It’s the time of the year where I start reminding my readers that November is a three work-week month and December is a two work-week month for many of us in the US. Please send a lot of goodwill and patience for folks who work in retail, hospitality, and travel, for it’s their peak season and they often have to deal with us on our worst behavior.

For me, November has 10 work days in it, with two half-weeks in the mix for good measure. An upcoming family trip will have me out of my office, but not necessarily out of reading and writing. Alas that I can’t turn thinking off, either – at least in a way that keeps me present with family. Having 10 work days this month means I’m having to eat much more of my own cooking than I’d like to.

I typically center two kinds of work for people to prioritize, and yes, deciding counts as work:

1. The key decisions that unblock other work or set up other work

2. The keystone projects that, once finished, set up or unblock other work

Sometime in November, many organizations will go into the annual freeze; many decisions, new ideas, and commitments are going to go into the “next year” bucket, either explicitly or implicitly. On the individual level, we start to do that, too, at least as it relates to professional work.

That’s why I center key decisions and keystone projects for November. If they don’t happen now, they’re going to drift into the back half of January.

Once we get over the chest-tightening that happens when we realize how momentous November can be, we can accept the gift of displacement. The constraint becomes a natural forcing function for us to get real now and make peace with what’s going to slide into next year.

As for me, I need to decide which of the manuscripts I’m going to push to done first so I don’t add another two months to the pub date. Premium subscribers, be on the lookout for an email about this next week.

Below are some posts and resources that will help you with your key decisions and keystone projects.

Resources to Help You Make the Most of the Weeks You Have

1. Get real about how much capacity you actually have.

For when the overload is a commitment count, not a productivity problem:

For when the weeks you do have need to be blocked, not hoped for:

2. Downsize before you defer or drop.

For when the easy yes turned into a pyramid of projects:

For when you need to decide what gets the three weeks:

3. Keep deadlines alive while people are away.

For when a project is stuck and it’s not clear whose job it is to do anything about it:

For when decision-makers are scarce and you need a yes before Thanksgiving:

4. Finish without the heroics.

For when the crunch is turning into a rally:

For when you’ve done the math and it still doesn’t all fit:

Join Us for Our November Events

Mark your calendars for our November events, open to our paid subscribers:

• Leadership Strategy Session (LSS): Wednesday, November 4, 2026, at 11:00 am PST November’s Focus: The annual freeze is coming whether your team names it or not. We’ll look at how to lead through it: which decisions have to land before people scatter, and how to keep the keystone projects moving on a half-staffed calendar.

• Monthly Momentum Call (MMC): Tuesday, November 10, 2026, at 11:00 am PST November’s Focus: Between a three-week November and a two-week December, a lot of work is about to slide into next year by default. Bring the decision you’ve been circling and the project that would unblock the rest, and we’ll work out what’s realistic before the “next year” bucket makes the call for you.

November Momentum Planners

The Momentum Planners were built to keep your most important work front and center. Download the free version of our November planners, now available only to subscribers.

Free subscribers: now might also be a great time for you to give our paid subscription a try. $10 a month will get you all our premium resources, our two monthly calls, the full digital suite of Momentum Planners, and more. Cancel anytime.

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While it will be obvious to many people and leaders that people need to check AI work and that team output will be checked by humans, we’re already seeing that many people are passing AI output to other humans and those humans are passing that AI output to other humans. In a 2025 University of Melbourne and KPMG study of more than 48,000 people across 47 countries, 66% said they rely on AI output without evaluating its accuracy.

It’s bad when it’s the leader that finally sees something that’s off and even worse when it’s the leader that starts the process. When the leader starts the process, seeing and calling out a problem is tantamount to questioning the leader without knowing whether it’s AI output or what the leader actually thinks. And often there’s no way to know: 57% of employees in that same study said they hide their AI use and present AI-generated work as their own. So many people are already disincentivized to question their leaders that the more common outcome is the AI work that comes from a leader will be reinforced by the organization rather than questioned.

Good team habits can mitigate this, of course. If we decide that we’re all going to be responsible for being the HITL for our own work before we pass it on, then we won’t necessarily need to call that out. If leaders make the obvious explicit that the onus is on someone who uses AI to check their work, then we at least won’t end up in a place where “Claude/ChatGPT said it” is a reasonable response when our work is wrong or slop.

This is going to become even more important as AI gets even better, for the tells we see today may not exist in a year. The AI companies are rushing headlong to make AI agents more human-like and they will likely be successful, mostly because we may stop paying close attention to our colleagues and correspondents to see the 10-15% difference between their work without AI and their work with AI.

We need to start asking this question now, for I’m concerned that there will be more folks who won’t even know what it means to check AI’s work before too long. This is not a joke: some of my colleagues who are in AI enablement and working with younger workers are already exasperated at the exasperation of folks not knowing what it means to check AI or how to do it.

If you’re not careful, there’s a dark side to theming your days: you can feel like you haven’t gotten anything done, even if you did the work of that day’s theme. It can feel this way even if you deliberately chose what you were going to be working on, too, so it’s not about the fact that you just jumped into things.

I’m writing about this because the last few Mondays have been this way for me. Mondays tend to be “Bookwork” days where I do a lot of writing and editing. I have larger swaths of time and, at the end of it, I haven’t finished a project or task. Pushed it forward, yes. Finished, no.

Compared to other days, there’s a lot less motion and a lot less external positive feedback. The parts of my brain that tick off “Done, good job” don’t.

And yet, because of these days, I’m now reviewing a couple of manuscripts that have accreted because I’ve been plugging away at them. That’s the nature of this kind of work. One day, you have a mess of words. The next day, you have a manuscript.

I often talk about the 10/15 Split from a place of simply having the peace of mind to step away from the work, knowing that everything has a home and plan. As a reminder, the 10/15 Split is a practice of reviewing your plan for 10 minutes in the morning and spending 15 minutes at the end of the day looking back over what you’ve done and making the plan for the next morning.

Today, I want to amplify that the other major benefit of the 15 part of the split is that it can help you with self-trust and commitments. When you see that you’ve followed the theme of the day, you have more trust that the work you decided NOT to do today can be done on its day - this a way of getting your backing back. It interrupts the impulse to take off running with an idea because you don’t know if you’ll actually do anything with it or make any progress with it.

Which means it’s especially important to do the 15 part of the 10/15 Split when you’re doing your solo best work. Even and especially if it feels like you haven’t actually gotten anything done for the day.

Before I jump into the practices and tooling, here are the puzzle pieces I’m working with:

1. I range widely across both media and topics. Documentaries, audiobooks, music, and magazines need to be accounted for and are rich sources of inspiration for me.

2. I like the convenience of e-books, but still retain more from physical books. This is consistent with research showing a modest comprehension advantage for print, especially with nonfiction and informational texts. Instead of it being an either/or, my practices and tooling need to address the constraints and opportunities of each format. I’ll often preview or do an initial skim of a book in the digital format and switch to buying a physical version if it’s especially rich or something I know is going to be a shelf-worthy book for me.

3. Since I left academia in the late 2000s, my research “database” and reference-capturing practices have become incoherent. #1 is the biggest contributor to this - I read a lot more diffusely than I did in the 2000s. It’s a lot easier to keep up with 3-5 philosophical books and a score of journal articles than it is 10-15 books and hundreds of links you half-remember.

4. I don’t want to spend a lot of time in the metawork of tending a system. The system needs to piggyback on what I’m already doing, not create a bunch of extra effort.

