something about this podcast by Dan Benjamin and John Roderick but I think the description from the webpage will suffice: “America’s top two podcast personalities are finally coming together in one podcasting event that will change the way you think about podcasting forever! Like a rock skipping over the placid waters of an alpine lake, Dan and John are all too well aware that this burst of kinetic energy will ultimately deposit them, like all human effort, at rest in the icy depths where no light can penetrate. Until then, they mean to thrill to the chase! To soak up the remaining light and banish thoughts of tomorrow! EXCELSIOR!”

  • Roderick on the Line: Merlin Mann and John Roderick. The pinnacle of the “two guys talking” genre.

  • Unattended Consequences: A new addition that introduced me to Patrick Rothfuss (as a podcast personality and amazing author). Pat and Max Temkin make a great duo.

  • Under the Radar: I’m not an iOS developer but for some reason I really enjoy this podcast. Hosted by “Underscore” David Smith and Marco Arment.

Looking to the Future

I might try to find some more educational or business related podcasts to add to the rotation. The vast majority of what I currently listen to is pure entertainment and I can’t help but feel if I added some more Exponent-esque shows to the mix I might expose myself to more ideas that might prove useful in my work.

I need to be careful with what I add, though, because podcast listening time often cannibalizes audiobook listening time and I’d rather spend more time on audiobooks in 2017. I kind of feel like I’m mostly at capacity right now so it will probably take unsubscribing from something or really just being blown away by something new to add it to the rotation.

What are your favorite podcasts from 2016? What should I give a trial run?

The Dueling Forces of Focus and Curiosity: Following Up on a Minimalism Experiment

A couple weeks ago I wrote an article about a minimalism experiment I was undertaking. My minimalism practice was already well developed so this experiment wasn’t about shifting from some kind of normal state into some slight decluttering, but about taking my pre-existing minimalist tendencies to a whole new level.

I won’t go over the parameters of the challenge in excruciating detail here (you’re welcome to read the original article if you want the gory details) but the basic gist was that I would basically remove every source of novelty or information in my life for a set period of time and notice the effect it had in my mind.

The impetus for the experiment was my own low-level frustration in not doing the things I knew I should be doing (writing regularly, meditating, and working out, mostly). Particularly when it comes to writing, I knew that I was not giving myself enough quiet time to work through or develop ideas truly worth writing about. I’ve had experience with the kinds of insights I can tap into when I systematically remove some of the noise in my life and I wanted to try to make that space for meaningful ideas and writing again.

Now, several weeks after my minimalism proclamation I feel like I owe people an update as to how everything has gone/is going.

First, my true extreme minimalism stage lasted an embarrassingly short period of time after publishing the original article. Within a couple days I found myself diving deeper into the world of third party apps across all my devices (iPhone, iPad, MacBook, and Apple TV) than I ever had before. Other aspects of the experiment stuck around for a bit longer. I didn’t listen to any podcasts for a couple weeks (although I have since caught up on the approximately 10 shows I’m subscribed to), my RSS reader remained empty for awhile (and now has about 8 sources in it), and only yesterday did I put my Withings wireless scale back in the bathroom.

Mentally, I noticed a couple of interesting things. First, and I’ve known this for months, maybe years, and have been wanting to write about it forever, but I seem to have two modes that I’ll call Expansive and Minimal. This whole experiment represents the desires of my Minimal mode. When the Minimal mode engages I look for ways to gain control over my environment and my mind. I declutter my already sparsely appointed apartment, I delete third party apps off all my devices and resolve to “run stock”, I look for ways to automate life tasks (hello Blue Apron, FreshDirect, and Cleanly) or I look to cancel every unnecessary subscription or service (goodbye Blue Apron, FreshDirect, Cleanly, Netflix, Apple Music, etc.). It’s hard to predict how it’s going to manifest and it’s very rarely rational to behold. The Minimal mode wakes from its slumber when I’m frustrated by the way I’m choosing to spend my time and generally feeling like I’m letting myself and the people around me down by not being better. I think it’s equal parts the desire to remove distraction and a way to punish myself for dropping the ball.

The Minimal mode’s antithesis is what I’ve been calling the Expansive mode. This is the equally enthralling state of mind where I break out of the confines of minimalism and decide to guzzle from the fire hose of information and entertainment and social interaction that our modern technology makes so easy to do. When the Expansive mode comes out to play I find myself following more people on Twitter, reinstalling Instagram, adding a bunch of stuff to my RSS reader and actively looking for new podcasts to check out. I’ll eschew the default apps that come with my devices and dive deep into finding the specific third party apps that allow the customization and features that let me use my devices like the semi-power user I am. I revel in novelty. I skip from distraction to distraction.

