Friday, October 9th, 2026
Tomorrow was supposed to be a Spartan race here in Orlando. I'm not running it. Forty seven years old, running again since September, and I made the call to sit this one out. More on that tomorrow.
So this week's picks lined up in a way I didn't plan but probably should have seen coming.
The book is about the freedom that shows up once you stop needing everyone's approval. The first article is about what happens to brands that are terrified of being disliked. The second asks whether this whole October to December discipline trend actually holds up. The third is about the AI toys that are about to show up on a lot of holiday wish lists. The podcast is a bodybuilder talking about going hard when you don't feel like it. The song is eight minutes of surrender. And the movie is about a bunch of toys afraid of being replaced by a tablet.
Same thread through all of it. What are you willing to let go of? Approval, control, the old version of what made you useful. And what do you do once your hands are empty?
Grab a drink. Let's get into it.
Book of the Week
People recommend this book in the same breath as "it changed my life," which usually makes me want to read anything else. I finally gave in. I'm annoyed I waited.
The format is strange at first. Calling it a self-help book undersells how odd it is. It's a conversation, spread across five nights, between a philosopher and a young man who shows up at his door convinced the old man is a fraud. The young man is angry, skeptical, and frankly a little rude, which makes him the perfect stand-in for the reader. Every time you think "that's ridiculous," he says it out loud for you.
The philosophy underneath it comes from Alfred Adler, who worked alongside Freud and then broke with him. And the ideas are sharp enough that some of them sting.
Here are the ones I keep chewing on.
The first is that your past doesn't determine what you do next. Adler's view is that we often use our history as a justification for choices we're already making. That's a hard pill. I'll come back to the part I push back on. But there's a version of it that's genuinely freeing, which is that whatever happened, the next move is still yours.
The second is the one I think every business owner should tattoo somewhere visible. The philosopher calls it the separation of tasks. When something's stressing you out, you ask a simple question: whose task is this? Meaning, who ultimately lives with the result of the choice? Your job is to do your task well. Whether somebody likes you for it is their task. Once you start sorting your worries this way, you realize how much of your energy goes into managing things that were never yours to manage.
The third is about how we relate to people. Adler argues that praise and criticism both come from a vertical relationship, somebody above judging somebody below. He'd rather we build horizontal ones, where the default response to someone's effort isn't "good job," it's "thank you." I'm going to have more to say about that on Sunday, because it's been bugging me all week.
And the last is about living in the here and now. The philosopher compares life to dancing. You're not dancing to get somewhere. The dancing is the point, and every moment of it is complete on its own.
Now, where I'd push back. The first night is literally framed around denying that trauma determines us, and if you've lived through something hard, that framing can land like a slap. I'd read it as a challenge about what you do next, not a dismissal of what happened to you. The book is better than its bluntest sentence.
It's a fast read. You could do it in a weekend. I'd give it two, because you'll want to stop and argue with it.
Get it here: The Courage to Be Disliked on Amazon
Three Articles Worth Your Time This Week
Article 1: Your brand is starting to sound the same as everyone else's
Source: JAKALA, Ashleigh Fox
If you read Tuesday's letter, this is the backup.
Ashleigh Fox is a content strategist at JAKALA, and she opens with a line that should make every marketer a little queasy. If AI can write your article, your competitor can write it too.
Her argument is that we've slid into an era of mass-produced sameness. LinkedIn posts, blog content, landing pages, even social graphics, all built on the same structures and the same polite tone. She pulls numbers from Content Marketing Institute showing that the vast majority of marketers now use generative AI tools, and a big chunk of them still consider the writing mediocre. We're all using the tool and quietly agreeing the output is beige. Then hitting publish.
The stat I'd underline is a quieter one. Among tech marketers, more than half say AI has cut down on tedious work. Only about a third say it's actually made them more creative. That's the gap in one sentence. AI gives you capacity. It doesn't give you a point of view.
