Idea Surplus Disorder

In this week's Idea Surplus Disorder, I'll share two great podcasts with the Filament team. We'll also discuss the death of daydreaming, explore the imaginary pressure of “what people will think,” identify the cause of meeting hangovers, and wonder if missing out is actually the point.

And as always, you’ll find a mix of fun finds, practical insights, and thought-provoking quotes to help you lead, live, and think more intentionally.

I'm Matt Homann, and I'm glad you're here.

Filamental Podcasts

I had a wonderful conversation with Dr. Myriam Hadnes on her Workshops Work podcast. Give it a listen or watch the video.

And our own Lauren Colbert took a deep dive on meetings with Chelsea Stuck. Here's the podcast and the video.

Ideas + Insights

I hate that our generation has witnessed the death of daydreaming:

Now that we have so many ways to fill even the smallest fragments of time, a subtle shift in our psychology of expectation also follows. We are more likely to experience waiting as an unpleasant delay rather than as anticipation. Waiting has become a problem to be solved, rather than a normal human experience. When we are accustomed to easily filling time, opportunities for anticipation, like opportunities for daydreaming, disappear.

What if missing out is the point?

What if missing out isn't a failure of optimisation but a condition of being human? What if the very fact that we cannot have everything is what makes anything matter at all? Scarcity isn't always the enemy of meaning — it's the condition that can make meaning possible

Related:

When I notice myself worrying about 'what other people will think,' I find I'm usually not worried about any single person's opinion. If I pick a specific person, I'm rarely concerned about what they will think. What I fear is the collective opinion in my head. It's imaginary.

Hybrid (still) isn't working:

You cannot effectively manage teams of remote or hybrid workers using the methods you relied on when all employees were in the office together. Doing so creates major problems for organizational culture, for how people are managed day-to-day, for how they are promoted, and for performance overall. Re-creating the cooperation and collaboration that happens in the office in a virtual context requires new rules and policies—as well as mandates that reel in some current practices.

And in a similar vein, let's not minimize the drawbacks of virtual meetings:

By now, the drawbacks of virtual meetings are well-known. In our focus groups, we examined two of the most pernicious: They dampen productivity, and they are less effective in generating useful ideas. We learned that virtual meetings are more frequent, in part, because they are used to address issues that people previously solved by sticking their heads in colleagues’ offices to ask for assistance.

The number of participants in virtual meetings tends to be larger than in in-person meetings, because there are no constraints on space. And because peripheral people are included, the meetings are less productive. We also heard that attendees of remote meetings often multitask and don’t pay full attention.

The result is that not only are participants not contributing meaningfully but also the hosts of meetings have to hold “postmeeting meetings” to explain to the people who were distracted what they missed.

Yet, a full return to office might not be doing what you think it is:

The return-to-office mandate can be a deal-breaker for those balancing childcare, eldercare, or other requirements with their career. In many cases, this falls on women in the workplace; however, it can affect any worker at some stage in their career journey. Upwork’s research said that nearly two-thirds (63%) of C-suite leaders whose companies have mandated an office return of some sort say the policy has led a disproportionate number of women to quit. Gartner’s research also showed women’s intent to stay at 11% lower with strict RTO mandates.

What causes your meeting hangovers?

• Irrelevance of the topics discussed (59%)
• Lack of a clear agenda or objectives (59%)
• Poor time management (53%)
• Lack of actionable outcomes or follow-up (48%)
• Unequal (39%) or low (38%) participation
• Ineffective facilitation (30%)

This list of modern-day social etiquette includes these gems:

• When someone tells a story, ask a follow-up question before telling your own. Part of etiquette is kind of feigning interest - if someone told you a story they are clearly passionate about, it is kind to ask a follow-up question to show that you listened.
• Take both AirPods out when you’re having a conversation with someone.
• Understand the purpose of a group chat - not for logistics, not for disagreements - those should happen 1:1. And don’t blow up peoples phone all day unless its something that’s gunna make them laugh later.
• Always help someone if they’re cleaning.

Thinking about a career change? This mega-prompt will help an AI work with you to explore the realities of your new job.

Finally, this is a fantastic "hack" to address impostor syndrome:

Replace “I don’t know what I’m doing” with “I’m learning as I go.” Yes, it can feel cheesy to talk to yourself, but research shows that these kinds of self-affirmations activate the brain systems associated with reward, so you’ll feel good about the process.

Fun Finds

• Forward an email to Snitcher and it will tell you if it is likely spam or phishing. Then it will delete it.
• This is pretty useful if you're a regular podcast listener: email a screenshot from your podcast player's screen to podcastmagic@sublime.app and you'll get a clip and transcript back in your inbox.
• A collection of buttons I'd like to press.
• Songscription turns any music clip into sheet music. Pure wizardry.
• How to avoid mosquito bites.

Words of Wisdom

Taste is the power of relishing or rejecting whatever is offered for the entertainment of the imagination. – Oliver Goldsmith

I don’t know anything about music. My job is to listen—to feel whether it’s alive. — Rick Rubin

And those who were seen dancing were thought to be insane by those who could not hear the music. – Friedrich Nietzsche

The only way we can make the most of our lives is to make the most of our moments. – Cleo Wade

I will only say that the worst jobs are not the hardest jobs. The worst job is the job you know is wrong for you, but you stay in it anyway. – John Hodgman

Smell is a potent wizard that transports us across a thousand miles and all the years we have lived. – Hellen Keller

They had drifted apart, as people do when they promise to stay in touch; the ones who are going to stay in touch don't need to promise. – Edward St. Aubyn

Up Next From Filament

Every month, Filament delivers an incredible mix of free programming and professional development. You can find links to sign up for all of our upcoming events, including PlayDays, EmpowerHer, NSFW, and SuperCollider here.

Now Reading

If you've made it this far, here's what I'm enjoying right now:

• The Four Conversations by Blair Enns: One of the best "sales" books I've read in a long time. Worth it just for the examples of language you can use with prospects on the sales journey.
• Alchemy by Rory Sutherland: A deep dive into counterintuitive thinking from one of the best advertising minds in the last fifty years.
• A Story is a Deal by Will Storr: I've just started this one on the science of storytelling, but am liking it so far.

In this week's edition of Idea Surplus Disorder, we'll explore why purpose at work is such a powerful engagement engine, how eroding trust shows up long before leaders notice it, and why we need better tools for measuring trust the same way we measure any other strategic asset.

We’ll look at organizational “debt” beyond the financial kind, practical ways to repurpose the time AI saves you, and a smarter approach to reading so you actually remember more.

Plus: the long-term costs of quick wins, when risks are worth taking, and one delightfully revealing Thanksgiving icebreaker.

And as always, you’ll find a mix of fun finds, practical insights, and thought-provoking quotes to help you lead, live, and think more intentionally.

I'm Matt Homann, and I'm glad you're here.

Ideas + Insights

Purpose at work matters:

Employees with a strong sense of purpose at work are 5.6 times as likely to be engaged in their jobs as those with a low sense of purpose. They are also much less likely to feel burned out or be watching for or actively seeking a new job. These outcomes reflect better individual experiences at work and are associated with improved organizational outcomes, including productivity and profitability.

... as trust in leaders erodes:

In Glassdoor reviews that mention senior leadership or management, the share of reviews that mention “disconnect” has increased 24% from 2024 to 2025. Similarly, related terms like misaligned (+149%), miscommunication (+25%), hypocrisy (+18%) and distrust (+26%) have all surged in Glassdoor reviews over the last year.

And if trust is so important, why aren't we measuring it better?

Trust measurement only works if leaders have the courage to expose blind spots and the discipline to respond. Like financial audits or compliance reviews, the point isn’t to prove you’re perfect, it’s to demonstrate that you’re managing risk through a rigorous and targeted process. Measuring executive trust requires an intentional approach, but the rewards are undeniable: a workplace culture where employees feel valued, stakeholders feel confident, and leaders are empowered to drive organizational success. When nurtured systematically, trust becomes the foundation not just for operational excellence, but for long-term resilience in an increasingly unpredictable business climate.

