Sabbatical Retrospective: Weeks 5 and 6

Another two weeks of sabbatical in the rear view mirror, another two-week retrospective on what I did, how I felt about it, and what I think is coming up next. This time around, I’m going to move the cut-and-dry statistics to the end of the article and jump into the crux of the retrospective quicker. Let’s get to it!

The first four weeks of my sabbatical were deliberately devoid of plans, intentions, or expectations. This was designed to give me time and space to see what emerged as important (if anything). While I think I could probably continue to bob along in that mode of existence for a long time, I wanted to start an easy transition out of it and into some sessions of deep work over. I knew I didn’t want to immediately dive into the deep end productivity-wise, but I also knew that I didn’t want to just float along as I had been.

Looking back at Weeks 5 & 6

Week 5 included driving to Buffalo (approximately 8 hours) on Thursday and back to Arlington on Sunday. In between those transportation days we were taking part in various wedding celebrations for a family member. Obviously not much “work” happened in that period of time, although I did manage a couple deep work sessions on some writing earlier in the week and a couple of times into Week 6. Week 6 started pretty slowly — possibly because of the recovery from aforementioned travel and wedding — but really started to pick up in the latter parts. 

As I wrote about in the latest issue of The Deliberate, on Thursday of last week I somehow got motivated to take care of a bunch of administrative tasks I had been dreading and avoiding for many months. With an afternoon of work I got a bunch of things off my plate and set myself up really well for some things that I want to do during the rest of my sabbatical. A few days later, I’m still riding that motivational high. In some ways that kind of felt like the transition between how I spent the first 4-5 weeks of my sabbatical (recovering,relaxing, etc.) and what I want to be doing next (taking action, doing things, trying things, and diving deep into meaningful pieces of work). It makes sense that a transition like this isn’t something you can necessarily will into existence. I wanted that transition to happen at the end of Week 4 but it actually happened in the middle of Week 6. I’ll take it.

The other thing that’s worth talking about briefly is I tried to officially do three personal experiments in week 5. They all seemed small enough on their own, but when I combined them together they started feeling simultaneously and paradoxically overwhelming and unimportant. This is a lesson I seem to need to learn over and over. Always do one personal experiment at a time — especially if it seems “too small.” By limiting the number of experiments I’m allowed to do at one time it makes them more important and it makes me take them more seriously. When I try to do too many at once it’s easy to let one or more drop off and you end up with a really hodgepodge set of results for the week. As a sort of recovery week from the debacle of Week 5 I decided to not do any experiments in Week 6.

What’s up for Week 7 and 8?

As I mentioned above, I made some decisions in Week 6 that will start to come to fruition in Week 7, 8, and beyond. A quick run through of what’s on my plate for the next two weeks:

• Meeting with a personal trainer to talk about some personal fitness goals I have and how he can help me.

• Taking my new road bike out for a couple of rides

• Using the gym membership I just signed up for — particularly for Olympic weightlifting I recently remembered I thoroughly enjoy

• Do a couple of sessions with my golf coach

Obviously, thoughts and intentions about my personal health have bubbled to the fore over the past few weeks and I’m taking some deliberate action in that realm. Other than these things, I’m excited to dig into one specific writing project over the next two weeks — figuring out if the constellation of things I’ve been writing about and care about can be massaged into a book that anybody other than me would be interested in reading. I’m going to take a crack at it over the next few weeks and see whether I can definitively answer that question.

The only added wrinkle is that Week 8 is going to be spent in Cape Cod rather than home in Virginia. This will be Emily’s main vacation for the summer and while I obviously don’t “need” a vacation, that is the headspace we will be occupying together that week. That being said, I don’t think there’s any reason that I can’t keep up with my writing, thinking, and exercise intentions while I’m there. So, other than some of the chaos that travel introduces to a routine, I don’t think it’ll be too different from what I’ve been doing at home for the past month.

After these two weeks I’ll officially be halfway through my sabbatical — which is truly bonkers.

The numbers

Here are some personal stats from the past two weeks, for those of you who find this part interesting. As always, the numbers below take the format of (Week 6 #/Week 7 #):

• Average hours slept per night: 7.12/7.9

• Average “quality” hours slept per night: 5.17/5.82

• Average deep hours slept per night: 2.03/2.02

• Average sleeping heart rate: 50/50

• Average steps per day: 10,981/11,123

• Average weekly weight: 206.77/207.37

• Days exercised (out of 7): 7/6

• Days read (out of 7): 7/6

• Days written (out of 7): 4/5

• Days meditated (out of 7): 3/1

On the reading front, this is what I’ve been getting into:

• Continued The Count of Monte Cristo by Alexandre Dumas

• Finished Code Girls by Liza Mundy

• Finished Empire of the Summer Moon by S.C. Gwynne

• Started Other Minds: The Octopus, the Sea, and the Deep Origins of Consciousness by Peter Godfrey-Smith

• Started Foundation by Isaac Asimov

• Started The Enlightenment: The Pursuit of Happiness, 1680-1790 by Ritchie Robertson

A relatively quiet two weeks in terms of video games and TV:

• Still playing a couple games of Starcraft 2 competitive ladder most days while deliberately trying to hone specific skills. Should be entering a Platinum 1 league as Random soon (have been sitting at #1 in Platinum 2 for a few days now)

• Playing the daily “Chaos Realm” map on Card of Darkness every day (takes like 5 minutes)

• Continuing to watch each episode of season 2 of Ted Lasso as they are released (how good was episode 3, eh?)

A few other things of note:

• Published issue #49 of The Deliberate

• Published episode #50 of Fields of Work

See you in two weeks!

Sabbatical Retrospective: Weeks 3 and 4

I’m on a 16 week sabbatical and to ensure I don’t utterly squander it I’m writing biweekly retrospectives.

I spent my first two weeks not doing much of anything (purposely) and “emptying the tank” in preparation for what might come next. Weeks three and four were largely the same, with some slight tweaks.

What did I do?

First, let’s review a handful of the weekly metrics I collect on myself, just to get an initial sense of how I’m doing. Each of the following metrics below follow the format of (Week 3 metric/Week 4 metric).

• Average hours slept per night: 7.05/7.77

• Average “quality” hours slept per night: 5.08/5.62

• Average deep hours slept per night: 1.9/1.9

• Average sleeping heart rate: 48/50

• Average steps per day: 13,570/15,842

• Total miles cycled per week: 0/11.6

• Average weekly weight: 207.1/208.3

• Days exercised (out of 7): 7/6

• Days read (out of 7): 7/5

• Days written (out of 7): 3/3

• Days meditated (out of 7): 4/2

A couple things are worth expounding on a little bit. The Steps number from Week 4 is definitely artificially high (and you’ll see why later). Weight is still trending upward, which isn’t ideal, and has been going up consistently enough to trigger some action on my part. Lastly, it’s surprising to see I missed two days of reading last week. I’m really not sure how that happened (or if that’s truly accurate) but it’s rare for me to miss one day, never mind two. 

With some basic personal metrics out of the way, let’s check-in on how else I’ve been using my time over the past two weeks. First, books:

• Started The Count of Monte Cristo (Apple Books/iPhone) by Alexandre Dumas

• Started Code Girls (physical book for reading in bed) by Liza Mundy

• Started Empire of the Summer Moon (audiobook) by S.C. Gwynne

• Started and finished The Adventure Zone: The Crystal Kingdom graphic novel

• Re-read Deep Work by Cal Newport

• Finished The Structure of Scientific Revolutions by Thomas Kuhn (audiobook)

Next, video games, TV, and movies:

• I’ve played at least a couple games of Starcraft 2 competitive ladder each day

• Picked up Hearthstone and Card of Darkness on iOS a little bit after having not touched either one in over a year

• Tried Magic The Gathering: Arena on iOS for a little bit (I used to love actual MTG when I was a kid so playing the digital version was a good and weird combo of novelty and nostalgia)

• Dabbled with Alto’s Odyssey again for just a couple minutes (I’m on the last achievement but I haven’t played it in so long I think I’ve lost all the skill I’d need to actually beat it…)

• Continued to do the NYT Mini Crossword and 3 games of Up Spell with Emily every night

• Started watching season 2 of Ted Lasso(!)

• Watched the second episode of season 2 of Tiny World

• Watched the first episode of Succession

• Watched the second episode of season 1 of I Think You Should Leave with Tim Robinson

• Re-watched Bo Burnham’s “Inside”

• Re-watched Harry Potter and the Goblet of Fire (Emily had just finished the book)

Finally, just a grab bag of other things I’ve been doing over the past couple weeks:

• No travel this week so mostly hung out at home in Virginia (and the apartment’s pool)

• Tried to do a week of very long walks. Did 20 miles on Monday of Week 4 but absolutely destroyed my feet with blisters and basically had to abandon the whole endeavor. I did manage to eke out 8.6 more miles on Tuesday and a couple shorter walks the rest of the week, but for all intents and purposes I basically bailed after Tuesday.

• Got dinner with a visiting friend at The Duck and the Peach in D.C.

• Got dinner with another visiting friend at Founding Farmers in D.C.

• Emily and I had our second salsa lesson and we got dinner afterward at Founding Farmers (and I wonder why my weight is going up…).

• Started rebuilding my informational ecosystem from scratch after having “emptied the tank” over the previous couple of weeks (much more on this soon)

• Went to the driving range a couple times and further learned that I’ve lost all semblance of being able to hit a golf ball consistently

• Made progress on our wedding website

• Continued to avoid eating a ton of raw vegetables (i.e. salads) to see if perhaps that has been triggering my intermittent yet acute intestinal distress. That hypothesis is currently supported by the evidence…

What went well?

Considering I had very low expectations for myself over the past two weeks, I’m tempted to ignore these two evaluative questions entirely. If I had to point to a couple things that felt like they went particularly well over this period:

• Re-reading Deep Work last weekend was good timing. I feel primed and ready to dive back into some substantive work now.

• I think I did a good job not thinking about work (and not feeling guilty about it)

• Emily and I practiced salsa a couple times prior to our second lesson and the second lesson itself went really well

• The fact that I finished a couple books and made progress on a few more is good

• I also spent a couple hours one afternoon re-populating Things. That app is such an important part of how I work so it felt good to take it from empty (which was kind of scary in and of itself) to filled up with good things that I’m excited to dig into

What didn’t go as well?

Again, I’m holding these lightly as the whole theme of the past two weeks was low expectations and guilt-free existence. That being said:

Keep moving and get out of the way. Photo by me.

• I missed a couple days in my very simple Sabbatical Log that I keep in Day One. It’s literally just a daily bulleted list of what I did but it completely slipped my mind for the second part of last week.

• As I alluded to, my Week of Long Walks experiment was kind of a bust and my heels still hurt.

• Even with zero expectations and a guilt-free ticket to do whatever I want, I think I’m spending too much time on my phone reading Twitter and Reddit in the morning.

• My weight has been heading, albeit slowly, in the wrong direction for a couple weeks. Too much delivery and restaurant food, not enough mindfulness around portion sizes.

What’s the plan for weeks 5 and 6?

If the first four weeks of my sabbatical were about unwinding, emptying, and floating then the next couple weeks are about deliberately refilling, channeling my attention in more productive directions, and starting to wake my somewhat atrophied concentration and writing muscles. My intention isn’t to go from zero to one hundred. But I do want to start setting aside a substantial chunk of each day to deliberately work on meaningful projects. To start, I think that’s going to mean restarting my usual morning routine and putting in 3-4 hours of focused work every morning. I think I’ll keep my afternoons will be a bit more unstructured and will allow myself to follow my nose a bit more.

Other than the overall intention to shift from a purely restorative mode into a slightly more productive mode, I know we have a little bit of travel coming up at the end of Week 5 (6 hour drive to Buffalo for a family wedding, a couple days of celebrations/obligations, and then a 6 hour drive back on Sunday). Travel always introduces more variables but I don’t anticipate it changing my plans very much.

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Sabbatical Retrospective: Weeks 1 and 2

I just wrapped up the second week of my sabbatical so wanted to take a few minutes to look at what I’ve done, what I’m thought and felt, and check-in with my overall intentions.

I told myself that I’d try to spend at least the first couple weeks, possibly the first month, of my sabbatical being very kind to myself. I didn’t want to immediately dive into some kind of productive activity even though there’s a large part of me yelling about using this time productively. I’m becoming increasingly convinced that it’s important to not give into that voice. There’s a kind of unwinding or slowing down that I think is extremely necessary and I can’t do it if I don’t give myself the time, space, or permission for it to happen.

Before I do any additional subjective retrospection, I think it’s worth capturing a handful of objective metrics from the past couple weeks (week 1/week 2):

• Average hours slept per night: 7.62/7.75

• Average “quality” hours slept per night: 5.53/5.38

• Average “deep” hours slept per night: 2.12/1.95

• Average sleeping heart rate: 51/48

• Average steps per day: 14,850/13,019

• Total miles cycled: 8.8/9.4

• Average weight: 206.4/206.7

• Days exercised: 7/7

• Days read: 6/7

• Days written: 2/2

• Days meditated: 2/1

In week 2 I tried to do a better job of just letting myself sleep until I naturally woke up. The only number that stands out to me as particularly interesting is the average sleeping heart rate of 48 in week 2. I think that’s the lowest I’ve seen in well over a year — maybe longer. Obviously, I de-emphasized cycling miles in favor of walking/running and really didn’t do much consistent writing or meditating. As far as what else I got up to over the past two weeks, here’s a brief log:

• Finished reading Tiamat’s Wrath by James S.A. Corey (The Expanse #8)

• Started and finished reading On Writing by Stephen King

• Started and finished reading The Wind Up Bird Chronicle by Haruki Murakami

• Wrote and published an article on SamSpurlin.com, What I’m Thinking About as I Embark on a Sabbatical

• Recorded and published an episode of Fields of Work

• Went to my first doctor checkup in several years. Got some bloodwork done and found out my cholesterol and triglycerides are higher than they should be. Woo!

