Friday, October 23rd, 2026
Every week I pick these things for different reasons, and every week they end up having the same conversation. This week the conversation was about the gap between who you were and who you're trying to become, and how long it takes to cross it.
The book is a short, plain spoken guide to being good at life that doesn't measure a good life by money or status. The first article says the habit you started three weeks ago probably isn't a habit yet, and that's normal. The second says the AI tools we lean on every day might be quietly making us worse at our jobs. The third says that if you're changing careers in your forties, you're not starting over, no matter what it feels like.
The podcast is about the ugly, awkward middle of getting good at anything. The song is two guys sitting with the wreckage of who they used to be. And the show is about a marriage where one person is trying to get back in instead of out.
Pour something. Let's go.
Book of the Week
First, a heads up so you buy the right one. There's another book out this month with almost the same title, a big hardcover from Ben Meer about building systems. That's not this one. This is Blake Mair's book, it came out at the end of June, and it's short. About ninety pages on Kindle. You can read it in an evening.
I like short books. Most business and self improvement books are a good magazine article stretched over three hundred pages so the author can charge twenty eight dollars and go on a podcast tour. Mair doesn't do that. He gets to the point and gets out.
The premise is simple and, honestly, a little countercultural right now. We measure a good life by wealth, status, and achievement. Mair says that's too thin a scoreboard. His definition of a life well lived is wider. Character. Meaningful relationships. Continual growth. Emotional resilience. Financial responsibility. Service to other people.
Read that list again and notice what's on it and what isn't. Money's on there, but it's framed as responsibility, not as the point. Achievement isn't really on there at all, at least not as its own category. Growth is. That's a different thing. Achievement is a result. Growth is a direction.
He's also clear about what the book isn't. It's not quick fixes and it's not motivational slogans. It's timeless principles meant to be used on a Tuesday, not admired on a Sunday. And the people he says he wrote it for include folks just starting their adult lives, people chasing growth, people looking for deeper meaning, and people rebuilding after setbacks.
That last group is why it's this week's pick.
When you're rebuilding, it's tempting to judge the whole effort by one number. Revenue. Followers. Pounds. Whatever your scoreboard is. And on a bad week that one number makes you feel like a fraud. A wider definition of a good life gives you more places to stand. Maybe the revenue was thin this month, but you kept your word to everybody, you showed up for your kids, you got stronger, you helped somebody who needed it. That's not a consolation prize. By Mair's definition, that's the actual game.
If you've got a son or daughter heading into their twenties, this is also an easy book to hand them. It's short enough that they might actually read it.
Get it here: How to Be Good at Life on Amazon
Three Articles Worth Your Time This Week
Article 1: Does It Really Take 66 Days to Form a Habit? What the Study Found
Source: The Nest Tools, Hamza Ahmed
You've heard it takes twenty one days to form a habit. You've probably also heard it takes sixty six. This piece walks through where the second number actually comes from, and it's worth five minutes because most of us are using it wrong.
The number traces back to a 2010 study out of University College London led by Phillippa Lally. Ninety six volunteers each picked one new daily behavior, like eating a piece of fruit with lunch or going for a fifteen minute run before dinner, and tried it every day for twelve weeks while rating how automatic it felt.
The median time to hit automatic was 66 days. But the range was the real story. Some people got there in 18 days. Others were projected to need 254. Exercise habits trended slower, with a median around 91 days, compared to 59 for drinking habits and 65 for eating ones, though the writer is careful to point out the difference between groups wasn't statistically significant in a sample that small.
And the twenty one day rule? It doesn't come from any habit study. It traces back to 1960s self help writing.
Here's the finding I'd tape to your bathroom mirror. Missing one day didn't materially affect habit formation. One miss doesn't reset you. People quit because they think it does.
So if you started something new in September and it still feels like work, you're not failing. You're on schedule. Give it until Christmas before you decide anything.
Read it here: Does It Really Take 66 Days to Form a Habit?
Article 2: Is AI ruining our skills? Early results are in, and they're not good
Source: Scientific American
This one made me put my coffee down.
It covers a growing pile of evidence that leaning on AI tools can erode the skills professionals spent years building. A survey of US health care workers found 70 percent of nurses and 77 percent of physicians are worried about exactly that.
Then there's the study that got everybody's attention. Endoscopy specialists in Poland, every one of them with at least 2,000 colonoscopies under their belt, were given an AI tool that flags precancerous growths in real time. It was available some days and not others. Before the tool came in, the doctors found at least one of these growths in 28.4 percent of colonoscopies. After it came in, on the days they worked without it, that rate dropped to 22.4 percent.
These are experts. Thousands of procedures. And three months of leaning on a tool made them measurably worse without it.
The second study was a coding experiment run by Anthropic. Fifty two software engineers did the same task. Half used an AI assistant. Afterward, everybody took a quiz on what they'd learned. The AI group averaged 50 percent. The group without it averaged 67. The AI users were especially bad at diagnosing errors, which suggests they got the work done without understanding it.
One researcher in the piece put it in a way I can't stop thinking about. People can perform at a high level because they're borrowing the skill from the AI, but they aren't building the skill themselves.
If you use these tools all day like I do, read this one. The answer isn't to quit using AI. It's to decide on purpose which skills you're willing to rent and which ones you need to own.
Read it here: Is AI ruining our skills? Early results are in
Article 3: Career change at 40: a reinvention, not a restart
Source: Natural Genius Academy, Anji Hallewell
Anji Hallewell spent twelve years on the hiring side of the table and the last nine coaching senior people through career changes, and this piece takes aim at one belief she says keeps people stuck for years. The belief that changing careers in your forties means starting from zero.
