What if paying off debt wasn’t the end of your financial journey, but the beginning of something bigger? In today’s episode, we meet three listeners at pivotal crossroads, each wrestling with how to align their money with what they truly want from life.
First, we talk with a couple who’s about to crush $100,000 in debt and launch a sanctuary for senior dogs and cats. They’re torn between selling a rental property to fund their dream now or keeping it to build long-term wealth. We explore the messy, beautiful tension between passion projects and financial security, and why the funding question might be entirely different than they think.
Then, we hear from a 51-year-old on the cusp of leaving her W-2 job to pursue an encore career. With a perfectly balanced tax triangle and her retirement number already hit, she’s wondering how aggressively to tackle Roth conversions and what pitfalls to avoid. We dig into RMD strategy, cash flow planning, and the art of using your money to do what you love, not just what you have to do.
Finally, we meet a 25-year-old planning to take an entire year off in 2027 to attempt a calendar year triple crown hike. He’s mapped out an incredibly clever tax strategy involving Roth conversions at a negative tax rate, but he’s wondering if he’s being too aggressive with his cash cushion. We talk about living in the future versus planning for it, and why optimizing shouldn’t come at the cost of the experience itself.
Listener Questions in This Episode
Victoria asks: Should we sell our rental property to fund our dream dog and cat sanctuary, or refinance and keep building our real estate portfolio? (4:32)
Gwen asks: With $3.2 million saved and a side business just getting started, how should I think about Roth conversions when I leave my W-2 job mid-2026? (32:15)
Soyman asks: Is my plan to convert $21k to Roth at a negative tax rate during my year-long hiking trip too risky with only a small cash buffer? (48:20)
Key Takeaways
- You don’t have to self-fund your entire nonprofit dream. Grant funding, donor networks, and philanthropic organizations exist specifically to support missions like animal rescue.
- The Airbnbs funding your sanctuary don’t have to be on the same land as the sanctuary. Income is fungible; location isn’t always necessary.
- A perfectly balanced tax triangle (equal parts taxable, traditional, and Roth) gives you maximum flexibility in retirement, especially when future tax rates are unknowable.
- RMDs aren’t just a future problem to solve later. Strategic withdrawals from pre-tax accounts in your early retirement years can prevent a bigger tax headache down the road.
- When you have flexibility in your timeline (like a 10-year farmland goal), you can be more aggressive with investments because you’re not locked into one specific year.
- Don’t let financial optimization undercut once-in-a-lifetime experiences. Plan for the future, but don’t live in it at the expense of the present.
Resource mentioned
Interview with Charity: Water founder Scott Harrison
Chapters
Note: Timestamps are approximate and may vary across listening platforms due to dynamically inserted ads.
(0:00) Setting the stage: values, goals, and big life transitions
(6:35) Launching a passion project without sacrificing retirement
(18:50) When paying off debt creates a financial inflection point
(42:10) Taking a year off, Roth conversions, and low-income planning
(58:40) Investing for long-term goals with shorter time horizons
(1:12:45) Roth conversions, RMD risk, and preserving tax flexibility
(1:41:30) Closing thoughts on aligning money with the life you want
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