5. I want the practices and tooling to easily integrate AI, but the interface needs to be for this human, not an agent.

My goal isn’t necessarily to read more, but to:

1. Retain more of what I do read

2. Quickly find what I’ve read, annotated, or commented on and eliminate needing to look through a few places I may have saved something

3. Comb connections between what I’m reading

4. Do a better job of referencing others’ work and pointing to the specific research I accumulate

5. Get the ideas from physical media into my digital system

Those givens and goals are useful constraints, but they’re not all the same kind of thing. The first four givens are firm. The fifth is part future-readying, part exploration; I haven’t used AI in this loop enough to know whether the juice is worth the squeeze. And goals 3 and 4 rest on a hypothesis rather than a plan: so much of my effort currently goes to “Where did I read that?” and “Where did I put that?” that it crowds out “How are these ideas connected?”

Whether cutting the cost of remembering and resurrecting frees up that capacity, or whether making connections turns out to be a different muscle altogether, is an open question. I also need to make peace with some system maintenance and curation being part of the mix; it just can’t be its own Thing to do or I’m not going to do it. (Clearly.)

Now to the tooling.

Readwise and Reader

Readwise* and Reader* are quickly becoming the center of the system, though they solve different problems.

I actually stumbled onto Readwise a few years ago through Mailbrew, another tool I was using to try to solve these same problems. I was using Pocket at the time and didn’t see the need for yet another read-it-later app, so Reader waited. I stopped using Mailbrew, but I hung on to Readwise because having it resurface what I’d read was that useful.

The demise of Pocket, which I’d used for years to save articles for later reading, created both a need and an opportunity here. I needed somewhere new to save all those interesting links I wasn’t ready to read yet. But rather than just replace Pocket with another read-it-later app, I could use the transition to solve a bigger problem: connecting what I’m reading with what I want to remember. That’s what pulled Reader in.

Reader is where I consolidate what I’m reading: articles, newsletters, PDFs, ebooks, and the rest of my digital reading, in one place where I can read, highlight, and annotate. Instead of having interesting material scattered across browser tabs, email inboxes, and various apps, I have one place to read and work with it.

Readwise collects highlights and notes from Reader, Kindle, and other sources, then resurfaces them over time. Resurfacing has nudged a few saved ideas into actual posts, but the bigger effect is quieter: I tend to highlight dense gems, and seeing one again months later gives me more time to roll it around.

I can continue reading physical books the way I prefer to read them—underlining passages, highlighting sections, and scribbling notes in the margins—then use my phone to scan those passages into Readwise. Its text recognition can turn photographed passages into digital highlights and I can add my own annotations alongside them. I can also dictate passages when that’s easier than scanning them.

This matters because physical books are often where I do my deepest reading and thinking, but they’ve also been one of the biggest holes in my digital reference system. I’ve accumulated years of marginalia and underlined passages that are effectively trapped on my bookshelves unless I remember which book contains them and go looking.

Being able to bring those ideas into the same system as my digital reading means I don’t have to choose between the reading experience that works best for me and the convenience of a searchable digital reference collection. There’s still some work involved in capturing physical highlights, and I’m figuring out how much of that work I want to do as I read versus batching it afterward. But that’s a much smaller problem than having two largely disconnected bodies of knowledge.

The combination gives me something I’ve been missing: a more coherent place to read, a way to bring my physical and digital reading together, and a system that helps me retain and retrieve what I’ve encountered.

Libby, Hoopla, and PressReader

One of the things I’m trying to do is make better use of the digital resources available through my public library. Portland has an amazing library system and I’ve been underutilizing it for years.

Three apps in particular are becoming important parts of my reading system: Libby, Hoopla, and PressReader. If you haven’t heard of them or haven’t paid much attention to what your library offers digitally, they’re worth checking out.

Libby is the library’s lending app for ebooks, audiobooks, and magazines. You borrow with your library card, popular titles have waiting lists, loans expire, and many ebooks can be sent to a Kindle. Before I traded in my last iPad Mini (which I still lowkey regret), I’d load it up with books and audiobooks before flights and business trips. It fit my actual travel-binge reading and listening patterns better than Audible did, so I stopped paying for Audible.

Hoopla covers ebooks, audiobooks, comics, graphic novels, movies, and music, and most of it is available immediately with no waiting list, though libraries cap how many items you can borrow a month. The comics are the draw for me: Y: The Last Man, Saga, a lot of 2010s Transformers and DC. I’d activate Marvel Unlimited for a travel or seasonal stretch, and Hoopla covered the things I was binge-interested or occasionally interested in but wasn’t going to buy or pay much attention to otherwise.

PressReader is newspapers and magazines from around the world, current issues included, depending on what your library subscribes to. Mine covers The Atlantic, The Economist, Foreign Affairs, The New York Times, The New Yorker, New Scientist, and MIT Technology Review, and, less loftily, Family Handyman, Popular Woodworking, Men’s Health, and Motorcycle Sport & Leisure. It lets me cherry-pick the articles I want without the dreaded stack of magazines flowing in faster than I can read them.

The advantage of all three is that they let me explore more without accumulating more. I’ve bought plenty of books, magazines, and comics over the years partly because I didn’t want to forget about them or lose access to something interesting. Library access gives me another option.

There are tradeoffs, of course. Borrowing limits, expiration dates, and availability mean these aren’t necessarily where I want to do my deepest reading or build a permanent reference collection. They’re better suited to magazines, comics, audiobooks, and previewing books long enough to decide whether I want to buy them.

That last part is particularly important. I can start with a digital copy, figure out whether a book deserves more attention, and buy the physical version if it’s something I want to read deeply, annotate, and keep on my shelf.

If you have a public library card, it’s worth checking which of these services your library supports. You may also have access through a university or another library system. There’s a surprising amount of reading material already available to you that you’re effectively paying for through taxes or tuition, whether you’re using it or not.

Upgrading My Dedicated Reader

I’m also considering upgrading to a better dedicated reading device. I already own a Kindle Paperwhite and a Kindle Fire, but neither quite does what I need for the system I’m building.

The Paperwhite is great for fiction and lighter nonfiction books, but it’s harder to use for deep reading that involves a lot of highlighting, annotating, and moving back and forth between sections. It also doesn’t handle the range of media I want to bring into the system, especially magazines, comics, and other visually rich material.

The Kindle Fire technically handles more of those formats, but mine is old, slow, and awkward to use, and the Fire OS store never had the apps I needed or expected. Even something as basic as running Chrome instead of Silk would have made a difference; the Fire became its own little island. The friction of using it outweighs the convenience of having it.

That leaves me considering two devices: an Alexa Tablet* and an iPad Mini.

The Alexa Tablet is compelling primarily because of its price and the fact that it’s a more capable Android tablet rather than being constrained by Amazon’s heavily modified version of Android (Fire OS). That opens up more options for reading apps and services without paying iPad prices.

The iPad Mini is compelling for different reasons. It fits into the rest of my Apple ecosystem, and I suspect it’ll provide a better overall device experience. More importantly, it would let me move quickly between reading and writing, which is something I do quite a bit. I often read something that sparks an idea I want to explore, or find myself writing something that sends me back to a book or article.

Of course, that flexibility could also be a disadvantage. A device that provides a lot of options also makes you choose among those options and allows distractions to creep in.

I’m holding off on making a decision until the next iPad Mini comes out in a few weeks. In the meantime, I’m trying to get clearer about what I actually need from a dedicated reading device rather than buying another piece of hardware and figuring out its role afterward.

Obsidian

Obsidian is a note-taking app built around linking notes to each other, so you end up with a web of ideas and references rather than a pile of files, all in plain text you control. It’s the tool people who do a lot of research and writing tend to land on.

I haven’t installed it, and that’s on purpose. I’ve considered adding Obsidian to the mix, especially since it could help with my goal of connecting ideas across the wide range of things I read and think about. It may eventually be necessary to consolidate my idea garden. As things stand, my reading system flows into my idea garden, but they’re still separate systems. Readwise and Reader help me capture and revisit what I’m encountering, while the idea garden is where I develop my own thinking about those things.

There’s a case to be made for bringing those two systems closer together. Obsidian might be the right tool for that but I’m holding off for now.

