The Hidden Advantage of Not Having a Plan
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👋 Hey dumdums,
Last Tuesday I spent forty-five minutes color-coding a spreadsheet to organize my weekend. Saturday would be "productive errands." Sunday was "creative restoration." I even scheduled a 3pm "spontaneous walk." Then my friend texted asking if I wanted to drive to a flea market two hours away, and I said no because it wasn't on the spreadsheet.
I spent my "creative restoration" block eating crackers and staring at a wall.
Plans are supposed to help us. But somewhere along the way, I started serving the plan instead of the other way around. Which got me thinking about why we worship planning in the first place, and what we're actually sacrificing on that altar.
Not having a plan sounds like laziness...
It sounds like something your disappointed father would cite at Thanksgiving. But there's a hidden cost to planning that nobody talks about: every plan is a bet on a future you can't predict, made with information you don't have yet.
The moment you commit to a plan, you start filtering out everything that doesn't fit it. Opportunities that don't match the roadmap look like distractions. Unexpected information feels like an inconvenience. You become a prisoner of Past You's limited imagination.
Nassim Taleb calls this "optionality." When the future is genuinely uncertain, the smart play isn't predicting correctly. It's staying flexible enough to grab whatever shows up. Plans feel like control, but they're often just pre-commitment to a path that might be wrong.
❝ A plan is a loan you take out against a future that hasn't agreed to the terms. ❞
The planless person isn't lost. They're liquid. Ready to pour into whatever container reality offers.
YouTube's Accidental Everything
In 2005, Steve Chen, Chad Hurley, and Jawed Karim launched YouTube as a video dating site. Their slogan was "Tune in, Hook up." They were so desperate for dating videos that they posted Craigslist ads offering to pay women $20 to upload clips of themselves talking about their ideal partner. But nobody did.
So they gave up. "Forget the dating aspect," Chen said. "Let's just open it up to any video." Eighteen months later, Google bought them for $1.65 billion.
Read the full story in The Guardian
Slack's Beautiful Failure
Stewart Butterfield spent three and a half years building Glitch, a massively multiplayer online game that barely anyone wanted to play. What his team did use obsessively was the internal chat tool they'd built to coordinate development. When Glitch died in 2012, Butterfield pivoted in 72 hours.
That chat tool became Slack, now worth over $27 billion. The plan failed. The accident won.
TechCrunch has the origin story
Instagram's Whiskey Problem
Kevin Systrom's original plan was Burbn, a check-in app for bourbon enthusiasts to share where they were drinking. The app flopped. But Systrom noticed users kept ignoring the check-in features and just posting photos. He stripped everything else out.
Instagram hit 25,000 users in 24 hours. Within 18 months, Facebook acquired it for $1 billion. Systrom's plan was a dead end. His willingness to abandon it was the actual product.
What Does Science Have to Say?
In 1976, psychologist Barry Staw ran a now-famous experiment showing that people who've committed to a plan will keep throwing resources at it even when it's clearly failing. He called this "escalation of commitment." Plans don't just guide us. They trap us. More on the research here.
Meanwhile, researcher Saras Sarasvathy studied how expert entrepreneurs actually make decisions. Her finding? The best founders don't predict and plan. They use "effectual reasoning," starting with what they have and staying open to wherever it leads. Planning is what MBA students do. Optionality is what successful founders do. Sarasvathy's research explained.
Dumb Word of the Day
Kairos (KYE-ross) noun
An ancient Greek word meaning the opportune moment for decisive action. Unlike chronos, which measures clock time, kairos is about recognizing when conditions suddenly align for something that wasn't in the plan.
Let's use it in a sentance: "I was supposed to be doing laundry, but a kairos moment arrived when my neighbor mentioned she was selling her vintage typewriter for $20."
This week, pick one day and delete your to-do list. All of it. Just start the day with nothing planned and see what you actually want to do when 9am arrives. Notice what opportunities show up when you're not already committed to something else.
The goal isn't chaos. It's discovering what your real priorities look like when Past You isn't calling the shots.
Thanks for getting dumb with me today.
Remember, the spreadsheet didn't go to the flea market, but you could have.
David 🎉
