The Thing We Never Talk About

Should you pay off your mortgage early or invest the money instead? In this solo episode, Tim walks through a real case study involving a couple who received a significant one-time windfall and want to know how to use it wisely. He compares three options — investing the full amount right away, paying off the mortgage entirely, or splitting the difference — across a twenty-year time line, and shares what the numbers actually revealed. The results might surprise you, and one of the most important factors turns out to be one that doesn't show up in any spreadsheet.
One Key Takeaway: When comparing paying off debt versus investing, the math usually favors investing — but only if you can actually stick to your investment plan over many years and decades.
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In this episode, Tim sits down with Richard Dansky — game narrative expert, fiction writer, and tabletop role-playing game designer — for a wide-ranging conversation about building a creative career across multiple formats and revenue streams. Richard traces his path from tabletop games starting in the '90s through nearly three decades of video game work, including a long tenure as the central narrative resource for Ubisoft's Tom Clancy franchise, while continuing to write fiction, contribute to tabletop games, and co-author a graphic novel along the way. He talks candidly about the economics of that kind of career: how he thinks about rates across different formats, why he has always lived well below his means, and why he wishes more writers understood their own professional value. He also shares hard-won wisdom about navigating rejection and knowing when to walk away from a bad deal.
Richard's question for Tim: How do you think  about melding various revenue streams, as these days every author's got to have a Patreon/Substack/YouTube channel/podcast/newsletter/online store/convention presence etc.
Key Takeaways:
Richard describes his entry into both tabletop and video games as largely relationship-driven — a reminder that in creative industries, showing up, being reliable, and knowing the right people often matters as much as talent.
He has maintained a remarkable ability to work across multiple formats simultaneously: video games by day, tabletop and fiction by night — treating each as a distinct creative sandbox with its own rules and rewards.
Richard's fiction acceptance rate is around 3.7%, which he notes is listed as above average. It's a useful reminder that rejection is the norm in creative work, not a signal of failure.
Richard describes the best financial habit of his career as consistently spending well below his means, and how knowing he can afford his lifestyle frees up mental and creative energy.
He argues that writers and narrative designers are frequently underpaid because the value of their work is hard to quantify, and that the industry actively works to make creative professionals feel their contributions are worth less than they are.
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Richard's website
Richard's LinkedIn profile, where he shares insight on game narrative design
The issue of Dark Yonder in which I first learned about Richard

Doing nothing with your money feels safe — but it comes with real costs, both financial and emotional. In this episode, Tim explains why cash is essential for short-term stability but loses value over time to inflation, and why investing anything beyond your cash reserve is one of the most important financial moves you can make. He also explores two emotional patterns that keep people stuck: "the leaky bucket", where money slowly disappears without intention, and the "but what comes next" mindset, where fear of making the wrong decision leads to making no decision at all. The solution to both, it turns out, is the same: define how much cash you actually need, stick to that number, and put everything above it to work for you through investing.

One Key Takeaway: Making no decision for what to do with your money is itself a decision — and it usually costs you.
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In this episode, Tim sits down with Angela Hugghins, esthetician & founder of Cult of Reason skincare, for a wide-ranging conversation about what it looks like to build multiple businesses on your own terms. Angela shares how she structured her solo practice to protect her hands, her energy, and her lifestyle after nearly 30 years in the industry, why she made a significant price jump despite fears of losing clients, and how she thinks about the break-even math before introducing any new product or equipment. She also talks candidly about the origins of Cult of Reason, the unexpected challenges of running a product business, and the recent purchase of a commercial building to house her businesses and generate rental income.
Angela's question for Tim: Now that we're landlords, what are the tax advantages of owning commercial real estate, how do we maximize rental income, and what other ways can we benefit from this new structure?
Key Takeaways:
Angela capped her working days at four per week after years of overworking, a deliberate lifestyle decision driven by the physical demands of her craft.
She hired a virtual assistant who spends just 30 minutes a day managing her emails and client communications — a small investment that she says has paid off in stress reduction far beyond its dollar cost.
After building a wait list of over 200 clients, Angela made a significant price increase, gave clients three months of advance notice without disclosing the exact amount, and lost only three or four people as a result.
Angela launched Cult of Reason to recreate a discontinued product she had relied on, starting with a single formula developed over two years through a custom cosmetics lab, funded entirely out of pocket.
She describes Cult of Reason as a passion project that is now self-funding, and identifies supply chain disruptions and tariffs on imported ingredients as challenges she hadn't anticipated when she started.
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Cult of Reason Skincare
Cult of Reason on YouTube

A surprising amount of what looks like a money problem is actually something else wearing a money costume. Tim shares a story from his early touring days, when a tour manager's blunt question — "Is this about the money, or is it something else?" — cut through a negotiation in under a minute. He applies that same question to financial planning, using the common example of someone wondering if they're saving enough for retirement: the real issue often isn't the math, it's an unresolved question about priorities. Tim walks through a framework for looking past the numbers to identify what you actually want, then reframing that priority as a matter of identity rather than obligation — a shift that makes it far easier to stick with a plan.
One Key Takeaway: Before assuming a financial question is just a matter of getting the numbers right, ask whether there's a deeper question hiding underneath it.
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