The danger with Obsidian isn’t that I couldn’t make it work. It’s that I could probably make it work too well. I know the rabbit warren it could be, and I know myself well enough to recognize how easily building and tending a sophisticated knowledge-management system becomes its own project. That tinkering time went into my Claude setups and workflows instead, because those solved real problems in my business and opened up capacity. Some of that capacity is now going to reading, which is why this is the active exploration at all.

Readwise and Reader may already do enough of what I need on the reading side, especially since they have an MCP that lets Claude crawl what I’ve captured, which is the AI piece I actually want: searching and making connections across my own highlights. And even if my reading system and idea garden remain separate for now, having a more coherent reading system would be a huge win on its own.

Reading Better Means I Think and Write Better

If you’ve started reading this post, let alone gotten to here, it’s probably a given to you that reading better means thinking and writing better. Reading, thinking, and writing form a complete loop for me, but my reading practices are the best leverage point for me now. It’s a puzzle worth solving for me, both because I enjoy all three and because they’re the foundation of my livelihood.

Readwise has a monthly subscription and, if I get another dedicated reading device, there’s a cost there that I tend to amortize over three years. Both together are comparable to the cost of a streaming service, but the relative value between a streaming service and reading is so lopsided toward reading that it’s laughable (for me).

The real tension for me isn’t the out of pocket cost, but how much tinker time it’s going to end up taking post-setup. Tinkering is both an occupational hazard and habit for me, so it’s something I’ll have to keep my eye on. In the meantime, I’m enjoying reading more, if for no other reason than I don’t have as many open loops going while I’m reading.

Today, I’m going to emphasize the “mirror” part of the equation, especially as it relates to the Thinking in Public project. A few people have checked in to see if I’m okay since I haven’t been posting as much lately.

When I woke up the morning I wrote the kickoff post, I didn’t know I’d be writing it. I hadn’t landed on it as the way forward and I didn’t overthink it. Contact with the real world has since reflected some things in my inner and outer world that I hadn’t seen in a while.

Consider this a learning-in-progress update.

Reflection #1: If I Don’t Release Ideas Soon, They Grow

I started by writing about whatever was on my mind first thing, but I quickly saw that my morning writing was far broodier and more ephemeral than I liked. Additionally, the first ideas weren’t necessarily the richest ones.

So I started waiting until I had some work and sessions under my belt to see which idea had stuck with me the most. It was also far more fun to write about a soulworm I’d shared with someone in a conversation than whatever I was gnashing about in the morning.

The unintended consequence was that waiting until the afternoon to both draft and publish was making my days longer than is healthy for me. And I’d often already done my broodier morning drafting, too, so I was drafting two posts a day.

Turns out that drafts are like avocados for me. After two nights of sitting, they shift from “I’m thinking about this” to my more standard “I’ve figured some things out, here are some action steps, and here’s a worksheet, too” posts. I’m only half joking.

Not only that, the posts start to sequence and schedule themselves. Monday’s “I’m thinking about this” draft turns into “the fourth in a series that runs on Wednesday.”

To mix too many metaphors, waiting for the catch of the day has been turning into premade meals.

The simple option of releasing them the same day runs into Reflection #2.

Reflection #2: The “Power Through” Switch Is Still There

As I wrote early in the project, I’ve been recalibrating my expectations about what a healthy, productive, on-purpose, and joyful day looks like. I’m trying not to tell myself a story that I have a quadrilemma on my hands and only get to pick two of those four desiderata.

An important reflection is that the exploration, writing, and feedback have reactivated the “Power Through” switch that’s been dormant for a while. You know the switch I’m talking about: it’s that moment when you realize you’re at the edge of your capacity and a reasonable person would step away. But if you step away, you might not get it back for this piece of work, and then it’ll go on the list of all the other things you’ve halted mid-process because you had to attend to trifles like eating, sleeping, and other beings’ needs.

Next thing you know, you look up and it’s 6:30, you’re overcooked, and other beings have formed a queue to voice their displeasure at your choices.

There’s a reason I deactivated and hid that switch. As I’ve said before, pain and fatigue are great motivators.

I now have the awareness to at least know when I’m about to flip that switch, so there’s progress. I’m also no longer willing to make flipping it a default. I’d rather be a model for healthier choices than a model for working to exhaustion simply because you started a challenge.

Thus I sit in the tension between the last two reflections. An idea growing on me is a more acceptable loss than my readiness dwindling.

Reflection #3: 80% of the Drafts Center On or Touch On AI

As I said in the centaur post, I have no interest in being an AI/prompt king or spending a lot of time talking about implementing AI, though I’m often reminded how much of an AI powerbuilder I’ve become when I talk about it. At the same time, so many of the deep issues I care about have deep AI interlinks.

AI has me reconsidering a lot of pre-AI givens. The post on Algorithmic Reality is an example and it’s merely a start.

It makes sense, then, that a lot of the less polished and filtered ideas relate to AI. I haven’t been thinking about most of them for twenty-plus years, the way I have with my other ideas. But I have had a few years of deep diving and implementation, so I’ve got a lot of accretion in play.

If I can get the Sequencer/Editor to chill, I’ll likely just get the AI posts out over the next few weeks to clear the content logjam I currently have. That’ll also help me avoid the “time to collect all of these ideas into a book” impulse that would result in my disappearing indefinitely.

These Are Puzzles Worth Solving for Me

In case it’s not clear, this is not a “welp, I tried and now I’m quitting” post. I’m not even sure I’m changing the “daily-ish” commitment yet, mostly because I know I’ll get far too rigid with myself if I do. I want to build a practice that has natural pauses and recalibrations I don’t feel I need to apologize for or justify.

I also know I could stop anytime with a simple “thanks, that was fun.” I’m squarely in the land of puzzles rather than problems, and for that, I’m very grateful.

May we all be so lucky as to have vexing puzzles that are worth solving. Your mileage may vary about solving them in public, though.

I shared the links below with her and thought I’d share them with you, too:

1. Share Your “Guide to Working with Me” - Early in the relationship, share your “Guide to Working with Me” so your teammates know how best to work with you sooner rather than later. It’s so much easier than waiting until they’ve pushed on one of your peeves.

2. Put the Recommendation Second - Say whether you want your teammates to lead with a recommendation or with a discussion of the problem. Don’t make them guess.

3. The COPP and DRIP Delegation Handshake - Agree on how work gets handed off and how it comes back. New directors will default to whatever their last boss expected unless you give them a shared handshake from day one.

4. Use Shortcodes to Increase Your Team’s Communication Speed and Clarity - Every team develops shortcodes. The question is whether they’re shared or idiosyncratic, and a reorg is when you get to choose.

5. Focus Blocks Are the Real Measure of Your Team’s Capacity - Leaders in transition are often stuck with old projects and responsibilities while they’re simultaneously creating new ones. Count focus blocks to make it a math problem rather than a character or competency problem.

My client’s context was a reorg, but you don’t need to be going through a reorg to implement these ideas and create better team habits. If you haven’t had these conversations in the last year, it’s probably time to have them again.

Premium subscribers: I’ve pulled all five into a clean, printable PDF for you and your team. It’s below.

New to my body of work on team-building and leadership? Continue the journey with the Team Habits Primer.

Go to the Team Habits Primer

October is the last full work month of the year. Once the holidays land, November gives most of us about three working weeks and December about two, so you and your team have closer to eight weeks of execution left in Q4, not twelve.

Pushing yourself or your team harder won’t make up the difference. What helps is sizing your commitments to the weeks you actually have and being honest about which projects are acceptable losses and which aren’t. When you focus on the work that matters most and let the rest go, the year can end with a few real wins rather than a long list of what didn’t get done. And when the holidays arrive, protect that time. Rest is a different way of being productive, not a distraction from it.

