The Thing We Never Talk About

Money has different jobs depending on when you need it — and confusing what works for one timeline with what works for another is one of the most common financial mistakes. In this solo episode, Tim walks through the difference between saving money and building wealth, using this definition of wealth as a guide: the ability to do what you want, when you want, with whom you want, for as long as you want. From cash savings for short-term needs, to CDs and Treasury bills for medium-term goals, to stock market investing for long-term goals like retirement, Tim lays out a simple framework for how matching your money to its purpose builds wealth both now and later.
One Key Takeaway: Saving money and building wealth are not the same thing. Match your money to its timeline: cash for the short term, stable interest-bearing accounts or investments for the medium term, and stock market investing for the long term.
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In this episode, Tim sits down with Serena Lander — self-employed artist, tattoo artist, and owner of a multi-unit property — for a conversation about building a creative life on your own terms. Serena traces her path from tattooing as a teenager in British Columbia, when she was one of only a handful of women in the craft in North America, through nearly four decades of working entirely for herself. She talks openly about her ambivalent feelings towards money and the practical decisions that have shaped her financial life like keeping overhead low and investing in things she actually believes in. It's a conversation about finding your own version of financial stability without abandoning the values that drew you to a creative life in the first place.
Serena's question for Tim: Can you share some ideas about setting goals in life and trying to engage more enthusiastically with your finances? I wish there was a way to make it more sparkly for myself so that I would do it.
Key Takeaways:
Serena started tattooing at 19 in British Columbia at a time when there were only a handful of women doing it in all of North America.
She has spent her entire career working for herself, supported early on by keeping her overhead extremely low.
Buying a house at the bottom of the market in 2011 and gradually subdividing it into four rental units has turned into a financial foundation she didn't originally plan for, with rental income now covering her mortgage.
Serena reflects on the punk rock and alternative music community's cultural aversion to money, and how that narrative — money as part of the system, financial participation as selling out — has made it harder for people in those communities to build long-term stability.
She finds it easier to engage with financial decisions when they are tangible and values-aligned, like adding solar panels to her house.
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Serena Lander on Instagram
Serena Lander's website

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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