Since that original article I think I’ve gone through both of these mindsets at least once, maybe twice.

Somehow I feel like the Minimal mode is the “right” one for me to be in and that if I could only find a way to remain like the urban monk I become during those phases I would somehow do all the things I feel like I should be doing that I’m currently not. Of course, though, it’s not that simple.

I’m trying to find my healthy middle way. I think I found my preferred baseline standard operating procedure a long time ago (it’s very minimal but it is much more reasonable than when I’m under the influence of my full blown Minimal mode). Because, spoiler alert, making physical and mental space in my life to be productive and do great things isn’t the secret to actually doing those things. The removal of distraction and novelty is not sufficient in itself to bring new creative endeavors into the world. On a logical level, I know that. But when I’m deep in the throes of hating myself for being so goddamn mediocre it can feel so much easier and straightforward to find some shit in my apartment to throw away, delete some apps from my phone, wipe my Twitter followers, and sit in the quiet comfort that, “Now there’s nothing left to distract me. I have no choice but to write/workout/read/whatever I’m not doing but feel like I should.”

I do think there is value to occasionally wiping the slate clean and starting fresh. I do think challenging myself to do with less is better than becoming accustomed to more. I do think eliminating distractions and carving out time and attention to dedicate to difficult work is a worthwhile endeavor. What I don’t believe, though, is that this is only “right” way to live and any time I stray away from it I am giving into temptaton or taking the easy way out.

The past couple weeks have made me more interested in what it looks like to live a deliberate and conscious life full of meaningful work in the midst of the chaos of life in NYC in 2016 while working at a start-up and while being an insatiably curious person with wide interests. True mindfulness is being able to take the device with the hundreds of third party apps and know how to flip it over and silence it when it’s time to write and not need to go through the acrobatics of neutering its functionality and hiding it because that’s the only way I’ll leave it alone long enough to do anything worthwhile.

True dedication to my craft is being able to carve out the time I need to do the things I say I care about (like writing) not by making grand gestures of wiping my calendar clean or cancelling every social commitment but by taking seriously the snippets of time that are underutilized or unappreciated right now. Or, even better, knowing how to create the space and distraction-free environment I know I need to wrestle with big ideas and complex tasks without having to become some kind of proto-digital hermit in the process.

Anyway, I suspect ill keep swinging between my Expansive and Minimal mindsets in the future but I’m going to try to keep the really deep, dark dives into either end of the continuum a much less frequent thing. Instead, I’ll try to hang out in the middle a little bit more and will get better about identifying how and when I should step a little further toward Expansion or Minimalization. When I’m in between article ideas or sitting on the front end of a new and large project then maybe that’s the time to open my aperture a bit further and indulge in more of my Expansive tendencies to get the information and perspectives and ideas that I can use as raw material later on. Once that raw material is gathered, though, and it’s time to actually crank on some kind of product I can put on my metaphorical monk robes, put my phone in a drawer, stop trying to perfect my “information consumption strategy”, and get lost in the Minimalism that lets me focus long and hard on one thing.

How to Prepare for a Vacation in the Digital Age

This article isn’t about the planning or logistics that go into taking a good vacation (less is always more when it comes to that anyway). It’s about how I’m setting up my devices and the expectations people have for me to simultaneously not detract from my vacation and enhance it (which are related but separate concepts). Your mileage may vary.

First, let’s get clear about what a vacation, or specifically this vacation, is for. It’s two weeks long with half of that time spent in (hopefully) warm and sunny Florida and half spent in decidedly less warm (but probably equally sunny) Michigan. The Florida segment will primarily be spent without obligations (familial or otherwise) while the Michigan segment will consist of staying at my parents’ house and being surrounded by my large immediate and intermediate family.

Regardless of the geographic characteristics of the vacation, the goals across the two weeks are largely the same:

  • Unplug my brain from work (both the day-to-day logistics and details of managing large scale organizational change efforts and the deliberate pondering of organizational design theory*)

  • Reboot my attentional sensitivity by abstaining from digital candy (my main vices are Twitter, Instagram, Reddit, and the ever so occasional glimpse at Facebook)

  • Reset my bedrock habits (full sleep with a relatively early waking time, daily meditation, daily exercise, and daily writing)

  • Indulge my curiosity through analog exploration instead of Wikipedia rabbit holes

  • Spend quality relationship building time with my very long term but also very long distance girlfriend (and who will be accompanying me on the first segment of this vacation)

With those basic goals in mind I had a clearer sense of what I need my devices to do to both get out of my way and also enhance what I want to do. Here’s what I did:

  • Moved all work specific apps (Fantastical, Safari, Airmail, Slack — for now) into a folder, turned off their notification privileges, and banished that folder to the back page

