One book, three articles, one podcast, one track, one movie. Filtered for people who are actually building something.
Every so often a week arranges itself around one idea without me planning it. This was one of those. The book, the articles, even the podcast I stumbled into on a walk, all of it kept circling the same thing. How do you tell whether you made a good call when the world keeps handing you results that don't match your reasoning?
Then Friday night I watched Adam Sandler hit a golf ball with a hockey slapshot and stopped thinking about any of it for two hours, which was probably the healthiest decision I made all week.
Grab your drink. Let's get into it.
Book of the Week
Annie Duke spent about two decades as a professional poker player before she started writing about decision making, and that background is the whole reason this book works. Poker is a game where you can play a hand perfectly and lose, play it terribly and win, and have to sit down and do it again the next hand without letting either result poison your thinking. Which is to say, it's business with faster feedback and better snacks.
The central idea is that we're wired to judge decisions by how they turned out. Duke calls it resulting, and once she names it you start seeing it everywhere. The founder whose reckless bet paid off and now gives talks about trusting your instincts. The manager who ran a solid process, caught a bad break, and got quietly sidelined. We reward luck and punish variance and call the whole thing meritocracy.
What separates this from the rest of the decision making shelf is that Duke isn't trying to make you more rational in the abstract. She's trying to make you better calibrated, which is a different and more achievable target. Certainty was never on offer. Every decision is a bet on an uncertain future, and the useful question isn't "am I right" but "how confident am I, and will I say the number out loud."
That last part is where the book earned its keep with me. She pushes hard on the practice of assigning explicit confidence levels to your beliefs, and on the social discipline of saying them to other people. It's uncomfortable. Saying "I'm about sixty percent on this" in a room where everyone else is speaking in certainties feels like weakness. Duke makes the case that it's the opposite, and more importantly, that it's the only way to ever find out whether your sixty percents are actually sixty percent.
The chapter on truthseeking groups is worth the price by itself. Duke argues that you can't calibrate alone, because you're the least reliable witness to your own reasoning. You need a small group with an explicit agreement to focus on process over outcomes, to steelman the other side, and to keep score honestly. Not a mastermind where everyone congratulates each other. A group where the highest compliment is someone telling you the flaw in your logic before it costs you.
She also has the best treatment of hindsight bias I've read. Your brain doesn't store the uncertainty you felt at the time. It overwrites it with what you know now, so every past decision looks either obviously right or obviously stupid. You can't feel this happening, which is what makes it dangerous, and it's why she keeps pushing you to write things down before you know how they end.
If you've got a decision in front of you right now that you keep circling, read the first four chapters this weekend. The rest can wait. Those four will change how you talk about the choice, and in my experience that's most of the work.
Get it here: Thinking in Bets on Amazon
Three Articles Worth Your Time This Week
Article 1: AI Agents for Small Business, Hype vs. Reality in 2026
Source: Thomas Wiegold
I've read a lot of AI agent takes this year and most of them are either breathless or dismissive. This one is neither, which is why I'm sending it to you.
Wiegold's framing is that the market numbers are genuinely real and genuinely misleading at the same time. Yes, a large majority of small businesses now report using AI in some form. But he points at the far more revealing figure, which is how few have actually integrated it into core operations. The gap between those two numbers is the whole story. Most of what gets counted as adoption is somebody with a subscription and a browser tab.
The line that stuck with me was his observation that most of the impressive agent demos circulating online are people configuring things for fun, not for measurable return. He's not sneering at that. He explicitly says experimentation matters. But he draws a hard line between weekend tinkering and something that runs in production and makes money, and he's honest that the distance between those two is enormous and mostly unglamorous.
What I appreciate is that he doesn't land on "so ignore it." He lands on specificity. Pick the workflow, measure the thing, and be ruthless about whether it actually moved. That's a boring conclusion and it's the correct one.
Read this one if you've been feeling behind. You're probably less behind than the noise suggests, and the fix is narrower than you think.
Read it here: AI Agents for Small Business: Hype vs. Reality in 2026
Article 2: The Pre-Mortem Practice, Spot Failure Before You Start
Source: Vikas Malpani
This one pairs so cleanly with the book that I almost didn't believe I found them in the same week.
The pre-mortem comes from psychologist Gary Klein. Before you commit to a plan, you imagine it's twelve months later and the thing failed badly, then you write the story of why. Not "it might fail." It failed. Past tense. The verb tense is doing real work, because imagining something as an accomplished fact unlocks reasons your brain won't produce when you're only considering a possibility.
Where Malpani goes further than most write ups is his insistence that a pre-mortem run once is a snapshot, and a pre-mortem run on a cadence is a practice. The failure most likely to kill you on day zero is rarely the one most likely to kill you on day ninety. So he puts a recurring quit-or-commit review on the calendar, separate from normal operations, and treats it as protected time.
He leans on Annie Duke for the reasoning behind that, which is the tie back to the book. Her point is that a founder's default state is to keep going, and a default of keep going means you only ever stop after the money runs out. A scheduled review converts quitting from an act of weakness into a routine decision. That reframe is worth sitting with if you've got something you've been dragging along.
His review has a question I've now stolen outright. Did any kill criterion trip since last time, and did I honor it, or did I quietly move the goalposts? I've moved goalposts. You've moved goalposts. Writing the question down where you have to answer it is a decent defense.