• Watched the Tampa Bay Lightning win the Stanley Cup.

• Hung out by the pool at our apartment complex a few times. Tried to not get sunburned.

• Conducted a coaching session with a client (agreed to keep meeting every other week throughout my sabbatical)

• Had a conversation with a friend about his experience with sabbatical and about a piece of software he’s working on

• Had dinner at La Collina in Washington D.C.

• Got a massage. Managed to stay awake the whole time, for a change.

• Got a fresh haircut.

• Recorded an episode of the Brave New Work podcast (was scheduled before I knew I was going on sabbatical and I didn’t want to reschedule it). I’m guessing it’ll come out in a few weeks.

• Had my first salsa lesson.

• Talked to a former grad school classmate about some career stuff she’s working through

• Had dinner at California Pizza Kitchen

• Lots of cooking dinner at home

• Made some bread and cookies

• Went for a couple 2 mile runs for the first time in months

Emptying the Tank

Other than these activities, the other thing that had my attention over the past two weeks was a general intention of “getting to empty.” This initiative actually started a couple weeks before the official start of my sabbatical. I’ve been going through as many services, files, backlogs, tools, and physical belongings as possible and asking myself, “Do I really need this?”

• Unsubscribed from all newsletters

• Unsubscribed from all podcasts

• Blocked myself from all social media

• Deleted all my RSS feeds

• Unsbscribed from as many services as possible

• Used default apps & tools wherever I could

• Went through my files and deleted anything I no longer needed (old project files, notes, etc.)

• Wiped out my Instapaper backlog

• Wiped out my Someday/Maybe project list

• Wiped out everything in my task management software

• Wiped out my backlog of potential personal experiments

• Simplified and consolidated my personal finances

• Donated or threw away as many unused physical items as possible

I’ve since relaxed a few of these restrictions (I resubscribed to a few of my usual podcasts and am no longer restricting access to Twitter or Instagram) but the overall effort will generally continue over the next two weeks, too. It’s amazing the nearly physical effect it can have to remove things that are ephemeral yet apparently carry considerable psychological weight (like lists of projects or tasks I feel like I should do or articles I said I wanted to read but hadn’t gotten to, yet). There are a few more things in this decluttering vein I think I still want to do and I may tackle a couple of them in Weeks 3 and 4 (potentially a complete online account audit/purge and a deep clean of my personal and work Google Drive).

Intentions for Weeks 3 and 4

As far as my intentions for the next two weeks go — it’s much of the same as the first two weeks. I’m still not going to hold myself to any expectations around sitting down and “working on” something everyday. I’d like to continue doing some light writing (like this) around what I’m doing and experiencing, but it’d be premature to really dive into a substantial project right now. Instead, I’m going to continue the process of clearing the decks as much as possible. Creating space and then giving myself permission to wander through that space is the name of the game right now. Realistically, that means trying to hit my Anchor Habits everyday, continuing to use Starcraft 2 as an arena to practice useful metacognitive skills, deliberately working on my golf game, and generally just doing whatever I want — as long as I do those things one at a time. The only additional thing I’m going to add to my plate this week is to try to notice and write down when I’m thinking about something I miss, want to do, or feel like I should do. There’s no commitment to actually do anything with that information (at least not right away). I’d just like to have a bit more of a running log of what’s going on in my brain when I take away the stuff that’s usually using up all its cycles.

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What I’m Thinking About as I Embark on a Sabbatical

For the last week I’ve been on sabbatical from The Ready. I have approximately 15 more weeks to go. What follows is a slightly cleaned up and elaborated version of an ICBD* exercise I shared with my colleagues before I signed off for the next few months. We generally use it with teams who are preparing to embark on some kind of new project or endeavor together, but it struck me as a potentially useful solo writing exercise, too. The idea is simple, ask yourself the following questions and you’ll probably feel much clearer about what you’re going to do and how you’re going to do it:

1. What are your intentions for this? Why are you here? Why do you want to be a part of this?

2. What are your concerns? What are you worried about?

3. What boundaries do you need? What will help alleviate some of your concerns?

4. What’s the dream outcome of this endeavor? What will it feel like? What will it look like?

Intentions

My first day of sabbatical was Monday, June 28th. My last day of sabbatical will be October 15th. I’m not 100% sure what’s going to happen between those two dates and I’m trying to be okay with that ambiguity.

There are obviously multiple very different paths available to me. I could really lean into not having any sort of structure or project and just see where my nose takes me over the next couple months. I’ll undoubtedly find some interesting things to do, read, and explore that I’d otherwise be incredibly unlikely to find in the course of my “regular life.”

I could pick one major project, like writing a book, and use my sabbatical to dive deep into it. It would come, potentially, at the cost of having more relaxation or unstructured time. But when would I have a better chance to focus on something like this?

Obviously, this is a false dichotomy. I’ll probably inhabit both of these ways of being — and others — over the course of these four months. The main thing that I’m holding myself accountable to is simply being deliberate with how I decide to use the time. That doesn’t mean I need to be super productive. I can be deliberate about playing video games, sitting by the pool, or going for long walks. What I don’t want to happen, though, is floating through my sabbatical without ever making any decisions about what I want my moment-to-moment experience to be. 

I’m up for some really focused and deep work (for example, I’m sitting down and writing this article) and I’m up for some extremely unstructured exploration. I’ll read. I’ll play some video games. I’ll go for walks. I’ll golf. I’ll probably go work on my brother’s farm for a little bit. I’m trying to hold it all very lightly… yet deliberately.

In broad strokes, though, my intention with this sabbatical is to get Healthy, Happy, and Hungry again. I intend to eat well and move my body such that the version of me that comes out the other end of this sabbatical in October feels and looks healthier than the version who went into the sabbatical in June. I intend to do things that restore my spirit and my outlook on my work and life. And finally, I want to come out of this sabbatical just yearning to get back into the work of my lifetime with The Ready. I want to be champing at the bit to get back into the mix of things and bring my newly restored self to the difficult work of transforming organizations and building a company capable of putting a dent in the universe.

Concerns

I could write an entire article only about my concerns. I’ll do my best to distill them to the most cogent and urgent.

In some ways, this sabbatical and the fact that I feel like I need it, and maybe have actually earned it, feels shameful. It’s an incredibly generous benefit. I’m already well paid and I sit inside an air conditioned room and mostly look at computers all day. There are so many people who are more deserving of a massive break from work. Why do I get this? What about people like my parents? My fiancee? My brothers? Or folks in truly essential yet low paid jobs that are 10x more physically draining than mine?

I’ve been around since the very beginning of The Ready. I was the first employee so I’ve been in the mix with everything that has happened... and now I’m going to be away for awhile. Will I still have a good reputation when I return? Will I be the only one who ever partakes in this policy and I’ll wear some kind of scarlet letter for the rest of my time there? What cool projects, moments, and things are going to happen while I’m gone?

I’m concerned I’ll feel too much pressure to make my sabbatical “worth it” and dive deep into some kind of work-adjacent project so that I can point to something at the end of it to justify the expense to the company. We explicitly didn’t write detailed expectations into the sabbatical policy but I know that one way I’ll try to soothe feelings of psychic distress and guilt is to make something so amazing and important that everyone thinks, “Wow! Sam sure did a good job on his sabbatical.”

And then, on the other side of that continuum, I’m worried I’ll under plan my sabbatical so drastically that I’ll just kind of float through it, get to the end, and realize I never really did anything worthwhile or truly restored myself. While I know I don’t want to make my sabbatical a super planned and rigid endeavor, I do know that I want to be deliberate about how I spend my time. There are things I want to think about, write, and explore that won’t “just happen.” I’ll need to make them happen if they’re going to happen at all.

Lastly, work has been my primary identity for… basically my entire adult life? I’ve either been working or going to school — or commonly, both — since 2004. I’ve never not worked. I worked through undergrad. When I graduated, I spent the first part of my twenties hustling to make a teaching career work while having graduated into the Great Recession. After beating my head against that intention, often while holding multiple jobs at once, I spent the rest of my twenties going to graduate school while working as a teaching and research assistant and while still writing my website and still taking on coaching clients and trying to start a consulting company and taking on freelance consulting gigs. Then, blessedly, The Ready. And continuing my PhD work while also being the first employee at a company in an industry I desperately wanted to be in but had no experience (cue the imposter syndrome and the manic sprint to self-educate myself into some feelings of competence). And throughout all of this my area of focus has been on the experience of work for other people. How can organizations be better? Are there better ways of working? What does the future of work look like?

So, yeah, I think about work a lot. If I’m not working, or helping other people work, then who exactly am I?

Boundaries

I made it clear to my colleagues (and implicitly, myself) that I’m going to try to take this sabbatical as seriously as possible. Which means I’m not going to hang out on Slack or be checking my work email. Both of those things have been excised from my phone and require some deliberate effort to log back into on my computer.

Although I don’t know the exact shape that this sabbatical will take (and I’m sure it’ll morph over time), I’m committing to sticking to my normal rhythms related to review and planning. Specifically, that means continuing to do my Sunday afternoon weekly review and planning sessions as well as my monthly sessions. They will probably be much shorter and less involved than when I’m working full-time, but they are at least some built-in checkpoints where I can ask myself how things are going and whether I want to make any changes to how I’ve been operating.

I’m also going to keep a very simple daily Sabbatical Log where I jot down what I did each day. I suspect it’ll be an interesting thing to look back on in the future and the act of having to write a few bullet points each evening will help me keep my attention deliberately engaged.

I’m sure I’ll come up with more boundaries over time, but I’ve generally found that the fewer and clearer there are the more useful they end up being.

Dreams

Luckily, I can think of several different dream scenarios that will leave me feeling like I treated this sabbatical with the respect it deserves and gave me the outcomes I need. I don’t need one specific outcome to feel like I got what I needed from this. As I mentioned in the Intentions section, the pithy one-liner for this sabbatical is “get Healthy, Happy, and Hungry.”

Some characteristics of the dream scenario for Healthy:

• Lose around 10 pounds

• Get my cholesterol and triglycerides lowered

• Get my food sensitivities and allergies sorted

• Run, cycle, and walk consistently

• Meditate consistently

Some characteristics of the dream scenario for Happy:

• Play a bunch of golf and drastically improve

• Play a bunch of Starcraft 2 and treat it as an arena for deliberate practice

• Read fiction

• Spend a significant amount of time in contemplation and writing in my journal

Some characteristics of the dream scenario for Hungry:

• Use this non-distracted time to develop my skills in concentration, focus, and deep work while learning about a bunch of organizational, consulting, and adjacent topics

• Develop a bunch of the amorphous ideas that have been bouncing around in my head for years into coherent pieces of writing

• Deliberately develop surprising and creative connections between my various interests and the domain of organizational design and transformation

I hope it’s not a cop out and I hope I’m not abusing the word… but truly the dream scenario of this sabbatical is that I can look back at how I spent my time over the last four months and say that whatever I decided to do I did it deliberately. I’m open to the idea that this sabbatical may take an unexpected left turn at some point. I’m open to the idea that I may decide to throw away all my intentions except one. I’m open to the idea that I may decide to do a bunch of things that are currently not even on my radar. The only thing I’m holding myself to is staying conscious, intentional, and deliberate through it all.

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If you’ve done something like this in the past and have any advice you think I should hear, please shoot me an email or send me a message on Twitter. If you’d like to follow along, might I suggest subscribing to my newsletter or following me on Twitter? 

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*This is an exercise that was developed by my former colleague, Bob Gower, and his wife, Alexandra Jamieson. If you’re interested in learning more about it, check out their book Radical Alignment and their company The Alignment Company.

Why Your New Strategy Will Fail

As organizational transformation consultants, we’re often invited to help functions, departments, and teams of all kinds within massive enterprises recover from failed strategy implementations. Regardless of the industry or organization, the narrative of each failure follows a familiar arc. A “new strategy” is developed over several months of backbreaking creative and consensus-building efforts. It ultimately results in a key artifact (usually an exceedingly beautiful deck of slides) that clearly articulates a smart and cogent shift in priority. There is (seemingly) buy-in from all the key players and generally a sense of, “Okay, this makes sense. Now we just have to implement it.” Inevitably, the strategy fails to manifest in any major positive changes and after 18–36 months of middling returns, it’s decided that a shift in strategy is needed and the cycle begins anew.

Why isn’t articulating a strategy enough? Why does it often fall down during implementation? What’s actually going on here?

New Strategy and Old Ways of Working

Mike Tyson likely wasn’t talking about organizations when he quipped, “Everyone has a plan until they get punched in the mouth.” If a carefully crafted strategy document is the plan in the aforementioned quote, then bringing that plan into contact with the rest of an organization is the punch in the mouth. Regardless of how inclusive the process was for developing the strategy, how many rounds of revision it went through, and how many senior leaders pledged to support it, the reality is that most deliberately developed strategies don’t survive contact with the rest of the organization — never mind the market.

The organizational environment into which a strategy needs to be implemented is one characterized by increasing complexity, volatility, uncertainty, and ambiguity. The conditions that organizations and leaders must navigate, both internally and externally, are only growing more difficult to predict and control. This diminishes the likelihood that the “right” people can make all the “right” decisions at the “right” time to successfully implement a strategy.

In a bygone era it may have been possible to play the role of leader as chess grandmaster. They saw the future more clearly than their opponent and could move their discrete pieces to and fro until declaring victory. As complicated as chess is, it still consists of a knowable subset of components that follow specific rules of engagement. Modern organizations are more like chaotic weather systems or biological ecosystems, neither of which can be known or driven like a game of chess. Instead, they may be influenced or managed, at best. This means leaders must adopt a different posture in order to meaningfully influence the way the work unfolds — a conscientious gardener rather than an all-knowing chessmaster. A chessmaster thrives when they can see the future better than their opponent and make one correct decision after another. A gardener must instead retain a posture of curiosity, of noticing, and of continuous interaction with the garden’s complex system. Put plainly, a strategy cannot be “chessmastered” into business outcomes because the organization and market in which it must be operationalized are much more like a garden than a game.

