The Thing We Never Talk About

Every year, financial “experts” roll out confident predictions about what the markets and economy will do next — and almost every year, they’re wrong. In this solo episode, Tim explains why financial forecasts are so appealing, why they’re fundamentally unreliable, and how chasing certainty can actually hurt your long-term financial health. Instead of guessing the future, he lays out a simple, durable framework for building stability, flexibility, and peace of mind in an unpredictable world. One Key Takeaway: You don’t need to predict the future to build financial security — simple habits, long-term thinking, and preparation for uncertainty matter far more than any market forecast.Links:Financial Forecasts Are Bullsh!tSign up for weekly Office HoursSend me a question to be answered on a future episode

Drumming instructor Todd Trainer joins Tim to talk about how an unexpected job loss pushed him into building a new career around teaching. He shares the story of growing his student base from DIY flyers to a full teaching practice, and why helping beginners find confidence & creativity has become some of the most meaningful work of his life. Todd also talks about adapting his teaching style for different learners and the philosophy that guides his approach to drumming instruction.Key Takeaways:Todd Trainer—best known as the drummer of Shellac—shares how losing a long-time job pushed him toward drumming instruction as a new career path. He started his teaching business in DIY fashion, putting up flyers & offering mobile lessons at his students' homes or rehearsal spaces. Eventually, Todd (and his wife, a designer) built a website that features scheduling tools & a payment system, which have been essential to the business’s success.His teaching philosophy emphasizes creativity, individuality, and imagination—encouraging students to develop their own unique style rather than chasing technical perfection. Todd finds deep fulfillment in teaching beginners, especially children, and describes how helping them discover their first drumbeat is one of the most rewarding parts of instruction. Teaching has become emotionally meaningful for Todd: the value exchanged between student and instructor goes far beyond the time they spend together.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Todd Trainer Drumming InstructionTwin Cities Drum CollectiveShellac of North America

Holiday spending can creep up fast — and the new year is the perfect time to reset. In this episode, Tim introduces the 4-Week Financial Detox, a simple step-by-step process designed to help you pause discretionary spending, reset your baseline expenses, eliminate costly subscription “leaks,” and refocus your money on what truly matters. Whether you’re rebuilding after the holidays or just ready to use your money more intentionally, this short reset can help you start the year with more clarity, control, and confidence in your financial life. One Key Takeaway: Small, temporary changes to your spending habits can create lasting improvements in financial health — especially when you focus your money on what genuinely enriches your life.Links:4-Week Financial DetoxSign up for weekly Office HoursSend me a question to be answered on a future episode

In this wide-ranging & deeply reflective conversation, guitarist Randy Randall (No Age, Hyphenate with Randy Randall) talks about the shifting economics of indie music, redefining success as he became a parent, and building a freelance career in marketing almost by accident. From his early days immersed in the DIY community to learning resilience in the gig economy, Randy shares an honest, unglamorous, and strangely hopeful portrait of what it means to be a lifelong creative worker. He & Tim dig into the real tensions between art and money, how freelancing in marketing actually aligns with his long history of conceptual art, and why optimism is essential when your livelihood depends on the next email, gig, or project.Randy's question for me:  When is it a good idea to put money in a traditional IRA versus when is it a good idea to put money in a Roth IRA?Key takeaways:Randy describes juggling multiple identities — musician, podcaster, and now freelance marketing professional — and the tension between what he wants to say he does and what actually pays the bills. He explains why touring slowed down: part parenthood, part industry collapse, part shifting audience habits — and how those changes pushed him into new types of work. Randy explains how he fell into freelance marketing during the pandemic, discovering it uses the same skills he honed through years of art-punk conceptual work. He discusses the unpredictable nature of gig-based creative work, where every project feels like “starting from zero” and momentum is never guaranteed. Randy and Tim dive into the emotional resilience required to freelance — balancing optimism, uncertainty, and the long game of sustaining a creative life. Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Randy's websiteHyphenate With Randy RandallTim's episode of HyphenateNo Age's Bandcamp pageLifeguard's "Ripped And Torn", produced by Randy

In this episode, Tim explains why cash flow is the foundation of every financial plan — and introduces a simple technique to make saving money easier and more consistent. By identifying your “invisible number,” the small amount you can save automatically without ever noticing, you can improve your cash flow, build long-term security, and reduce friction in your financial life. Tim breaks down how this approach works, why automation matters, and how small, steady habits can quietly transform your financial trajectory.5 Key Takeaways:Cash flow is the foundation of financial planning. Every major financial decision — investing, buying a home, planning for retirement — depends on knowing what you earn, spend, and save.Income = spending + saving. This simple equation underpins every cash-flow conversation and highlights the trade-off between what you use today and what you set aside for the future.Your “invisible number” makes saving effortless. This is an amount of money small enough to transfer automatically without affecting your daily life — your savings grow without conscious effort.Increase your invisible number slowly. After a few months, bump it up in small increments until you begin to notice it — then dial it back slightly and automate that amount indefinitely.Tie your number to something you buy without thinking. A daily coffee, a sandwich, a beer — if you’d spend it without hesitation, you can likely save it without noticing, too. Small, automated transfers add up meaningfully over time.Links:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletterThe cost of a cup of black coffee at Starbucks