Productive Flourishing

What a week in US politics. I’ve been thinking and feeling about it all week and I’m as relieved as I am worried. I’m reckoning with a protective bitterness I’ve had since the end of 2024 and I think it’s going to take some time to shake it.

One of the recurring thoughts ahs been the word ‘will’ in the context of these political times. It has three distinct meanings:

1. The intent or preference an agent has. “If it is her will, let it be so.”

2. An agent’s backbone or tenacity. “They’re strong-willed.”

3. The verb of commitment. “I will do it.”

I think it’s time for a lovechild between Reconstruction and the New Deal. We have rights to advance and restore — and need to (re)build the institutions to protect them — at the same time that we have what amount to public works projects in AI, green tech, health care, and education.

The political game of punts and recovered fumbles every 6–8 years isn’t going to deliver what we need now and what the next generations will need. It’s going to take a sustained political will, in all three senses.

We, the people, need to clarify our will in the first sense: a positive agenda we want our electeds to pursue, not just a list of things we’re against. We need the will in the second sense to put as much heat on them as we put into reactionary rallies when things don’t go our way. And we need a lot of will in the third...

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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...

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October’s Monthly Momentum Call replay is above. If you’d rather listen than watch, the audio version is just below.

As more and more work shifts to being AI-assisted or AI-managed, we’re going to have to start asking who the HITL (Human in the Loop) is and where the HITL is in the process of work being created.

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.

Subscribe to Productive Flourishing to do your best work that won’t be replaced by AI, but perhaps will be...

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One of the ways I encourage people to get more progress and sanity is to give days recurring themes. By default, Mondays are “catch up + get started + team meeting” days for a lot of people, regardless of whether that makes sense or was consciously chosen to be that way. Similarly, Fridays tend to be a check out and/or social day for a lot of people.

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...

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After reading Reading Is Becoming a Minority Practice (Again), a few people asked about the reading practices and tools I’m exploring. This is the answer, with the caveat that it’s still in motion. Since we’ve established that the T in Thinking in Public could just as easily be for ‘thrashing’, let’s add ‘tinkering’ to the mix, too. Fair warning that this is a long one.

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...

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In Start Finishing, I wrote that best work projects are both mirrors and bridges. I usually talk about the bridge part, in the sense that they help you get to the life and work you want to have.

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.

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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.

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...

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A leader I’m working with is in the middle of a reorg and picking up new directors. It’s a precious and rare window where the teams don’t have new norms yet and are actually expecting some changes.

New team habits will form in the first few months, so it’s a good time to intentionally establish the team habits you want.

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...

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🌟 While we no longer record the Q&A discussions during our Leadership Strategy Sessions, we continue to record the opening teaching. Enjoy a special preview of what we shared about sizing your team's commitments for the rest of the year. If you want to see the complete teaching and take part in upcoming sessions, consider upgrading to join us live next month.

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...

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This morning I read Rose Horowitch’s “The End of Reading Is Here,” which I found as I was looking for more good sources to read and rebuilding my reading practices and tools. Because I’d already been thinking a lot about reading, writing, comprehension, and recall, it piqued my interest.

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...

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