What does this mean for how we think about the implementation of strategy? To start, we should swap “implementation,” which implies a one-time activity, for “implementing,” which suggests ongoing and unceasing effort.

Any strategy document is a shared artifact filled with creative and nuanced thinking. Given the cross-functional reality of how work gets done in any large bureaucracy, no one team, function, or organization can operationalize a strategy in isolation. Instead, many stakeholders with many incentives (both explicit and implicit) need to simultaneously share responsibility for whether it becomes an animating and unifying force in the organization. How can something that touches so many parts of an organization, with such varied incentives and unique concerns, fulfill the hopes and dreams it was designed to achieve without being ground to a halt by the bureaucracy that originally spawned it?

The Intersection of Strategy and Operating System

An organization’s OS ultimately determines whether the intentions embedded within a shift in strategy find fertile soil and grow or fall upon the ground and whither. An OS comprises the assumptions, principles, practices, and behaviors that are encouraged, supported, and rewarded across multiple facets of an organization. It is the mostly invisible yet pervasive milieu that every employee of an organization simultaneously exists in and helps create.

Developing and implementing a strategy is an attempt at being deliberate about what an organization is going to do and how it’s going to do it. An organization’s current OS is always perfectly optimized for the results it’s currently getting. In this way, strategy and organizational operating systems are intimately connected, whether that connection is explicitly called out or not. Said another way, if we try to operationalize a new strategy into an organization’s original OS, which presumably created the need for a shift in strategy in the first place, then we risk being thwarted by the very forces that prompted our desire to change.

Therefore, for a new strategy to change the course of an organization or team, it must go hand-in-hand with holistic OS change.

How Legacy Operating Systems Sabotage Strategy

First, bureaucracy optimizes for minimizing risks of commission, rather than risks of omission. The risks of taking the wrong action are talked about openly but there’s rarely much conversation about the risk inherent in failing to do something — and the latter can create equally problematic outcomes. This inability to notice the opportunity costs at play manifests as an unwillingness to do things that are unproven or unknown in favor of just doing what is already being done but (hopefully) slightly better. To the extent that a strategy represents an organization’s intention to step into the unknown, it’s going to bump up against this propensity for not taking risks and all the rigamarole, theater, and political shenanigans that inevitably accompany such risk aversion.

Second, most large bureaucracies struggle with having a coherent approach to enterprise-wide problems. Employee identities are often more strongly aligned with business area, function, or program than to the overall enterprise. Making an initiative “cross-functional” often means guaranteeing every possible faction equal representation, so working groups and meetings quickly inflate to untenable sizes. A new strategy can’t simply be a statement of what an organization needs to do; it must describe key challenges and opportunities that can only be handled by a truly coherent coalition with shared goals, values, and ideas about how to best pursue this work. Addressing this type of cross-functional challenge in the same way other “cross-functional” challenges are typically approached is likely to create a slow-moving morass of committees and status meetings.

Third, formal structures and value-creation structures are often disconnected in traditional bureaucracies and there’s very little ability to dynamically team around new opportunities. Bureaucracies grow and ossify as the work of the organization becomes more known and the focus (perhaps rightfully!) shifts to extracting efficiency even over investigating new opportunities. In some cases, the rigid structures and policies that typify bureaucracies do make certain types of tasks and work more efficient. However, a shift in strategy inherently presupposes organizational mobility. It requires a restructuring of teams, workflows, decision rights, and mindsets toward fluidity and a willingness to handle ambiguity as a new and unknown domain is mapped. Handing a mandate of change to a bureaucracy that has been optimizing for efficiency is like expecting someone who has been training intensely to run a 100 meter sprint to run a marathon instead. The will and the motivation might be there, but the muscles and the cardiovascular ability have simply been optimized for something else.

Organizational Transformation Is Strategy Implementation

Strategic shifts are the perfect time to unlock larger organizational change — and actually require organizational change to be successful. Much of the time, organizations are simply propelled forward by inertia. The bigger and more bureaucratic an organization, the more inertia it has. It takes something special to disrupt that force and steer momentum in a new direction. A deliberate attempt to chart a new strategic path, whether organizationally or within a specific function, is precisely the type of event that can interrupt the status quo. How can this interruption be used as an opportunity to upgrade your OS, and how can this newly upgraded OS unlock the potential your strategic shift represents?

Allow teams pursuing new strategic imperatives to operate outside the usual bureaucratic environment. Strategic pivots require speed, and nothing prohibits organizational speed more than red tape. To the extent that a new strategy requires teams to do new work, try to protect those teams from the bureaucratic stranglehold that will inevitably try to bring them into the fold. Giving these teams and initiatives breathing room will not only set them up for greater success, but will also advance the cause of chipping away at the most pervasive organizational debt. Nothing shines a light on stale bureaucracy more than proof that meaningful work can happen quicker, with less pain, and without causing harm to the rest of the organization.

Use a shift in strategy as a platform for rapid and deliberate experimentation. Making room for meaningful experimentation can catalyze progress toward a new strategic direction. Rapid iteration and learning is the backbone of strategic implementation. No matter how good the thinking was that went into the articulation of a strategy, it’s impossible for it to fully predict the future. Good strategic implementation strives to validate or invalidate the assumptions upon which it’s built as quickly as possible. Pursuing the strategy then becomes a fluid and ever-evolving process that finds new opportunities that never could have been predicted when the original thinking was being done.

Start the way you intend to finish. A strategy designed to allow an organization to adapt to the market cannot be executed by an organization that cannot adapt to the strategy. Just as no organization has successfully transitioned to more agile ways of working through waterfall practices, it’s safe to surmise no organization trying to become more fit for complex and uncertain realities has done so through command-and-control, plan-and-predict, bureaucratic methods. To that end, implementation of a strategy is unlikely to be a linear process. It’ll have stops and starts, loop back on itself, and reveal things that were impossible to predict when the strategy was originally drafted. The grace and adaptability of your approach to bringing a new strategy to life will largely determine whether or not it’s successful.

A Shift From Strategy to Meta-Strategy

Disruptive reorgs, monumental pivots in strategy, and other “big moves” are signs that an organization is operating (and struggling) under a legacy operating system. Proponents of these approaches always underestimate the amount of unproductive churn they generate and overestimate how much they will fundamentally change an organization’s trajectory. Organizations that have transcended these dramatic interventions have built operating systems that allow them to be constantly sensing, responding, and experimenting with what the market is telling them. They understand that it’s not about perfect execution of a strategy, but rather the imperfect yet ever-better implementation of a meta-strategy — the ongoing care and maintenance of their evolutionary organizational operating system. They no longer need dramatic swings in strategy, because they are able to pursue opportunities at the drop of a hat and pivot away from dead-ends before they become an existential crisis. This is where true opportunity lies; this is what the best companies in the world have uncovered; and this is what you and your organization can achieve by uniting strategy implementation with holistic organizational transformation.

Sam Spurlin is a Partner at The Ready, an organizational design and transformation partner that helps you build a better way of working. We work with some of the world’s largest, oldest, and most inspiring organizations to help them remove bureaucracy and adapt to the complex world in which we all live. Learn more by subscribing to our Brave New Work podcast and Brave New Work Weekly newsletter, checking out our book, or reaching out to have a conversation about how we can help your organization evolve ways of working better suited to your current reality.

Thank you to Zoe Donaldson and Alastair Steward for their editing and feedback prowess. Any particularly cogent bits are likely covered in their fingerprints and the mistakes are purely my own.

Building a Morning Writing Routine in Real Time

I’m actively trying to build a new routine. On the first day of that new routine I did a stream of consciousness exercise to capture everything I was thinking about in that moment. I’ve decided to publish it, lightly edited, as a potentially useful glimpse into the mind of someone who is trying to deliberately build a new routine while using the self-knowledge gleaned from years of personal experimentation. The specific details of what I’m trying to do here may not be relevant to you, but the categories of reflection below may help you unlock challenges you’ve faced in your own endeavors.

Check out the entry for this experiment in my Deliberate Experimentation Dashboard for a rougher but more real-time look into how this is going, too.

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Routine as Archaeology or Creativity?

I love routine. A good routine feels like uncovering something that has always been there and building something completely new. “Uncovered” because there’s a sense of comfort and a sense of, “Ah, this is how things should’ve always been,” when you land on a routine that works but “built” because it’s very rarely something that shows up fully formed. It gets modified, torn down, rejiggered, and tweaked over time. Eventually, it solidifies into something simultaneously essential and also not part of your deliberate consciousness. Essential because its absence is keenly felt (or, more positively, doing it propels you to the next part of your day with the right mindset and the right momentum) and subconscious because it’s nearly automatic.

I have a slate of routines. Some are relatively fresh and still being built. And others have become so automatic I may have trouble noticing them as routines. Right now, as I write this, I’m trying to lay the foundation for a new routine related to writing. My hypothesis is that I can spend roughly 7:00-8:00 AM nearly every day doing some kind of writing (or writing adjacent) activity. That writing may not always look like this — a nearly stream of consciousness draft focused on getting as many words out of me as possible — but could include editing previous writing, outlining in preparation for future writing, or even doing deliberate research and note-taking.

What I’m most interested in, though, is whether I can make this 7:00-8:00 AM block something sacred.

The Mechanics of Potential Self-Sabotage

While the foundation to this routine is brand new, it’s being built in a neighborhood of much more mature routines. Its neighbors are “Wake Up at 6:00 AM” and “Read For Awhile Right After Waking Up.” These two routines have been bedrocks for as long as I can remember. In fact, “Write From 7:00-8:00” could be thought of as being built on property previously claimed by “Read For Awhile Right After Waking Up,” because “awhile” has usually included time beyond 7:00 AM. I guess that means “Read For Awhile Right After Waking Up” needs to become “Read From 6:10ish to 7:00.”

I’ve played with this routine in the past and have watched it start strong only to fade over time. The most common force that overtakes it is a sense of anxiety over what my upcoming work day entails and feeling like I need to steal time away from writing in order to be properly prepared for what’s coming up later in the day. It would be foolish of me to think this will never happen. Sometimes there’s a major meeting in the morning that requires my attention in the early morning hours in order to be adequately prepared for it. Sometimes things get overwhelming and reserving some time early in the morning to do “real work” helps restore the equilibrium I need to feel good about my job. But these can be exceptions and they don’t need to represent failure to the point of abandoning the original intention of writing for an hour in the morning.

I have worked hard to become a very productive and focused consultant. I can accomplish everything I need to accomplish during a normal 9:00ish to 5:00ish work day. I take those hours extremely seriously so that I can have this guilt free time in the morning to work on my craft. And, even more importantly, I try not to conceptualize myself as having set “work hours.” It’s easy for me to fall into a trap of thinking my job is to work a certain number of hours each week when really I need to consistently be thinking about my work as creating outcomes that matter to my clients and The Ready. Those outcomes are divorced from a set schedule. Sometimes the most impactful work I can do is take an entire afternoon “off” and think through a problem. Sometimes it’s sitting down to work through a problem after dinner. 9 to 5 is a useful default constraint. Useful in the sense that it’s what I hold very lightly as an ideal. I can transcend it when it makes sense to but otherwise it’s a good chunk of time that allows me to order my life outside of work.

I know I need to be vigilant about that part of me that thinks I need to work early in the morning to prepare for the rest of my day. I wonder if there’s any part of that drive that’s based in self-sabotage? “I can’t be a writer because I have this intense job that requires me to work a ton of hours. Oh well.” There’s probably a small part of me that subconsciously thinks this way. I know there are things I can do, though, that helps keep those thoughts at bay.

I think a lot of it actually starts the day before. When I don’t crisply end my day it can feel like I’m carrying a lot of amorphously open loops with me throughout the evening and into the next morning. Crisply ending my day means taking the ten to fifteen minutes at the end of the day to truly end the stuff I’m working on and set some intentions about when I’ll pick them up again tomorrow or later in the week. It’s about looking at my calendar for the next day or two and figuring out what I need to do to feel prepared for whatever is coming up — and when I’m going to do that preparation. When I’ve done those things my brain can let go of the anxiety that drives me to spend time in the morning making sure I’m completely and utterly prepared for the day —time that I’m trying to invest in writing.

I can also set myself up for success by doing my best to not schedule meetings early in the day. Early meetings are the #1 thing that make me feel like I need to use the time between 7:00 and 8:00 for consulting work. Anything that happens at 10:00 AM or later (or even better, after noon) makes me feel like I have time to prep starting around 9:00 AM.

What Does ‘Writing’ Even Mean, Though?

What about how to use the time itself? What am I supposed to be writing or doing during this newly sacred block of time? The simplest answer is, “Writing.” The somewhat more specific answer is, “Working on writing that will help me move my career into a more writing-centric mode.” Articles for public consumption and anything that might become a book are at the top of the prioritization list. Writing of a completely personal nature is fine, too since that writing is often the seeds that sprout into something bigger. Where it starts to get a bit more fuzzy is when thinking about the work that has to happen around writing that isn’t actually making words appear. Editing, researching, taking notes, etc. My thinking, as of right now, is that every day should consist of at least some actual writing (maybe “drafting” is a better word) and that as long as I make some net new words appear I can use some of the remaining time for editing, thinking, taking, notes, and researching. What I want to avoid, though, is spending this time reading or researching and somehow tricking myself into thinking that I’m doing what I set out to do. I could imagine spending the whole time, even the whole time for a couple days in a row, reading and taking notes on something. But it’s something I’ll need to keep an eye on because it’s a very attractive escape hatch for my particular type of brain. Writing is hard. Reading, researching, and thinking about writing is easy (and fun).

