The Thing We Never Talk About

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

Film and video editor Max Goldblatt joins Tim to talk about building a creative career across indie films, digital content, and nearly a decade of touring. He shares how early exposure to editing shaped his path, how short-film work opened doors to feature projects, and what it takes to balance passion, stability, and financial responsibility in an unpredictable industry. Max also reflects on navigating rate negotiations, imposter syndrome, and the realities of sustaining creative momentum over time.Max's question for me:  My kid is three. School is expensive. I know that a 529 plan has some limitations, like what if she doesn't go to college? Is there a smart and flexible way to set her up for success?Key takeaways:Max Goldblatt is a film, TV, and digital video editor based in Los Angeles, working both on independent films (his “passion work”) and as a lead editor for a production company that handles a range of clients, including MasterClass.He learned the craft early by watching his father, editor Mark Goldblatt, spending spring breaks in editing rooms for major films like Starship Troopers, True Lies, and Armageddon.Before establishing himself as an editor, Max spent nearly nine years touring, first as a videographer for his cousin Pete Yorn and then as a merch manager for various artists (including Sufjan Stevens).He now balances steady staff work with independent feature opportunities, with his company allowing him to step away for film projects and return afterward, providing stability during volatile industry periods.On finances, Max says he’s always been frugal and cautious, started a Roth IRA early due to childhood acting income, avoids credit card debt, and prefers a “save first, spend within means” approach rather than rigid budgeting.Links:Send me a question to be answered on a future episode.Sign up for the Keep It Easy newsletter.Max's websiteThe trailer for Sacremento, a feature film edited by MaxSt Vincent's MasterClass (edited by Max)Ringo Starr's MasterClass (edited by Max)

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: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.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.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.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.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:Sign up for weekly Office HoursSend me a question to be answered on a future episodeSign up for the Keep It Easy newsletterThe Congress.Gov page on HSAsEnergy Efficient Home Improvement Credit