Organizations incur lots of different types of debt (technical, cultural, etc.) but rarely measure anything but the financial kind well:

When borrowing the “debt lens,” here’s a framework anyone can use:

1. Name It: Be explicit — “This is debt.” Label the shortcut and its likely cost.
2. Track It: Maintain a register, backlog, or log of known debts. Visibility prevents denial.
3. Plan for Repayment: Dedicate cycles, budgets, or policy reviews to address it.
4. Balance Incentives: Reward long-term resilience, not just quick wins.
5. Communicate Transparently: Treat debt as part of the system, not a hidden flaw.

Read a lot? You're likely highlighting too much:

Highlight and underline very selectively – ideally no more than 10–20% of the text. Mark only the most important points or phrases that capture the essence. Why It Works: Over-highlighting is a form of mental laziness that can hinder memory (you end up bypassing the decision of what’s truly important).

Want to find ways to leverage the time in your job that AI frees up? Try this:

AI creates gaps in your work—30 seconds while it generates code, two minutes while it fixes your test, five minutes while it researches. During the next one, don't scroll. Stare at what you're working on and write:

What else could I be doing right now on this project? What detail am I skipping that I'm curious about? What part of this work do I keep rushing past?

Don't force it. Just notice what comes up. Do this for a week. You're not looking for a grand revelation—you're looking for a pattern in what keeps showing up.

Stigler’s law of eponymy:

"No scientific discovery is named after its original discoverer.” Stigler’s law is itself an example of Stigler’s law.

The long-term consequences of quick wins:

Quick wins can feel smart in the moment. They create momentum, please stakeholders, and deliver visible results. But every shortcut has a cost. When we fail to account for that cost, we’re not just buying time — we’re borrowing from the future. And the future always comes knocking.

On the other hand, we should take risks when...

(1) the worst outcome is manageable and (2) the best outcome is life-changing. Look for opportunities where it won't kill you if it goes poorly, but you'd be blown away if it goes well.

Finally, here's a fun icebreaker for the Thanksgiving dinner table:

What is a “rich person thing” you would be totally into if you became rich?

Fun Finds

• Dithering
• Deceptive Practices on a Need to Know Basis
• Corners of the Internet Database
• The Two Types of Jokes
• A brief history of people talking to computers
• Unparalleled Misalignments: words in phrases that match, but really don't
• Mail.google.com/mail/#sub shows you all the gmail emails you are subscribed to and makes it easy to unsubscribe.
• A world map of influential ideas.

Words of Wisdom

The logic of algorithms tends to repeat what “works,” but art opens up what is possible. Not everything has to be immediate or predictable. Defend slowness when it serves a purpose, silence when it speaks and difference when evocative. Beauty is not just a means of escape; it is, above all, an invocation. When cinema is authentic, it does not merely console but challenges. It articulates the questions that dwell within us and sometimes even provokes tears that we did not know we needed to express. – Pope Leo XIV

What can we gain by sailing to the moon if we are not able to cross the abyss that separates us from ourselves? – Vivek Murthy

People ask you for criticism, but they only want praise. – W. Somerset Maugham

Attention is the rarest and purest form of generosity. – Simone Weil

Art is the act of making things we don’t need, but which make the world a better place.  — Brian Eno

You can be relevant as hell and still be boring as f*ck. – Martin Weigel

When you fall in love with the process rather than the outcome, you don't have to wait to be happy. – Shane Parrish

We act as though comfort and luxury were the chief requirements of life, when all that we need to make us happy is something to be enthusiastic about. – Charles Kingsley

Up Next From Filament

Every month, Filament delivers an incredible mix of free programming and professional development. You can find links to sign up for all of our upcoming events, including PlayDays, Wavelength, NSFW, and SuperCollider here.

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In This Edition

In this week’s Idea Surplus Disorder, we dig into what happens when AI becomes so seamless we forget it’s shaping our thinking. You’ll see why screen-free spaces still matter, why “interesting work” may beat traditional happiness hacks, and how leaders broadcast expectations through tiny, often unspoken cues.

We’ll also unpack the gap between what organizations say is their strategy and what they’re actually doing, the rising need for “proof of work” in an era of effortless fakery, and why so many employees feel emotionally numb in the face of constant change. Plus, two practical tech tips you’ll want to steal.

And as always, you’ll find a mix of fun finds, practical insights, and thought-provoking quotes to help you lead, live, and think more intentionally.

I'm Matt Homann, and I'm glad you're here.

Ideas + Insights

What are the implications when AI becomes a tool we forget we're using?

When we use a tool, it becomes part of us. That’s not just the case for hammers, pens, or cars, but also for a notebook used to organize thoughts. It becomes part of our cognitive process. Computer are not different. While I’m typing this text, my fingers are flying over the keyboard, switching windows, opening notes, looking up words in a dictionary. All while I’m fully focused on the meta-task of getting my thoughts out, unaware of all the tiny miracles happening.

Our minds are susceptible to outside cues. When we read news articles we tend to believe what seems plausible. When we review code we generally expect it to behave the way it looks, even when we don’t have the context to assess that. The same is true for text: When we let a model transform notes into a blog post, a lot of context and nuance is added. We read it and believe the output to be what we thought. It’s subtle.

Should we make education (and meetings) completely screen-free?

It’s time to remove laptops from classrooms. Across 24 experiments: Students learn more and get better grades after taking notes by hand than typing. It’s not just because they’re less distracted—writing enables deeper processing and more images. The pen is mightier than the keyboard.

The secret to happiness? Do "interesting" work:

When you’re procrastinating on a project, wondering why your outwardly successful career doesn’t feel as vibrant as it could, or feeling stuck on a difficult life-choice, it’s worth asking if you’ve forgotten the importance of building your days, as far as you’re able, around what actually interests you.

Meaningful projects aren’t always fun; life certainly isn’t always easy; and the moment in history through which we’re living definitely isn’t calming and relaxing. But maybe it is always, or almost always, possible to find and pursue something that’s truly and enliveningly interesting about the place in life in which you find yourself, and the paths that are open to you to take. “May you live in interesting times” isn’t really an ancient Chinese curse. But we do live in very interesting times; there are things you could do today that would deeply and absorbingly interest you. It might be worth seeing where they lead.

"Tells" aren't just something in poker games. Leaders have tells, too:

Be aware of your “tells.” Leaders at all levels, recognize that you are a powerful informal management system. Your attention, your questions, and your emotional reactions in meetings send the clearest signals of all about “what good looks like.” Make sure your personal cues are in alignment with your stated goals.

Strategy is as much about what you're doing now as what you say you want to do:

For those who see themselves as waiting to do strategy until they have tackled their execution challenges, their Strategy-in-Use becomes a cumulation of short-term fixes of pressing problems rather than a coherent and purposeful set of choices. The lack of such a purposeful set of choices is what causes the company to be beset by continuous ‘operational/executional challenges,’ which causes the leader to postpone tackling strategy again, which causes more challenges, which cases delay, and so on.

The biggest problem with a substantial gap between Espoused Strategy and Strategy-in-Use is that it is very difficult to improve your current position if you don’t know where you are today. If you want to get to Kansas City, it is sure important to know whether you are starting out from Boston or Los Angeles! If you want to improve from your current outcomes by improving your strategy, it is absolutely essential to know what your current strategy is. That has little or anything to do with what you say, it is a product of what you have done and are doing.

Honest people swear more:

A team of researchers from the Netherlands, the UK, the USA, and Hong Kong report that people who use profanity are less likely to be associated with lying and deception.

We are going to need "proof of work" for everything:

Society has always relied on its own implicit version of Proof of Work for all kinds of things. We have operated on the assumption that if a document, a photo, a technical report, slide deck, student essay or any “cognitive artifact” was complex, it was hard to produce. That difficulty was our proxy for truth. If you saw a photo of a car accident, you trusted it because faking a realistic photo required immense skill and time. If a student turned in a ten-page paper, the artifact itself proved they had engaged with the material.

AI is effectively removing that proof of work from human society. It has driven the cost of that production to zero. We can now trivially generate voices, images, video, code, homework, research papers, political analysis, news articles, medical reports and on and on. [We've created] a world where digital artifacts are impossible to trust because they are too cheap to create.

