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.
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:
- 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.
- 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?
- 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.
- Ask someone you trust but who thinks differently: “What do you believe about X that I probably don’t?” Listen without defending.
- 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.