Is Technology Destroying My Intuition?

A Personal Experiment Recap and Reflection

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Are my systems turning me into a robot?

There are two dueling forces within me that seem to be locked in a never-ending battle. On the one hand, I love simplicity and minimalism. I love using default settings and apps, simplifying my needs, and generally reducing the number of requirements I need to be productive and happy. On the other hand, I love using highly specific software that has features beyond the basics. For the tools I use everyday, I love finding the best and then customizing them to my exact specifications and I love using technology to create systems and processes that help me offload the need to remember to do thing. These opposing forces ebb and flow within me and you can usually tell my current status by just taking a peek at the software I’m using (and since I’m writing this in Bear instead of Notes my expansive/non-minimal aspect must be winning right now).

I recently found myself reflecting on all the systems and processes I had created to get myself to do the “right things” at the “right time.” As a huge proponent of the Getting Things Done (GTD) personal productivity approach, I’m very good at offloading my tasks into an external system. Every thought that starts with, “I should do…” is regularly captured in a piece of software and a decision is made about what to do about it on a very regular cadence.

Even beyond my robust GTD system, I enlist technology for several other jobs in my life. I use an automatically recurring checklist in the morning and in the evening to help me get through my morning and evening routines successfully. Every day at the same time 5–7 reminders pop up on my devices to encourage me to do things like, “Read for a bit,” “Journal,” and “Meditate.”

Finally, I’m also using technology to track several different categories of data about myself, both physical and mental. I track sleep and physical activity with my smart watch, subjective experience with Exist.io, computer usage with Moment and Rescue Time, and finances with Mint, just to name a few.

All of these external systems I created for myself are designed to help me focus my attention and effort where it is most needed. At least, that was the theory… but what if I’m actually harming myself instead?

What if my GTD system is making me capture and make decisions on the inessential at the expense of what I really needed to be doing? Would I be more likely to work on what really matters, the truly essential, if I didn’t have a system that tracked all my work and instead I had to make decisions based on my gut?

Are my automatic morning and evening checklists offloading the responsibility to notice how my routine is making me feel in favor of just mindlessly checking items off a list? Do I really need a piece of technology to tell me to take the actions I know make up routines that are important to me?

Is my quantified self habit causing me to take certain actions not because of how they make me feel but because they move certain numbers up or down? Shouldn’t I be doing things because I like the way they make me feel and not because they make my graphs prettier at the end of the year?

In a nutshell, am I outsourcing my intuition by using processes and technology to take care of large aspects of my life?

Would I be a more sensitive, calm, and responsive person if I stopped relying on these systems and instead tried to get in touch with my own thoughts, feelings, and sensations? The more I dug into what an experiment to test this might look like the more nervous I got, which told me I was probably on the right path.

Ultimately, I decided to commit to 30 days where I removed as many of these sources of information, tracking, and outside support. I would revert back to a place where I didn’t have any kind of technology telling me what I should be doing or feeling with the hope that it would re-awaken what I was calling my intuition — my ability to notice how I’m feeling in the moment and make decisions or take action based on that information.

I won’t bore you with the day-by-day play-by-play, but some of the things I ended up doing included:

  • Stopped tracking my sleep

  • Stopped filling out my weekly personal metrics spreadsheet with things like steps, sleep duration, number of workouts, journal entries, and meditation duration.

  • Stopped weighing myself daily

  • Didn’t use an app to track workouts or meditation sessions

  • Didn’t use automatically recurring checklists in the morning or evening

  • Turned off as many notifications as possible

Importantly, there were a few things I didn’t do (although I definitely thought about it):

  • I didn’t stop using Things or the GTD methodology for tracking my work

  • I didn’t turn off Mint since it tracks my finances passively and I knew I didn’t want a big hole in my yearly data

Doing those two things felt too unsafe to try right now so I excluded them from the experiment.

The Results

The one thing that always bothered me about being a PhD student was this expectation that we were supposed to always know how our experiment would turn out. I’m not sure anybody ever explicitly said that, but the message was still there. By the time you had reviewed all the literature and prepared the methods and done pilots and worked through every possible contingency, running the experiment was just a matter of getting the data you needed to write up your findings (and if you disagree with that please point me to where all the “failed” experiments are being published… nobody moves forward in the academic world with failed experiments).

That was definitely not how I approached this experiment. It was truly an experiment in every sense of the word. I didn’t know what the results would be. On the one hand I was hoping that maybe this would unlock some kind of blissful, free, and responsive state of mind that would liberate me from all my systems and keep me much more rooted in the moment. That would have been an interesting and exciting result of this experiment. On the other hand, I had a sneaking suspicion that there was a reason I felt drawn to things like GTD and recurring checklists and quantified self. That removing these important aspects of how I make sense of the world would make me feel like I was adrift with nothing to latch onto.

The real results were somewhat more mixed.

I think I started to see some glimpses of my intuition coming back. I definitely became more aware of my body and my mind by creating more space. On the positive side, removing nearly all notifications was something that created a noticeable improvement in my state of mind. I felt like I could have longer thoughts that had the freedom to roam and grow. In a notification heavy world those thoughts would often be cut off before they could become something interesting.

By the end, though, I decided to revert to my previous systems and habits almost completely. I learned that these systems I’ve created for myself give my brain and energy positive direction. Without them, I would start ruminating or obsessing over things that would just end up making me feel bad.

