No. 641 – August 10, 2025
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Tiny Thoughts
Telling yourself you’ll do it tomorrow is how dreams die.
The problem with success is that it teaches you the wrong lessons. What worked yesterday becomes religion, and religions don’t adapt.
People think good decision-making is about being right all the time. It’s not. It’s about lowering the cost of being wrong and changing your mind.
When the cost of mistakes is high, we’re paralyzed with fear. When the cost of mistakes is low, we can move fast and adapt.
Make mistakes cheap, not rare.
Insights
Poet Christine Evangelou on a cluttered mind:
“A crowded mind leaves no space for a peaceful heart.”
Steve Jobs on courage:
“Have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.”
Philosopher Arthur Schopenhauer on the need to not only accumulate information but also to reflect and digest it:
“You may accumulate a vast amount of knowledge but it will be of far less value to you than a much smaller amount if you have not thought it over for yourself; because only through ordering what you know by comparing every truth with every other truth can you take complete possession of your knowledge and get it into your power.”
The Knowledge Project
Ryan Petersen is the founder and CEO of Flexport, the platform that coordinates global logistics from factory floor to customer door. In this conversation, he’s refreshingly transparent about the mistakes and painful lessons he’s learned building several companies.
He opens up about stepping down as CEO, his struggles with self-confidence, and what happened when he was forced to step in and save his own company. Along the way, we explore why micromanagement might be the secret to better leadership, how tariffs reveal the hidden complexity of global trade, and what it takes to scale a company without losing control.
There are stories and lessons here you won’t find anywhere else.
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Thanks for reading,
— Shane Parrish