In the Q&A, we got into what it looks like to see the full picture before you commit, including:

• Spotting when one big initiative is really three active projects, and resourcing it that way

• Making the case to your manager when you’re carrying two jobs

• Moving people between base teams (steady operations) and expedition teams (new initiatives) without the move feeling like a loss of status

• Talking with the people a change affects before you design around their reaction

Join us for our next Leadership Strategy Session on Wednesday, November 4, 2026, at 11:00 a.m. PST.

Premium subscribers can watch the full opening teaching and access all related resources shared during the call. 👇🏽

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It’s definitely worth a read and she navigates a lot of the traps that articles and books like this can fall into. She also discusses the role AI plays in this, which made it fresh. This is an extension of her article, not a counterpoint.

That said, I’m unsure that she handled the decentralization of reading as much as I think it’s in play. Consider this morning’s reading: I bounced from Substack, to The Atlantic via Kindle Unlimited, to Libby, and through a few more articles I’d saved across different platforms. I’m unsure that any single “counting” source would be able to track that behavior in any coherent way, as it didn’t generate something tracked like an aggregate sale (BookScan) or something like the Nielsen ratings.

By virtue of my reading books, articles, and long-form blog posts — and being a writer — it’s clear that my reading and writing habits are outliers. I’m writing this at 2 p.m. and haven’t seen, let alone watched, a video of any kind yet, which is another sign that I’m an outlier. To be clear here, it’s not a matter of extreme willpower and focus as much as I’ve set up my digital ecosystem such that I have to go to see short-form content, as I can get sucked into it just as much as anyone else.

My quibble about decentralization and how I bounced around may not be generalizable for her broader thesis that there’s a cultural shift away from reading. Rogue philosophers are rarely a good sample for anything.

From here, I’ll build on some of the quotes from her article.

“When children watched an animated video of a story, they used the region associated with imagination about half as much as they did when looking at static illustrations while listening to an audio recording. Children also used their cerebellum–a part of the brain associated with learning–less when watching a video.”

There’s plenty of mounting evidence that the way we’re reading — or not reading — is leading to worse critical thinking skills. I hadn’t yet considered that imagination may be affected.

Given what else I was writing about this morning, we’re going to need even more imagination to address what’s here and coming in the next few decades. I feel much more optimistic about AI being able to help with critical thinking than I do about it helping us be more imaginative, so if imagination is in jeopardy over generational scales alongside critical thinking, I’m concerned we’re going to have even fewer adult humans able to imagine solutions to the problems humanity hasn’t yet faced.

Or, better stated, we’re going to have less distributed imagination, with more of it concentrated in magnet schools, supercampuses, and private think tanks that are often only available to folks who can afford not only to go to them, but to have the education and preparation to go to them. Divergent thinking and novel approaches to problems are unlikely to emerge from what amounts to an affluent monoculture.1

“Now that being a reader is optional, it can function as an identity marker. When you see someone on the train reading printed matter, it feels like a statement. Perhaps inevitably, such statements have become the stuff of online ridicule: Brandish a book too ostensibly in public, and you might find yourself accused of ‘performative reading.’ […] Today, reading is again clustered among a small minority of the population, but being a person of letters confers less status than it once did.” (Emphasis mine)

I believe the bolded statement is doing a lot more work than its brevity lets on. If there’s less social status accrued to being a reader and seemingly even fewer economic benefits to it, the main reason left for reading is the enjoyment of it. Between doing something cognitively harder and clicking on the next link or swiping, people are going to do the latter.

I also think this dovetails with trends writes about in “You Are No Longer Invited to Dinner.” The precipitous drop in inviting people over for dinner, cards, or parties also removes a lot of the default social gatherings that I think were part of the way books were omnipresent in our lives. Horowitch notes that “Netflix has reportedly told directors and screenwriters to assume the audience isn’t paying attention and to constantly remind viewers what’s going on.” If our personalized entertainment media tells us what’s going on, there’s less room for us to do anything but tell someone else what’s going on, and telling them spoils the discovery that makes it entertaining. Aside from the entertainment, there’s not much else to talk about with people who’ve not already seen it with you.

Up until the mid-2010s, I would get asked what I was reading multiple times a month. I may get asked once or twice a year now and don’t volunteer it that much anymore, either. It could also just be that the questions have switched from “what are you reading?” to “what do you think about [topic]?” More chilling to me is that I just realized today that I no longer maintain and curate a mental list of books to be able to answer questions about them.

I’m legitimately curious about your experience with this, at the same time that the fact that you’re reading this probably makes you a non-generalizable example, too.

“Presented with human and AI-produced text side-by-side, even M.F.A. candidates have been shown to prefer the work of machines.”

In 2024, ’s “People prefer A.I. art because people prefer bad art” added to the despair I was feeling about my writing aspirations. As much as people decry AI slop, research suggests that, en masse, it’s what’s preferred. If enough people prefer the words that a prompt could spit out, why bother with all the toil and effort it takes to do original work? At the time, prescriptive nonfiction — ostensibly the type of writing I do — seemed like it was going the way of horses.

My despair was somewhat worse because my work is part of what’s been used to train LLMs without my consent and so much of it is publicly and freely available. Depending on which platforms you use, your AI tool may be able to generate 75% of the essence of what I’d say. If you’re just looking for bullet points and action prompts, it may do it reasonably well.

In yet another connection, I think the sales drops among megasellers behind Tim Ferriss’s “Has AI Already Killed How-to Nonfiction?” amount to buying non-readers shifting their behaviors in favor of either not reading at all or getting their information from LLMs. “Buying non-readers” is exactly what it sounds like: people who bought books but never read them, at all or past the first three chapters. Much as I said above about trackable activities, “book purchases” were long assumed to be a proxy for “book reading,” but that was a house of cards the whole time.

Part of what made that despair so heavy was that the focus my health journey prompted and walking away from the acquisition had both pointed me back to writing more articles, short books, and other writing-forward projects. I’d come back with a focus at exactly the time AI and short-form video were making what I feel I’m best suited to do less viable.

It wasn’t until I came back around to embracing that I write for people who want to read and think, even if that requires a bit more work and a few more minutes, that I got out of that despair. But even then, it took me a few quarters.

It’s become ever clearer to me that the game is going to be decidedly different going forward. If reading is again clustered among a small minority, as Horowitch put it, then my job could be easier and more aligned with what I want to do. Instead of chasing a bunch of non-readers, I can just write to those of you who are already here.

“Books used to be an essential source of knowledge, memory, wisdom, and morality. They were written by older generations and passed down to the young in a vertical transmission of culture, the social psychologist Jonathan Haidt told me. Now information moves horizontally, from young person to young person. This makes dynamic figures such as MrBeast and TheBurntPeanut the guardians of American culture. The decline of reading didn’t turn the world upside down. It turned the world sideways.” (Emphasis mine)

A few months ago, I was watching The Secret Lives of Mormon Wives and had a pit in my stomach when I fully appreciated that reality TV shows like this were no longer derivatives of our culture, but instead, they were creating and reinforcing culture. More MrBeasts and drama starlets have crossed over into mainstream media than the Mark Robers of the world. We’re getting the culture our attention says we want.2

When I grew up, we knew The Real World wasn’t and Jerry Springer was over the top for entertainment purposes. Between then and now, the intermingling of social media and reality TV has started to create culture and, apparently, American presidents.

When you’re leading through a RIF, there will be days where everything feels impossible.

There’s a saying I come back to in times like these, often attributed to Star Trek’s Jean-Luc Picard: “You can do one impossible thing at a time.”

You’ll think you’ve accounted for every variable and then someone tells you their visa is at risk. Or they just bought a house. Or they’re about to go on parental leave. Or the person you most trusted has quietly turned against the plan.

You’ll think you’ve hit the emotional bottom, only to find the basement you’re sitting in has sub-basements. This is normal.

