The Thing We Never Talk About

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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In this episode, Tim  talks with Tony Rolando, musician, instrument designer, and founder of Make Noise Music, about building electronic musical instruments, growing a niche manufacturing business, and staying creatively grounded as success scales. Tony shares how his background as a musician shaped the unconventional design philosophy behind Make Noise’s modular synthesizers. They discuss the realities of scaling a creative business, including hiring, cash flow, and the tradeoffs between growth and personal freedom. The conversation also touches on Tony’s evolving relationship with money, health, and what it means to use success to support a meaningful life.
Tony's question for Tim: With the way the current administration is increasingly isolating the US from the global economy, I have had the thought that I should shift my investments to be heavier in European and emerging markets. Add to that, that my retirement portfolio is almost entirely SRI and I sometimes feel it makes even more sense to shift to the European market. Do you have thoughts on this? 
Key Takeaways:
Tony began Make Noise in 2008 after leaving a low-paying job at Moog Music, initially building modules by hand with no formal business plan.
Early Make Noise designs emerged from Tony’s personal musical needs—creating modules that didn’t yet exist in the small modular synth market at the time.
Tony approaches instrument design as a musician first, deliberately stacking functions into single controls to make instruments more expressive and playable.
As Make Noise grew, Tony learned that hiring employees gave him his personal life back—but did not necessarily increase his income.
Tony shares personal reflections on money, saving habits, health challenges, and the importance of actually using money to enjoy life.
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Make Noise Music
Make Noise's YouTube page
Tony's Bandcamp page

With investing tools cheaper & more accessible than ever, why would anyone still pay an advisor to manage their investments? In this solo episode, Tim breaks down how the biggest benefit of investment management isn’t better stock picks or secret knowledge, but help with follow-through, emotional decision-making, and actually doing the things you already know you should be doing. The episode closes with practical guidance on how to decide whether managing your own investments or delegating that responsibility makes the most sense for you. One Key Takeaway: Paying for investment management isn’t about access to information or tools—it’s about whether having support helps you make better decisions and stick with them over time.
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