“So to me, this is not a money management question.”
That’s what I told a listener partway into this episode — right after she told me she’s 42, makes $140,000 a year, and has $686,000 saved.
She wasn’t asking if she could afford a family gap year. Her numbers already answered that.
She was asking something harder: is it worth walking away from a job she loves, when she’s not sure it’ll still be there when she gets back?
Joe and I dig into that one first. Then we help a dad of four decide whether to stop maxing his IRA to pay down the mortgage faster — even when the math argues for investing instead. We close out with a smarter way to think about saving for college, from a longtime listener who says nobody explains this part well.
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Listener Questions
Mandy asks: I really loved your most recent podcast on the July jobs report that came out. I saw something recently in the news stating that 100% of the labor workforce decline was actually female, and that 100% of it was females leaving the workforce. I wasn’t sure how accurate or correct that information was, and I was curious if it is accurate, what is the reason behind it and what factors are impacting that?
Nieves asks: I recently quit my job and moved to Madrid, Spain for a year to pursue an MBA. I received a scholarship for the program, but I had to use most of my savings for a €20,000 deposit that will be returned after I complete a six-month internship following the MBA. I also took out a €30,000 loan for living expenses for the next 12 months at an interest rate under 4%. I’m 30 years old and have around $150,000 in my old 401(k), $50,000 in my Roth IRA, and a duplex in St. Louis, Missouri that I bought in 2021 for $240,000. The mortgage, including taxes and insurance, is about $1,500 a month, and it brings in around $3,100 a month in rent. One of the units is a midterm rental, so I have additional expenses associated with that unit. I’ve been thinking about selling the property because my tenants have started paying late and the property needs a new roof and a few other repairs. I don’t have enough cash to replace the roof out of pocket, and managing the property from abroad has become stressful. I could likely sell the duplex for around $250,000 to $275,000, and I currently owe $180,000 on the mortgage. How do you know when it’s okay to let go of an investment that is objectively a good long-term asset? I’m struggling with whether selling would be a smart simplification for peace of mind or if I’d be giving up a valuable long-term asset.
Key Takeaways
- It’s Not a Money Question, It’s a Life Question: When the numbers already check out, the real question isn’t “can we afford this” — it’s what you actually want the next year or two of your life to look like.
- Value Comes From Scarcity: A specific window — like taking a trip while your kids are still young enough to remember it as a family adventure — has real value, even if it’s hard to put a number on. The same trip taken later isn’t the same trip.
- Aim to Retire Often, Not Just Early: Instead of racing toward one big finish line, it can make more sense to build in breaks throughout your working life rather than saving all your freedom for the very end.
- Debt Payoff Isn’t Always a Math Problem: If carrying debt genuinely raises your anxiety, paying it off can be the right move even when investing would technically win on paper. Peace of mind has a return too.
- A Mortgage Term Is a Ceiling, Not a Deadline: Taking a 30-year loan for the payment flexibility doesn’t mean you’re locked into 30 years of payments — you can still pay it off in 10 if that’s what fits your plan.
Resources
The real question behind quitting a job you love or paying off debt anyway? Your money mindset. Take our free quiz to find yours: https://affordanything.com/fiire
Camp Fi, the financial independence retreats Paula and Joe swap stories about this episode: https://campfi.org
Heavy Metal Money, Chris Luger’s personal-finance podcast: https://heavymetal.money
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Chapters
Note: Timestamps are approximate and may vary across listening platforms due to dynamically inserted ads.
(7:12) Can you afford to quit a job you love?
(11:09) Three things that actually predict job satisfaction
(17:05) Why this window with your kids won’t come twice
(22:20) Why retiring often beats retiring early
(30:14) Why bad trip experiences count as good data
(34:18) Why paying off debt can beat the math
(36:49) Why coasting on your current savings pace is risky
(44:26) How to think like a CFO about your mortgage
(51:09) Why one bucket per goal makes saving easier
(53:46) Why your 401k isn’t really about retirement
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