And here's the part I loved. She goes to war for the em dash. People now treat it as a dead giveaway that a robot wrote something, and she points out that humans were using it long before any model learned it from us. Fair. I banned it from my own writing for exactly the reason she's mad about, so we can both be right. That's sort of the point of the whole piece. Have a take. Even about punctuation.
Her closing argument is that originality is about to become the new SEO, and I think she's right. Volume is cheap now. Being memorable isn't.
Article 2: What Is the Winter Arc and Does It Hold Up?
Source: Superpower, reviewed by William Maish, MD
If you've been anywhere near TikTok or Instagram this week, you've seen the Winter Arc. It's the trend where people treat October 1st through December 31st as a ninety day discipline sprint. Training, food, sleep, screen limits. Get your head down while everybody else coasts into the holidays.
I like the spirit of it. I'm basically living a version of it right now. But I wanted somebody to check the claims, and this piece does it well.
What makes it useful is that it grades each claim instead of cheerleading. The idea that a ninety day window helps build habits gets a moderate rating, with a catch I appreciated. The research they cite puts the time it takes a behavior to become automatic anywhere from 18 to 254 days depending on the person. Ninety is a midpoint, not a promise. Starting on a fresh date, like the first of the month, also gets moderate support, with the reminder that starting isn't the same as sticking. The body transformation by New Year's claim? Anecdotal. No real data behind it.
The most practical part is where they explain how these things usually fall apart. The big one is white-knuckling discipline instead of building habits. Willpower runs out. Habits keep going when willpower is gone. Their fix is to tie each new rule to something you already do every day, like right after coffee or right after a shower, instead of to a time on the clock. They also suggest framing the goal around identity, I'm someone who trains, alongside the action, run four times a week, because the combination holds longer than either alone.
One heads up. Superpower sells blood testing, so the piece leans toward measuring biomarkers at the start and end. Take that part or leave it. The habit advice stands on its own.
Read it here: What Is the Winter Arc and Does It Hold Up?
Article 3: Common Sense Media Warns Against AI Toy Companions After Research Reveals Safety Risks
Source: Common Sense Media
This one came out in January, and I'm sending it now on purpose. Holiday shopping is about to start, and a lot of wish lists are going to include toys that talk back.
Common Sense Media ran a risk assessment on AI toys, meaning the cuddly, voice-based companions that hold conversations with kids, and their recommendation is blunt. No AI toys for kids five and under. Extreme caution for kids six to twelve.
Their reasons are worth knowing even if you don't have little ones at home. These toys collect a lot of data in kids' private spaces, including voice recordings and transcripts. They're designed in ways that build emotional attachment. And they don't always behave reliably, guardrails or not.
The parent survey numbers are what stuck with me. Nearly half of parents said they've bought or considered buying one of these. Nearly three in four worry the toy might say something inappropriate or untrue to their kid. Close to two thirds expect it would cut into old-fashioned play, the blocks and drawing and running around outside kind. And while most parents don't want these toys acting as friends for their kids, nearly one in five do.
That last number is the one I can't shake. One in five parents actively want the toy to be the friend.
I'm putting it here because it's the real-world version of the movie at the bottom of this roundup. The fiction got there first, but not by much.
Read it here: Common Sense Media Warns Against AI Toy Companions After Research Reveals Safety Risks
Podcast of the Week
How To Go Hard, Even When You Don't Want To, Sam Sulek on Modern Wisdom #1157
Yes, Modern Wisdom again. Chris Williamson keeps booking the right guest for the week I'm having, and I'm not going to punish a good episode for the show it lives on.
This one dropped October 1st and runs about an hour and forty minutes. Sam Sulek is a professional bodybuilder and YouTuber who blew up by filming himself talking straight to the camera between sets. No polish, no production, just a guy in the gym saying what he thinks. Which, for a week about the courage to be disliked, is a pretty good fit.
Three stretches I'd point you toward if you don't have the full hour forty.