There's a bit of a wild card, here, that is also worth exploring for a moment. When I’ve done this in the past the writing I’ve focused on has been 100% focused on non-fiction. I’ve never even considered writing fiction before. For whatever reason I’m feeling the smallest of itches telling me to explore writing fiction. I don’t know where that voice is coming from but it feels like I should honor it. I have no idea what form it’s going to take but I’d be very okay if this morning writing session became dedicated (or at least partly dedicated) to figuring out what that voice wants to say. I’ve never thought of myself as a fiction writer and my gut tells me that I’d be terrible at it. I’m so goddamn literal and rational all the time. But also, life is long and my interests are varied. God knows I read a lot so why not try listening to the voice that says it wants to be a fiction writer and see if anything comes out of it? Nobody ever has to see it. Expectations can stay comfortably low and I can look at myself squarely in the mirror and say I didn’t hide from trying new things.

The Mechanics of Execution

The mechanics of this intention are interesting to me, too. I’ve already talked about the timing, 7:00-8:00 every weekday (weekends are to be determined). That’s because I’ve learned that going right from waking up to writing is really tough for me. I’ve tried that experiment and learned that my brain takes a little time to wake up and reading a book and drinking coffee for the first 30-45 minutes of the day is basically the best part of my day. In the past my brain has rebelled when I tried to make it write first thing in the day. It/I get mad about having to give up the best part of my day to do a difficult thing and eventually my willpower dries up and I’m back to not writing. So, this time around I’m trying to use this self-knowledge rather than ignore it. Starting at 7:00 gives me enough time to read and get that first cup of coffee in me.

Other mechanics to think about include what I’m actually doing the writing on and what my environment is like during the writing session. My inclination is to do the writing on my iPad rather than my laptop and external monitor. Laptop + external monitor is where I spend 95% of my normal workday. I like the idea of shifting this decidedly non-consulting activity away from the tools I used to do my regular job. My iPad can become my default writing machine and my laptop + external monitor can become my default everything else machine. I think it’s possible to build associations with different tools and environments and to that end I think I’ll try to listen to the same music every morning, too. Tycho already has very strong associations with productivity and writing in my brain, so I’m going to milk that for all it’s worth. If it’s between 7:00ish and 8:00ish and I’m writing I’ll have Tycho being piped into my ears.

One last thing to figure out, then, is how to end each session. I’m a big fan of parking on the down slope so that it’s easy to pick up where I left off in the following session. The literal way to do that is to stop in the middle of a sen…

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If you like wrestling with the what and how of deliberate attention then you’ll probably like my newsletter, The Deliberate. Subscribe here for a weekly(ish) exploration of what it means to cultivate attention in a complex world.

A Goodbye Note to Twitter

I’ve read a lot of “goodbye Twitter” articles over the past few weeks. They almost always seem to start with a litany of negative symptoms that the author thinks Twitter is causing. I understand the inclination — it’s easy to identify the things that aren’t going well. The things that don’t feel right. It’s exciting to think about these burdens being lifted from your shoulders.

I’ve noticed that many of these missives end with some sort of admission that the author has either come back to the service (while promising that their eyes have been opened to the reality of the situation and this time they won’t become addicted) or never really left at all. Something about the standard approach to leaving social media behind doesn’t seem to really do the trick.

So, I’m going to try a different tack with this article. Let’s start with trying to better understand what I’m excited to be moving toward -- the future that ideally becomes more attainable by stepping away from Twitter.

Channeling creative energy into larger and more complex outputs

For someone with creative ambitions, Twitter seems uniquely constructed to undermine me. The development of an idea and the steady chipping away at it, is something that takes time and patience and an extremely high boredom threshold. I’ve found some of my most prolific bursts of creativity have come during times when I was experimenting with removing Twitter from my life. Without Twitter, the motivational and creative steam I need to run the Industrial Era steel mill that is my creative process is allowed to build and build and build. Twitter is a vent that lets that steam escape at periodic intervals. If I don’t let it build to the level where I feel like I have to do something creative or else something bad is going to happen to the intricate workings of my factory-brain then I have a tendency to make nothing other than tweets. Some people have a way of making tweets art. My tweets are not art. My tweets are my procrastination made visible.

Let me articulate it more simply: creative, professional, and personal endeavors that are likely to involve frustration and a willingness to sit with boredom are interesting to me because I don’t think I’ve made very many of those things. Twitter is too easy a creative outlet and I think it undermines my ability to do cooler stuff than I currently do. If I remove this extremely convenient  escape hatch from my range of options, might I have an easier time sticking with difficult things? It’s not guaranteed, but I think it gives me much more of a fighting chance.

MORE: Better, longer, and more complex writing on SamSpurlin.com and TheReady.com, more consistent and interesting issues of The Deliberate, exploring freelance writing opportunities, exploring writing a book, etc.

LESS: Having a halfway decent idea and throwing it on Twitter to see what people think, with the vague idea of turning it into an article, only to never touch it again. Tricking myself that writing a couple pithy tweets is the same thing as writing.

Channeling curiosity by consuming longer, more complex and more nuanced information

I love the feeling of consuming news essentially as it’s happening. It feels like I’m there. Like I’m in the mix and seeing what’s happening in real time. It’s almost like watching a movie or playing a video game. I’m a scraggly barn cat getting squirt with milk right from the cow’s udder. 

And holy shit is that an unwholesome way to consume news.

Getting news from Twitter is like how I imagine kitesurfing works: you become intimately familiar with the moment-to-moment reality of the surface of the water because every little wave and updraft has a visible impact on your ability to stay upright. It’s what allows you to keep looking like a supremely cool dude catching some righteous waves and not getting a face full of surf. Just navigating that environment likely takes every bit of skill and attention that you have and it can seem like that’s what the whole ocean is. It’s all consuming and it’s fun.

I don’t know that news should be all consuming and I’m pretty sure it probably shouldn’t be fun the way kitesurfing is (presumably) fun. If a kite surfer is a master of the intimate surface, I’m interested in becoming whatever it is that cares more about what’s going on far below the surface. A submariner? A whale? What’s going on down there? How is it affecting what’s going on up at the surface? (Why would I pick an aquatic metaphor when I grew up in the Midwest?)

MORE: Reading long magazine and journal articles, newspapers, books, and other sources of information that aren’t ripped from the breaking news headlines.

LESS: Trusting algorithms to put the “right” stuff in front of me, staying extremely up to date on everything. Feeling like knowing what is happening is the same thing as understanding why something is happening.

The opportunity to be more deliberate in refilling my creative and inspirational reservoirs

There’s a whole world of interesting, inspiring and thought-provoking stuff out there that I don’t think I’m doing a very good job exploring because “the algorithm” doesn’t surface it to me. The algorithm is great at figuring out what it thinks I’ll find interesting within the bubble of the people and topics I already follow or have expressed interest in. But that’s not how I want to explore the world. I want to explore things that I’m unlikely to find interesting. I want to choose to go this way and not that way. I want the search for inspiration and beauty and art to be a vigorously proactive exploration, not delivered to me as some kind of passive buffet of lukewarm things I’ve kind of liked before.

MORE: Deliberately choosing fiction, movies, music, and other art. Asking people for recommendations. Aimless wandering. Following my nose.

LESS: Mindless consumption of the admittedly cool and mostly unsurprising stuff Twitter likes to show me.

Untangling myself from the need for validation from others

Twitter pushes some very primal and maladaptive buttons in my brain. I’m a huge sucker for validation from others. Without making this a quasi-therapy session, let’s just say that I’ve never really felt like I belong much of anywhere. Never quite good enough, or with the right qualifications, or the right experiences to really be part of the in group. Classic Impostor Syndrome stuff, I know. One way I’ve learned to calm down that voice in my head that tells me I’m not good enough is to collect words of affirmation from people I admire. Or, now that we’re in the social media age, Likes and Retweets and Mentions from people I admire — which are the digital equivalent of pats on the head.

That is no way to live. I’m tired of tweeting something and then watching my notifications anxiously while I see who did or didn’t throw me some kind of digital reward. I’m tired of being a pigeon pecking a lever and waiting for food to come out at random intervals.

It’s time to learn how to not give a shit (or at least less of a shit) about what people think. It’s time to learn to give myself the affirmation that Twitter makes far too easy to rely on others to provide.

MORE: Developing my own sense of taste, exploring unpopular ideas without fear of social ramifications.

LESS: Hoping the right people see my stuff and think it’s good. Trying to be clever in public.

Giving myself space to explore nuance

I’m not one to decry “cancel culture.” In most cases, cancel culture is just a stupid way of saying “having to face the consequences of acting shitty.” But I’ve seen enough Twitter mobs to know that they don’t always get it right. I’ve seen what happens when any sense of nuance gets destroyed with the wrong thing going viral.

A couple weeks ago a podcaster and musician I’ve followed for literally over a decade became a meme because of a series of ill-advised tweets. He became “Bean Dad.” To the mob that formed, his series of tweets became evidence that he was a child abuser and anti-Semite. Anyone who has listened to his multiple podcasts every week for years knew this was not true. We had the context of who he is. His struggles and triumphs with mental health. The obvious pride and joy he has at being a father. And, yes, how being a bit of a dick is part of his brand. None of that nuance matters, though, when you have a bad day, tweet something stupid, and the mob wakes up. 

Being a surly person is not generally part of my brand. I’m not super sarcastic and I generally don’t try to make myself stand out on Twitter by being shocking in any way. But I do have bad days. I do make lapses in judgement. I am not perfect. 

Twitter is a nuance destruction machine. I like nuance. I don’t know that I’m particularly good at it, but it seems like the type of thing worth getting better at navigating. Being nuanced in my writing and thinking. Being nuanced in understanding what others are saying and arguing. I think the world would be a better place if we spent less time speaking or thinking in polar dichotomies. Nuance requires room to breathe and a platform where brevity is its calling card is not particularly well-suited to nurture particularly nuanced takes on just about anything. At the very least, if I want to practice being more nuanced then I need a place to do it… and Twitter ain’t it.

MORE: Exploring the contours, depths, and jagged edges of what’s going on in the world. More peace of mind knowing I’m not one poorly worded or ill-advised joke tweet away from having my professional life upended.

LESS: Certainty in, well, everything.

Some Pertinent Questions

I’ve been chipping away at this article for days, making it longer and longer, rewriting and rewriting, because I think part of me is afraid that once I finish it I’ll need to go ahead and pull the plug. So, in the spirit of a.) capturing those fears in an effort to allay them and b.) doing so quickly, I’m going to knock this next section out FAQ-style.

Aren’t you going to feel isolated?

Maybe! But I’m going to remember that I have lots and lots of people who I could text, email, or gasp call. I’m also going to keep my Open Office Hours going and I’m known to plaster my email all over the place, so I have a feeling I won’t be hurting for human interaction.

Aren’t you shooting your future professional endeavors in the foot?

Maybe! I guess I won’t necessarily be known as a quippy and fun organization design thinker/consultant on Twitter. Luckily, even though it’s easy to think that’s a large part of my job, it turns out it really isn’t. In fact, trading Twitter time for writing time (or speaking time or getting better at my craft time or even just true rejuvenation time) will probably do much more for my professional endeavors than maintaining a fun Twitter feed.

Are you going to be worse at your job?

Maybe! I used to find lots of interesting articles related to organizations and organization design in my Twitter timeline. Luckily, there are lots of other places to find good things to read and reading fewer things deeper is probably good for me anyway.

Aren’t you bailing on the actual hard thing (learning how to use social media with moderation)?

Maybe! I agree that if I truly had mastery over my attention I probably wouldn’t write a multi-thousand word article about leaving Twitter. I just... wouldn’t ever open the app. Alas, it turns out I am mostly human and I have the foibles and weaknesses of anyone who has struggled with curtailing a pleasurable yet harmful behavior. I’ve learned enough about myself through my personal experiments to know I’m a cold turkey kind of guy.

What will you do when you want to have a short break? When you’re waiting in line for something? After dinner when you just want to kill some time before bed?

I don’t know! Probably be bored some, or even most, of the time. It’s probably going to suck at first but I’m guessing it will suck less over time. I’m excited to find out.

You think you’re better than me?

God, no.

Let’s Wrap This Thing Up

I haven’t come to this decision lightly. I’ve been making it for the past couple years... and then all at once. I’ve experimented with removing Twitter and other social media from my life for varying lengths of time. As anyone who I’ve followed for a long time knows, I unfollow and re-follow people multiple times a year as I go through phases of trying out new (coping) strategies. What has always united these experiments is that I always felt good while I did them. I always felt calmer and happier. I would write more. I would read more. And then, inevitably, I’d have a down evening or feel like I earned the ability to kill some time and the next thing I knew I’d be re-downloading the apps and re-following the usual suspects and without much of a deliberate decision I would have slid back into my status quo. And things would be fine for awhile! I would convince myself that using this tool was actually super important and useful. This time would be different! 

And the discomfort and disquiet would slowly grow until I did another experiment. And the cycle would continue.

No more. No more cycle. Time to chart a new path.

Goodbye!

P.S. There are still many ways to connect with me if you’re so inclined. My email is sam@samspurlin.com and I legitimately like receiving email from strangers. I literally have a link where you can sign up to have an honest to god conversation with me about literally anything right here. I also write here at SamSpurlin.com and I have a newsletter called The Deliberate and I have a podcast called Fields of Work. So, I’m around. Say hi.

Looking Back At My Year of Writing

A common theme emerges yet again — I spend most of the year feeling like I should be writing more and when I finally gather up all my public writing for this end of year article I’m pleasantly surprised by how much I actually wrote. I’m starting to think that mismatch between my expectations and reality may be more of a permanent fixture than I’d like.