Generation Numb:

One-half of workers say they feel numb, indifferent, or “nothing at all” when their employers announce changes. Another 30% say that shifts in rules, ways of working, or strategy inspire feelings of overwhelm and anxiety. Among all respondents, 17% say unclear priorities or constant change are the biggest source of negative emotions at work.

These are two great tips I found this week:

• You can add a US passport as your digital ID to your wallet app on an iPhone running iOS 26.1 or later. You still need to carry your passport overseas, but you can pull out this ID for TSA clearance at 250 airports in the U.S., including SFO, LAX, JFK and LGA. To do this go to your wallet, hit the + in the upper right, then choose “Driver’s License and ID Cards,” then “Digital ID.” You’ll be prompted to hold your phone’s camera over the photo page of your passport and then you need to touch your phone to the chip embedded in the back of the passport. Then you’ll be asked to take a selfie and do some prescribed head movements to verify you are real. Finally, your application will await verification. Once verified (mine took only a few minutes) your passport ID will appear in your wallet. 
• If you want a quick way to see all your receipts in Gmail, I recently noticed that in my personal account a “Purchases” label category was automatically created and added to my sidebar. Unfortunately, this feature is not available in my Google Workspace account. I use both personal and work emails for shopping, so to mimic that view I type “category:purchases” into the search box to display messages that include receipts, purchase confirmations, invoices, and statements. This is especially helpful during the holiday season.

Finally, some thinking on long-term thinking.

Fun Finds

• MyTaxReceipt shows you a breakdown of how your U.S. federal taxes get spent.
• Time Magazine's Top 100 Photos of 2025
• Window Swap gives you a look out of windows all over the world.
• A collection of stunning time-lapse videos of plants growing.
• Twenty-five things to tell your children.
• Busy Simulator with recurring app notification noises.

Words of Wisdom

An object in possession seldom retains the same charm that it had in pursuit. – Pliny the Younger

Sustainability without profitability has no impact and profitability without sustainability has no future. – Cécile Béliot

History is where everything unexpected in its own time is chronicled on the page as inevitable. – Philip Roth

One who looks around him is intelligent; one who looks within him is wise. – Matshona Dhliwayo

I don’t know what I think until I write it down. – Joan Didion

Up Next From Filament

Every month, Filament delivers an incredible mix of free programming and professional development. You can find links to sign up for all of our upcoming events, including PlayDays, Wavelength, NSFW, and SuperCollider here.

;Thanks to everyone who took last week's survey. I'll leave it open for another week before throwing Idea Surplus Disorder into the garage for a new year's tune-up. Look for a new-and-improved version in 2026!

In This Edition

In this week’s Idea Surplus Disorder: Is facilitation a radical act of care, what can we learn about collaboration from forest firefighters, and should we be bored more?

Also, clear-eyed guidance on when AI supports good thinking, how to use the Minto Pyramid for clearer communication, and when to take a deep dive.

And as always, you’ll find a mix of fun finds, practical insights, and thought-provoking quotes to help you lead, live, and think more intentionally.

I'm Matt Homann, and I'm glad you're here.

Ideas + Insights

Is facilitation a radical act of care? At Filament, we think so:

Modern business is filled with siloes, and work is delivered in decks where different teams own a section. A well facilitated workshop allows people to discover their interconnectedness and identify how they might work together to produce more creative work.

Good facilitation is about tending to the conditions that allow people to show up as their best and most creative selves. Those conditions aren’t technical, they’re human. They’re about safety, belonging, clarity, and trust.

And I love these "rules" from the same article:

• Highlight a desire to hear from everyone; this isn’t a performance for the loudest.
• Ask unexpected questions, and let them breathe.
• You don’t have to hold all the answers, but you do have to hold the space.
• It’s not what you say, it’s how you show up.
• Bring people together in real life to go deeper.

Lessons in handoffs from fighting forest fires:

During a forest fire, the outgoing chief goes through five steps during a conversation with the incoming chief: Here’s what I think we face. Here’s what I think we should do. Here’s why. Here’s what I think we should keep an eye on. Now talk to me (i.e., tell me if you (a) don’t understand, (b) cannot do it, (c) see something that I do not).

Be bored more (via):

Essentially, Dr. Andreasen found that the brain defaults to creativity. When we sit with boredom, when the mind is allowed to float freely, the brain engages in what she termed REST (“random episodic silent thinking”). And during REST, Dr. Andreasen writes, the brain “uses its most human and complex parts...areas known to gather information and link it all together—in potentially novel ways.

Looking for a company guide for when to use AI (LLMs) and when not to? This one from Oxide is quite good.

LLM-generated prose undermines a social contract of sorts: absent LLMs, it is presumed that of the reader and the writer, it is the writer that has undertaken the greater intellectual exertion. (That is, it is more work to write than to read!) For the reader, this is important: should they struggle with an idea, they can reasonably assume that the writer themselves understands it — and it is the least a reader can do to labor to make sense of it.

If, however, prose is LLM-generated, this social contract becomes ripped up: a reader cannot assume that the writer understands their ideas because they might not so much have read the product of the LLM that they tasked to write it. If one is lucky, these are LLM hallucinations: obviously wrong and quickly discarded. If one is unlucky, however, it will be a kind of LLM-induced cognitive dissonance: a puzzle in which pieces don’t fit because there is in fact no puzzle at all. This can leave a reader frustrated: why should they spend more time reading prose than the writer spent writing it?

This can be navigated, of course, but it is truly perilous: our writing is an important vessel for building trust — and that trust can be quickly eroded if we are not speaking with our own voice. For us at Oxide, there is a more mechanical reason to be jaundiced about using LLMs to write: because our hiring process very much selects for writers, we know that everyone at Oxide can write — and we have the luxury of demanding of ourselves the kind of writing that we know that we are all capable of.

Will a significant percentage of a company’s employees in less than three years be two types of employees that barely existed a year ago?

These are agentic (AI) employees who will have their own email addresses, own logins and will be managed by newly trained HR and Talent teams.

Another group will be fractionalized (human) employees who have all the benefits of employees including health care but work 3 or 4 days a week as a result of AI replacing some work. This move to fractionalized employees will also be turbo-charged by new marketplaces are allowing people to have a primary form of income and health care augmented by other forms of income.

To communicate more clearly at work, use the Minto Pyramid:

1. Start with the conclusion: Capture your audience's attention early on by first telling them the main takeaway, message, recommendation or simply your conclusion. This may be the opposite to how we've been taught to communicate but it's more efficient, especially in writing and with audiences who have limited time or attention. This principle is also called BLUF – "bottom line up front". It originated in the military but is now widely used in the business world.

2. Provide key points: With the main takeaway already communicated, it's time to support it with key arguments or main points. These should still be fairly short. Write them as summaries of your main points. This part should explain the "why" behind your conclusion or recommendation.

3. Support points with detailed information: You might still need to make your key points credible. Do that by giving more detailed information that support them: facts, evidence, numbers, results. This is the part where you can really go into detail if you want to.

Finally, for true mastery, we must be prepared to take a "deep dive" into something new:

If our goal is to get not just smarter or more knowledgeable, but wiser, we cannot be content to learn in half measures. We must go as deep as we possibly can. We don’t just read a book on a topic. We have to read everything we can find on it. We dn’t just ask a question or find an expert. We have to find do expert we can and ask them every question they’re willing to answer. We don’t just look at what’s there. We have to explore the remotest corners, every facet, from every angle. We have to hear from people we agree with and from people we disagree with. We have to go out and get real experience.

Fun Finds

• Why is everyone running in romcoms?
• Why do we have two nostrils and not just one?
• A periodic table of imaginary elements from movies, television, and books.
• A map of every (and I mean every) building in the world.
• All of human history in just one hour.

Words of Wisdom

You don’t remember the times your dad held your handlebars. You remember the day he let go. – Lenore Skenazy

It is not the strongest of the species that survives, but the one most responsive to change. — Charles Darwin

Those who don’t believe in magic will never find it. – Ronald Dahl

An idiot in motion will always go further than a genius at rest. – Kpaxs

You never know what worse luck your bad luck has saved you from. — Cormac McCarthy

Show me a company that has fun, and I guarantee that good work comes out of it. – Steve Edge

Up Next From Filament

Every month, Filament delivers an incredible mix of free programming and professional development. You can find links to sign up for all of our upcoming events, including PlayDays, Wavelength, NSFW, and SuperCollider here.