A RIF doesn’t unfold like a project plan. It slams forward in lurches, layers, and ambushes. You can’t outpace it and you can’t solve the whole thing at once.

What you can do is manage one impossible thing at a time. Focus on the next consequential conversation, the moment that requires your presence, or the decision that unlocks the next five. Lead from there.

Colin Powell has some old-school wisdom that helps, too: “It will look better in the morning.”

It might not feel better and it might not be completely solved. But you’ll have another day and another chance to face the next impossible thing.

That’s what this kind of leadership is: not the absence of difficulty, but the commitment to face it imperfectly and with purpose until it’s done.

1. “An objective phenomenon exists independently of human consciousness and beliefs.”

2. “The subjective is something that exists depending on the consciousness and beliefs of a single individual.”

3. “The inter-subjective is something that exists within the communication network linking the subjective consciousness of many individuals.”1

Harari calls these phenomena, but he’s just as comfortable calling them layers of reality, and that’s how I’m using the word here. When I say “reality,” I mean the reality we actually live in, the one all these layers build together.

So much of what matters and drives us is in that third layer. Meaning, money, status, politics, religion2 - all live in that realm. And as I wrote in How Much of Your Work is an Epicycle?, we will do a lot of work to make sure objective reality matches our inter-subjective beliefs, even when the data from objective reality doesn’t fit.

Over the last few years, I’ve been thinking that there’s a new layer of reality: algorithmic reality. As the name suggests, it’s the level of reality that’s generated by algorithms - machine learning, AI, search engines, and so on. Virtual and augmented reality are mostly algorithmic and are likely to be even more so in the future.

It’s none of the other layers. When algorithmic reality corresponds with objective reality, it’s because it’s been fed by humans. And while these algorithms can sometimes be more truthful about where we put our attention via what we click, search, and engage with, it’s not subjective reality.

Most of the information we get via smartphones, tablets, computers, TVs, and so on is mediated by algorithms. The more AI-native devices get, the more what we see is going to be algorithmic.

For instance, what you’re going to see when you search for something is likely different than what I’m going to see when I search for the same thing. The results are going to be tailored to what the algorithms predict will be useful or interesting to me. We’re training these devices to curate what we want to see, even if we’re not intending to do so.

You’ve no doubt experienced this if you’ve clicked on something out of curiosity and then ads and content about that thing shows up everywhere else you’re reading for weeks. You’ve also probably seen how your social media feeds all of a sudden show a lot more of that, too.

If this were just about getting annoying content for a few weeks, it wouldn’t be a big deal. But we know that manipulation of algorithmic reality has affected elections and affects how we see ourselves, our neighbors, and world. Especially given how much of algorithmic reality is based on outrage, shock and awe, and sound bites.

And that’s the point: subjective, inter-subjective, and algorithmic reality interact with each other. This is how we end up in echo chambers and the virtual version of gated communities. We only hear what we’ve trained the algorithms to feed us and we only interact with people like us. Even when we know we’ve curated our information and online social circles, it’s really easy to forget that what we’re seeing and who we’re interacting with is curated by algorithms.

And even if you go out of your way to get as much unmediated information and meet people outside of your social circles, most folks you talk to are still going to be influenced by their own or others’ algorithmic realities. Influential people and the media can redirect attention away from what they don’t want us to see and toward what they want us to, simply by changing the terms and/or giving us another chew toy for our attention.

The inescapability of algorithmically-mediated information and relationships is why I think it should be on the list alongside the other realities. Algorithmic reality is no less a part of the reality we live in than subjective and inter-subjective reality, but it’s also not those.

And the more people adopt AI into hourly work and lives, the more dominant algorithmic reality is going to become for how individuals understand the world. But that “understanding” isn’t going to be of the world; it’s going to be of unconsciously curated information and groups.

I don’t have a tidy resolution to provide here. For my part, for stuff that really matters to me, I try to use the very same technology that would otherwise narrow what I see to broaden it. I ask AI to steelman contrary positions and invalidate my beliefs. I try to read and learn about people with radically different beliefs than I do, at the same time that I need to be honest that there are a lot of viewpoints that I’ve had my fill of and am no longer willing to entertain, be charitable towards, or give any attention.

Therein lies the tension: I know that even as I go out of my way to diversify my information and groups, I’m still going to be navigating algorithmic reality. Absolute skepticism is too laborious to maintain, so I just have to accept that what I’m seeing is not only mediated by my feelings (subjective reality) and other people’s beliefs (inter-subjective reality), but by computers and algorithms, too.

And maybe there’s some grace and humility to find in that.

It’s really easy for an easy yes to a new commitment to blow up into a whole lot of work or overwhelm us. I’m going to repurpose the project pyramid from Start Finishing to illustrate what happens.

New commitments often come in at the turquoise-colored blocks or above. Covering for a teammate who’s out often comes in there, too.

But if you’re like most folks ‘round here, you’re already at or above the five projects of that size that you can carry well. Even if you can pause one of your active projects quickly, there’s still some transition work that is itself a project for a few weeks that’s happening at the same time you’re spinning up the new project.

This liminal period will be messy and you’re likely going to feel scattered and overloaded, especially if you didn’t anticipate this new project hitting your deck. You’ve taken on all the projects and tasks that live underneath that quarter-sized commitment. And handling all of that is going to spread all of your time blocks even thinner.

The mess and the feelings are temporary and much closer to a situation than a problem. Once you’ve worked through the projects of leaving yourself breadcrumbs and adjusting to the displacement - there will be displacement - you’ll have a period where you have footing again. And if you’re like most of us, you’ll get your footing just in time for another project to stride in.

There’s a natural tendency to cut back on restorative activities during these periods when, in reality, you’re likely going to need more restorative activities. Most of us would understand that if we increased our physical load, we’d need more fuel and rest to compensate for it. But most of us make our daily bread by emotional, cognitive, and relational labor, so taking on new quarter-sized and larger projects amounts to increasing those loads even more. In the same way that we’d need more rest and fuel for physical loads, we need the same for the loads of our work.

I know some readers are going to nod knowingly, then barge on ahead with #MaximumEffort anyway. I get that some folks really have to, as well. But you can’t expect yourself to perform as if you had the margin, fuel, rest, and clarity needed for the next leg.

You also can’t expect to get to all the things you had on deck before you said yes to the new commitment. That yes created its own new pyramid of work. It’s going to crowd out other things and you’re going to feel the weight of it for a bit. You can feel the sting of it, but that may just be the sting of residue that requires no further action.

A problem is something that must or needs to be solved. It’s usually manifest because it’s painful, annoying, disgusting, or dissonant.

A puzzle is something that could be or would be good to solve. It could be “good to solve” because you enjoy the process of solving it or because the outcome you’re looking for would be a nice-to-have, not a need-to-have.

A situation is something that either doesn’t need to be solved or will resolve itself on its own. Situations sometimes look and feel like problems because the situation may not be what you want or need. You know you have a situation when it resolves with a true “It is what it is.” You may not like the is-ness of it, but the is-ness is not something to dwell upon. How you accept the is-ness is.

All of them rest on the same foundation: there’s a gap between the world and your vision, goals, needs, or wants. The difference is what to do about the gap.

If you’ve been in a coaching session with me or at one of our community events, you’ve probably heard me say something like “Okay, I hear about the situation. But I’m not sure I hear a problem yet.” Or “Oh, that’s a neat puzzle. Are you making it a problem?”

What happens next is the point: they stop and interrogate what’s really going on. Sometimes they can quickly point to something pressing or hot. Sometimes they see the issue is tied to a strategic or future-building item. And a lot of the time, they see that they don’t actually need to do anything.

The question is always useful because it makes them articulate what’s really going on. Thousands of reps over decades strengthened my ability to see the difference, at the same time that people have different contexts, values, and needs.

