Intro

Most leaders want to believe they're building something durable: a company that matters, a culture that sticks, a system people can rely on. But what if most organizations don't have the staying power of a great city like Venice...and instead are more like a gold rush town? What if that same company is more likely to change you than you are to change it? In this episode, Sam sits down with John Cutler, writer of The Beautiful Mess and Head of Product at Dotwork, to pull on the threads John has been obsessively following for years: how organizations actually work, why seeing patterns and being able to act on them are completely different skills, how leadership is like game design, and why embracing the mess might be smarter than chasing clarity.

Learn more about John and Dotwork:

• Read his newsletter
• On LinkedIn
• Dotwork

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Mentioned references:

• Dr. Cat Hicks
• John's post about "the slide"
• W. Edwards Deming
• "Hollow Knight and Silksong"
• John's post with Tom Kerwin
• Ashby's Law of Requisite Variety
• This Beautiful Mess (the emo band)
• John's old Medium posts
• North Star Framework
• Team Topologies, book by Matthew Skelton and Manuel Pais

00:00 Intro + Check-In: What was your first job and did you learn anything from it that you still use today?

02:34 Finding your organizational trigger words

08:41 Can you really change your company?

11:12 Most companies are more like gold rush towns than lasting institutions

15:26 Finding joy at work when the company won't love you back

18:29 Every leader is a game designer

21:45 Stepping back and seeing the system

27:55 Why chasing clarity at work might be the wrong goal

33:20 Having all the data and asking the wrong questions

35:34 How Dotwork is rethinking organizational strategy tools

40:42 Building flexible operating systems that leaders will actually use

44:14 Building a generalist career in a specialist world

50:21 Leave us a review and share the show with a friend

Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.