  • Deliberately decided which apps to leave on my front page. The ones who made the cut are Kindle, iBooks, Overcast, Instapaper, Music, Camera, Byword, and 2Do. A few words of explanation…

  • Obviously, I aim to spend much of this vacation with my nose (or ears) buried in a book. I have many, many hours left in the audiobook version of Ron Chernow’s George Washington biography and have yet to choose a book to actually read. I’m leaning toward Wise Man’s Fear (book one was insanely good) or some other fiction

  • I have a bit of an Instapaper backlog. Even though most of those articles are ostensibly work related I’m fortunate to find those topics intrinsically interesting. Once I clear that backlog I’ll probably move it off the front page

  • I also have a very small podcast backlog. I think I’ll give it the Instapaper treatment — clear the backlog, pause refilling it until after vacation, and then move it off the front page

  • Camera makes the cut because I want to take pictures over the next two weeks. I’m terrible at remembering to do this but am nearly always glad when I do

  • 2Do (my task management app) may seem like a weird app to include on the front page given my goals related to unplugging from the work. However, I need it close at hand because I will be using it copiously to dump the various thoughts that come to mind related to work. It’s the starting point of my GTD system and I’m a firm believer in thinking ideas once and then saving them somewhere I know I can trust to deal with them later

  • My iPad is setup the same way but with the addition of Byword (which is where I’m writing this right now as I fly to Florida). Writing is something that’s incredibly important to me and I’m hoping to spend a significant amount of time over the next two weeks just writing about whatever seems urgent and/or interesting when it’s time to sit down and type. This is my favorite iOS app for doing that. Some entries may find there way to Medium but chances are most will end up in Day One (my long running digital journal)

Outside of the actual app arrangement itself, I’ve also gone in and silenced nearly every notification that is even somewhat likely to happen over the next two weeks that isn’t absolutely critical (e.g. email is silenced but my banking app can still tell me if someone is trying to use my credit card to pay for illicit pet monkeys in Nova Scotia).

I dropped a note in my Twitter profile about being away for the next two weeks, but that’s probably more in service of my own vanity than the unlikely situation that anyone would notice or care about my absence. Turned off notifications, too. The burst of dopamine every time someone likes a tweet feels nice, but I’ll be searching for more natural dopamine hits on this vacation (that sounds like I’m talking about drugs… more like sitting on a beach with my feet in the water or petting a dolphin on the head).

I don’t get many emails, but I’ve gone ahead and setup a simple vacation responder letting people know when I’ll return. People who really know me already have my phone number and are welcome to call or text in a true emergency.

Work-wise, I’ve cleared my plate everywhere I could, talked to my team about covering key meetings in my absence, and trust that nothing too bad can happen in two weeks (right?).

Now, it’s all about easing into the mental space of not needing to be “on.” It’s about resisting the muscle memory of flipping open Tweetbot or Slack and making sure I’m “on top of things.” It’s about soothing and calming a mind that is often moving faster than is useful or enjoyable.

So with that I’ll close my iPad, pop in my headphones, and listen to the soothing dulcet tones of a gentleman telling me about the life of the first American president. I’ll feel the urge to make a humorous quip on Twitter or see how many people recommended this article but instead I’ll just turn up the volume and remember that Washington didn’t help lead a revolution or cross the Delaware — and I won’t do whatever my equivalent is — without letting the inessential and inconsequential crowd out the necessary hard work of recharging physically, mentally, emotionally, and spiritually.

And last I checked there’s no app for that.

  • My notebook will be ready to record any insights that I hope bubble through my subconscious and make it the surface of my awareness. You better believe I’ll be capturing those. Those mind nuggets are gold!

How Does a Minimalist Pack? A Quick Retrospective on a 1-Day Business Trip

Anything I do more than once I expect to get better at. Traveling is one of those things. My job has me traveling a fair amount and each trip is an opportunity to perfect the way I do it. I also like challenging myself to pack as lightly as possible.

This trip was for a quick 1-day sojourn to Chicago from New York City. It would have me leaving Wednesday evening and coming back to NYC Thursday evening. I spent the vast majority of Thursday at the client’s office delivering a workshop.


The first gathering of stuff.

Let’s take a look at my first stab at packing for the trip:

  • Slacks, undershirt, grey button up shirt, socks, underwear, athletic shorts

  • Mittens & scarf

  • 12” MacBook Retina & power cord

  • iPad Air 2 w/ charging brick and cord

  • Apple Watch series 1 (not pictured) and its ridiculously long charging cord

  • iPhone 7 Plus (not pictured) and Lightning EarPods

  • Medium size Moleskine notebook & pen

  • Toothbrush, toothpaste, deodorant, pomade, contacts, comb, NightGuard (dentist’s orders…), glasses & case, sunglasses & case, dopp kit

  • Wallet

  • 15 The Ready Vol. 1 magazines (not pictured)

  • A stack of post-it notes (not pictured)

  • A handful of sharpies (not pictured)

  • 100 ping pong balls (not pictured)

Not being happy with my first attempt at anything I took a look at everything laid out on the table and decided to see if I could make another attempt at removing the nonessential.