True problems and puzzles don’t resolve themselves. They persist until somebody does something to change them. When we make puzzles problems, we live in a place of continual artificial urgency. When we make problems puzzles, we’re ignoring the reality that something needs to change.

Not sure which you have? Ask what happens if you don’t solve it. If something real breaks or degrades, it’s a problem. If the honest answer is nothing, but it’d be nice, it’s a puzzle.

Whether situations create problems is contextual. If I don’t need to do anything outside and have nothing that’s going to be affected by getting wet, then rain is merely a situation. If I rode my motorcycle to meet someone and it unexpectedly started raining, that could be a problem. Or it could just be that I need to ride home in the rain, take a warm shower, change clothes, and avoid emotionally over-investing in the situation.

When we make situations into problems, we amplify the drama and crises in our lives. They’re going to resolve on their own timelines, regardless of what we do about them. But we humans would rather futilely try to change something to assert our control than surrender to reality or other people’s agency. Better to have a healthy shrug than an unhealthy and emotionally expensive urge to fix everything.

On the work front, the situation people most insist is a problem is how behind they are. It feels like a problem because their integrity or reputation seems to be on the line. But flip the scenario: if a valued colleague or friend were in the same spot, they’d apply a lot of grace and see that it’s simply that person’s turn on the fall-down ride.

On the personal front, it’s being sick, injured, or navigating a new diagnosis. Those situations often cause real physical problems. The problems people intensify, though, are around how they’ll be seen and how people will treat them.

The aforementioned shrug can also be a dodge. Sometimes we call a real problem a situation because “it is what it is” costs less than changing something. The tell is that situations resolve on their own timelines and relabeled problems keep coming back around, unsolved.

Truly understanding the difference between all three allows for better prioritization, more peace of mind, and better expectations for ourselves. It may mean letting some puzzles and situations slide off your deck so you can focus on real problems. Or it may reveal the opposite: a project list so full of problems that no puzzles ever get a focus block. Putting out fires all day and never getting to your puzzles gets old.

The next time something has your attention and you feel the urge to fix it, take a beat and evaluate whether you’re dealing with a problem, puzzle, or situation. Adjust accordingly.

I felt a stiffness in it that was unlike other posts that I’ve shared or was working on. Or maybe some strain. Or maybe a lack of spark. If you read it, you probably felt it, too.

At first I thought it may simply be the subject matter. But I actually love writing about teams, leadership, team dynamics, and so on. And I get excited talking to clients about team/org composition and I get excited when people get the difference between base and expedition teams and how it addresses some funk in their teaming.

What I couldn’t see all afternoon and evening was that the strain was coming from how the post got made, not from what it says. The post held up. The way I made it didn’t.

As I was falling asleep, I accepted the simpler answer: the problem was never in the post. By the time I started drafting it, I was tired, compressed, and frustrated.

Prior to drafting that one from scratch in the afternoon, which is already typically not my best writing time, I had worked on two other posts that I was much more excited by. Both of them ended up landing in my typical 1,000 +/- 200 word range.

And it was actually the fourth post I had worked on yesterday. I had edited another post earlier in the morning to add an attribution and that post would’ve been a good one to send yesterday, too. But it was also too long, landing in my typical word count range.

When I’m in a writing groove like I’ve been in for a while, it takes me 30-50 minutes to get to that typical word count. Since drafting doesn’t take me long, I can draft and ship in one focus block. Sometimes I can do it in 30-45 minutes.

Getting my natural drafts down to 300-500 words can take me hours and I usually feel like the posts are off. When I’ve done short writing sprints in the past, I always just assumed that my unsettledness was because I’m used to writing longer posts and that I’d get used to the short ones. And there was a part of me that’s always felt that if I was a better writer, I’d be able to land the shorter posts.

While the latter bit could be a lot of my own head trash, internet and editorial norms play a big part in it. In the mid-2010s, I wrote for fancy magazines that always pushed the 500-800 word limits, but really, the editors wanted shorter posts. Editors were much happier with a 500 word post than an 800 word post, so I’d take the extra hours to hone my work down to those limits, accepting that the slight dissonance I felt every time was just part of playing the game.

Eventually, I stopped playing because the effort and process were no longer worth it to me. I sometimes kick myself because had I just kept at it, I’d likely have a much larger platform now. But, who knows, there’s also a good chance that I would’ve sacrificed the joy of writing on the altar of success.

In fairness to the editors, it’s well known that shorter posts get read. Posts that are read get shared and commented on. Posts that are too long go into the “read later” bucket that no one actually gets to. The editors were doing their jobs and also trying to get my work read. (Thank you, long-suffering and under-appreciated editors!)

As I was thrashing, I posted on Substack Notes and responded:

The trade Carrie mentioned is the one that vexes me.

I think I was chewing on the post all night because I was thrashing about why I claimed that these TiP posts would be 300-500 words. Was it to make it easier on me or because it’s an easier ask of you? Why had I made myself the editor who would eventually make the writer bail?

The average reading rate is 238 words per minute. The difference in reading times between a 500 word post and a 1000 word post is about two minutes. The difference in writing time for me to get most of my ideas into that word count is many hours. And that’s assuming I actually don’t bail on editing or run out of energy.

As you now know from Learning to Live and Work with New Limits, I don’t have the energy I used to. A focus block or two of editing means I’m either going to burn myself out or I’m not likely to publish. Overworking drafts is already why I haven’t been publishing – I don’t need to replicate the pattern by another vector.

So, by the time I got to yesterday’s post, I was tired, compressed, and frustrated because I needed a couple of minutes. I didn’t need those minutes to work on the posts; I needed a couple extra minutes of your reading time.

As I drifted off, I thought about how many other places in my life I had ended up in dissonant or compromised places because I didn’t take an additional minute or two that someone would’ve gladly and graciously given to me. So many corners cut and apologies given, neither of which were needed.

My heart hurt a bit for me, but also for you. Because I know you’ve done the same and may be prone to do it in the future. (Caught you!)

Going forward, I’m going to take the additional minutes I need to make this fun, sustainable, and aligned for me. And if you need a few extra minutes from me to do the same for your efforts, please take them.

In case you’re wondering, yes, I am laughing at myself because it’s not like you come to me for short posts and it’s nowhere close to on-brand for me. When will I learn to stop trying to be something no one expects or is asking me to be? Apparently TiP can mean Thrashing in Public as much as Thinking in Public.

p.s. I reread the post with fresh eyes. It’s good enough and I’m glad I got it out on its own merits. That the process of getting it out catalyzed this post so early is a wonderful bonus.

October has arrived, and with it, overwhelm. If I’m honest, I hit overwhelm a while back but kept pushing myself, thinking I could just get x thing done, or past y deadline, and all would right itself again. You can guess how well that wishful thinking went.

And I know all too well that feeling overwhelmed is a direct result of being overloaded. Or perhaps a more appropriate word for this time of year: overcommitted. Little by little, month by month, I’ve accumulated my fair share of commitment debt, and with only three months left in the year, it feels like that debt needs to be reduced or paid. Debt coming from:

All the things I had planned for 2026. A past version of me was perhaps overly optimistic, considering the best-case scenario, and didn’t account for the project pileup that inevitably happened when that best-case scenario didn’t pan out.

And also all the things I “planned” (intended) to do in 2026. Things that never quite made it to project status because there was no actual plan in place.

And then there were the things that showed up unexpectedly. The opportunities, events, projects, and tasks that only added weight to what I was already carrying. Along with the new ideas and possibilities the unexpected tends to bring along.

Let’s not forget those back-burner projects. The ones that have been left sitting, waiting for better timing, resources, or someone else to be available. And now, with three months left in the year, every damn pot seems to be boiling over all at the same time.

And of course, there are always those things that take up my time, energy, and attention but somehow never make it onto the project list. Like getting sick, traveling, navigating a big change, or tending to relationships.