Looking back at the writing I did for SamSpurlin.com I see a renewed interest in trying to write about my experiences with personal experimentation. I started the year by sharing how my Focus Months were going. And then again at the end of the year I started writing about my foray into weekly experimentation. This is something that’s likely to continue into 2021 and beyond. Instead of being embarrassed at how introspective and specific to me exercises like that tend to be, I’m going to challenge myself to write them in a way that is both interesting and useful to other folks. No more shying away from the weird things I do that I personally think are interesting.

Beyond the personal experimentation recap articles I also got down some key ideas that I’ve been wanting to explore for a long time. Namely, the idea of personal development being an exercise in exploration (or an expedition, as I call it in the article) and the basics of my system for “deliberate personal development.” These are related ideas that I’ve only just started poking around the edges of. These will likely make an appearance in 2021, too.

SamSpurlin.com

1. Looking Back at a Year of Growth, Grief, and Calm

2. The Year of Intensity/Simplicity

3. How to Engage With an Overwhelming World

4. Introducing Focus Months

5. In February I'm Going to Write a Shit Ton

6. The End of My First "Month of Write"

7. "Month of Sit" Recap & a Look at April

8. Personal development is an expedition, not an exercise in perfection

9. Carving Out Your Space to Contribute

10. Recapping My Second "Month of Write" and Looking Ahead to a "Month of Read"

11. Exploring the hard reset

12. Trying to understand my resistance to second brains, digital gardens, and other interesting note-taking concepts

13. Experiment #1: Do The Work Before Wallowing

14. Experiment #2: Green Tea is the New Coffee

15. Experiment #3: Sustain the Home Routine

16. Experiment # 4: Morning Meditation

17. My System and Method for Deliberate Personal Development: An Introduction and Overview

The Deliberate

Thirteen issues means I put a new one out at a little over one per month. If I had conceptualized this as a monthly newsletter then I’d be thrilled. For some reason, though, I’ve always thought of this project being weekly in nature (or maybe biweekly, at most). I don’t think I’ve ever stuck to that cadence for more than a couple weeks so it might be time to face the music and admit to myself that this is never going to be a weekly newsletter.

I think I’m okay with that.

The main thing I like about having a newsletter is that it makes me more attentive to the things I’m seeing and reading. When I’m regularly writing I find myself engaging with the world from a posture of readiness. “Is this something to write about? Is this something worth sharing? Oh! What about this thing?” When I’m not regularly curating and writing the newsletter I can find myself floating through the world in a much more passive mode. Interesting ideas just kind of slide off my brain and don’t find anywhere to latch onto. It’s more tiring to be in that active frame of mind but it’s also much more satisfying than the alternative. 

If you’d like to follow along with The Deliberate in 2021 be sure to subscribe.

1. Why All The Tracking? (TD #27)

2. How To Deal With an Overwhelming World (TD #28)

3. Digital Declutter 2020 Edition (TD #29)

4. Things Fall Apart (TD #30)

5. Sitting and Writing and Quarantining (TD #31)

6. Bottom Up Personal Development (TD #32)

7. Extracting Some Insights From a Down Week (TD #33)

8. Making Space to Write (TD #34)

9. A Checklist For When You Feel Bad But You Want to Stop Feeling Bad (TD #35)

10. Exploring the Hard Reset (TD #36)

11. The Privilege of Extra Unused Attention (TD #37)

12. Clearing the Decks (TD #38)

13. Frivolous (TD #39)

If you found yourself reading and enjoying anything I wrote this year I want to thank you for giving me some of your time and attention. I tell myself that I mostly write for the intrinsic enjoyment and meaning that I’m able to derive from it but I’d be lying if I said I’m immune to feedback. I love when people share what I’ve written, send me an email, say hello on Twitter, or any other avenue of communication. 

Thanks for keeping me going during a weird year.

My System and Method for Deliberate Personal Development: An Introduction and Overview

For as long as I can remember I’ve always been overwhelmed by the number of things I wanted to do or try. As a voracious reader of personal development books I seemed to have a never ending torrent of good ideas raining around me at all times. Ideas about how I could be better. Ideas about new habits to start or stop. Ideas about how to build a life that I’m proud of. Being the overachiever that I am, I would find myself trying to do all the things all the time. I wouldn’t ever consciously stop one personal development intention and start a new one because I never got super clear about what I was actually trying to do. I would just let all these good intentions and good ideas kind of wash over me and because I am not some kind of prodigy this would obviously always mean I was failing on at least a handful of vague intentions at the same time. Instead of feeling like I was making and keeping commitments to myself I was always operating under a vague sense that I wasn’t doing the things I said I wanted to do (even though, overall, I was definitely doing a lot).

Eventually, I homed in on two key concepts for the system I ended up developing for myself: limiting work in progress (WIP) and iterative experimentation.

As anyone familiar with the Theory of Constraints knows, putting a cap on the number of things that are allowed to be “active” at once actually increases the flow of items through a system. If you have a backlog of 10 items you’ll actually complete them faster if you only work on 1 or 2 at a time, rather than trying to chip away at all 10 simultaneously. In the case of personal development, we don’t actually care about finishing things quickly — but we do care about finishing things (which is really more of a psychological state than anything else). The power of this idea was fairly obvious to me in a work or school context, but I started to wonder if it applied in a broader personal development context, too. 

Secondarily, as I got deeper into my work with organizations through my job at The Ready I came to better understand the power that continuous experimentation can have when a team is trying to do something new. While I had always been interested in self-experimentation, especially as part of the quantified self movement, I developed a new appreciation for what disciplined and iterative experimentation looks like and what it can unlock through my work at The Ready. I started to apply this experimental mindset to my own personal development endeavors with really surprising results.

The combination of limiting WIP and adopting a habit of continuous experimentation was what helped me start to feel good about my personal development efforts for the first time. In the rest of this article I will show you the system I developed for myself as simply and directly as possible.

The goal is to create an external system that can hold all the ideas for potential experiments you get from the world around you (books, podcasts, etc.), help you develop those ideas into full-fledged yet tractable experiments, help you limit the number of experiments you are pursuing at once, guide you in learning from the experiments you’ve done, and help you uncover the core personal insights that are the ultimate goal of the whole endeavor. 

The Tool

It sounds like a lot, but a relatively simple Kanban board can do most of the heavy lifting for us.

A Kanban board is a tool that helps you visualize work and the various states in which it could be. The simplest version has three columns: To Do, Doing, and Done. We aren’t going to complicate it much more than that.

Our Deliberate Experimentation Kanban is going to have the following columns: Inbox, Backlog, Active, Done, and a separate, but related, area called the Insight Library.

Inbox

This is the list where you can throw any vague idea or intention to ensure you won’t lose it. You haven’t committed to anything that’s on this list. It’s simply the top of the funnel for things you might want to potentially do. Anything can go in here. Musings, questions, thoughts, a word or two... anything to get the thought off your mind and into the system.

To Do

When you move something out of the Inbox because you’re pretty sure you want to do it soon, you move it to the To Do list. Here you’ll fill out the Basic Experimentation Template and make sure you’ve thought through the details. These ideas are ready to go... but aren’t active yet.

Active

This is where you put the experiment you are currently doing. Every day you’ll check-in and add relevant data or reflections to the card. Ideally you won’t have more than 1 or 2 experiments active at a time (remember, limit WIP!).

Done

This is simply where you put the experiments you have completed. In order to move an experiment from Active to Done you need to fill out the End of Experiment Retrospective questions. This is where you’ll make sure you extracted all the lessons — and maybe even extract an Insight or two!

Insight Library

The last part of the system actually lives outside of the Kanban board itself as a separate document that I call my Insight Library. The whole reason we’re doing personal experiments is to uncover these key insights about ourselves. We’re systematically trying new things so that we can systematically explore our beliefs, assumptions, and abilities — all the stuff that makes up who we are as people. It’s about uncovering, discovering, and maybe even changing, more and more of our identity over time. As we do more experiments we will capture new insights about ourselves or adjustments to insights we’ve made in the past. This slow but deliberate accrual of our own personal Insight Library is personal development.

The Routines

A Kanban board is not enough... it must be paired with a few key routines related to how we use the tool.

First, there’s the ongoing habit of throwing ideas into your Inbox as you come across them. It’s being able to notice when you’re thinking, “I should try...” or, “I wonder what it’d be like to...” and capturing those ideas into your system as soon as possible. Sometimes these ideas will pop up out of thin air and other times you’ll capture them as you read a book, watch a YouTube video, or have a conversation with a friend. They can come from anywhere and the more you practice the better you’ll get at capturing them right away.

Second, there’s the daily routine of reflecting on how your active experiment(s) is going. I usually do this in the evening before I go to bed. It’s as simple as logging into your Kanban and tapping out a sentence or two about how it went today. Sometimes, if the experiment is extremely cut and dry, logging the day’s data is as simple as writing “Yes” or “No.”

Third, there’s the weekly routine of retrospecting on the whole experiment (assuming you ran the experiment for a week — some experiments are longer than that). This is where you pause and ask yourself some general questions about what went well, what didn’t go as well, and what you learned.

Finally, there’s the trimesterly(ish) routine of going through all your completed experiments and mining them for potential Insights and new experiment ideas. Sometimes you need to accrue many weeks of experiments before patterns and themes start emerging. A lot of the time you’ll notice them without having to do this quarterly routine but I like to schedule some time every 4 months or so to do a deep dive into my completed experiments to see what I can find.

It sounds like a lot, but generally each of these can be done in only a couple minutes. Setting up some automatically recurring reminders and building them into your overall routine makes them something that you’ll learn to look forward to over time.

What else do you want to know about this system? What isn’t clear? What doesn’t make sense? I intend this to be the beginning of a lengthy series expounding on this approach and your feedback will help me better understand where I’m not clearly describing what’s in my head. Let me know on Twitter (@samspurlin) or in the comments below!

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Curious to learn more about this system as I experiment with it in real time? Join my newsletter, aptly called The Deliberate, to get behind-the-scenes writing and thinking.

Experiment # 4: Morning Meditation

I don’t have a dedicated place in my day for my meditation practice. When I manage to do it, it seems to be in the evening and it always feels like I’m somehow getting lucky. Other daily habits have places in my daily routine where they feel natural and good. I’d love to figure out what that could be for meditation and I’m wondering if it might be right after I wake up? 

I learned a couple weeks ago that I’m not as reliant on coffee as I thought I was so I think I could get up and meditate right away and then go into my morning coffee routine. As silly as it sounds, I’ve struggled with meditation right after waking up in the past because I couldn’t figure out the order of operations with my coffee routine. Option A is making coffee and then not drinking it for twenty minutes while I meditate. Meditation is difficult enough as it is... smelling coffee and knowing that it’s waiting for me the whole time feels like doing it on Hard Mode. Option B is making a cup of coffee, drinking it and then meditating. This seems rational but at that point, roughly thirty minutes later, I’ve kind of lost the “wake up and meditate right away” vibe and more often than not it’s difficult to put down whatever I’m reading and go do a harder thing (i.e meditate). Option C, which always seemed too hard, was to meditate immediately and then go make coffee after finishing the session. That’s the version I’m going with for this experiment.

For the next week, as soon as I wake up and use the bathroom I’m going to immediately do the twenty minute Daily Meditation in my meditation app of choice before doing anything else in my day (including making coffee). Under normal circumstances this means I’d be cutting into my morning reading time. In vacation mode, I don’t really need to worry about that. If it goes well, I can cross that bridge when I re-enter real life in January.

So, how did it go?

A week later and here I am. I successfully meditated for seven days in a row but I did not do each of those sessions immediately upon waking up. I think I managed to do that for five of those sessions. A couple things worth noticing:

• Somehow I went to bed a couple times this week with my phone sitting on the table next to my bed — which is not how I normally operate. On those occasions I found myself scrolling through Twitter in the morning rather than immediately getting out of bed and putting my butt on a cushion.

• Broadly, I noticed it can be tougher to get out of bed and get moving when the first thing on the docket is twenty minutes of meditation. Usually, making a hot cup of coffee is my animating force.

• That being said, I felt good when I did the morning meditation. A nice mix of calm, focused, and accomplished.

• I think this is probably the best spot in my day for meditation to live. I’ve still got a long way to go to make it feel automatic but I at least showed myself that it’s possible.

Experiment #3: Sustain the Home Routine

I’m in Florida for a month without my stationary bike — my primary source of exercise — and I need to figure out another way to burn some calories and keep myself mentally healthy. Normally I’d go for 30-60 minute ride a couple times a week as my primary means of exercising (in addition to a very low-key morning walk which is much more about waking up than it is about getting stronger). If I was only going to be here a week or two I wouldn’t worry too much about it but because I’m here until early January I don’t think it’s wise for me to throw all plans of exercise to the wind and just roll with the punches. Because I will end this month too fat. Fat and sad. And nobody, especially me, wants that.

And really, it’s about more than exercise. Without going into a bunch of detail that makes me look even more privileged and out of touch than I already am, I’m fortunate to be spending the month of December in Florida with very little work to do. Emily and I drove down (to avoid the Covid hotbeds of airports and airplanes) and are socially isolating in a condo that we’re inhabiting by ourselves (and we just got tested for Covid today). I’m very lucky to be able to do this. And I very much need the break. But four weeks is way too long to be in “vacation mode” the whole time.

So, to preempt that, I’m calling this week’s experiment Sustain the Home Routine. It’s about hitting the same major beats of my daily routine at basically the same time and not throwing all my structure out the window just because I’m in a new location and a non-work setting. It would be very easy for me to ignore all the routine that I rely on and love when I’m in more “normal” times just because I’m on vacation and in a new location. Without a little bit of vigilance I’ll eat like an idiot, exercise not at all, and just kind of flit from one somewhat pleasing activity to another before ultimately ending the day not feeling particularly rejuvenated or good.

