Lessons Learned From The World’s Toughest Milkman

Skipping through Openculture last night, I came upon an indie documentary called ‘I Thought I Told You to Shut Up!’ and all kinds of thoughts ensued. I’m including it below, watch and then let’s talk about the lessons learned from The World’s Toughest Milkman. Reid Fleming is a counter-culture icon, and his journey can teach us a lot about the life of a creative professional:

I’ll be honest – I knew nothing about David Boswell or Reid Fleming until last night. From what I hear, Reid Fleming’s humor is similar to mine, and it’s reflected in some of the scenes I wrote in Mesh. Real comedy, and life lessons, often come from that weird left corner of the universe. Listening to the sad story of Boswell’s good intentions, you can’t help but empathize. An honest artist with a family to feed can be a tasty morsel in the mouth of the Tinseltown Machine.

Even people like Matt Groenig acknowledge Reid Fleming’s impact on the world of comic art, while simultaneously saying ‘yeah, but that’s Hollywood.’┬áSo what lessons can we derive from the fate of the World’s Toughest Milkman? I’ve identified a couple:

  • There’s a universe of art and ideas out there that most of us don’t know about
  • Ideas are easy, execution is hard
  • Real artists ship, but that ship can sink! I need to make sure Mesh gets on the right boat, headed to the right destination
  • Mesh needs, not only people who want to read it, but toughness and competence – I’m going to run into the same types of people Boswell did, and I must be prepared

The unpolished authenticity of Reid Fleming is not to be ignored – it’s very similar to the gritty, authentic universe I’m building over here. If I want that universe to be inhabited and loved, I need to be tough.

Just like Reid Fleming.