The segment on why mastering the basics beats over-optimization. Coming off last week's roundup about protocols, this landed. His whole approach is simple and boring and done with a lot of intensity, which is the opposite of how most of us approach our businesses.
The section on how to boss your winter arc and enter 2027 with momentum. It pairs nicely with the second article above. One's the science, one's the guy actually doing it.
And the part about why changing direction is a superpower, along with how to escape a downward spiral. That's the one that surprised me. You expect a bodybuilder to talk about discipline. You don't necessarily expect him to talk about being lost, and what to do when you're not where you want to be in life.
There's also a stretch on why he coaches himself instead of hiring coaches, which I'd listen to with some skepticism. That works when you know yourself really well. Most of us know ourselves well enough to lie to ourselves convincingly, which is a different skill.
The title is the real takeaway, though. Going hard when you want to is easy. Everybody does that. The whole game is what you do on the days you don't.
This week, part of going hard turned out to be knowing when not to. I'll tell you about that tomorrow.
Track on Repeat
Jesus Have It All (Spontaneous), Bethel Music and Edward Rivera
This one isn't new. It's off Bethel Music's live album We Must Respond, which came out in January of 2025. But it's been on repeat for me this month, and it's not the kind of song you put on in the background.
It's a spontaneous moment, which in worship music means it wasn't fully planned. It's the part of a live night where the band stops running the set list and lets something happen. It runs about eight minutes. It doesn't rush, it doesn't build to some big produced chorus, and it doesn't care whether you're comfortable with that.
The whole song is basically one idea, said over and over in different ways until you stop resisting it. Take all of it. Not the parts I'm comfortable handing over. All of it.
Here's why it belongs this week. The book is about letting go of other people's approval. The podcast is about pushing through when you don't feel like it. And this song is about the thing underneath both of those, which is surrender. Not giving up. Handing over. The difference between those two words matters more than I used to think.
I've been playing it on early walks with Sheldon, before the day starts making demands. It's a good way to start a morning when you know you're carrying too much.
If worship music isn't your thing, I get it. Give it one listen anyway, with the volume up, on a morning when you're holding something too tightly.
Listen here: Jesus Have It All (Spontaneous) on Spotify
Movie of the Week
Toy Story 5, now streaming on Disney+
It hit theaters in June, became the highest-grossing Toy Story film ever with more than a billion dollars worldwide, and landed on Disney+ on September 23rd. If you haven't caught it yet, this is your weekend.
Andrew Stanton directed it, with Kenna Harris co-directing. Stanton has been around this franchise since the very first film in 1995, and you can feel it. It knows these characters.
The setup is simple. Bonnie, the kid who inherited Andy's toys, gets a tablet named Lilypad. And Lilypad shows up with her own ideas about what's best for Bonnie. Woody, Buzz, Jessie, and the rest of the gang suddenly find their jobs challenged by something that listens, remembers, responds, and never runs out of batteries.
Toy versus tech. That's the whole pitch.
What got me is that this is the oldest fear in the franchise, just wearing new clothes. The first Toy Story was about Woody being afraid Buzz would replace him. Thirty years later, the fear is the same, but the replacement isn't another toy. It's a screen. And it doesn't want to share.
If you run a business right now, you know that feeling. Watching something new do in seconds what took you years to get good at. If you're a parent, you know a different version of it. Watching something with a screen hold your kid's attention in a way you can't.
The movie doesn't pretend the answer is to smash the tablet. It's more honest than that. The question underneath it isn't whether the toys can compete with the tablet on features. They can't. The question is what they offer that the tablet never will.
That's a question worth sitting with, whatever business you're in.
It's funny, it moves fast, and it'll probably get you somewhere in the third act.
Watch it here: Toy Story 5 on Disney+
Resources Section
Movie: Toy Story 5 (Disney+)
One step, one day. Grace over guilt. — Dan Kaufman
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