More specifically, these are the basic “beats” of my day that I’m expecting myself to adhere to for the next week:

• 6:00 up, make coffee, and read a book

• 7:00ish out the door for a walk

• 9:00 - 12:00ish knock out whatever work I need to do

• 12:00ish lunch that I make (not delivery or fast food)

• 3:00ish snack so I have enough energy for an afternoon workout

• 5:00ish some kind of workout, probably a run

• 6:00ish make dinner

• 7:00ish dinner

• 10:00ish bed

What may seem like a ton of structure to some is actually the perfect scaffolding for me. It ensures I’m doing the most important stuff without hyper scheduling my day (especially since I’m ostensibly on vacation). I’m hoping that this little bit of extra planning and discipline will actually make me feel more rejuvenated than if I just followed each and every whim that I have.

End of Experiment Retrospective

The experiment this week was to basically hold onto the normal beats of my daily routine even though I’m in a different location and ostensibly on vacation. A month is too long to be in full-on vacation mode and I know I’m the type of person who derives a lot of comfort and satisfaction from keeping to a relatively consistent daily routine.

 How did I do? I’m going to give myself a letter grade for each of the areas I said I wanted to focus on:

• Waking up & going to bed on time: Pretty much nailed it. Got up a couple minutes late (like, < 10 minutes) a couple times but that’s a pretty negligible miss. A-

• Going for a morning walk: 7:10, 7:06, 7:04, 10:52, 7:10, 12:10 were the times of my morning walks this week. The 10:52 day I deliberately decided to go later because I was down to the last few pages of a book I had been reading for a long time. The 12:10 walk was on Saturday and I’m deliberately much more relaxed about when things happen on the weekend. A

• Make lunch rather than buying: Made lunch every day. Booya. A

• An afternoon snack: I don’t keep records of this so I don’t know exactly how I did. I’m guessing pretty well because when I get my 3:00 PM reminder on my phone I get SO PUMPED to eat a snack. Snacks are the best. Probably an A?

• An evening workout: I’ve been trying to do a bit of a run/walk as my workout. I haven’t run in months so it has been very slow going. More walk than run, if I’m being honest. I made it out there on Monday, Tuesday, Wednesday (active recovery), and Friday. The only day that felt a little bit like a miss was Thursday, but honestly my body was not feeling all that great so I think the extra rest day was smart. Nothing on Saturday other than a bonus walk (on the beach). A-

• Making dinner rather than buying: Nailed it. We did a great job using our groceries this week. We even skipped Friday Pizza Party in favor of an equally fun dinner we made ourselves. A

Overall, I call this experiment a resounding success. I definitely felt pretty good and didn’t get into that listless state where I find myself kinda mindlessly drifting from one distraction to another for large swaths of the days. That’s always enemy #1 for my happiness so experiments that help me keep that at bay are very much worth it. As I suspected, a decent daily routine gives me something to build around and as long as I don’t become an utter slave to it, then I think it’s a mostly positive thing for me to focus on — even on vacation.

Experiment #2: Green Tea is the New Coffee

Sometimes personal experiments are extremely connected to deep and important changes I want to make in my life. This is not one of those times. This is going to be an experiment borne of two parts logistical necessity and one part morbid curiosity.

I’m not a huge coffee drinker, in volume, but I am a huge coffee drinker, in love. I love fancy fresh beans. I have a fancy electric kettle with a gooseneck that allows for precise pouring. I use an AeroPress. I drink two cups every morning and almost never exceed that.

That being said, I’m pretty sure I’ve had at least one cup of coffee every day for like… 15 years? Longer than that?

I don’t like knowing that I’m reliant on a drug to feel good in the morning and I’m curious what it’ll be like to not drink coffee for a week. Also, I messed up my coffee delivery subscription and I’m currently out of coffee until Wednesday. But I did just buy some very nice green tea that arrived late last week.

For the next week I’m going to replace my two morning cups of coffee with green tea.

Hypothesis: I’m going to miss coffee a lot. I’m going to feel kind of bad. But by the end of the week I’ll have worked through whatever caffeine withdrawal I might be feeling and I’ll be proud of the hard earned self-knowledge I’ll have gained. Or something like that.

End of Experiment Retrospective

This went wildly better than I expected.

Monday night’s sleep.

I thought that because I love my morning coffee routine so much it would be a total drag to not do it for a week. Luckily, it looks like my two cups per day habit isn’t enough for me to be hopelessly caffeine addicted.

Monday night (the first evening after replacing my morning coffee with green tea) was the only time I really felt any negative physical symptoms. A nice dull headache settled in by the afternoon of that first day and I felt absolutely wiped by 8 PM. I dragged ass until 9 PM before deciding to just give in to the inevitable and hit the hay. I then slept hard.

The rest of the week I went to bed and got up at my normal times (10 PM/6 AM). I didn’t feel terrible in the morning and I was able to go through my day feeling fine.

So, the takeaway from this isn’t that I’m now going to give up coffee. Instead, I’m going back to my morning coffee routine feeling much better about it. I know now that I’m not hopelessly addicted to caffeine. I just like coffee and I like the ritual of making it my fussy way each morning. It’ll feel nice to go back to it knowing I can drop it again without crushingly adverse consequences if I ever need or want to. I have a feeling that’ll make it taste that much better.

Experiment #1: Do The Work Before Wallowing

Sometimes I get extremely wrapped up in my own head about all sorts of things. I start doubting whether I’m any good at my career, whether my clients secretly think I’m doing a terrible job, whether I should quit my job and go do something completely different. I start beating myself up for not writing more or reading more.

It’s okay to feel bad sometimes. Honestly, sometimes feeling bad is the pre-requisite to feeling really good later. But I don’t like feeling bad for seemingly no reason.

Over the past few years I’ve done a pretty good job finding the minimum viable habits necessary to have a decently high probability of having a non-terrible day. Doing these habits doesn’t guarantee that I’ll have a good day but it almost guarantees I won’t have a truly dismal day.

What’s silly, though, is that I’ll sometimes find myself circling the psychological drain without having yet completed my daily habits (what I call my Anchor Habits and which consist of doing some sort of minimal deliberate exercise, reading at least fifteen minutes of a book, meditating for at least ten minutes, and doing one session of any length of writing). How can I look at myself in the mirror and say, “Yep, this is some righteous wallowing,” when I haven’t done the things I know tend to make me feel better?

If I notice myself wallowing without having completed my Anchor Habits, I must complete my Anchor Habits before resuming wallowing. If I’ve done my Anchor Habits and I still feel like shit, well, that’s how it goes sometimes.

End of Experiment Retrospective

Key Stats

• Number of “Anchor Days” (days where I completed all four of my daily habits): 4 (the last time I had at least 4 Anchor Days it was August and the last time before that was April)

• Total Anchor “Points”: 22 out of a possible 28 (average YTD is 18)

I didn’t mention this in the setup for this week’s experiment, but there was a pretty huge confounding variable that surely messed with my experiment a bit this week — a very short work week and the Thanksgiving holiday. This was obviously a pretty atypical week so I don’t know how much of what I experienced can really be attributed to the experiment. That being said, subjectively it seemed to help. I did a pretty okay job actually “doing the work” (doing my four daily habits each day) this week and I felt pretty good all week. I didn’t actually record any data about how I felt at the end of each day, so this is entirely subjective and likely biased by how I’m feeling in this moment as I’m writing this, but overall it felt like a pretty psychologically healthy and overall positive week.

As always, the two Anchor Habits I was least consistent with were Writing and Meditating. Neither one of these has a really locked-in time slot in my daily routine like Reading and Exercise do. I did start to circle 9:00 PM as my meditation time and having it be the last thing I do before I get ready for bed. Writing seemed to mostly get slotted into the after dinner time slot (when it happened at all) … but it was pretty inconsistent. In my ideal world I would give more of my “prime” hours (i.e. the morning) to writing so I don’t always feel like I’m scraping the bottom of my energy and motivation barrel when it comes time to write.

I consider the experiment a success and while I’m not going to officially do it again next week, this is an example of one of those experiments where I intend to more or less keep it going indefinitely even though I wanted to focus on it intensely for a week to help get it going again. The whole point of having daily Anchor Habits is that I do them every day. The key thing, though, is remembering to ask myself if I’ve finished my Anchor Habits for the day if and when I find myself in a psychologically dark place again.

Trying to understand my resistance to second brains, digital gardens, and other interesting note-taking concepts

All the coolest kids are building “second brains” and “digital gardens” and public note-taking libraries and I’m sitting here like a rube with no robust note-taking system. I am one of the most knowledge worky of all knowledge workers — a management consultant. I mostly spend my days having conversations with executives about how their organizations can be better, with teams who are trying to constantly evolve the way they work, and occasionally writing things that support both of those endeavors. And in my “off time” I try to write semi-insightful things on this website and in my newsletter. If there’s anybody who could benefit from having a note-taking system that generates insights that can be turned into smart words (spoken or written), it’s me.

And yet, I don’t. And I don’t think I’m going to any time soon.

The cynic and small mean person inside me sees these folks expounding the value of their digital gardens and wonders if they’re missing the point. I don’t actually follow any of them closely enough to know if this is true (it’s probably not) but if all the work being put into the note-taking system isn’t resulting in actual outputs then it seems like misplaced effort. It’s like a chef collecting a huge library of impressive and rare ingredients but never actually making anything with them.

My process is a lot more like coming home from the grocery store with the ingredients in hand and basically immediately turning on the stove and getting to work. I know that if I don’t capitalize on the motivation and the available ingredients when they are easily at hand I’m unlikely to do much of anything with them. The optimist in me says it makes me very efficient and somewhat, if sporadically, prolific. I suppose a critic would say that this process encourages a level of superficiality enforced by immediacy. How nuanced and expansive can I be if I don’t have a place for ideas (ingredients, maybe? I’m letting this metaphor get away from me) to go ferment for awhile. Other than my brain, that is. My first brain, not a second one.

Perhaps I’m not giving myself enough credit for what I do. I may not have a digital garden, but I do have a digital windowsill with a couple herbs sitting on it (I will wring every bit of utility out of this metaphor; just watch me). I have what I call my “Spark List” which is a simple text file with every scrap of an idea that I’ve ever had that I think I might want to write about at some point. When I want to write but don’t have something sitting at the front of my awareness I’ll sometimes go shopping in my Spark List for something to write about. 

I’ll also do stream of consciousness writing about a variety of topics and they almost always get saved in Day One which is ostensibly a journal but has really become a catch-all place to store writing that doesn’t have much of a home anywhere else. It doesn’t get any meta-data attached to it other than the date at which I put it into the program. Once every few months I’ll go through Day One and read those entries and see if it sparks anything to be added to the Spark List. Otherwise, Day One gives me an “On This Day” notification every morning that shows me everything I’ve saved in the program on the given date since 2011 (which is when I started keeping a journal). Mostly what I’ve learned from this is that I’ve been thinking about and struggling with the same things for the better part of a decade. Something to be said for consistency, I guess?

I look at what people have built with Roam and I think, I should do that. I look at what people are doing with Notion and I think, I should do that. I look at what people have made with DEVONthink and I think, I should do that.

For now, though, I’m going to keep the shortest distance between inspiration and output as possible. That’s the best way I know how to work and diving deep into the world of note-taking sounds exactly like the kind of productive distraction that would keep me fat, happy, and distracted for months while I never actually make the things that the notes are supposed to support. Maybe all those years of writing the same things into Day One have taught me something about myself after all?

Exploring the hard reset

I’m no computer expert so I’m not exactly sure what causes them to periodically lock up and require a hard reset — holding the power button down for an uncomfortably long time and interrupting whatever runaway process or hopelessly locked instructions is causing a computer to be completely unresponsive. I’ve always imagined the computer being a little bit concerned but also grateful that I’ve come along to release it from whatever is ailing it. A chance to start over, get rid of the extra stuff that is causing the slow down, and re-engage with the world with clear memory, greater simplicity, and a newfound sense of optimism.

That’s kind of what I’ve been doing to myself for the past couple weeks.

For reasons old (my compulsion to always do more and better) and new (a worldwide pandemic that has thrown a wrench into every plan and routine) I’ve been feeling a bit like the computer that is sluggish and verging on unresponsive. Inching closer and closer to where the usual troubleshooting actions are no longer effective and instead needing someone to hold my power button down until the screen flashes black and the normal boot up sequence starts again. Too many processes running at the same time. Too many open loops competing for the same limited memory resulting in a user interface that feels like it’s being dragged through mud. Like trying to stream a video through dial-up — stuttery, pixelated, and generally an unpleasant mess to interact with. 

Moving beyond the computer metaphor that I only understand enough of to barely muddle my way through, I recently realized that my 2020 theme of Simplicity/Intensity has been heavily weighted toward the Intensity end of that duality. Each month I’ve been taking a habit and trying to be deliberately intense about it. So far, though, I haven’t done much to explore the simplicity or spaciousness that I wanted to temper the intensity that tends to come more naturally and be more interesting to me. 

So, even though I’m still in the midst of my first Month of Read, I’ve also been experimenting with scaling way back across many different aspects of my life. Scaling back the number and complexity of the tools to do my basic work. Scaling back the number of open loops I have running at any one time. Scaling back the expectations and the negative self-talk that push me toward greater achievement while simultaneously making me unhappy. Scaling back the number of places I appear online and the number of feeds that need tending. It has meant looking at everything around me and asking myself whether I could do without something, at least for a little bit, just to see what it’s like. 

And although I’ve done a lot so far the process is still ongoing. Shedding the obvious dead weight results in new layers of things to consider. Things that weren’t obvious at first glance are brought into the light and analyzed for the first time. Old projects, old intentions, and old personal commitments that haven’t been re-examined or updated by the current version of myself. Old identities and expectations that no longer serve their intended purpose and instead are just consuming limited mental RAM.