Read it here: The Pre-Mortem Practice: Spot Failure Before You Start
Article 3: Why the Smartest Solo Entrepreneurs of 2026 Are Staying Small
Source: Millennial Magazine
I went into this one expecting a puff piece about the joys of the one person business and got something considerably more honest.
The setup is familiar. Software and AI now let one person do work that used to take a department, so a lot of builders are choosing ownership and control over outside money and fast growth. Fine. We've all read that.
Then the piece does the thing I wasn't expecting, which is to take a hard swing at its own premise. Staying small is not the same as staying calm. It quotes founder mental health data that is genuinely rough, and makes the point that running a one person business can concentrate the pressure rather than relieve it, because there's nobody to hand the hard thing to at two in the morning. It also notes that a solo operation is a single point of failure. If you get sick, the business gets sick.
And it does something almost nobody does, which is put realistic numbers next to the famous outliers. The people making millions alone are real and they are outliers, and the average nonemployer business in this country makes a fraction of what the highlight reel implies. The article's conclusion is that a lean business is best understood as a route to a sustainable income, not a lottery ticket.
I needed to read that. There's a version of the small business gospel that's really just hustle culture wearing a cardigan, and this piece calls it out. Calm is a practice you build. It isn't a size you arrive at.
Podcast of the Week
I put this on during a walk expecting the standard Shark Tank origin story and got something with a lot more grit in it than I bargained for.
Herjavec's background is the part people tend to skip past. He came to Canada as a kid from Yugoslavia with a family that had close to nothing, and the early jobs were the early jobs. Waiting tables. Delivering things. The kind of work that doesn't make it into the keynote. What he does well in this conversation is refuse to sand that down into a tidy underdog arc. He talks about it as a period that shaped his relationship with risk in ways that were useful and in ways that weren't.
The mindset shift in the title is less about positive thinking than about time horizon. His argument, roughly, is that most people are running a short game while telling themselves it's a long one, and the tell is how they respond to a bad quarter. If a bad quarter changes your strategy, you never had a strategy. You had a hope with a spreadsheet attached.
There's a stretch in the middle where he talks about the years after his first company sold, and it's the least polished part of the episode and the best. He's candid that the money didn't resolve the thing he thought it would resolve, and that he had to figure out what he was actually building for once the obvious answer stopped working. If you've ever hit a milestone and felt strangely flat afterward, that section will land.
He's also refreshingly blunt about sales, which is his real expertise and the thing he's least precious about. His view is that most people fail at selling not because they lack technique but because they haven't decided they're allowed to ask. That's a mindset problem wearing a skills problem's clothes, and I've watched it play out with enough consultants to know he's right.
Worth the listen, especially on a walk where you're not taking notes and can just let it run.
Listen here: The Mindset Shift That Made Me Millions on Spotify
Track on Repeat
Ten years. That's the thing I keep getting stuck on. This track came out in December of 2016 and here it is with an anniversary edition, and I remember exactly where I was and what I was building when it first showed up, and almost none of that still exists in the form it was in.
For anyone who doesn't know it, this was Armin van Buuren's first real move into psytrance, made with the Israeli duo Vini Vici, with vocals and tribal chanting from the French band Hilight Tribe. It shouldn't work as well as it does. It's got a bassline that behaves like a machine and a vocal that sounds like it was recorded around a fire, and the friction between those two things is the entire song.
I don't put this on to relax. I put it on when I've got something in front of me that I've been avoiding and I need my body to catch up with my intentions. There's a stretch in the back half where the whole thing drops out and rebuilds, and I've timed more than one hard task to start exactly there, which is a slightly ridiculous system that works every single time.
The anniversary framing hit differently than I expected. A decade of the same few minutes doing the same job for me across three completely different chapters. Most of what I was building in 2016 is gone. This survived.
Not background music. Put it on properly.
Listen here: Great Spirit (10th Anniversary Edition) on Spotify
Movie of the Week
Look. I'm not going to sit here and tell you this is a good film.
Adam Sandler brought Happy back nearly thirty years after the original, with Christopher McDonald returning as Shooter McGavin, Julie Bowen and Ben Stiller back as well, and a cameo list that runs from Bad Bunny to Travis Kelce to a pile of actual PGA pros including John Daly and Jack Nicklaus. The critics were not kind. The Hollywood Reporter called it a whiffed shot. And then it went out and posted the biggest opening weekend Netflix has ever had for a film in the US, which tells you something about the distance between what critics measure and what audiences actually want on a Friday night.
Here's why it's in the roundup, though, and it's not just that I laughed.
The premise underneath the jokes is a guy who was great at something a long time ago, walked away, and has to work out whether he's got any business coming back. The game moved on without him. Everybody hits it further now. There's a real question sitting under all the vulgarity about whether returning to a thing you used to be good at is courage or just an inability to let go.
I turned 47 this month. I've been rebuilding a business. I'm in physical therapy twice a week trying to get a knee to do what it used to do without thinking about it. So yes, a broad comedy about an aging athlete deciding whether he's still got it landed on me with slightly more weight than Sandler intended. That's my problem, not the film's.
Watch it with somebody. Don't watch it alone taking notes like I apparently do now. It's a two hour permission slip to stop being serious, and some weeks that's the most useful thing on the menu.
Watch it here: Happy Gilmore 2 on Netflix
Resources Section
Movie: Happy Gilmore 2 (Netflix)
One step, one day. Grace over guilt. — Dan Kaufman
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