Her argument is that it almost never does. The skills that made you good, reading a room, building trust fast, structuring an argument, managing a difficult person, don't vanish when you change industries. They travel with you. What changes is the container they sit in.
She also makes the case that a good pivot is tested, not leapt. Real conversations with people doing the work now. A small paid project that lets you feel the new terrain before your mortgage depends on it. Field research before commitment, the same way you'd validate a market before launching into it.
But the section that got me was the one she calls the guilt nobody names. Guilt about disrupting the household income. Guilt about the years your family spent supporting the version of you that now wants to change. She says she's watched directors who can talk through market risk with total calm go quiet when the subject turns to what their teenager will think of a pay cut.
Her answer isn't a pep talk. It's a plan. A well built pivot answers the guilt with sequencing and evidence, so the people who depend on you aren't being asked to trust a leap.
You can probably guess why a guy whose podcast is called Grace Over Guilt liked that section.
Read it here: Career change at 40: a reinvention, not a restart
Podcast of the Week
15 Success Habits to Mastering Anything in Life, The Ed Mylett Show
Ed Mylett has a way of saying things I've heard a hundred times so they land like the first time. This weekend special came out October 10th, and it's really two episodes in one.
The first half is Ed on his own, breaking down the stages every pursuit goes through. His version goes something like this. Every skill starts out ugly. Then it gets awkward. And then, eventually, things start to mesh. His point is that the awkward stage is where most dreams quietly die. Not because people aren't capable, but because they quit right before it starts to work.
That line hit me in the chest, because I'm in the awkward stage of about four things right now.
He also gets into what he calls hidden progress, what's happening underneath the surface when it feels like nothing is working, and he walks through seven moves for connecting what you want to what you actually do each day. There's a part where he challenges you to look honestly at your own scoreboard, and he admits to one habit he does out loud that probably looks a little crazy to people around him. I won't spoil it.
The second half is a conversation with Jon Gordon, the leadership author who works with elite coaches and teams. Ed describes him as someone who earned his optimism the hard way, and he doesn't let Jon off easy. He presses him on how he actually lived his ideas when things got hard. Jon lays out a framework of five forces that pull people off course, with an answer for each.
The episode runs about an hour and a half. If you only have twenty minutes, listen to the first section on the stages of mastery. Then go do the thing you were about to quit.
The tagline of the episode is that you're making more progress than you think. I needed that this week. Maybe you do too.
Track on Repeat
WHO I WAS, NF and mgk
This came out last November on NF's EP, Fear, and it's been on repeat on my runs and at my desk for two weeks straight.
It's the first time NF and mgk ever worked together, after years of fans asking for it. The beat is stripped way down. A finger picked acoustic guitar, some piano, not much else. No stadium theatrics. Just two guys taking turns going through the boxes in the attic.
mgk goes first, and his verse is raw. He talks about his father's death, about broken relationships, about how the most he ever earned didn't fix the empty feeling. And then he gets to the part that stopped me cold. He talks about hiding from God for more than twenty years, and coming back, and not being asked to explain himself or prove he still qualified. Just being welcomed home like a son.
If you know the story of the prodigal son, you know exactly what he's describing. The father doesn't wait for the speech. He runs.
mgk says he recorded the whole verse in one take, the same day NF sent him the beat, and they kept it. You can hear it.
NF's verse is the opposite in tone. Careful, precise, wound tight. He's working through old anger and the habit of shutting down, and what makes his part land is that he's not just worried about himself anymore. He's worried about what he passes on to his kids. As a dad, that part got me.
There's also a little detail I love. NF is famously a perfectionist, and he left the studio chatter in. You can hear somebody asking for the vocal to be turned up. He left the rough edges on purpose, which feels right for a song about not hiding who you were.
It's three minutes long. Play it loud. Then think about who you used to be, and whether you've forgiven him yet.
Listen here: WHO I WAS on Spotify
Show of the Week
The Diplomat, Season 4, on Netflix
If you haven't watched The Diplomat, start at the beginning. If you have, you already know why it jumped straight to the top of my list.
Keri Russell plays Kate Wyler, a career diplomat who got handed the job of US ambassador to the United Kingdom when she didn't want it, while her marriage to Hal, played by Rufus Sewell, slowly came apart around her. Hal is brilliant, charming, ambitious, and absolutely exhausting. The show has always been half political thriller and half the most honest portrait of a complicated marriage on television.
Season 3 ended with Kate finding out Hal had been working behind her back with President Grace Penn, played by Allison Janney, on a move involving a stolen nuclear warhead that the British didn't know about. That's a lot of trust to blow up in one episode.
Season 4 dropped on Netflix on October 15th, all eight episodes at once. Debora Cahn is still running the show, and Janney and Bradley Whitford, who plays her husband Todd, are now full series regulars. Cahn told Netflix the season is built on the foursome of Kate, Hal, Grace, and Todd, and the official synopsis says two marriages threaten to eat each other alive.
So, a calm one.
Here's the moment from the teaser that made it this week's pick. Kate tells Hal she isn't trying to get out of the marriage. She's trying to get back in.
That's a different sentence than most of us know how to say. When something we committed to gets hard, whether it's a marriage, a business, a friendship, or a promise we made to ourselves, the easy move is to look for the exit. Getting back in is harder. You have to face what happened, own your part, and choose the thing again on purpose.
Kate is not a perfect person. Neither is Hal. That's the point. Nobody on this show gets to be the clean hero, and the people worth rooting for are the ones who keep choosing to come back to the table.
Watch it here: The Diplomat on Netflix
Resources
One step, one day. Grace over guilt. — Dan Kaufman
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