You'll notice things look a little different this week.

While I was recovering, I reviewed all of your survey feedback (thank you!) and spent some time thinking about what I actually want this newsletter to be.

Three years in, it was time to simplify. But not to shorten. I was surprised how many of you wanted to keep it "as is" with all the ideas, quotes, and fun finds.

But I wanted each section to have a clearer purpose — and for the whole thing to feel more like mine. Not just a collection of links, but a point of view.

Here's the new structure:

• What I'm Writing — an essay of mine, a post from the Filament blog, or some musings on LinkedIn
• My Favorite Find — the one idea I can't stop thinking about
• Worth Your Time — four more ideas that earned their spot
• This Week's Question — one question worth asking your team (or yourself)
• Random Things for Smart People — because not everything has to be workplace related
• Words of Wisdom — borrowed brilliance to close us out

Let's see how it feels

What I'm Writing:

Two weeks ago, I wrote about retiring 10% at a time. Here's an excerpt:

I'm not retiring. But I'm starting to practice.

Beginning this year, I'm taking two random days off each month. Not vacation. Not sick days. Retirement days. Two days a month is roughly 10% of my working time.

The honest truth is I've never been retired before, and I don't know anyone who does it particularly well. So I'm hoping to learn now, while I still have the energy and curiosity to figure it out.

The guilt is real, by the way. But I've watched too many people sprint to a finish line only to arrive too exhausted or too sick to enjoy what they'd been running toward.

I'd rather practice now.

Read it on LinkedIn instead→

My Favorite Find:

I read hundreds of blogs and dozens of newsletters every week, and I always find more ideas than I can share. This week, I really loved Addy Omani's reflection on the lessons learned from fourteen years at Google. Some are software developer specific, but most will resonate no matter what you do, including:

Being right is cheap:

Getting to right together is the real work.

You can win every technical argument and lose the project. I’ve watched brilliant engineers accrue silent resentment by always being the smartest person in the room. The cost shows up later as “mysterious execution issues” and “strange resistance.”

The skill isn’t being right. It’s entering discussions to align on the problem, creating space for others, and remaining skeptical of your own certainty.

Most “slow” teams are actually misaligned teams.

When a project drags, the instinct is to blame execution: people aren’t working hard enough, the technology is wrong, there aren’t enough engineers. Usually none of that is the real problem.

In large companies, teams are your unit of concurrency, but coordination costs grow geometrically as teams multiply. Most slowness is actually alignment failure - people building the wrong things, or the right things in incompatible ways.

Novelty is a loan you repay in outages, hiring, and cognitive overhead.

Treat your technology choices like an organization with a small “innovation token” budget. Spend one each time you adopt something materially non-standard. You can’t afford many.

The punchline isn’t “never innovate.” It’s “innovate only where you’re uniquely paid to innovate.” Everything else should default to boring, because boring has known failure modes.

The “best tool for the job” is often the “least-worst tool across many jobs”-because operating a zoo becomes the real tax.

More Thinking Worth Your Time:

To explore the impact of friends at work, KPMG has conducted Workplace Friendship research. Their latest results showedworkplace friendships:

• Workplace friendships are valued at 20% salary premium
• 57% of people would take a job with salary 10% below market value if it offered close work friendships (vs a role with 10% over market salary but no friendships)
• Three-quarters of workers say that financial constraints prevent them from socialising with colleagues outside of work
• 87% say friendship-enabling cultures are crucial for retention

There's nothing "just" about "just hopping on a call."

Your colleague asks you a reasonable question. You could take 5 minutes to write a cogent reply. You have everything you need to reply well. Multiple teammates would benefit from reading your reply. But instead, you say, “Let’s hop on a call.”

When you say this, sometimes what you really mean is: “I don’t want to do the work of clarifying my own thinking. And I believe it’ll be easier to think out loud and answer in a live conversation.”

My response to you is: I do not want to hop on a call because you are too lazy to write a cogent message. If you don’t want to invest 10 minutes to write a reply to a reasonable question, why should I listen (with no 1.5x button) as you meander in real time? GTFO.

There’s nothing “just” about “just hopping on a call.”

We're judging our decisions all wrong:

“Resulting” is (Annie) Duke’s term for judging a decision’s quality by its outcome. A good decision can lead to a bad outcome (and vice versa) because of factors outside your control.

When you overfit decision quality to outcome quality, you risk repeating errors that preceded a lucky good outcome and avoiding good decisions that didn’t work out due to bad luck.

Are you trapped in a Prison of Rightness?

⁠⁠What actually hurt was the feeling of resistance to being wrong, the cognitive dissonance between who I was at my outermost and innermost layers — a feeling that would build and build for as long as the dissonance was maintained.

Being wrong, and saying so, is by contrast liberating — like your mind is tangled up in a very complicated knot of stories and anxieties, but by pulling out just the right thread, the whole thing falls apart.

Acknowledging what is true is so much cleaner, psychologically, than maintaining everything necessary to avoid acknowledging it. Feynman famously said, “you must not fool yourself, and you are the easiest person to fool,” but I think I disagree. Fooling yourself takes work.

This Week's Question:

Ask each of your team members: What are you stuck on?

Posing the “stuck” question communicates that feeling challenged is not an experience that needs to be hidden or feared. It’s expected. That perspective is useful because it fosters resilience. It’s much easier to weather adversity when we anticipate being tested. In contrast, when struggle arrives unexpectedly, it shakes our confidence and leads us to question our abilities.

Random Things for Smart People

• One difference between animated chipmunks Chip ’n’ Dale is that Chip has one tooth and Dale has two.
• How do they get the bubbles in Champagne?
• Defending adverbs
• Rock Paper Scissors Strategies
• The ultimate guide to dinner parties

Words of Wisdom

The real problem is not whether machines think but whether men do. — B.F. Skinner

Even spontaneity gets better with practice. – Rick Rubin

Leadership is disappointing people at a rate they can absorb. – Claire Hughes Johnson

Persistence is the runway that gives your talent time to take off. – Barry Demp

Working smart isn't the opposite of working hard. It's the result of working hard. – Shane Parrish

In this week’s Idea Surplus Disorder, we start with a simple but powerful icebreaker that helps people connect through lived experience, not small talk.

From there, we explore why preparation so often masquerades as progress, when it makes sense to delegate work to AI (and when it doesn’t), and how writing becomes real leverage when we stop waiting for the perfect moment.

We also look at the habits worth leaving behind in 2026, the ways AI is reshaping our collective intelligence, and a question designed to pull teams out of default pessimism and into clearer, more optimistic action.

As always, I'm Matt Homann, and I'm glad you're here!

What I'm Writing:

One of my favorite icebreakers is The Fortune Teller and the Four-Year-Old. It is a distinctive yet simple activity that offers a refreshing departure from traditional icebreaker exercises. It’s designed to create immediate connections between individuals who may not be well-acquainted.

Here’s how it unfolds:

• Start by dividing the attendees into pairs. One participant in each pair assumes the intriguing role of the 'Fortune Teller', while the other adopts the curiosity of a 'Four-Year-Old'.
• The Four-Year-Old's mission is to ask the Fortune Teller questions about their imagined future, such as "What will I be when I grow up?" or "Whom will I marry?"
• Instead of providing fictitious predictions, the Fortune Teller responds with stories taken from their own history. For instance, in answering "What will I be when I grow up?" the Fortune Teller might share, "You’ll grow up to be an accountant in a bustling firm in Chicago." This response, disguised as a prediction, is a sharing of the Fortune Teller's own life lessons and experiences.
• To delve deeper, the Four-Year-Old is then encouraged to ask further questions about the Fortune Teller's narrative, adding depth to the conversation before moving on to their next query.
• After dedicating about 15-30 minutes to this engaging exercise, the pairs switch roles, allowing everyone to gain insights from both perspectives.

This simple exercise is a minimal time investment that yields substantial dividends, including stronger team bonds, improved communication, and a heightened sense of empathy among team members.