I also learned that without my systems that prompt me to take positive action, to do the things I know I should be doing, I mostly end up not doing any of those things at all. I worked out very little over the course of this experiment. I meditated very little over the course of this experiment. I wrote very little over the course of this experiment. I know that I feel better when I do all three of these things regularly. For whatever reason, when I removed all external structure I didn’t keep doing these things that I know are positive for me.

Does this mean that I’ve been tricking myself and that I’d actually be happier if I stopped doing them? If I can’t do them without collecting data about them or being reminded by a technological system does that mean I shouldn’t be doing these activities? I wrestled with this for awhile because for a significant amount of time I thought this might be the case. Was I doing my habits for the wrong reasons?

Ultimately, I decided that it’s better to do the right things for the “wrong” reasons than it is to not do them at all.

I’m happier when I’m working out, meditating, and writing regularly and if there are tools, systems, or processes that help move me in that direction then I should embrace them with open arms. It was actually extremely eye-opening to realize that what really matters is simply doing these activities and that it doesn’t matter what it requires to get my ass on a cushion, my feet in a gym, or my fingers on a keyboard. The real battle begins when I close my eyes and start breathing, lifting those weights, or moving my fingers; I don’t need to make it harder than it has to be. If a recurring checklist makes it easier to meditate, great. If being able to track my workout data over time makes me more likely to go lift weights, awesome. If keeping track of how many times I write in my journal every week makes it more likely that I’ll sit down and write, excellent.

I admire the folks who don’t need systems to get themselves to do the things they know they need to do. What this experiment showed me, though, is that I’m not one of those people. And instead of feeling badly about that, I’m going to lean into this realization and continue building the external systems that help me be the best version of myself — completely guilt free.

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You Can’t Hide Mediocrity Behind Quantity

Recently I embarked on an experiment where I challenged myself to write and publish something everyday. I wrote quite a few articles during that time. Some were trite and navel-gazey but a few others tried to tackle more substantive ideas.

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Like any good experiment, I definitely learned something.

Publishing everyday isn’t the skill I need to develop. Writing everyday is.

Trying to publish everyday was certainly challenging and it pushed me to sit down and spend more time in front of the keyboard than I probably would have otherwise. I got a little bit better at quickly identifying something to write about and cranking out something coherent. Being able to write clearly and cogently is definitely a useful skill, but it’s also one that is squarely in my comfort zone. It seems like I’ve always been able to write quicker and at greater length than most people (I remember all the dirty looks my friends gave me during in-class essay tests in high school).

Unfortunately, when it comes to writing, quickness is not a particularly distinguishing characteristic. I’m not trying to write breaking news or get something published under a tight deadline so the fact that I can crank out a couple hundred words without thinking twice isn’t super useful. What is useful, however, is writing something so impactful and insightful that people share it with their friends or are compelled to reach out to me or change how they think about a tricky subject — all characteristics that are unrelated to how quickly I created it.

This experiment in daily writing actually coincided with another event that really helped me understand my own approach to work. At The Ready we work in duos and we try to be very deliberate about retrospecting and learning from the work we do and how we do it. For the last 6 months I’ve been partnered with Spencer Pitman and a few weeks ago we had our last retrospective. If you know Spencer you know that everything he does oozes with quality. All you need to do is spend a couple minutes checking out his writing or his decks — the dude makes incredibly impressive stuff.

I know he never said these words but I remember walking away from our meeting with the stark realization, “I compensate with feeling creatively or professionally vulnerable with sheer quantity of output.” My combined affinity for perfecting my own personal productivity and my natural gift for being able to work quickly tend to create a strategy of overwhelming people with okay content.

Spencer takes the opposite approach. He doesn’t create a ton but everything he does make causes people to stop in their tracks and say, “Woah.”

I, on the other hand, seem to be operating with some version of this in my head:

“I don’t know if what I’m doing is any good, or if I’m even capable of doing something excellent, so instead I’m going to create more ‘pretty good’ stuff than you think is even possible for one person to create and you will probably be impressed.”

This approach to creative work is a way for me to hide from the uncomfortable reality that doing great work requires skills I’ve yet to master — patience, editing, and taste, to name a few. My experiment of writing and publishing everyday was helping me develop skills I already had while letting me ignore skills I find uncomfortable.

“I can’t edit this piece for clarity or impact! I told myself that I’d publish something everyday! I can’t tackle a trickier idea because I don’t have the time to really tackle it the right way!”

With this new understanding still settling into my brain I’ve decided to embark on a new experiment. I’m still aiming to write everyday but I will no longer expect to publish something everyday. I’m hesitant to put an official interval on my publishing efforts, but I’m shooting for publishing something roughly every week or so. I want to give myself time to step away from a first draft, revisit with fresh eyes, rewrite and edit as needed, and put something into the world that I can be proud of on its own and not just because I wrote it quickly. I want to take the time to write articles that take me more than one session to draft because they require more careful thinking and care.

I’ve been sitting on some ideas that need more than a rushed evening writing session to bring to fruition. Removing my arbitrary daily publishing deadline has given me the space, and the motivation, to try to tackle these. Therefore, you’ll definitely be seeing my writing less frequently. The world doesn’t need another mediocre Medium author peddling half-baked (or even three-quarter baked) ideas so I’m taking myself out of the kitchen — for now.

I’ll be back when I have some fully baked bread, and better metaphors, to share.

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.

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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:

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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

MacBook

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

AirPods

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.

Nearly

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.