Didn’t make the 2nd cut.

I decided to not bring:

  • Mittens & scarf (I was only going to be there for a day and would spend most of it indoors anyway)

  • Sunglasses (landing at night, spending the whole day inside, and then flying out again in the dark)

  • Comb (I don’t actually have a hair style that requires a comb — I dunno why I grabbed it in the first place)

  • iPad (since I was bringing my computer and my phone and the flight was short I figured I didn’t have much use for a third device)

  • Athletic shorts (realized I wasn’t going to have time to workout)

After removing those things, this is what was left to go into the bag:


A couple things to note:

  • I decided to only bring the iPad charging brick (as opposed to my iPhone brick and/or Apple Watch brick) because it would super charge my phone and watch and I didn’t necessarily need to charge both of those things at the same time.

  • At the last second I decided to bring my Beats noise cancelling headphones but not the charger and cord. My reasoning was that the flight was short and that I should be able to get there and back without needing to charge them. I was right.

  • I definitely could have worn the same pants on the plane and then to the workshop the next day and it wouldn’t have been a big deal. Although, I guess I’d really be rolling the dice on keeping them stain-free for two days in a row (I have a magic ability to somehow always get food on myself).

  • I regret not bringing my scarf and mittens. It was 19 degrees at one point and I walked from the hotel to the client’s office (roughly half a mile).

  • I forgot to grab an adapter (USB-C to VGA) at the office before I left so I had to buy one when I got there.

  • If I didn’t have to bring workshop material (magazines, ping pong balls, post-its, and sharpies) I probably could have just brought my backpack and not needed my carry on as well.

Overall, pretty solid attempt. Didn’t really bring anything that wasn’t used and didn’t leave much behind that I really wish I had with me — which is generally my metric for determining whether I did a good job packing.

Getting to Essential and Creating Space

I’ve been trying to articulate why my radical minimalism experiment feels so necessary. I took a stab at it in yesterday’s article but I thought I would take another shot at it right now.

I think there are two driving forces behind this effort. The first is the relatively simple idea of figuring out how little I need to truly be happy and productive. I’m healthy, straight, white, and male so the cynical way to understand this feeling is to think that my life is so peachy keen that I need to manufacture my own challenges. Cynical but probably more true than I’d like to admit.

My life is pretty great and I don’t really have any hardships worth pointing to.

And maybe it’s because of this cushy reality I feel like I have to take deliberate steps to not lock myself into the warm and dulling embrace of having every desire and whim met at a moment’s notice (but God, what a douchey thing to say, right?).

Perhaps this is my attempt at ensuring my success, to the extent I have any, originates from something other than privilege and fortunate external circumstances. Perhaps if I pare down my belongings and my attachments and my desires I’ll be left with a nugget of something that is me. And if all my success doesn’t escape or if I’m able to continue doing great work when the gap between capital M Me and what I produce isn’t intermediated by stuff then maybe I’m worthwhile after all?

This is taking an existential turn.

The second force at play is that I’m worried my participation in modern society is destroying the state of mind required to create something truly great. I’ve always believed that I was capable (destined?) to make a meaningful impact on the world. A book? A company? A talk? A theory? I’m not 100% sure the medium it will take but I am 100% sure that it will take more effort, time, and focus than anything I’ve ever done. Looking at the ebb and flow of my daily life right now I don’t see how that’s ever going to happen. I mean, it’s not like I’m going to suddenly suck at my job or anything like that. It’s more the realization that I could continue doing what I’m doing and have a perfectly mediocre life or I could really fuck-shit-up (FSU) and have a shot at doing something great.

It may be sad that the best way I can see to FSU right now is to basically stop using social media, put away my electronic entertainment devices, and sit in silence a bit more (more privilege, ftw). But hey, for me (and a lot of other people I know) that’s the modern version of FSU. Maybe I’ll find/be subjected to something different to do down the road (taking a long sabbatical? moving to another country? contracting a life changing illness?) but for now this is my best shot at shaking things up.

The hope is that this newfound space and silence will not only give me the raw time I need to create something great but also the time I need for the ideas bouncing around in my head to coalesce. Some ideas can be skimmed off the surface of the mind and implemented pretty quickly (and sometimes they’re even pretty good) but I have a feeling the really groundbreaking stuff requires the uncertainty and agony and frustration of silence when all you really want to do is listen to a goddamn podcast or shoot some aliens.