Moreover, it encourages participants to reflect upon their own life journeys, fostering greater self-awareness and understanding toward others.

So the next time you find yourself in a gathering with individuals you're keen to connect with on a deeper level, try out this fortune-telling exercise. It could be the key to establishing faster, more effective connections and meetings.

My Favorite Find:

I read hundreds of blogs and dozens of newsletters every week, and I always find more ideas than I can share. I'm not sure I "loved" Things That Aren't Doing the Thing, but it sure resonated with me.

Here are just a few of the things that aren't the thing:

• Preparing to do the thing isn't doing the thing.
• Scheduling time to do the thing isn't doing the thing.
• Making a to-do list for the thing isn't doing the thing.
• Hating on yourself for not doing the thing isn't doing the thing. Hating on other people who have done the thing isn't doing the thing. Hating on the obstacles in the way of doing the thing isn't doing the thing.
• Reading about how to do the thing isn't doing the thing. Reading about how other people did the thing isn't doing the thing. Reading this essay isn't doing the thing.
• The only thing that is doing the thing is doing the thing.

A Few More Things Worth Your Time:

Should you delegate something to AI? Ethan Mollick shares the three variables to consider:

1. Human Baseline Time: how long the task would take you to do yourself. 2. Probability of Success: how likely the AI is to produce an output that meets your bar on a given attempt. 3. AI Process Time: how long it takes you to request, wait for, and evaluate an AI output

A useful mental model is that you’re trading off “doing the whole task” (Human Baseline Time) against “paying the overhead cost” (AI Process Time), possibly multiple times until you get something acceptable.

The higher Probability of Success is, the fewer times you have to pay AI Process Time, and the more useful it is to turn things over to the AI.

Writing is leverage:

Writing is one of the few tools that can reliably change how you think. It forces you to commit to a line of thought and to turn half-formed ideas into something you can examine.

People who write regularly don’t just produce more and better work, they understand themselves and their work more clearly. Regular writing also makes you better at explaining things, whether that’s in emails, presentations, or conversations. You develop an instinct for what works and what doesn’t when communicating complex ideas. Plus, you create a record of your thinking that becomes valuable over time – patterns emerge, forgotten insights resurface, and you can see how your perspective has evolved.

But most people never get that leverage, because they treat writing as something that requires the right mood, the right idea, or the right moment.

Here are a few distractions to leave behind in 2026 (out of 12 in the full post). What's on your list?

• Scrolling as a way to recover from stress. After a long day, your brain wants relief. Culture offers the fastest version: endless content. But relief and restoration are not the same thing. Scrolling often leaves you more restless than when you started—because it never resolves anything. It just fills space. Try a different question this year: “What restores me?” Then do that instead.
• The “I’ll just check real quick” habit. Quick checks are rarely quick. They’re gateways. A message becomes a thread. A headline becomes an hour. A quick lookup becomes a detour through ten other topics. This year, make checking intentional. Put it in a time window. Keep it contained. Stop paying with your day.
• Consuming more opinions than you can think through. Information isn’t neutral. It shapes mood, worldview, and stress level. You can care about the world without absorbing every hot take. And you can stay informed without living in a constant state of agitation. Choose fewer sources. Choose better sources. And choose time limits that protect your mind.
• A to-do list that never meets a calendar. Lists feel productive. They’re also easy to ignore. If you want traction, put tasks into time. Timeboxing is one method that forces clarity and reduces the anxiety of an endless list. HBR breaks down why it works. Your calendar becomes your plan.

AI is changing humanity's collective intelligence:

Generative artificial intelligence (AI) does not transport bodies, but it is already starting to disrupt the physics of collective intelligence: How ideas, drafts, data, and perspectives move between people, how much information groups can process, and how quickly they can move from vague hunch to concrete product.

These shifts are thrilling and terrifying. It now feels easy to build thousands of new tools and workflows. Some will increase our capacity to solve problems. Some could transform our public spaces to be more inclusive and less polarizing. Some could also quietly hollow out the cultures, relationships, and institutions upon which our ability to solve problems together depends.

The challenge—and opportunity—for scientists and practitioners is to start testing how AI can advance collective intelligence in real policy domains, and how these mechanisms can be turned into new muscles and immune systems for shared problem-solving.

This Week's Question:

It’s easy to default to the negative, especially for the natural pessimists on every team. But asking, “What happens if everything goes right?” unlocks optimism and forces clarity about what “everything” actually means. That shared clarity becomes the starting point for doing remarkable work together.

This week's question is inspired by the podcast Best Case Scenarios, hosted by Kevin Kelly and Dan Pink, in which they ask experts to share the best possible good news scenario in the next 25 years in fields including energy, transportation, biotechnology, and brain science.

Random Things for Smart People

• Stuck in a loop? Unloop helps you map it and get unstuck.
• Logorrhea is excessive and often incoherent talkativeness.
• Text Behind Image is a super-simple way to, you know ...
• Take the Correlation Experiment test.
• Bubble Wrap was originally designed to be 3D wallpaper.

Words of Wisdom

Mastery is the revenge of the patient on the privileged. – Shane Parrish

Where I was born and where and how I have lived is unimportant. It is what I have done with where I have been that should be of interest. – Georgia O'Keeffe

The universe is not only stranger than we suppose, but stranger than we can suppose. — J. B. S. Haldane

To handle yourself, use your head; to handle others, use your heart. – Eleanor Roosevelt

There will come a time when you believe everything is finished. That will be the beginning. – Louis L’Amour

In this week’s Idea Surplus Disorder, we talk about misalignment in our expectations, our attention, and our systems, and begin with my post about a deceptively simple tradeoff that clarifies what “done” really means and prevents weeks of unnecessary overwork.

From there, we examine why humans have become startlingly poor listeners in an age obsessed with communication, how AI can accelerate effort rather than ease it, and why our fixation on proof can quietly strangle experimentation.

As always, I'm Matt Homann, and I'm glad you're here!

What I'm Writing:

Would you like it done 75% Tomorrow or 95% Next Week?

Most of us have been on both sides of this moment: someone asks for something, and neither person has a clear picture of what "done" looks like.

The requester wants a quick, directional answer. The person doing the work assumes they need to deliver something polished and thorough. And so begins the quiet spiral of mismatched expectations, where someone over-invests in something that didn't need to be perfect, while the person waiting wonders why it's taking so long.

One question cuts through all of that: "Would you rather have it at 75% tomorrow, or 95% next week?"

Why it works: It clarifies what "done" actually means. It makes the cost of quality visible, since the last 20% often accounts for 80% of the effort. And it reveals the work's real purpose. A request for 95% signals the deliverable is going somewhere important. A request for 75% suggests it's likely an input into a larger conversation.

The hidden benefit: This question gives the requester permission to ask for less. When you offer 75% as a legitimate option, you're making it safe for someone to say, "Actually, I just need something to react to." The person doing the work gets realistic expectations. The person asking gets what they need faster.

Read the full post →

My Favorite Find:

I read hundreds of blogs and dozens of newsletters every week, and I always find more ideas than I can share. This week I've been thinking a lot about listening, and stumbled upon Jeff Bullas' post about why AI listens better than humans do, and found these sobering stats.

Artificial intelligence is revealing just how catastrophically bad we’ve become at the very skill that makes us most human. And the evidence is more damning than you might imagine.

Research from Harvard Business Review shows that people retain only 25% of what they hear in conversations. Meanwhile, studies reveal we spend approximately 60% of our communication time talking about ourselves, when we’re supposedly listening to others.

Brain imaging shows we’re actually mentally rehearsing our response within 8 seconds of someone starting to speak. A University of California study found that the average listener interrupts within 11 seconds of someone starting to talk. Not minutes. Seconds. That’s barely enough time to form a complete thought, let alone express it.

Even more telling: Research shows that in business meetings, executives listen at only 25% efficiency, meaning they miss, misunderstand, or forget 75% of what they hear.

A study published in the International Journal of Listening found that immediately after a 10-minute presentation, the average listener can recall only 50% of what was said. Within 48 hours, that drops to 25%.
According to research by Faye Doell at Loyola University, about 75% of the time people engage in “narcissistic listening”—redirecting conversations back to themselves rather than exploring the other person’s experience.

