start again no. 58: getting comfortable with "i'm not sure"

Hey 👋🏽,

How do we get better at making decisions?

I thought about this this week while chewing on a question shared in response to last week’s recap of Jason Calacanis’s Angel and an article about How Billionaires See Themselves (thanks Hannah!).

Realizing how little I actually knew, I enlisted the help of many of you via text, phone and carrier pigeon to begin to do the work required to have an opinion.

Hannah’s question was a forcing function to finish professional poker player and Columbia/UPenn grad Annie Duke’s Thinking in Bets. In the book Annie talks about how beliefs are typically formed:

  • We hear something

  • We believe it’s true

  • We maybe/sometimes refine that belief later

Beliefs are the basis of all of the bets we make. We make bets everyday with the things we do and don’t spend our time and money on. If we create feedback loops for our beliefs to continuously change with new information and experience, we’ll make better bets and create better outcomes. 

We’ll also begin to get comfortable with uncertainty, saying “I don’t know, let’s find out together.” We’ll welcome opinions that differ from our own and begin to move towards objectivity. Maybe, just maybe, we’ll even change our minds.

It was fun this week to connect with friends about ideas and opinions with curiosity, staying open minded throughout inquiry, sensing and working through resistance to learn. Answering questions with more questions and reading made me want to create a forcing function for deeper exploration of thought, like figuring out how to create a turtleocracy within my network.

What big questions are you thinking about currently? I’d love to know.


I see you, I love you, let’s have a great week,

H

About me: I’m the COO of Animalz, a global content marketing agency and a cycling instructor. I live outside of washington, DC with my partner, 5yo and dog Duke Ellington.