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3 / Are you mistaking the stories in your head for facts?

August 21, 2022

Welcome to Issue #3

I love using metaphors with clients. A metaphor takes something abstract, like “being CEO,” and pulls everyone present into a context they understand so the abstraction becomes something familiar to play with.

My favorite metaphor (okay, technically, it is a simile) lately is how a startup is like a mountain climbing expedition and the CEO is the expedition’s guide.

The guide supplies a map that lays out which mountain the group will climb, where each day’s campsites are, the selected route, features in the landscape like rivers, bridges, and more. The guide gets to know their crew members, assigns responsibilities according to relevant skills, and so on.

In a startup, the CEO supplies a vision that lays out an objective (sell $2M of this thing this year!), milestones to achieve the goal, potential obstacles (failing to solve customer needs!), hiring and assigning responsibilities, and so on.

When climbing a mountain, the map doesn’t match the territory. That bridge you were planning on using to cross the river? It turns out that’s gone. The guide has to work with the team to come up with a solution. The same goes for a startup. The CEO lays out a (top-down) vision at the start of the quarter, and four weeks in, something unforeseen happens, and the team has to adjust (bottom-up).

This metaphor can help a CEO understand their role, and it can also give the team a shared language to maneuver the challenges that inevitably arise over the lifetime of a startup. Climbing a mountain is hard, accidents happen, and people get grumpy (especially when hungry and tired), but the team has to remember that everyone is in it together to achieve their shared goal.

Big Idea #3: Fact vs. Meaning

I learned this from a coach of mine back in 2014. I've since seen the idea in various formats, but I'm unsure where it came from originally.


One of the most common traps I see the founders I coach falling into is mistaking the stories in their heads for facts.

Facts are things we all observe. They are things that have happened, witnessed, and we can agree they happened. If I hit you in the face with a water balloon full of 35°F water, we’re not going to argue about whether you just got hit in the face with an icy cold water balloon—unless I’m a dirty liar, which for the sake of simplicity we will assume I am not.

Not only am I not a dirty liar, but I am also not a sonofabitch, so I did not mean to hit you in the face with the water balloon—I’m just an untrained liquid projectile launcher. But anyone who has ever been hit in the face with a water balloon knows that it’s easy to jump to the conclusion that their assailant definitely did that shit on purpose. The meanings we create about the facts we observe are not facts—they are interpretations or stories we tell ourselves about the facts.

The meaning we give a fact—like getting hit in the kisser with a slushy latex bag of water—can dramatically change how we react.

  • Meaning 1: Supposing you’re charitable, you may decide I didn’t do it on purpose, I slipped, it must have been an accident, and gawdang, that was kinda funny.
  • Meaning 2: Supposing you don’t really trust me, the meaning you make up may be that I am most definitely a sonofabitch, I meant to do it, and I’m looking to put the hurt on you via tap-water trajectile.

If you’re in the meaning 1 camp, you’ll likely forgive me, laugh about it, and move on. As for meaning 2 camp, things will get ugly one way or another.


That may have sounded like an application or practice, but there’s a lot more under the hood to put to work here, starting with writing a no freezing water balloon in the office policy.

The first thing to take away here is that everybody makes up stories about stuff that happens. You have done this today—I guarantee it.

The second thing to take away is that people are especially prone to making up stories when there are missing facts. For example, if I’m late to a meeting, you don’t know why I’m late. You know I’m not there. So until you can get more information, you have to sit there not knowing. And people hate not knowing. So we make up a story to avoid living in the scary Land of Unknowing.

The third thing to take away is that the key is to begin to notice when you’re making up stories. I like to call this “noticing when you’re living in Meaning Land instead of Fact Land.” People are almost always (but not always) living in the Land of Meaning when they’re feeling negative emotions toward or about themselves, other people, or circumstances.

Don’t believe me? Remember when Alexis interrupted you this week (fact)? You told yourself a story (they’re rude and self-absorbed). Remember when you couldn’t find the motivation to work past 3pm yesterday? You told yourself a story (all the other founders are working until 8pm and definitely not exercising to beat the evening rush). Remember when there was an S3 outage on launch day? You told yourself a story that Lord Bezos, Destroyer of Milk and Honey, personally cursed your team.

Stories don’t always have to be negative. For example, Positive stories are behind the misalignment of confidence and competence in the Dunning-Kruger Effect.

Negative or positive, the point is that *you do not see Reality—*you’re not living in the Land of Facts, you’re living in the Land of meaning.

So once you notice you’re in meaning Land, it’s helpful to try three things:

  1. Draw a T-Chart like the one in the graphic where the left side is labeled “Facts,” and the right is labeled “Meanings.” This way, you’ll be able to see where you’re at.
  2. What information could I get in order to shift back to the Land of facts? This often takes the form of a question: “Hey, why did you throw that water balloon at my face?”
  3. What about my relationship with this person or situation made me come up with that meaning? This is more about self-reflection. Would you have assumed the same intention if someone else hit you with a flying bag of water?


Things happen, and then people come up with stories about those things—especially when they are missing information. Our interpretations—the meaning we make—color what we think Reality is. They can make someone a villain or a hero, but they’re often made up. If you’re feeling frustrated with yourself, someone else, or a situation, draw up yer ol’ fact vs. meaning T-Chart and get clear which Land you’re in. Once you’re sure you’re camping out in Fact Land, you can figure out whether you need more information to assess the situation, whether that’s by talking to someone else or spending some time reflecting.

Reads & Resources


I have a Notion database where I collect all the articles, tweets, videos, and more. Inside there’s a tag called “Super Resource” with a dynamite emoji, and I’d add two of those tags to Michael’s talk at Heavybit on Pricing if I could. The link has the transcript and video, and you can download the slides. My favorite part is when he explains why it’s possible to charge $260 for a toaster.

From Twitter

I don’t know if it’s just me, but I feel like Paul has been much more active on Twitter than usual. It’s hard to think of somebody who has seen more companies go from 0-100 and everywhere in-between than Paul. The gist of this tweet? Only hire someone if the lack of that person is the main thing holding back growth.


“The Unicorn Launcher” is a new podcast with Executive Coach Matt Mochary and two Australian tech founders. I particularly liked this episode because it’s a great example of what people can expect to get out of a real coaching situation with lessons for personal and professional parts of a leader’s life.


If you’re a CEO or product leader and haven’t read this book, that’s a lot like being a Christian without having read the damn Bible. This has to be one of the top 5 books I recommend my clients read. Marty Cagan has been studying best practices for product management at the Silicon Valley Product Group since he was the VP of Product at Netscape from ‘96-’01. One thing you can expect after reading this is to do away with product roadmaps once and for all.

Dice Roll

A friend of mine sent me a tweet with an excerpt from Dee Hock’s book (the founder of), where Dee suggests managers should be spending only 5% of their time managing their subordinates, 20% managing their peers, 25% managing up, and 50% of their time managing themselves. I think this is one I’ll be thinking on for a long time.

That’s all for this week. I’m looking forward to what’s next!