Hello Reader, My wife Taylor hosts a podcast called Doomed to Fail with her co-host Farz. The premise: take history’s most notorious disasters and epic failures, analyze the red flags, and ask the uncomfortable questions: How did things go so wrong? Could this have been avoided? They invited me to talk about a mental model that answers both questions. It’s called second-order thinking. And I wanted to share the core ideas with you here, because this pattern is everywhere. The Scene That...
9 days ago • 5 min read
Hello Reader, Austria and Germany share a border, similar cultures, and comparable healthcare systems. Ask citizens of both countries whether they support organ donation, and roughly 85% say yes. Yet Austria has a 99% organ donor registration rate, and Germany sits at 12%. Same values. Same medical infrastructure. Opposite outcomes. The difference? Austria uses opt-out registration. Germany uses opt-in. In Austria, you are considered a donor unless you actively decline. In Germany, you're not...
17 days ago • 3 min read
Hello Reader, February 1, 2003. Space Shuttle Columbia disintegrated over Texas during reentry. Seven astronauts die. NASA investigators later traced the failure to a foam strike during launch (a piece of insulation that hit the wing at 500 mph). Engineers knew about the strike. They analyzed it. They presented their findings to management sixteen days before the disaster. Their slide said: "Review of test data indicates conservatism for tile penetration." Management saw no red flags. The...
24 days ago • 3 min read
Hello Reader, Athens, 461 BC. Workers haul limestone blocks under the Mediterranean sun, building walls that will connect the city to its port at Piraeus. The Athenian navy has just played a crucial role in helping to defeat the Persian Empire. Their democracy is flourishing. Trade routes are expanding. They're becoming wealthy, confident, and powerful. Fifty miles south, Spartan leaders watch. They see the walls rising. They calculate what those fortifications mean—Athens can now withstand a...
about 1 month ago • 4 min read
Hello Reader, My product roadmap started with three clear phases. Then marketing requested one automation. Sales needed a dashboard feature. Operations wanted a process update. Leadership suggested an innovative integration. Six months later, I was still in phase one. Nothing had shipped. My team was exhausted. I'd become a product therapist, managing expectations instead of executing the plan we all agreed on. The problem wasn't that the requests were bad. It's that I never defined when to...
about 1 month ago • 4 min read
Hello Reader, Someone offers you a coin flip. Heads, you win $100. Tails, you lose $100. Fair odds. You decline immediately. They adjust: Heads, you win $200. Tails, you lose $100—positive expected value, mathematically advantageous. You still decline. That's Loss Aversion. Losing $100 hurts approximately twice as much as winning $100 feels good. Your brain weighs potential losses roughly two to one against equivalent gains. You're not evaluating decisions on math. You're evaluating them on...
about 2 months ago • 3 min read
Hello Reader, The executive team agrees: the Q4 strategy is solid. Everyone nods. The plan gets approved. Three months later, the market has shifted, and your assumptions were wrong. No one wants to admit they saw the warning signs but stayed quiet because the group had already made up its mind. You didn't fail because of bad people. You failed because agreement felt safer than reality-testing. Enter Scrum: a two-week work cycle with four mandatory checkpoints: Sprint Planning (commit to...
about 2 months ago • 3 min read
Hello Reader, You schedule two-hour blocks for deep work. Twenty minutes in, you're answering Slack messages. You try again tomorrow. Same result. You download a focus app, turn off notifications, and move to a quiet room. Thirty minutes this time, then you're back in reactive mode. You adjust your tactics—using better tools, stricter rules, and more discipline. But the pattern persists. Most people would continue to tweak the execution. That's single-loop learning: fixing the symptoms...
about 2 months ago • 6 min read
Hello Reader, You sit down to write the report. Three hours later, you're still staring at the same paragraph, feeling guilty about checking email six times and wondering why you lack discipline. You're not undisciplined. You're fighting your own biology, and your biology wins every time. That's the Pomodoro Technique, though most people miss the real insight. It's not about productivity, but rather about recognizing that your brain operates in natural cycles of focus and fatigue, and that...
2 months ago • 3 min read