We’ve become a civilization of broadcasters with no receivers.

And here's the kicker on why humans might prefer talking to AI instead of other humans:

This isn’t about AI being sophisticated. It’s about human listening becoming so rare that simulation feels like revelation.

A Few More Things Worth Your Time:

You're not the only one with imposter syndrome:

A majority — 71% — of U.S. CEOs say they experience imposter syndrome, according to a new Korn Ferry survey of about 400 executives.

The Covid-19 pandemic intensified long-standing challenges for C-suite executives, and even four years later, leaders are struggling to cope with the colossal change it brought to the workplace.

In the past, CEOs might have faced one or two major changes to the business landscape during their tenure, but “never this many, and never all at once.”

This is something I've been noticing in my own day-to-day: AI doesn't reduce work, it intensifies it.

In our in-progress research, we discovered that AI tools didn’t reduce work, they consistently intensified it. In an eight-month study of how generative AI changed work habits at a U.S.-based technology company with about 200 employees, we found that employees worked at a faster pace, took on a broader scope of tasks, and extended work into more hours of the day, often without being asked to do so.

That may sound like a win, but it’s not quite so simple. These changes can be unsustainable, leading to workload creep, cognitive fatigue, burnout, and weakened decision-making. The productivity surge enjoyed at the beginning can give way to lower quality work, turnover, and other problems.

What worked last time is the enemy of what (might) work next:

Somewhere along the way, “evidence-based” began to mean “already validated”. Ideas are expected to arrive with proof attached. Decks become heavier, rationale gets more elaborate. And anything genuinely new – and by that I mean, anything that hasn’t yet had the chance to succeed – struggles to survive the damning weight of the process.

The bittersweet irony is, that the more money there is on the line, the harder it becomes to justify the very experimentation that once created that value in the first place. Point-of-proof becomes a prison. Analysis and data goes towards trying to recreate some of the success of an existing project, rather than pushing work to somewhere untrodden.

Because the real problem isn’t a lack of brave ideas: it’s the impermeable systems we’ve built around them. Incentives quietly shape behaviour, and most creative systems reward speed over surprise and predictability over possibility. Nine times out of ten, fluency will always trump friction. We say we want bold thinking, but we design processes that punish it.

This Week's Question:

What is it I'm not seeing? Though the post (excerpt below) is literally about looking at things, the question works equally well when you're presented with any sort of problem.

We live in a heavily visual world in which our capacity to see things is paradoxically declining.

From the moment we wake up until we fall asleep, usually with a mobile device in our hand or at our bedside, we are continuously exposed to fleeting and fragmented imagery, each of which captures our attention for a few seconds at best, before we move on to the next.

We watch but we don’t see.

Random Things for Smart People

• A molly guard is a safety cover that you need to move out of the way before pressing an important button, and is named after Molly, an engineer’s daughter who was invited to a datacenter and promptly pressed a big red button.
• The origin story of Super Mario Bros.
• Screen Toys are silly things to do with a mouse and your screen. Super fun on a big screen.
• Old Crap is an online museum of vintage computers.

Words of Wisdom

Everyone who started something had no clue how to do it at the beginning. But they figured it out by making mistakes. Make your number 1 trait your "figureoutability". – Viola Davis

Never try to discourage thinking, for you are sure to succeed. – Bertrand Russell

People often ask me, “How do you find the time?” And I answer, “I look for it.” – Rob Fitzpatrick

Wisdom is the art of knowing what to overlook. – William James

Craft is what we are expected to know; art is the unexpected use of our craft. – Ed Catmull

I'm hitting "send" on this newsletter a day late from London after two canceled flights and an unexpected evening in an airport hotel.

This week: a reframe that gave a roomful of cautious leaders permission to take risks, a simple question from Kevin Kelly that might change how you start your mornings, and a handful of tools for thinking more clearly about the things you're most certain about.

As always, I'm Matt Homann, and I'm glad you're here!

What I'm Writing:

A few years ago, I was facilitating a strategy session with about twenty-five senior leaders. The ideas on the table were strong, but nobody wanted to take a risk. Then the CEO said something that changed the entire conversation: "I'm happy for us to pay tuition to learn a lesson, but I'll be damned if I'm willing for us to pay to take the same class twice."

That one sentence solved two problems at once. It gave people permission to experiment, and it created an obligation to make sure the learning actually traveled. In this post, I unpack why "failure" shuts people down, why "tuition" opens them up, and the one rule that keeps the reframe from becoming an excuse.

Read the full post →

My Favorite Find:

Things feel heavy right now for a lot of people. Uncertainty at work piled upon uncertainty everywhere else. And when everything feels like that, optimism can start to seem naive

Which is why I keep coming back to this piece by Kevin Kelly. It's not about positive thinking or pretending things are fine. It's about what happens when you decide, deliberately, to stay open to the possibility that help is already on its way.

Kelly spent years hitchhiking, cycling across America, and wandering through Asia, and he noticed something: generosity showed up every single time, but only when he was willing to receive it. His daily question wasn't will something good happen, but how will it happen today?

That shift — from whether to how — is one of the most useful reframes I've encountered in a long time.

So ask yourself, how will the miracle happen today?

A Few More Things Worth Your Time:

How to talk to anyone – and why you should:

A lot of people have given up taking a chance on other people: that they might want to listen, that they might want to talk. But they have also given up taking a chance on themselves: that they might be able to navigate a conversation with someone new, cope with knockbacks and steer a path through any misunderstandings.

The key is to lower the stakes. Make it less of a big deal. Don’t focus on what could go wrong. Also, don’t focus on how amazing this could be. You are just saying, “It’s cold today, isn’t it?” You are not asking someone to join you on a quest for world peace. Similarly, if an approach is made towards you and you don’t want to respond, just be confident and clear either with your gestures (look down, don’t make eye contact) or with speech: “I can’t talk right now.”

Oliver Burkeman reminds us that no matter how sophisticated they feel, our tools are still tools:

There’s no reason this can’t involve immersing yourself in all manner of digital tools. But you’ll be relegating them to their proper role as tools, useful in some contexts and too limited to be useful in others, as opposed to gods you must appease, regardless of the cost to your experience of life.

The reason “you’re not ready for what’s coming next”, in other words, is that we’re never ready for what’s coming next.

I’m not suggesting that when you grasp this insight you’ll immediately cease worrying about the future and be free of anxiety forever. (That hasn’t been my experience.) But it can free you up sufficiently to notice a different way of approaching life: not by anxiously bracing against impending doom, but by taking a deep breath and settling down a bit into the basic uncertainty of it all.

Does every item on your agenda have a Directly Responsible Individual?

A DRI is assigned to agenda items for all to see. Employees expect to see a DRI next to an agenda item, and everyone knows that the DRI will be driving action. In addition to this utilitarian purpose, a DRI serves a number of other purposes, including (1) getting more people involved in the meeting, (2) providing a nice opportunity for skill development in leading meetings, and (3) making the meeting more stimulating for other attendees as more voices are incorporated.

Once upon a time, authority mattered, but now our systems reward being right over being fast:

What matters now is how fast something moves through the network: how quickly it is clicked, shared, quoted, replied to, remixed, and replaced. In a system tuned for speed, authority is ornamental. The network rewards motion first and judgment later, if ever. Perhaps that’s why you feel you can’t discern between truths, half-truths, and lies.

Networks compress time and space, then quietly train us to live at their speed.

People do what the network rewards. Writers write for the feed. Photographers shoot for the scroll. Newsrooms frame stories as conflict because conflict travels faster than nuance. Even our emotional lives adapt to latency and refresh cycles. The design of the network becomes the choreography of daily life.

I feel so many in my LinkedIn feed are training me to ignore them:

Every time you send a generic, low-effort automated email, you are taking out a loan against your reputation. You are teaching your market that:

You don’t know them. You don’t value their time. You are just a bot.

And just like financial debt, Brand Debt compounds. Six months from now, when you actually have something valuable to say, they won’t hear it. Because you already trained them to skip over your name.