Commitment debt can show up at any time, but in October it seems to be particularly painful. We’re just far enough from the end of the year to feel like there’s still time to make good on it, but seasoned enough to know November and December will compress the timeline. It’s time to make some hard choices. Otherwise, reality will make them for us.

~ Maghan

Resources to Help You Clear the Way for What Matters

If you're feeling the weight of your own commitment debt, join me. Here's where I'm starting, along with a few resources to help along the way.

1. Get real about what you are carrying.

   For when you need to sort out all your projects:

2. Determine your acceptable and unacceptable losses.

   For when you need to scale back so you can focus on what matters most:

   For when letting go needs to be a team habit, not a one-time fix:

3. Give yourself (and your team) permission to let go.

   For when you need to make peace with the tough choices that come with letting go:

   For when you or your team needs your permission to let go:

4. Pay down the debt.

   For when you need to stop fiddling and call it good enough:

   For when it's time to get the work that made the cut done:

Join Us for Our October Events

Mark your calendars for our September events, open to our paid subscribers:

• Leadership Strategy Session (LSS): Wednesday, October 7, 2026, at 11:00 am PDT
  October’s Focus: October is the last full month to shape how your team finishes the year. That means deciding not just what moves forward, but what doesn't. We'll look at how to lead a strategic withdrawal, so the work that matters most isn't competing with everything else for your team's time, energy, and attention.

• Monthly Momentum Call (MMC): Wednesday, October 21, 2026, at 11:00 am PDT
  October’s Focus: With the end of the year in sight, the pull is to fit it all in. But if you don't decide in October what you'll drop, defer, or downsize, November will decide for you. We'll look at how to make those calls so your best work gets the room it needs.

October Momentum Planners

The Momentum Planners were built to keep your most important work front and center. Download the free version of our September planners, now available only to subscribers.

Base teams work in the known, the predictable, and the routine. Their job is to create or manage a predictable outcome, process, or spec. If they do that, they’re successful.

Expedition teams work in VUCA (Volatile, Uncertain, Complex, and Ambiguous) arenas. Even when they know where they’re going, they’re not sure what they’re going to find there. And they sometimes don’t even know how to translate or transport what they find back to base. Learning and discovery tend to be the win conditions for expedition teams.

Just as there are different teams, there are different players. Some folks are base team players. Give them the checklists, spreadsheets, and routines all day and they’re happy.

Expedition team players want to live on the edge. That’s where the thrills and discoveries are. That they may not pull off whatever they’re trying to do is a feature, not a bug.

Some people can toggle between the two, but they’re rarer because they have to be able to switch from solving for VUCA to embracing VUCA.

As I said in Team Habits, team dysfunction (or high function) can often come down to team composition.

A team that needs to be an expedition team that’s stacked with base team players is going to struggle. The team will spend so much time getting ready and trying to factor in all the unknowns that they’ll eat up too much of their expedition and implementation time. And the few expedition team players will be so frustrated at having to pull the base team players along that they’ll be worn out before they actually get anywhere.

A team that needs to be a base team that’s stacked with expedition team players is also going to struggle. The team will always be trying to go somewhere new, flashy, and sexy rather than sticking to the knitting. The few base team players will have to follow the expedition team players around with their checklists and procedures and spend so much time cleaning up messes that they’ll just wish they could do it on their own.

One kind of team— and one kind of player— isn’t inherently better than the other. The goal or outcome to achieve determines the kind of team you need, and the kind of team needed determines what players are needed on that team.

In late 2024, as part of finally going to the Veterans Administration (VA) for some service-related issues I’ve been dealing with since my deployment in the mid-2000s, I discovered that I had all but one of the markers for fibromyalgia and chronic fatigue. I knew I had PTSD, hypervigilance, IBS, hip/spinal issues, hearing loss, and tinnitus, but the markers were new information to me.

It also explained a lot of the aches, pains, wipeouts, and doctor visits over the last couple of decades. I had already figured out what activities I could and couldn’t do, but I didn’t know why.

The particular way fibromyalgia and chronic fatigue show up for me creates a challenging balance: I need to work out and move a lot or I’m in pain, but if I work out too much, I can have a fatigue wipeout. I’d gotten used to working in level 4 – 7 pain - that was my normal - but fatigue makes it hard for me to do anything, including everyday tasks and working out.

You read that correctly: if I’m not active enough, I’m in pain. If I’m too active, I can get crippling fatigue and can’t be active.

The can there is important. I’m still figuring out what combination of activities I can do that lead to fatigue and which don’t. And what duration for each activity is recovering, strengthening, and/or fatiguing.

Aside from physical activity, the other major pain and fatigue trigger is stress. I’ve learned that it’s not just distress, but eustress, too. For me, though, a lot of the activities that create eustress tend to be much more moderate and include activity, nature, music, and other elements that calm my nervous system.

Prior to learning that I had fibromyalgia and chronic fatigue, it didn’t feel like there was much I could do to be out of pain and have high energy. That’s why I had just accepted the daily pain as my reality and the fatigue as a ride-along to the pain or a random “I overdid” it occurrence.

Pain is a hell of a motivator. Or, better stated, it’s a hell of a motivator when you know you can avoid or lessen it.

So I ended up with the simple goals of increasing movement, decreasing stress, and accepting that I could no longer work a “normal” schedule, let alone the hours I’d built my life and career on. What were previously productivity experiments became health imperatives.

At the top level, it was a simple math problem. But at the root level - at least in the beginning - it was an identity problem. I’ve never been able to succeed by being good enough. I had to be better to get a chance to play and to stay in the game, at least in the creative class I work in and with. I still feel this way, though with less underdog energy.

And one of the ways I’ve been better is to outwork folks and be more consistent over time. I’m rarely the smartest, richest, best connected, or most accomplished person in the room, though I’m often among the most balanced across some of those.

I can’t outwork folks in the short time slices that online careers live in. I can’t be everywhere. It’s not simply that I don’t want to - I can’t anymore. I also don’t want to.

Competitive dynamics aside, I can’t do as much as I want to do and am used to being able to do. I know this is normal as we age, but I have the normal aging decline plus this pain/fatigue condition.

The easiest way for me to adjust to these new conditions has been to think of it like a 20-lb rucksack that I can’t take off. I’ve had to do everything most folks have to do with this 20-lb rucksack and I’ll have to keep carrying it with me. Everything is harder, but with pacing, patience, and making better commitments, I can still get on down the road.

So, yes, it’s going to be one of my five projects. But now I know it’s a project and can quit pretending like it’ll go away.

I got my disability rating in late 2024. Officially being a disabled veteran is a whole other identity reckoning that I’m still working through on a lot of levels. That said, I’m really grateful to have the medical treatment, bodywork, and meds that are helping me manage pain and my nervous system (mostly) covered by the VA rather than spending nearly a grand a month for care.

As part of that care, I started taking Duloxetine in October 2025 and it’s been a godsend for pain, fatigue, and nervous system regulation, at the same time that it’s had other effects on my focus. After a year of taking it, I think I’ve figured out the focus/attention cycles and the support structures I need. Gone are the days of just getting up and cranking, as it’s now a whole two-hour uptake process.

On the work front, the diagnosis and walking away from nearly being acquired in 2024 has led to a deep reckoning about what matters to me, what I no longer can do, and what I no longer want to do. I took the fears and pre-grieving from both as signals for what I really cared about. I’m better at adding the full energetic costs of activities when I’m considering whether to do them or keep doing them. My ideas and goals have a harder time getting a Yes enough to get turned into a project.

What became ever clearer to me is that writing and advising were my unacceptable losses. It’s taken me a few years to get those recentered and you’re reading this on the other side of the void I’ve been in.

I’ll likely share more details about the changes I’ve made and where things may be headed as we go along, but this health journey has been both a catalyst and foundation for so much of my thinking and reconsiderations. It’s not something I want to be defined by, but it’s also not something that I can or want to ignore.

