As the year winds down, Tim shares five practical steps you can take right now to lower next year’s tax bill. From maximizing retirement contributions to understanding energy-efficiency credits, this episode focuses on simple, actionable strategies for creative professionals and self-employed listeners. Tim breaks down how tax-deferred accounts, health savings accounts, and even small investment decisions can make a meaningful difference — without the last-minute stress of filing season. 

Five Key Takeaways:

1. Contribute to tax-deferred retirement accounts. Deposits into IRAs, 401(k)s, and similar accounts reduce current-year taxable income. Remember: new accounts must be opened before December 31 to count for this tax year.
2. Use a Health Savings Account (HSA) if eligible. HSAs offer a triple tax advantage: contributions are tax-deductible, growth is untaxed, and qualified withdrawals are tax-free.
3. Offset gains with losses. Selling underperforming investments in non-retirement accounts lets you claim up to $3,000 in capital losses per year to reduce taxable income — but watch for wash-sale rules.
4. Take advantage of home energy credits. Energy-efficient home upgrades (like HVAC systems, doors, or windows) can qualify for valuable federal credits, but some expire at the end of 2025.
5. Consider strategic charitable giving. While deductions only apply if your itemized total exceeds the standard deduction, bundling several years of giving into one tax year can increase tax efficiency for higher earners.

Links:
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The Congress.Gov page on HSAs
Energy Efficient Home Improvement Credit

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 Tim: why would someone invest in life insurance? Is that an alternative to the stock market?

Key takeaways:

1. John Dugan is a longtime drummer & writer who now works as a content specialist in the design industry. 
2. 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. 
3. Though he played extensively in touring bands, music never paid his bills; he always held another job to maintain stability. 
4. John learned the value of maintaining an emergency savings buffer early, influenced by frugal parents and reinforced by the realities of touring life. 
5. 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:
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John's website
Chisel's Bandcamp page
Uniflora, John's son's band

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:

1. 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.
2. 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.
3. 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.
4. Tackle high-interest debt first. No amount of investing can outpace credit card interest, so pay those balances before focusing on long-term investments.
5. 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:
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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 Tim: 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:

1. 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).
2. He describes early failures and rejections as essential to building resilience and understanding his craft.
3. Ben blurs boundaries between literary and genre fiction, arguing that good storytelling transcends category.
4. A former university professor, Ben believes in being a "good literary citizen": sharing knowledge with newer writers and opening doors when possible.
5. 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 website
The End Times (physical subscription)
The End Times (digital subscription)
Red Moon, Ben's breakout novel
Ben's page at Marvel Comics
Ben's page at DC Comics

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:

1. The 4% rule (and its partner, the 25× rule) provides a simple way to estimate how much you’d need to make work optional.
2. Even if you never plan to “retire,” saving and investing buys you freedom and flexibility later in life.
3. Your target nest egg is determined by your annual spending—spend more, need more; spend less, need less.
4. Consistent small actions—saving a little more, paying debt faster, investing regularly—compound into big results.
5. Financial independence isn’t about quitting work; it’s about creating options and reducing obligation.

Links:
Sign up for weekly Office Hours
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Sign up for the Keep It Easy newsletter
William Bengen's Wiki page
Investopedia's page on the 4% Rule

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 Tim: Regular IRA, Roth IRA, or SIMPLE IRA?

Key takeaways:

1. Longevity through discipline: Mike has supported himself solely through writing since 1992 — proof that persistence can outlast uncertainty.
2. Money is part of the craft: Understanding taxes, mileage, bookkeeping, and contracts enables creative independence.
3. Multiple income streams matter: Like his farmer father, Mike learned to diversify work to stay sustainable.
4. Integrity over exposure: Turning down a high-profile appearance taught him the value of aligning work with values.
5. 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 website
His new book Improbable Mentors & Happy Tangents
Population: 485, Mike's breakout memoir about small-town life and volunteer firefighting

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:

1. 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.
2. 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).
3. Abundance is about “more than enough.” But abundance depends on how much you think you need, not just how much you have.
4. Freedom > possessions. Wealth is really about time and freedom, not just money or material goods.
5. 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 Hours
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Sign up for the Keep It Easy newsletter
Morgan Housel

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 Tim: what is going to happen with tariffs in the next 12 months?

Key takeaways:

1. Sam reflects on his unusual career path—from surfer & skateboarding industry work, to marketing & touring, and eventually to chocolate making.
2. 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.
3. 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.
4. 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.
5. He connects golf to entrepreneurship, noting both require persistence, resilience, and the ability to face setbacks with optimism (and a lesson from his grandmother).

Links
Send me a question to be answered on a future episode.
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Videri Chocolate Factory – Sam’s chocolate business in Raleigh, NC

Golf Golf Golf – His indoor golf simulator business

Simon Sinek Podcast – Referenced for entrepreneurship insights

Mark Twain: A Life by Ron Chernow – Biography Sam mentioned listening to

Tree Farm Golf Club – South Carolina golf course he cited as a model of hospitality

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:

1. Aim for an emergency fund with at least 3–6 months of expenses (or more if self-employed) in an FDIC-insured savings account.
2. 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.
3. Though volatile in the short term, stocks and other investments historically outpace inflation over long periods.
4. The barbell model: balance the stability of cash with the growth potential of investments to create financial strength.
5. Start small and stay consistent—invest extra cash gradually, automate contributions, and avoid moving the goalposts on your savings target.

Links:
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Musician Macie Stewart has been performing since her teens, from early bands like Kids These Days to co-founding Finom & becoming a fixture in Chicago’s improvised music scene. In this episode, she talks about finding community at Constellation (an excellent Chicago venue), balancing the realities of freelance income with creative freedom, and what success looks like for her today. One key takeaway: building a sustainable creative life means balancing financial practicality with artistic curiosity and community.

Macie's question for Tim: how to make a yearly budget when income fluctuates so greatly? 

Key takeaways:

1. Macie began touring as a teen and later found her way into Chicago’s improvised music scene through current bandmate Sima Cunningham.
2. Although she's been a working musician for many years, only in the past five years has she fully realized music can be her career.
3. Macie supports herself through touring, session work (especially strings and arranging), licensing, scoring, grants, royalties, and collaborations.
4. She saves regularly, uses a high-yield savings account, contributes to a Roth IRA, and focuses on building stability as a self-employed musician.
5. For Macie, success means creative freedom, sustainable touring, and the ability to pursue unconventional projects like theater or dance collaborations

Links
Send me a question to be answered on a future episode.
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Macie's website
Finom's website
Constellation in Chicago

Kids These Days wiki page

Sound & Gravity festival