There were some fun reminders in this list of 26 Useful Concepts, including:

• The One Percent Rule: In online communities, around 1% of users produce almost all of the content. As such, what you see online is not representative of humanity, but merely of a loud, obsessive (and often narcissistic, psychopathic, low-IQ) minority. Social media is literally a freakshow.
• Amara’s Law: We tend to overestimate the short-term impact of new tech, and underestimate the long-term impact, because hype inflates expectations, and thus disappointment, and thus scepticism. As such, it’s possible for AI to be both a bubble and the most transformative tech since fire.
• Cammarata’s Razor: If you want more agency, ask yourself what you’d do if you had ten times more agency. Then do it.

This Week's Question(s):

From Thomas Gilovich's book How We Know What Isn't So (via Bookfreak) comes a handful of questions we should ask when we're certain we've made up our mind:

1. Identify a belief you hold strongly. Now ask yourself: “What evidence would convince me this is wrong?” If you can’t name any, that’s a warning sign.
2. Think of a recent “streak” or “pattern” you noticed — in sports, luck, or daily life. Consider: Could this be random variation that I’m interpreting as meaningful?
3. Notice the next time you encounter information that supports your existing view. Pause and apply the same critical scrutiny you’d use for information that contradicts it.
4. Ask someone you trust but who thinks differently: “What do you believe about X that I probably don’t?” Listen without defending.
5. Before sharing a surprising “fact” today, ask yourself: “Did I verify this, or did I believe it because I wanted it to be true?”

Random Things for Smart People

• Old Crap is an online museum of vintage computers.
• The Elliot Report compiles direct phone numbers and email addresses for customer service executives at hundreds of companies — airlines, hotels, car rentals, banks, cable providers, and more.
• Here's a list of book recommendation tools, including Most Recommended Books filtered by famous recommenders.

Words of Wisdom

Everyone who started something had no clue how to do it at the beginning. But they figured it out by making mistakes. Make your number one trait your "figureoutability". – Viola Davis

Sometimes I wonder whether the world is being run by smart people who are putting us on or by imbeciles who really mean it. – Mark Twain

Never try to discourage thinking, for you are sure to succeed. – Bertrand Russell

This is how we grow: by being defeated by greater and greater things. – Rainer Maria Rilke

People often ask me, “How do you find the time?” And I answer, “I look for it.” – Rob Fitzpatrick

Craft is what we are expected to know; art is the unexpected use of our craft. – Ed Catmull

FILAMENT'S LAST MINUTE MEETINGS

We've got a few open dates for Filament's Last Minute Meetings on March 24 and 31, and April 1 and 2. You can get more information here.

I'm hitting "send" on this week’s Idea Surplus Disorder from the Dublin airport after a week abroad —and I'm really looking forward to being home!

This week: a simple framework that fixes the most common reason meetings go sideways, some hard-won wisdom from Kevin Kelly, why AI (still) can't write like you do, and a surprisingly moving piece about what happens when the world stops needing what you're best at.

Plus tools for making better gut decisions, a beautifully designed archive worth exploring, and a few things that made me smile.

As always, I'm Matt Homann, and I'm glad you're here!

What I'm Writing:

Most meetings don't fail because of bad agendas or the wrong people in the room. They fail because nobody agrees on what kind of conversation they're actually having. Is this a brainstorm? A debate? A decision? When that's unclear, people show up in different modes and talk past each other.

Filament's Dream, Debate, Decide, Do framework solves that with a single question asked before the meeting starts: Which of these four are we doing right now?

• Is it a Dream meeting? Come with ideas.
• A Debate meeting? Arrive with a point of view.
• Are we Deciding? Let's be clear about what we're deciding on and who the decider is.
• And if we're Doing? We'll leave with clear tasks, accountability, and measures.

It's a small habit with a surprisingly large effect on how meetings feel and what they actually produce.

Read the full post for a breakdown of each mode and how to use them.

My Favorite Find:

I read hundreds of blogs and dozens of newsletters every week, and I always find more ideas than I can share. Today's favorite find is a book: Kevin Kelly's Excellent Advice for Living: Wisdom I Wish I'd Known Earlier.

It's a collection of his observations from a life lived as the world's most interesting man. One that stopped me dead in my tracks as I was "finishing" our new website is:

Be prepared. When you have 90% of a large project completed, finishing the final details will take another 90%.

And another that gives me the ambition to keep learning and using AI:

A worthy goal for a year is to learn enough about a subject so that you can't believe how ignorant you were a year earlier.

A Few More Things Worth Your Time:

Why your AI (still) can't write like you:

Why does AI writing still sound like AI writing, even as the models get smarter? The most reliable fingerprints of your personal style come from the words you write subconsciously: articles, pronouns, and function words that emerge in a distinctive pattern as you focus on the meaning of a sentence.

Related: What's Happening to Writing

Anne-Laure Le Cunff shares her Gut Decision Matrix that starts with two questions to ask when you have a strong gut reaction to something: 1. Is this instinct or intuition? 2. Are you in immediate danger, or is this a more complex situation?

If your response is instinct in immediate danger, it usually makes sense to act right away. These survival mechanisms evolved specifically to deal with situations where hesitation could be costly.

However, instincts can misfire in modern contexts. When a situation is more complex, it’s often better to slow down and question the instinctive response before acting on it.

If you have domain-specific expertise or experience in similar fast-moving situations, a strong intuition may be worth acting on quickly. In these moments you may not have time for deliberate analysis, so it can be reasonable to rely on your brain’s automatic pattern recognition, which can detect important signals faster than conscious reasoning.

Finally, in slower-developing or more complex situations, it’s best to treat intuitions as hypotheses and examine them through additional thinking, evidence, or testing before committing to a decision.

When you've loved your job, but your job hasn't loved you back:

It still makes me sad, though, that what I’ve spent 45 years of my life toiling at will likely end up as a footnote, the providence of folksy artisans and historical reenactors. I didn’t leave a dent in the universe so much as splatted against it. The world no longer has a need for what I somewhat sardonically call my art. We are all product managers now, pleading with obtuse underlings to go back and try again and to get it right this time. I remain a father and husband and son and friend, but the need for what I can do — the need for what programmers can do — is shrinking, and my conception of myself and my usefulness along with it.

That was something I did that mattered. I’ll miss it.

The Steve Jobs Archive is a beautifully designed compilation of his work, teachings, and others' reflections on his legacy. Letters to Young Creators is a great place to start.

This Week's Question:

For every project you undertake, can your team complete these four prompts?

• The purpose of this work is ______.
• To achieve that, we will ________.
• My role in the process is _________.
• And it will be successful if _______.

Random Things for Smart People

• In Every Language is a Wikipedia search engine that lets you see how different regions of the world depict the same thing.
• A Reading List for Strategists Who Want to Think Dangerously
• How one unappetizing weed became dozens of different vegetables, including kale, broccoli, and Brussels sprouts.
• The 80's were brown.
• Jimi Hendrix was a systems engineer.
• The origin of Casual Fridays

Words of Wisdom

Imagination is the most potent force in the universe. It's the one skill in life that benefits from ignoring what everyone else knows. – Kevin Kelly

You just have to be very careful about doing things you are fundamentally not going to be proud of, because they will damage you. – Naval Ravikant

It is not because things are difficult that we do not dare; it is because we do not dare that they are difficult. — Seneca

If all you did was look for things to appreciate, you would live a joyously spectacular life. – Esther Hicks

What you celebrate becomes what you are: choose with extraordinary care. – Patricia Mou

FILAMENT'S LAST MINUTE MEETINGS

We've got a few open dates for Filament's Last Minute Meetings on March 24 and 31, and April 1 and 2. You can get more information here.

Welcome to another Monday edition of Idea Surplus Disorder. This week: lessons in technology disruption from ATMs and the iPhone, a deceptively simple question that helps you see your own work more clearly, and a reminder to stop scanning for red flags — and start looking for green ones.

Plus, why our systems keep rewarding complexity over simplicity, what twenty-year-old project management lessons still get right, and a single question worth asking yourself the next time you feel stuck in your own work.

As always, I'm Matt Homann, and I'm glad you're here!

My Favorite Find:

I read hundreds of blogs and dozens of newsletters every week, and I always find more ideas than I can share. Today's favorite find is this simple reminder from Seth Godin:

We were taught to look out for red flags. Little signs that something is wrong, that we should be careful or even turn around.

