In this episode, Tim sits down with Katie Cunningham, a freelance producer and writer-director, for a conversation about risk, identity, and how she built a creative life on your own terms. Katie shares the story of leaving a corporate marketing job in 2022 to write and direct a self-funded short film (even though her finances weren't necessarily ready for the leap), and how that decision led to later creative success. She talks candidly about what it took to rewire a long-held identity as someone who was "bad with money," the practical systems that changed her relationship with her finances, and Produce Your Life, a project she launched to apply a production mindset to everyday life. It's a conversation about building financial confidence step by step and trusting yourself enough to take the leap before everything feels perfectly ready.

Katie's question for Tim: Can we talk about rewiring my internal story to look directly at and take responsibility for money instead of remaining in a state of chaos?

Key Takeaways:

1. Katie left her corporate marketing job in 2022 to pursue writing and directing, despite knowing that it was a financial risk.
2. Before making the leap, she spent months consolidating scattered retirement accounts and reviewing her spending to trim unnecessary expenses — unglamorous groundwork that gave her a clearer picture of where she actually stood financially.
3. As a new freelancer, Katie embraced a period of deliberate "unmooredness," traveling and taking on flexible freelance production work without a fixed home base, which matched the freedom she identified as a core value.
4. Katie's rules for deciding which jobs to take are built around how a project sustains her lifestyle costs, or whether it's an opportunity to learn from someone she admires (even at a lower rate).
5. Katie's biggest piece of advice for freelancers is to know exactly what their lifestyle costs every month, since that number changes everything about which gigs make sense to take and removes a huge amount of background financial stress.

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Katie's website