The idea is not to move forward indefinitely as some kind of modern ascetic (I’m pretty sure the fact that I’m typing this on an iPad while living in an expensive apartment just outside of Washington DC prevents me from authentically claiming that path anyway). It’s more like a systematic dismantling of as much of the scaffolding I’ve intentionally and unintentionally built around myself over the last few years so I can better see the building — the person — underneath it all. When I was living in NYC there were certain construction sites that I only ever saw with scaffolding draped all over them. Scaffolding so dense and so seemingly permanent that it seemed to be an actual part of the building. And then, suddenly and dramatically and without warning, I would find myself walking the same path as always only to realize that somehow, improbably, a new building stood where before I usually saw the accoutrements of construction. Overnight the fundamental appearance of a building would change as the scaffolding was removed and the construction equipment moved away.

And there was almost always something beautiful standing there.

My personal construction project isn’t completed (and I don’t think I ever want it to be) but it’s time to take stock of what’s there before moving on to new projects. I’m hoping removing the detritus will give me a better appreciation of what’s already there and some new motivation to embark on the next phase of whatever it is I want to do. 

Recapping My Second "Month of Write" and Looking Ahead to a "Month of Read"

In February I conducted my first Month of Write and was very disappointed. In April I decided to take another crack at it quicker than I had initially planned in order to see if I could get the bad taste of February out of my mouth. Whereas in February I didn’t really have a plan other than “write more,” in April I specifically wanted to see myself get up at 6:00 AM everyday, sit down at my iPad or computer by 6:15, and write consistently from roughly 6:15 to roughly 7:30 (I originally intended to do 7:45 but quickly learned that that end time unnecessarily complicated my mornings).

As you might expect, April went much better than February.

First, a few objective stats:

• Words Written: 17,702 (compared to 6,500 in February)

• Days Written: 18 (compared to 13 in February)

• Published articles/newsletters: 7 (compared to 3 in February)

And now a few subjective reflections:

• I started really strong. The first week of this month I was an absolute machine. The routine felt incredible. I felt like a real writer. I was focused and energetic and just so goddamn writerly.

• Each week’s writing total went down. The second week was okay, the third week was spotty, and the last week was a travesty. 

• This decline was not super surprising. The first couple weeks of any new habit are always the easiest. It’s once the novelty starts to wear off that you really start to run into problems.

• I started to get distracted by work urgency as the month went on. I had several early morning meetings where it felt like I had to use the time I set aside for writing to prepare. I need to figure out a way to keep my intense job as constrained as possible into normal work hours.

• Even as my output tailed off across the month, I did a pretty good job getting up on time everyday. I would just sometimes get sucked into reading or looking at my phone or working on “regular work.”

• Finally, I started to wrap my arms around a large writing project in a way that I haven’t in a long, long, long time. I wrote around 7,000 words that I didn’t publish but I’m excited to keep nudging forward.

And a few more lessons (how is a “lesson” different from a “reflection”?):

• I created a process for daily writing that I’ve never used before but I really like. Basically, I create a separate file in Ulysses for each day. I then do all of that day’s writing in that sheet, regardless of the “type” of writing I’m doing. At the end of the writing session I can copy and paste what I created into it’s final resting space. For example, a typical day might contain a couple hundred words that are a journal entry that eventually lives in Day One, the first two thirds of an article I’m eventually going to publish on my website, and the beginning of an outline for an issue of The Deliberate. I’ll copy and paste these various chunks to the places they need to go but I’ll leave behind the “master” log of all the writing I do each day.

• It’s a really nice way to have a sense of progress since I can see each day’s note in the sidebar and see how many words I wrote.

• It lets me set myself up for the next day’s writing by ending each day’s writing session by creating tomorrow’s document and pre-populating it with my ideas or thoughts about what I could write about.

• The writing association with Tycho that I’m trying to build is slowly getting stronger. As I tailed off in my productivity last month I realized I had gotten sloppy with putting my headphones on and turning on Tycho as quickly as possible. 

I’m really looking forward to the day where I can make writing a larger part of my day job. The only way to do that, though, is to make writing a larger part of the rest of my life. Developing these skills and putting more of my ideas out into the world is what will allow me to eventually make that jump to more of a writing-focused career. The nice thing about my current writing routine, though, is that it’ll serve me just as well now as it will in this fictional future state where I can write all day. So, until then, if it’s between 6:15 and 7:30 in the Eastern American time zone then my butt should be planted in front of my desk, Tycho should be bumping in my ears, and I should be making words appear in Ulysses.

Month of Read

I have four Anchor Habits that I try to do everyday: exercise in some capacity, meditate, write something, and, most enjoyably, read something substantial. We’re now into May and I’ve given each of these habits (and writing twice!), except for reading, a month of their own. The time has finally come to rectify that. Welcome to the first Month of Read of 2020!

This month creates a bit of a conundrum for me. The basic idea was that although I try to do these four Anchor Habits in a minimal capacity everyday, I can be extremely hit or miss on them. I thought that by really focusing on one of them per month would help me get more consistent. And so far, that hypothesis has been right! However, I’m already incredibly consistent with my reading habit. As of this writing I’m rocking. A 62 day streak of having read at least 15 minutes per day. Reading is a part of my day that already feels like a reward and it’s pretty deeply baked into my daily routine.

So, what to do in a month where I’m supposed to really focus on it?

My initial inclination was to give myself a specific focus or restriction. Something like, I can only read fiction, or poetry, or I have to read something deliberately difficult, or read slower, etc. Something that would push me out of my normal comfort zone. However, for each of my other Focus Months where I was focusing on a habit for the first time, I kept it deliberately simple and basically just had the intention of, “Try to do the thing more than I normally would and see how you feel.” So, in the spirit of simplicity I’m going to do the same thing with this Month of Read. I’m just going to read as much as I can (which is kind of what I already do but I’m sure I can find some parts of my day where I could switch over from something low-quality, like browsing Twitter, to reading) and actually track the amount of time I spend reading in a time-based reading log (which is not something I normally do).

At the end of the month I’ll have a better sense of how much time I spend reading in a month where I’m really trying to spend as much time reading as possible. In the remaining two months of 2020 where I’ll focus on reading again, I’ll put some kind of variation or focus or restriction on the intention to make it more interesting.

Feel free to follow along in this Notion card to see how I’m doing during the month: https://www.notion.so/samspurlin/Read-as-much-as-I-can-every-day-3c855fdb064a43fa9e04577663543283

Carving Out Your Space to Contribute

Why do I sometimes feel ashamed of the stuff I like to read and write about? Is that shame trying to tell me something useful or is it keeping me from contributing valuable ideas to the world? 

Productivity Pornographer or Philosopher?

On the useful side of things, it’s definitely keeping me from participating in the “productivity porn” and “hustle porn” racket. There are definitely parts of my personality that are drawn to those topics in a way that I know isn’t helpful or healthy. I know that writing about productivity for the sake of productivity is not anything the world needs more of. There are too many people already hawking suspect productivity advice that papers over problematic views about the world and the role of work in our lives. I mean, I like reading and writing a good productivity hack as much as the next middle-aged white knowledge worker guy but that’s not exactly elevating the discourse about meaningful work. I like candy bars too but I’m not about to eat a candy bar only diet.

Speaking of elevating the discourse, I think that’s the other vector into my shame about what I feel drawn to write about. There are some folks who take an incredibly philosophical point of view and tone in writing about work and personal development that I find both admirable and completely unattainable with my writing and thinking ability. In my darker moments I look at someone writing and thinking at such a high level about this stuff that I feel like I shouldn't add anything if I can’t operate at that level. 

Considering I just articulated two ends of the same continuum, there’s obviously a lot of white space in the middle where I could probably feel pretty comfortable exploring. I know I’m not going to write absolute drivel about 10 productivity hacks to supercharge your productive productivity (even if I sneak a quick look at those articles from time to time...) and I’m not capable of writing a far-reaching philosophical treatise on the nature of work and the human condition. That doesn't mean those are my only two options, though.

Charting My Place in the Middle of the Continuum 

To stay away from the drivel end of the continuum, I think it helps to articulate that I specifically ascribe to a definition of productivity that’s broader than simply the amount of work you’re able to get done. It’s much more about overall meaningful engagement with the world — work or otherwise. It’s about feeling like an active agent in the world rather than a passive object. Anything from “tips and tricks” to life philosophies that help you feel more engaged with the world falls into the realm of productivity to me.

And on the other end of the continuum I don’t think it’s particularly helpful to keep the discourse around meaningful engagement with the world at the level that only philosophy professors can engage with. To the extent that I can use my experience in the academic world to bring those concepts and ideas down to a level that’s more digestible to the average person then I am providing a useful service. I’ve been out of the academic world long enough to know that what often passes as good writing in academia is utterly impenetrable to even very bright people and that making ideas accessible can be incredibly valuable.

As a reminder to myself and a public stake in the ground, these are the areas where I have something to contribute and I should be pushing myself to publish as much as possible on:

• Everything I’ve been thinking about with reformed workism and deliberate attention

• Everything I’ve learned about the reality of being an employee in an organization — legacy, self-managing, small, large, or otherwise

• The intersection of organization design and the individual experience of work

• The connection between using tools and software to make yourself a more effective agent in the world

• The remnants of my academic training in positive psychology and how it applies to individuals and organizations

• My own personal experiments/experiences with how I’m applying these concepts to my own life

Shame is the ultimate in unhelpful emotions when it comes to trying to make a positive impact on the world or do anything that remotely opens you up to potential rejection or judgment. For a long time I don’t think I really understood that a lot of my creative blockage was being caused by the shame I felt in either contributing to the anti-intellectual and unhelpful productivity hack genre or being unable to elevate my thinking and writing to the almost equally unhelpful “productivity philosopher” level. Now, I think I’m finally starting to realize that my advantage and gift is being able to explore much more of the continuum while staying away from either extreme end.

Shame and Comparison

In an effort to make this a little bit more generalizable and less navel-gazey, I have to imagine that this dynamic I just walked myself through is something that other folks experience, too. At its heart it’s a problem of comparison. The transparency of the internet has given us a much wider pool of people to compare ourselves to and believe it or not, there’s a lot of incredible people out there in the world. The most useful advice I’ve heard about this dynamic is that it’s profoundly unhelpful to compare your backstage to other people’s front stage. Meaning, you only have access to the polished final project that people project into the world (no messiness to be found anywhere!) whereas you're intimately familiar with all the personal discord that accompanies everything that you produce.

That’s why I love seeing “behind the scenes” content from the creators I really like. Show me your process. Help me understand that you don’t just crank out stuff that I adore with never ending productivity and effortless grace. Show me your struggle so that mine feels a little bit more normal.

Finally, the other piece of advice that I read somewhere a long time ago that sometimes soothes me in moments of uncertainty is that even if it seems like someone has already done what you’re trying to do, they haven’t done it in your voice. The writers and creators I follow most closely are not constantly sharing brand new ideas. Many of them cover well-trodden ground. However, it’s their voices and personalities that keep me coming back and interested in what they’re doing. That can be a difficult generosity to extend to ourselves but when I’m able to do so the quiet, doubting voice in my head is placated and I can actually focus on doing what I want to do.

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Personal development is an expedition, not an exercise in perfection

I don’t think personal development is an exercise in trying to reach some idealized state. Or at least, not some kind of universal idealized state that’s the same for everyone. I’m not interested in personal development because I’m trying to become more like somebody else who I think is admirable in some way. I’m interested in personal development because I’m trying to better understand and learn about myself. I believe that most of us only have visibility to a small sliver of our own personalities, capabilities, and general self-knowledge. Who “I am” is a bit of a black box, I think. I see the parts that are brought out of the shadows by the demands of my normal day-to-day life and the challenges I experience navigating it. But I get the sense that this is only a small portion — that there are parts of me that exist but I don’t regularly see or experience because they aren’t generally needed to navigate my normal life. I want to find those hidden parts. I want to understand those under utilized parts. And that’s why I pursue personal development. I want to see and understand and interact with the parts of me that are below the surface.

Or let’s try another metaphor on for size: an unmapped territory. The visible parts of me and my personality are like an extremely well-mapped neighborhood. There’s a ton of details on the map and it’s extremely precise. But as you get further from the center it starts to get a bit fuzzier. There aren’t as many road names and the features are more vague until eventually, once you get far enough away from that extremely well-mapped center, it simply shows fog and here be dragons. Personal development as I conceptualize it, then, is the systematic series of forays into that fog to update and add detail to the map that is me. It’s looking at that fuzzy map and the warning of dragons and asking, “Do there actually be dragons? Let’s see if we can find them.”

This is deliberately in contrast to a deficit view of personal development where I’m constantly trying to become better because I’m not enough. Or, because I’m not close enough to some sort of ideal person (or writer or athlete or consultant or whatever aspect of my identity isn’t feeling up to snuff at the moment). Approaching personal development from this angle is a qualitatively different, and I would argue less pleasant, experience. I’m certainly not immune from falling into this kind of comparative mindset. It’s easy to look at someone and immediately use them as some kind of measuring stick that almost always seems to find you wanting. That’s not a fun way to go through life and if you look at personal development through that lens I wouldn’t be surprised if it wouldn’t be attractive to you.

Limit work in progress in all the things — including your good intentions about yourself

But, let’s say that for whatever reason you’re already of the mind that personal development is an inherently rewarding experience and that being on a quest to better understand yourself is attractive to you. In my experience, one of the most difficult things about thinking this way is being overwhelmed by the options in front of you at any one time. And if your reading diet has as many non-fiction books in it as mine does you are constantly finding good ideas for things you’d potentially like to try. If you’re like most people, those ideas end up floating around in your head in some kind of liminal state for awhile until you eventually forget about them and go back to whatever your current default behaviors are. If your lucky, you might try something different long enough to slightly adjust your default behavior. If your like me, however, you’ll spend most of the time feeling like your failing at enacting new behaviors because you have too many in your head at once and no real clear commitments about what you told yourself you would do. 

