The Thing We Never Talk About

Getting stuck in a “comfort zone” is often a sign that something isn’t actually all that comfortable—especially when it comes to money and long-term decisions. In this episode, Tim explores why so many important financial moves get stuck in the “I should” category, why waiting for the perfect moment usually makes things worse, and shares five practical, low-pressure ways to break out of an uncomfortable status quo and start making progress. One Key Takeaway: Real change doesn’t start with a perfect plan—it starts with small actions that gets you moving in the right direction.

In this episode, Tim sits down with Sarah Williams for a wide-ranging conversation about her creative path, professional evolution, and the realities of building a sustainable career on her own terms. Sarah shares her journey from early employee to co-owner & co-CEO, and how her leadership evolved as the company grew. She also reflects on burnout, delegation, financial stability, and redefining success beyond revenue. They explore how money, confidence, and self-trust intersect with creativity, especially when your career doesn’t follow a traditional path. Sarah 

Sarah’s question for Tim: how do you see the relationship between financial health and mental and physical health? Growing up I always had a lot of anxiety about Money. As I've gotten older and looked to create more financial security for myself, my family, and my business, that feeling doesn't really go away. How do you think about these challenges?
Key Takeaways:
Sarah Williams shares her path from being the first employee at her company to becoming co-owner and co-CEO, and how long-term commitment shaped her leadership style.
She discusses the difference between building a lasting brand identity versus chasing short-term marketing trends and quick wins.
Sarah reflects on learning to trust her instincts while also developing systems that support sustainable growth.
She talks openly about learning to delegate and empower others as her role shifted from “doing everything” to leading a team.
The episode highlights the importance of aligning personal values with professional goals in order to build a sustainable, fulfilling career.
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Beardwood&Co

In this episode, Tim breaks down everything you need to know about Individual Retirement Accounts (IRAs) and how they fit into a long-term financial plan. He explains the differences between Traditional and Roth IRAs, who can contribute, how much you can save, and how taxes work both now and in retirement. Tim also covers investment choices inside an IRA, rules around withdrawals, and advanced options for self-employed people like SEP and SIMPLE IRAs. Along the way, he shares practical strategies for balancing short-term flexibility with long-term growth. One Key Takeaway: An IRA is one of the most powerful tools for building long-term financial security—but only if you understand how it works and use it intentionally.
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In this episode, Tim talks with cartoonist, writer, and teacher Emily Flake about building a creative career through multiple income streams, persistence, and adaptability. Emily shares what it’s really like to work in fields where rejection is common, success is unpredictable, and financial stability requires constant adjustment. Together, they explore the tension between creative fulfillment and practical money decisions, including saving, budgeting, and long-term planning. One Key Takeaway: A sustainable creative career is built less on sudden success and more on resilience, flexibility, and steady habits that support both artistic and financial health.

Emily’s question for Tim: I’m a freelancer whose income varies wildly, and not only am i terrible with money but I’m actively afraid of thinking about it. I play chicken with my bank account, which is a checking account, because i don’t have a savings account. Don’t you dare even ask if I have a retirement account. I’m 48 gd years old. I guess my question is: how fucked am I?
Key Takeaways:
Emily Flake describes how her career has been built from many different income streams, including cartooning, writing, teaching, comedy, and running creative programs, rather than from one single job.
She explains that publishing work in prestigious outlets like The New Yorker brings visibility and credibility, but does not guarantee long-term financial security.
Emily talks about the ongoing reality of pitching work, receiving rejections, and learning to persist in an industry where “no” is far more common than “yes.”
She reflects on how she balances creative fulfillment with practical concerns like paying bills and maintaining steady income.
Emily speaks candidly about her discomfort with money, budgeting, and long-term financial planning, and how this has affected her decisions.
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Emily's website
St Nell's Humor Writing Residency
Emily's contributor page at The New Yorker

Managing money with an up & down income can feel overwhelming, especially when it comes to planning for the future. In this episode, Tim introduces the “Reservoir System,” a simple, intuitive framework for managing cash flow when your don't know how much you'll make this month or this year. Using the metaphor of managing a town's water supply, he explains how checking, savings, and investment accounts each serve a distinct purpose, and how to know when to keep cash on hand, when to save, and when to invest. This episode is especially helpful for freelancers, creatives, and self-employed people who want more stability without relying on traditional budgets. One Key Takeaway: Financial stability with an irregular income comes from prioritizing cash reserves first, then savings, and only investing once your short-term needs are fully covered.
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