John Dugan - Content Specialist in the Design Industry
In this episode, Tim talks with writer, drummer, and content specialist John Dugan about creative work, shifting career priorities, raising kids in a music-rich environment, and how financial needs and perspectives evolve over time. John reflects on decades in bands including Chisel, his transition from journalism into content strategy for the design world, and what happens when art, family life, and money all need to coexist. They also discuss saving habits, risk tolerance, reunion shows, and supporting the next generation of artists—including John’s teenage son’s band, Uniflora.John's question for me: why would someone invest in life insurance? Is that an alternative to the stock market?Key takeaways:John Dugan is a longtime drummer & writer who now works as a content specialist in the design industry. He shifted from “cool, low-paying jobs” in journalism and cultural criticism to a more sustainable career path once he became a parent and needed greater financial stability. Though he played extensively in touring bands, music never paid his bills; he always held another job to maintain stability. John learned the value of maintaining an emergency savings buffer early, influenced by frugal parents and reinforced by the realities of touring life. He continues to think about risk vs. caution in personal finance, recognizing that while he tends to be risk-averse, some well-timed risks can meaningfully shape financial outcomes.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.John's websiteChisel's Bandcamp pageUniflora, John's son's band
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1:02:56
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1:02:56
Listener Mailbag 01
It's the first listener mailbag episode! Tim answers real money & personal finance questions from listeners about ethical investing, managing debt, and overcoming money-related shame. He explains how to easily invest according to your values, how to balance saving while paying off student loans, and when to use savings to tackle credit card debt. The conversation ends with a thoughtful reflection on emotional well-being — how to move past financial shame and build confidence through small, consistent wins.Key Takeaways:Ethical investing is more accessible than ever. Lower cost ESG & SRI funds allow everyday investors to align their money with their values without paying high fees.Perfection isn’t required. There is no “clean” money, bank, company, or country — but choosing options that most closely reflect your ethics is better than sitting out entirely.The 50/30/20 rule still applies — with flexibility. When paying off student loans or other debt, treat recurring payments as essentials (the 50%) and keep aiming for 20% savings when possible.Tackle high-interest debt first. No amount of investing can outpace credit card interest, so pay those balances before focusing on long-term investments.Let go of shame and rewrite your story. Shame is a story we tell ourselves — and if you're going to make up a story about yourself, it might as well be a good one! Start collecting evidence of good habits, look for supportive accountability, and celebrate even small wins.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletter
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28:54
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28:54
Benjamin Percy – Storyteller
Benjamin Percy has built a career bridging literary fiction, comics, and Hollywood storytelling. As the author of acclaimed novels, comic book arcs for Marvel and DC, and scripts for film and audio drama, Ben joins Tim to discuss the craft and discipline behind a self-employed creative life. He talks about writing routines, handling rejection, learning to navigate the business side of art, and balancing creative ambition with family life. The conversation explores how consistency, humility, and persistence turn creative work into a sustainable career. Ben's question for me: AI worries me for all the standard reasons, but it also worries me because I anticipate the over promise and overspending will reach a point of bubble bursting correction. Is there any sense, even a vague one as to when that might happen, and how to shield yourself from the fallout?Key takeaways:Benjamin's storytelling spans novels, comics (Wolverine, Batman, Green Arrow), screenplays, and podcasts, and writing across mediums has helped him become a better writer (and pay his bills).He describes early failures and rejections as essential to building resilience and understanding his craft.Ben blurs boundaries between literary and genre fiction, arguing that good storytelling transcends category.A former university professor, Ben believes in being a "good literary citizen": sharing knowledge with newer writers and opening doors when possible.Longevity in creative work comes from patience, adaptability, and the ability to keep going through uncertainty.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Benjamin's websiteThe End Times (physical subscription)The End Times (digital subscription)Red Moon, Ben's breakout novelBen's page at Marvel ComicsBen's page at DC Comics
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1:05:43
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1:05:43
Quick Nest Egg Calculation
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
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