Luckily, there’s a thought technology that comes from our understanding of how work flows through a system that I think is useful in this context, too: limiting work in progress. Somewhat counterintuitively, the most work in progress that exists in a system the less smoothly it flows through that system. By limiting yourself to less pieces of work in progress (with everything that still remains to be done waiting to be pulled from a backlog) you’re able to do much more than if you tried to do everything at once. This applies to personal development intentions, too. Trying to do everything at once is a recipe for frustration and for not actually changing much of anything.

A great tool for visualizing and limiting work in progress is a Kanban board. A kanban board is a simple tool for showing a list of work items sitting in a backlog, a list of work items currently being worked, and a list of work items that have been completed. These “work items” move from left to right through the system such that anybody can walk up to the board (or load it on their computer) and see the state of the system. They can see the work that’s yet left to be done, the work that’s currently happening, and everything that has already been accomplished. Why don’t we use this same idea for personal development endeavors, too?

What if instead of getting inspired by something you read in a book or article and immediately try to implement in your life (likely on top of whatever inspired you last week or the week before) you captured the idea and put it on a backlog? Then, on a regular cadence you could consult your backlog of ideas and promote a reasonable number to “active” status. As part of promoting something from the backlog you’ll also do some thinking up front to understand what it is you’re actually trying to do. Like a good scientist, you’ll have a hypothesis about what will happen and you’ll have a sense of what metrics you’ll need to look at to validate or invalidate your hypothesis. At the very least, you’ll know that on a certain date you will look at an experiment you were running and ask yourself a few questions like, “How did it go?,” “Did I learn anything about myself?,” “Does this tell me anything about what I should do next?”

That’s what I’m trying to create. An approach to help you capture, process, and implement personal development intentions so that you can come to better understand yourself over time. A system to help you keep from being overwhelmed with all the ideas you have about things you want to try or ways you think you could be “better” (however you want to define that word). By bringing some structure to this whole process I can spend more time and energy actually trying new things rather than trying to hold it all in my head. Holding it all in my head means I inevitably forget good ideas and almost guarantees that I feel badly about myself as I try to do a bunch of half-formed ideas/intentions at the same time — seeing very few of them to completion and generally feeling like I’m not doing “enough.”

Don’t (just) build habits, uncover insights about yourself

Over time, as I do more and more experiments/experiences I’ll occasionally shake loose an insight that helps me better understand myself. While these insights feel blindingly obvious when they occur to me, they’re also the type of thing that are likely to be forgotten faster than I would like. That’s why I want to capture them and keep them somewhere where I can regularly review them. This body of insights about myself and the world is my best articulation of who I am and a visual representation of my growing self-knowledge. It’s the map that I want to be adding more and more details to as I do more forays into the unknown.

The whole point of caring about personal development and doing experiments is to knock loose, uncover, craft, or otherwise get my arms around these key insights about how my brain works, what my personality is, why I think or believe the way I do, etc. These insights, then, can shine a powerful light on interesting paths to pursue in my personal development efforts. Which then creates new insights (or tweaks previous ones). The cycle continues. And because there’s no specific end point that I’m shooting for, no idealized state of perfection, I’m glad the cycle continues. The cycle itself is full of meaning and excitement.

Is finding joy in this cycle something that’s completely unique to me? Is it only interesting to a very small number of people who are similar to me? Or is it something that can be taught to anyone who has a little bit of curiosity about themselves and how they interact with the world? I honestly don’t know but this is the path of inquiry that I’m going to explore until I figure it out.

"Month of Sit" Recap & a Look at April

Is there a better time to try to develop a healthy meditation practice than during a global pandemic? 

My March focus for my Intensity/Simplicity theme was my meditation practice. As a reminder, I’ve decided to take each of my four daily habits (Read, Write, Move, and Sit) and focus on one at a time each month for all of 2020. January I focused on Move and tried to run a bunch. In February I focused on Write and tried to write a “shit ton.” March, then, has been focused on Sit.

Like with the other two months, I didn’t step into March 1st with a specific goal in mind. I figured for this first go around with each of the habits I would just try to see what it is like if I made a general intention to do each one “more.” In the case of January I think that worked pretty well. I definitely ran more than usual, at least. February was mostly a failure. I would put March somewhere between the two. As I sit here today on April 1st I see I have a 73% completion rate on actually sitting down and meditating every day. That comes out to 8 days missed out of 31. In February I missed 19 days so I definitely took a step in the right direction.

As part of this experiment I also re-read Mindfulness in Plain English to help ground me in what I was trying to do — and why. I did that in the first couple days of March with the vague intention I would read some other meditation-related books throughout the rest of the month but that never actually happened. I did re-subscribe to the Audio Dharma podcast and while I don’t listen to everything that shows up in that feed there’s usually at least one or two talks I’ll listen to each week. 

I did a combination of completely silent meditations using the app Enso as a timer and some guided meditations using Calm. The purist in me thinks the guided meditation craze ala Headspace or Calm or 10% Happier or Wake Up and the rest of the Relaxation as a Service companies is kind of a cop out and that you don’t “need” anything other than a place to sit and some quiet to meditate. However, in the absence of a teacher I do think I picked up a couple techniques via the guided meditations that helped. 

Finally, I had a vague intention to not only meditate “more than usual” but to find a place in my daily routine where it could become just an automatic part of my day. I played with a couple spots and I think I’ve landed on in the morning after I read/have coffee as my favorite timeslot with just before bedtime as a backup. I definitely learned that the later in the day it got before meditating the less likely I was to actually do it. 

Now, with all the arguably unimportant preliminaries out of the way, did I actually learn anything about myself by meditating more than usual this month? Honestly, no. But that’s okay. I have enough on-again off-again meditation experience to know that 30 days of extremely limited meditation (between 10 and 20 minutes a day) is not enough for anything to “happen” (to the extent that anything ever happens in meditation). I didn’t expect to become enlightened or have some kind of breakthrough — and I didn’t. I did notice that on days when I meditated I felt calmer and more in control of my emotions. I’m not sure if that’s a result of simply having done a thing I intended to do (I can get similar feelings from writing or reading or exercising) or was a result of the actual meditation experience itself. At the end of the day, it probably doesn’t matter.

April: Month of Write (Redux)

The nice thing about coming up with some kind of experiment or personal development program is that I get to make the rules. I had a general intention to spend the first four months of 2020 rotating through the four daily habits I mentioned earlier. Having done Move, Write, and Sit that would mean April is a Month of Read. However, I’m going to call an audible.

I’m still really annoyed about how poorly my Month of Write went in February, so I’m going to hold off on doing my first Month of Read and do another Month of Write instead. This time, though, I’m putting a little more structure into play. No more am I just going to vaguely try to “write more.” Instead, I’m specifically trying to sit at my desk and try to write from 6:15-7:45 AM everyday this month. The topic of the writing doesn’t really matter but the goal is to more or less keep my fingers moving for the vast majority of this time. Personal journaling and other stream of consciousness writing is what I’ll turn to if I’m not making any progress on an article for SamSpurlin.com or The Ready or The Deliberate or any other major writing project.

Basically, I’ve paid enough lip service to the idea of being a prolific writer and if I don’t figure out how to build it into my days, even though I have a very demanding day job, then I’m never going to figure it out. The day job may be demanding, but it’s flexible (and stands to benefit from my greater writing output, too). My life is also the simplest it’s ever going to be. It doesn’t necessarily get easier from here. I’m not married and I don’t have kids. If those things are in my future then it’s not like there’s some future writerly state where I’ll have more time or attention to dedicate to this. If I can’t lock in the practice now while I’m relatively free to do as I please then I’m worried I never will.

Along with the specificity of “sit at my desk from 6:15-7:45 AM everyday and try to write,” as a goal I’m putting in a bit more scaffolding to help me accomplish this.

First, I know my phone is the central character here who can foil my plans. If I look at email, Slack, Twitter, or Reddit before sitting down to write I’m much less likely to actually get it done. Therefore, part of my process is to not get my phone off its charger until after I’ve finished my morning writing session. The problem is that I generally use my phone as an alarm clock. However, with that setup I’m guaranteed to touch my phone mere seconds after I wake up; right when my willpower is lowest and I’m most likely to convince myself that looking at Twitter for a few minutes will “help me wake up.” The fix is simple enough, though. I bought an analog alarm clock so now I have no reason to touch my phone immediately upon waking.

Second, I can sometimes dilly-dally when it comes to making coffee in the morning. This is usually caused by getting lost in my phone but the resistance to getting up and actually making the coffee might be bidirectional with the phone problem. To that end, I’m making it as easy as possible to make coffee in the morning while still meeting my annoyingly high standards (fresh beans, pour-over or AeroPress) by filling the electric kettle the night before, putting beans in the hopper of the grinder, assembling the AeroPress or pour-over cone, and getting a mug out of the cupboard. It’s not much, but I’m hoping the fact that all I need to do is push a button and twist a knob to get hot coffee and prepped grounds will make it easier to actually get out of bed and to the kitchen.

Finally, I’m really taking seriously the idea that I can create an association with a specific type of music and a specific kind of work. I already listen to a ton of instrumental electronic music while I do other work and the band Tycho is my absolute favorite. When I sit down to write every morning I’m going to turn on my Tycho playlist and that’s the only thing I’m ever going to listen to while working (and I won’t listen to Tycho outside of these morning writing sessions, either). I’m hoping that I can get to the point where hearing a Tycho song immediately puts my brain into a state that’s particularly conducive to writing. 

I’ve been operating under this program for the last week of March and have been averaging somewhere between 2000 and 3000 words of fresh prose each morning — so the early returns are certainly promising! The trick, though, as with all monthlong experiments, is to keep this momentum going when getting up “early” and writing for 90 minutes is no longer the fun new thing and is instead “just a thing.” 

The End of My First "Month of Write"

Welp.

That didn’t seem to go very well.

My month of writing as much as humanly possible (actually, I guess I called it a “shit ton”) has come to an end and I can’t help but feel I mostly failed. Before the self-flagellation begins let’s start with the objective facts and then I’ll dive into a bit about what happened and what I think I learned.

This month I wrote approximately 6,000 words (plus whatever this article ends up being) spread across one issue of The Deliberate, one issue of Brave New Work Weekly, two published articles on Medium, and 10 journal entries. I did this writing spread across 13 days. The word output isn’t what’s getting me down — it’s the fact that I basically only managed to write for 50% of the days in a month where my primary focus was to write as much and as consistently as possible.

There were definitely some external factors at play that somehow didn’t manage to make their way into my daydreams about what this month was going to be like (funny how reality has a way nosing it’s way into everything). The past couple months have been perhaps the most hectic and stressful I’ve ever had while working at The Ready. I’m putting in far more hours than I want to be in order to make some (ostensibly) short-term projects successful. We’re expanding our scope at the client, I’ve been leading an initiative to work with external writers at The Ready, and my partner and I have been hiring and training a new member. I’ve also been on the road for much of the past month with trips to NYC, Charleston, SC, and Dallas, TX all happening in the past three weeks.

I don’t share these external forces as excuses. Only as useful context for understanding why it was difficult for me to accomplish what I had set out to do with this experiment.

I had hoped to build a set writing routine into my default day. Perhaps carving out an hour or so in the morning or maybe closing out my day with a strong writing session. I didn’t have strong feelings about when it happened, I just wanted to see myself prioritize writing every day. WIth a 50% completion rate that obviously didn’t really happen. I didn’t really stick with any specific time of day long enough to truly understand whether I could’ve made it work for me. I seem to find it difficult to write first thing in the morning but I’m so cognitively drained by the end of the day evening writing sessions don’t really happen either. It seems that the only way I’ll write as much as I think I could or should is if I bake it into the prime part of my day. Perhaps in calmer times that will be possible but when spinning as many plates as I was this month there was no way I was adding another plate without causing some catastrophic problems for myself.

It wasn’t 100% negative, though. One thing I learned over the past month was that I have an underdeveloped process — and respect — for the brainstorming, planning, researching phase of writing. Early on I wasn’t giving myself credit for days where I simply outlined a potential article or pulled together notes but I quickly realized that was stupid. Writing is more than sitting down and drafting prose and if I don’t give myself mental credit for doing the stuff that allows me to draft then I’m shooting myself in the foot for no good reason. Along with the mental permission to consider outlining/mind mapping a legitimate part of my writing process I also realized I don’t really have a robust process for taking an idea from a nugget to a fleshed out article.

My bailiwick is smallish ideas that can be captured in 1,000–2,000 words. A blog article, basically. I don’t want to just be a blog article writer, though. I want to be able to push an idea across many writing sessions and many rounds of revisions before I share it with the world. If everything I write has to be conceptualized and drafted over the course of one working session then I’m really putting a ceiling on the type, amount, and quality of the writing I can produce. I think I have a newfound respect for figuring out how to do all the work that surrounds a productive session of actually making prose appear on the screen.

In my remaining two “Months of Write” that I have in 2020 (tentatively scheduled for June and October) I have a couple ideas that I’m batting around.

1. Shooting for a specific word goal.

2. Working on one “piece” of writing the entire month.

3. Picking a specific part of my day and making the focus of the month the installation of a writing routine in that part of the day.

4. Forgoing all public writing for the month and just exploring ideas in complete privacy for a month.

While my guardrails for this month were deliberately broad and pretty vague, I’m wondering if I might benefit from some tighter constraints the next time around.

And while I didn’t hit 100% on this month’s aim of writing everyday I do feel like I learned some things about how I can become a better writer and I’m looking forward to taking another crack at it in a couple months.

I’m Sam and I write about time and attention at The Deliberate and help organizations become more adaptive at The Ready. I Tweet and post really mundane pictures on Instagram.