I’m writing you today from the south of France, where I’ve been taking a little breather before a busy fall. This episode is a reflection on some of the most popular questions that came up around the launch of Never Play It Safe. In the particular lies the universal — and the questions from our community reflect challenges so many of us face.

Matt asked about starting a coaching/consulting side hustle. My answer? Don’t try to solve everything from the couch. Start small. Run tiny experiments. Serve people by solving the problems you’ve already solved for yourself. From there, Dylan jumped in with a question about making a film project with a comedian friend. We dug into what it means to treat creative collaborations like real businesses — agreements, responsibilities, financing, and the all-important element of play.

• Side hustles that stick: why solving your own past problems makes you a better coach or consultant
• Tiny experiments: the fastest way to test ideas and get real data instead of planning forever
• Collaboration as play: how operating agreements and clear roles keep partnerships fun instead of frustrating
• Burnout recovery: why rediscovering play is the antidote to grazing through work like a cow instead of hunting like a lion

The big idea? The best way forward isn’t overthinking — it’s showing up, experimenting, and rediscovering play in the process.