What would it take for work to become optional? In this solo episode, Tim walks through a simple framework for estimating your “enough” number—the amount you’d need in savings & investments to reduce or even eliminate the obligation to work. Using the 4% and 25× rules, he explains how to calculate a target nest egg amount, why it’s useful even if you never plan to retire, and how small, consistent habits can turn into huge long-term growth over time. Whether your dream is full retirement or just the freedom to choose when & how you work, this episode offers clear & practical insight for building that future.Key Takeaways:The 4% rule (and its partner, the 25× rule) provides a simple way to estimate how much you’d need to make work optional.Even if you never plan to “retire,” saving and investing buys you freedom and flexibility later in life.Your target nest egg is determined by your annual spending—spend more, need more; spend less, need less.Consistent small actions—saving a little more, paying debt faster, investing regularly—compound into big results.Financial independence isn’t about quitting work; it’s about creating options and reducing obligation.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletterWilliam Bengen's Wiki pageInvestopedia's page on the 4% Rule
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16:35
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16:35
Michael Perry - Self-Employed Writer
For more than 30 years, Michael Perry has built a life around words — from essays and bestselling books to one-man shows and live events. In this conversation, Mike shares how his blue-collar roots shaped his approach to creative work and money, why he still keeps his nursing license “just in case,” and what it really takes to sustain a self-employed creative life. He and Tim talk about saying no to the wrong opportunities (even when Oprah calls), learning business skills on the fly, and how low overhead, multiple income streams, and a willingness to keep “shoveling” have allowed him to keep doing what he loves.Mike's question for me: Regular IRA, Roth IRA, or SIMPLE IRA?Key takeaways:Longevity through discipline: Mike has supported himself solely through writing since 1992 — proof that persistence can outlast uncertainty.Money is part of the craft: Understanding taxes, mileage, bookkeeping, and contracts enables creative independence.Multiple income streams matter: Like his farmer father, Mike learned to diversify work to stay sustainable.Integrity over exposure: Turning down a high-profile appearance taught him the value of aligning work with values.Freedom, not fame: For Mike, success means autonomy, stability, and the ability to keep creating on his own terms.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Michael Perry's websiteHis new book Improbable Mentors & Happy TangentsPopulation: 485, Mike's breakout memoir about small-town life and volunteer firefighting
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1:18:29
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1:18:29
What Is “Wealth”?
What comes to mind when you hear the word “wealth”? In this episode, Tim explores how our ideas about money are shaped not just by math & spreadsheets, but by deep emotional lessons from family, culture, and experience. He unpacks why textbook definitions of wealth often fall short, shares perspectives from author Morgan Housel, and offers a new way to think about building abundance: creating more “perfect average days”. Along the way, Tim explains how saving and investing can buy you freedom, time, and peace of mind—keys to living a life of true wealth.Key takeaways:Wealth is more than a number. Financial education often emphasizes the math side of money—budgets, compounding, spreadsheets—but emotional lessons from family and culture shape our views about money just as strongly.Early experiences—such as seeing family members struggle with debt, investing, or real estate—can create lasting beliefs about what’s “safe” or “risky” (even if those beliefs aren’t accurate or helpful).Abundance is about “more than enough.” But abundance depends on how much you think you need, not just how much you have.Freedom > possessions. Wealth is really about time and freedom, not just money or material goods.Instead of chasing endless big goals (which look great on social media), let's reframe wealth as the ability to afford more “perfect average days”—days filled with comfort, connection, and choice. Saving and investing is a way to buy those future days of freedom.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletterMorgan Housel
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15:33
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15:33
Sam Ratto - Chocolate Maker
Sam Ratto is the founder of Videri Chocolate Factory in Raleigh, NC, and recently started Golf Golf Golf, an indoor golf simulator business. In this episode, Sam shares his winding path from surfing & skateboarding culture, launching a bean-to-bar chocolate company, and building a new hospitality venture around his love of golf. He talks about the realities of small business finance, lessons learned from failures, and how he balances entrepreneurial risk with personal stability. One key takeaway: The creative path to entrepreneurship isn’t linear—financial discipline and resilience help make bold risks possible.Sam's question for me: what is going to happen with tariffs in the next 12 months?Key takeaways:Sam reflects on his unusual career path—from surfer & skateboarding industry work, to marketing & touring, and eventually to chocolate making.He highlights lessons from running a business: the importance of self-motivation, honesty with oneself and employees, and the heavy mental load of constant financial stress.Sam shares how he learned disciplined personal money habits from his fiancé, including paying off credit card debt and adopting cost-cutting practices like packing a lunch.Golf Golf Golf emerged from his love of golf and recognition that indoor simulators offered a hospitality-driven, lower-overhead business in a growing market.He connects golf to entrepreneurship, noting both require persistence, resilience, and the ability to face setbacks with optimism (and a lesson from his grandmother).LinksSend me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Videri Chocolate Factory – Sam’s chocolate business in Raleigh, NCGolf Golf Golf – His indoor golf simulator businessSimon Sinek Podcast – Referenced for entrepreneurship insightsMark Twain: A Life by Ron Chernow – Biography Sam mentioned listening toTree Farm Golf Club – South Carolina golf course he cited as a model of hospitality
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1:14:50
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1:14:50
The Problem With Too Much Cash
In this episode, we unpack why having the right amount of cash in savings is essential—but why holding on to too much can quietly hurt your financial future. While an emergency fund provides short-term stability and peace of mind, excess cash loses value every year to inflation. By contrasting the short-term safety of savings with the long-term growth of investments, the conversation highlights the importance of balance. Practical frameworks like the “barbell model” and simple steps for gradually investing extra funds show how to move beyond just saving to start building lasting financial security.Key takeaways:Aim for an emergency fund with at least 3–6 months of expenses (or more if self-employed) in an FDIC-insured savings account.Cash is great in the short term—but lousy in the long term. Inflation erodes buying power over time, making cash unreliable for long-term goals.Though volatile in the short term, stocks and other investments historically outpace inflation over long periods.The barbell model: balance the stability of cash with the growth potential of investments to create financial strength.Start small and stay consistent—invest extra cash gradually, automate contributions, and avoid moving the goalposts on your savings target.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletter
The Thing We Never Talk About is an educational podcast about personal finance for creatives and other weirdos. We'll discuss managing cash flow with a lumpy income, when to save & when to invest, and how to reduce stress & build confidence when it comes to your money. No hot stock tips, no complicated strategies, and no finance bro jargon. We'll hear from artists, musicians, creative professionals, and other weirdos about how they navigate these questions for themselves. The Thing We Never Talk About is hosted by Timothy Iseler, CFP®, a former recording & touring audio engineer with 18 years experience in the music industry.
Ireland