Don’t let that distract you from being on the lookout for green flags.

We might need encouragement to leap forward. If you look for the green flags, you’re more likely to find them.

A Few More Things Worth Your Time:

ATMs didn't reduce the number of bank tellers, but the iPhone did:

The ATM tried to do the teller’s job better, faster, cheaper; it tried to fit capital into a labor-shaped hole; but the iPhone made the teller’s job irrelevant. One automated tasks within an existing paradigm, and the other created a new paradigm in which those tasks simply didn’t need to exist at all.

And it is paradigm replacement, not task automation, that actually displaces workers—and, conversely, unlocks the latent productivity within any technology. That’s because as long as the old paradigm persists, there will be labor-shaped holes in which capital substitution will encounter constant frictions and bottlenecks.

Forget your single conversation with ChatGPT. What would a fully-automated, infinitely-scalable, genius-level firm be able to accomplish?

Even people who expect human-level AI soon are still seriously underestimating how different the world will look when we have it. Most people are anchoring on how smart they expect individual models to be. (i.e. they’re asking themselves “What would the world be like if everyone had a very smart assistant who could work 24/7?”.)

Everyone is sleeping on the collective advantages AIs will have, which have nothing to do with raw IQ but rather with the fact that they are digital—they can be copied, distilled, merged, scaled, and evolved in ways human simply can’t.

What would a fully automated company look like - with all the workers, all the managers as AIs? I claim that such AI firms will grow, coordinate, improve, and be selected-for at unprecedented speed.

The Corporate Bullshit Receptivity Scale measures how much people like empty organizational rhetoric. High scorers thrive in corporate environments but are measurably worse at their jobs than people who keep things to the point:

Results show that corporate bullshit receptivity is distinct from a general affinity for corporate speech, negatively associated with measures of analytic thinking, and positively related with other bullshit-related constructs in theoretically-consistent ways. Importantly, corporate bullshit receptivity is positively associated with several workplace perception variables and is a robust negative predictor of work-related decision-making.

Complexity looks smart. Not because it is, but because our systems are set up to reward it:

Pay attention to what you celebrate publicly. If every shout-out in your team channel is for the big, complex project, that’s what people will optimize for. Start recognizing the engineer who deleted code. The one who said “we don’t need this yet” and was right.

At the end of the day, if we keep rewarding complexity and ignoring simplicity, we shouldn’t be surprised when that’s exactly what we get. But the fix isn’t complicated. Which, I guess, is kind of the point.

Twenty years after writing Making Things Happen, Scott Berkun shares his favorite lessons from the book, including:

• Project management in many organizations is project rescue in disguise.
• All schedules are guesses.
• Stupidity travels down. Fools at the bottom are easy to ignore. Stupidity from the top is hard to escape.
• Odds of success improve the smaller and clearer your goals are.
• Projects in trouble should have smaller teams and simpler ambitions.
• Most project failures were people problems first.
• Avoid blame. If you hide it or shame it you will repeat it.

This Week's Question:

If I were replaced, what would my replacement do?

By temporarily removing ourselves from the singular ­first-person point of view, which is inextricably informed by our memories, prejudices, hopes, and hurts, we are able to see and think more clearly, unencumbered by our personal experiences and feelings — and our need to look good or defend ourselves.

Random Things for Smart People

• The Happy Map
• Dicing an onion, mathematically.
• Extreme macros of insect wings.
• The First Night Effect is why you don't sleep well your first night in a strange bed.
• An Art Discovery Engine

Words of Wisdom

Vulnerability doesn’t come after trust—it precedes it. Leaping into the unknown, when done alongside others, causes the solid ground of trust to materialize beneath our feet. – Daniel Coyle

It is much easier to be fired for being illogical than for being unimaginative. – Rory Sutherland

Bureaucracy filters out noise, but sometimes, what sounds like noise is actually the first signal of something transformative on the way. – David Cleevely

If creativity were really expensive, it would be taken more seriously. – Graham Fink

Resources are likely to come to you in greater abundance when you are generous and inclusive and engage people in your passion for life. – Rosamund Stone Zander

In this week's Idea Surplus Disorder, we'll talk about the limits of our tools, the limits of our attention, and the quiet cost of outsourcing our thinking – and begin with a finding that reframes what AI can and can't actually do for us right now.

From there, we examine why showing more proof might earn you less trust, how our reliance on technology erodes our judgment in ways we rarely notice, and why three or four hours of real focus might be all any of us actually have in a day.

As always, I'm Matt Homann, and I'm glad you're here!

My Favorite Find:

I read hundreds of blogs and dozens of newsletters every week, and I always find more ideas than I can share. Today's favorite find is about an under-discussed limitation of our current versions of AI: as of now, they can't keep learning:

Despite our expectations, current LLMs do not learn from each other, nor do they learn when you correct them again and again. They currently do not have a robust way to remember their mistakes or corrections, nor to get smarter more than once a year when they are retrained from 4.0 to 5.0.

Every time you correct ChatGPT’s mistake, it forgets by the next conversation. Every time a robot fails at a task, it will fail the exact same way tomorrow.

This is why AIs can’t hold a real job in 2026. At this moment we lack the software genius to install continuous learning (at scale) to the machines.

A Few More Things Worth Your Time:

Burning the midnight oil? You can only seriously focus on work for just 3-4 hours at a time.

There aren't many hard-and-fast rules of time management that apply to everyone, always, regardless of situation or personality. But I think there might be one: you almost certainly can't consistently do the kind of work that demands serious mental focus for more than about three or four hours a day.

Yes, it's true we live in a system that demands too much of us, leaves no time for rest, and makes many feel as though their survival depends on working impossible hours. But it's also true that we're increasingly the kind of people who don't want to rest – who get antsy and anxious if we don't feel we're being productive.

The usual result is that we push ourselves beyond the sane limits of daily activity, when doing less would have been more productive in the long run.

Does technology trick us into thinking we're adding more "value" when we're actually degrading trust?

Technology has made it easier to pad what we present. more slides, data and "proof." But proof and trust are inversely correlated in creative work. The more you have to prove, the less they trust you. The less they trust you, the more you have to prove.

And speaking of technology, in what ways are we escalating our reliance on the tools we use?

Want to think about the future differently? Jane McConigal suggests we play the game One Hundred Ways Anything Can Be Different in the Future:

Here’s how it works: First, you pick a topic, like work, or food, or learning. Then you list one hundred things that are true about it today. The simpler or more obvious the fact, the better.

Next, you rewrite each fact, one by one, so that ten years from now the opposite is true—no matter how ridiculous, at first, the new ideas sound.

Finally, you look for clues, or evidence of change already happening today, that these ideas are plausible and realistic.

Ideas can be acted upon in four ways:

• First, you must generate the idea, usually from memory or experience or activity.
• Then you have to retain it—that is, hold it steady in your mind and keep it from disappearing.
• Then you have to inspect it—study it and make inferences about it.
• Finally, you have to be able to transform it—alter it in some way to suit your higher purposes.

This Week's Question

This week's question is inspired by Hearding Tigers by Todd Henry: What are we working on? Todd's advice:

Build a list of every project your team is working on, and define the core problem that it’s solving. Then write a one-sentence problem statement that clearly articulates what the team is trying to accomplish.

Random Things for Smart People

• Channel Surfer is a YouTube "channel guide" that looks like cable TV.
• The HTML Review is an annual journal of literature made to exist on the web
• How the spreadsheet reshaped America.
• I'm loving the Acme Weather iPhone app from the makers of Dark Sky (IYKYK).
• Every photo Curiosity Mars Rover has taken since 2013.

Words of Wisdom

Luck can find you, but it has to find you working. – Daniel Arsham

If you do not change direction, you may end up where you are heading. – Lao Tzu

Consensus is the process of avoiding the very issues that have to be solved. – Margaret Thatcher

The foolish person winds up doing at the end what the smart person does at the beginning. – Kevin Kelly

It is tiring to deal with someone who has made an enemy of you when you do not think of them at all. But, of course, this is often why they hate you. – Christopher Buehlman