Decision memos to bosses and boards typically follow a standard format: Issue, Discussion, Recommendation. IDR is solid, and it’s the house style of staff colleges, law schools, and policy programs. I teach my clients to reorder it.

Issue, Recommendation, Discussion.

Here’s why. In practice, the recommendation gets buried under seven or eight pages of discussion. Decision-makers take forever to find what’s being asked of them, and discussion-first invites them into the weeds of the decision before they need to be there, debating details instead of championing or approving the broad thrust.

The components carry their own disciplines:

Issue. Statable in two or three sentences. If you can’t state it that tightly, one of three things is wrong: you don’t understand the issue well enough, you’re writing at too low an altitude, or you don’t understand what your decision-makers need to see to decide.

Recommendation. What to do. It goes second.

Discussion. One to two pages, prose or a bulleted summary. Same discipline as the issue: what the decision-makers need to know and no more.

When I teach this, the pushback comes fast: “Don’t I need to build my case first? Isn’t leading with the recommendation abrupt?”

No. A well-written issue and recommendation do much of the case-building on their own, because together they tell your decider what you were considering and optimizing for. The issue opens a gap. The recommendation closes it. The discussion shows how it was closed.

A tight recommendation does something else, too: it shows your decision-makers what blind spots you may have missed, and it lets them introduce parameters you weren’t considering. They can often do that without reading the discussion at all. If you spot trends in what they add, you’ll know what to seed your next recommendations with.

Worried that leading with your recommendation anchors your deciders into rubber-stamping it? It tends to run the other way: a recommendation they can see is one they can push on. The buried recommendation is the one that slides through unexamined.

Consider what burying the recommendation actually costs. Your decision-makers have to wade through pages to find what you’re asking of them, so the memo goes into the “print out and deep thinking” space people pretend they have in their schedules. The response, when it finally comes, is often some version of “So, what are you asking me for?”

The advanced version of the mistake inverts. People who’ve learned to lead with the recommendation sometimes skip the issue, and the recommendation floats unanchored. That response sounds like “Okay, it took me a while to figure out what we were talking about and why it mattered.” Both mistakes produce the same outcome: slower decisions.

Leaders often get queasy about IRD. It can feel presumptuous, as if you’re telling your decision-makers what to decide before you’ve earned the right to. Burying the recommendation is that queasiness expressing itself structurally: discussion-first is an attempt to earn trust on paper. The memo was never going to be the instrument that builds the trust case, though. Operate as if you already have the trust of the people you’re writing to.

If you’re unsure whether your decision-makers would prefer the recommendation or discussion up front, ask them what they’d rather receive. In my experience, the answer is the recommendation up front, every time, because decision-makers look for the ask first and then calibrate how deeply to engage based on the scale of the ask. If your organization mandates a memo template, the reorder still works: put the recommendation in the cover note or executive summary and let the template be the template.

This also explains why IDR remains the standard in large, impersonal organizations: IDR doesn’t rely on trust. The facts and the case are what they are, whoever wrote the memo. If you’re writing to people who know you, though, discussion-first leaves that relationship unused.

The format also works in the other direction. Founders and executives writing to their teams can run the same structure with one change: the R becomes Resolution rather than Recommendation. A recommendation asks someone above you to decide; a resolution tells the people you lead what you’ve decided, and the discussion still shows your work at the altitude they need it.1

How is this different from BLUF-ing your memo? Depending on how you write the BLUF, it may be the same thing — a three-sentence BLUF can carry all the relevant information. Typically, though, trying to do that stuffs the BLUF full of discussion items your reader doesn’t need yet. IRD keeps the layers separate so each can do its job.

You already have their trust, or you wouldn’t be the one writing the memo. Write like it.

New to my teaming work? Keep going with the Team Habits Primer.

Here’s the summary:

Shorter, daily-ish posts where I think out loud about whatever I’m chewing on. More unfiltered and unpolished, likely including more shop talk and personal wonderings alongside core themes.

I could list a lot of audience-facing and strategic reasons why I’m doing this, but they all cut against doing it equally well. The main reason I want to do it is because I’m creatively constipated after a few years of thrashing, making publishing harder than it needs to be, and behind-the-scenes stuff that I’ll likely talk about in pieces going forward.

If you’ve been on one of our community events, you’ve probably heard me say “Your cage; your key.” I’m eating my own cooking here.

As the summary suggests, TiP posts will span more than what I’ve made “core” areas. They’ll also be more fragments and snippets I pick up throughout the days.

Some writers are using social media, including Substack Notes, for similar kinds of efforts. That feels backwards to me, as you’ve already signed up and, like me, the last thing you’re probably wanting is Yet Another Social Media place to be. TiP posts will be hitting your Inbox.

By short, I mean they may be 300-500 words. TiP is doing some work for me that Twitter used to do; I hope it does the same “quick idea discovery” work that social media does for some.

Because Substack makes it awkward to add people to sections, I accidentally added everyone to the new section. I decided to accept the “mistake” as probably closer to what makes sense. If you’d rather not get short posts, it’s easy enough to unsubscribe from this section, Thinking in Public, and get whatever else you were already getting.

As exciting as it is to kick the shackles off, I’m going to give this a six-month evaluation period. I know I’ll be excited the first few weeks. I also know that I’ll feel the displacement consequences four to six weeks from now. Six months is a long enough new project cocoon.

My ask: hit the “love” button or comment if you’re liking the new content. It’ll be fuel for when my excitement wanes and will amplify my own excitement and curiosity.

And if you don’t want to get TiP content, please unsubscribe from the section. I won’t be looking much and will be focusing on who this is for - me and people who dig it. You won’t hurt my feelings and I’d rather not increase the noise in your Inbox.

You can tell it’s a TiP post because you’ll see “Charlie Gilkey (TiP)” as the sender. And unsubscribing is as easy as hitting unsubscribe in the footer of your email, then turning the toggle off for Thinking in Public. See the pic below.

That’s it for today. See you tomorrow with whatever I’m thinking about enough to share.

Post-publish edit: I’m going to create a muse board with folks who reply or email me, which will help me center who I’m writing to. and are already added, as are others who’ve emailed me.

We hope you’ll join us for our next Monthly Momentum Call on Wednesday, October 21, 2026, at 11:00 a.m. PDT.

Session Highlights

What came up in this month's conversation1.

Flow comes from conditions you set up, not from open time.

• Focus. It takes energy and attention as well as time. A clear afternoon with nothing left in the tank won’t get you into flow.

• Challenge that matches your skill. Too easy and you’re bored. Too hard and you’re anxious. Aim for work that stretches you without feeling impossible.

• Clear goals and feedback. A goal you never test against the world is a wish. Perfectionism gets in the way here because it keeps you from shipping, and without shipping you get no feedback.

• Self-trust. Trust the skills you have, or your ability to figure it out. IABCD (intention, awareness, boundaries, courage, discipline) is the toolkit for building it.

Verb the noun.

Intention, awareness, boundaries, courage, and discipline are nouns, and nouns just sit there. Ask what you’ll do to create each one. The same goes for identity. If you want to be a writer, write. If you want to be a leader, lead.

When the tools aren’t working, look for loss of backing.

From The Dictionary of Obscure Sorrows:

loss of backing

n. An abrupt collapse of trust in yourself—having abandoned a resolution, surrendered to your demons, or squandered an opportunity you swore you’d take seriously this time—which resets your expectations and makes it that much harder to guarantee that your word is worth anything, even to yourself.

If you keep reaching for a new system, an accountability partner, or the one person who’ll fix everything, loss of backing is often what’s really going on. You rebuild that trust by shipping. You don’t have to start with the big annual goals. Start with your week and prove to yourself that you can ship, week after week. Once that feels steady, move to the month, then the quarter.

Pick a Goldilocks goal.

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