Afford Anything | Get Smarter With Money

#748: 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

A listener with $686,000 saved and a job she loves wants to take her family on a year-long trip — but Paula says her real question isn't about money at all. Later: a dad chooses to stop maxing his IRA to pay off a mortgage, even though the math says otherwise.

Joe joins from the road to help answer three listener questions: a family weighing a year off against a job she loves, a dad debating whether to stop maxing his IRA to pay off a house, and a longtime listener with a smarter way to save for college.

In this episode, we discuss:

How to decide whether a job you love is worth walking away from for a family gap year

The three factors that actually predict whether you'll love your next job

Why "retiring early" might be the wrong goal — and what to aim for instead

How to know if you're financially ready for a career break, and what to prep first

Why paying off your mortgage can beat investing, even when the math says otherwise

How to structure your mortgage term like a finance pro (and why the 30-year can win)

Why saving in separate, labeled accounts makes it easier to actually hit your goals

Whether you're weighing a big life pivot, deciding what to do with extra cash, or just trying to make saving feel less abstract, this episode offers frameworks — not just formulas — for making the call.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(07:12) 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

🔗 OTHER 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 (Joe recorded this episode from his place): https://heavymetal.money

👉 Got a question of your own? Leave a voicemail for Paula: https://affordanything.com/voicemail

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#747: We have good news on multiple fronts to share about the job market, the stock market, the commodities market, and volatile news around the bond market.

And we begin it with some great news coming out of Nepal.

Welcome to the First Friday episode for September 2026.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(00:00) Rescued workers in Nepal

(04:53) Strong August jobs report

(10:14) Conflicting employment data

(12:27) Strong jobs, weaker stocks

(17:43) Why bonds matter more

(23:17) Inflation drives Treasury yields

(29:45) Hidden risks in bonds

(36:50) Treasury buyback controversy

(43:32) Liquidity versus warning signs

🔗 RESOURCES MENTIONED

👉 Build a Life of Financial Freedom with our free workbook: https://affordanything.com/fiire

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#746: We begin today’s episode with a discussion of the disastrous flash flooding in Nepal, a personal topic for Paula given her family there. There’s both a human story, one of the resilience of the Nepalese people and the strong community bonds there, and an economic story, where poor infrastructure and a lack of economic development have hindered disaster response and exacerbated the tragedies of recent events.

Listeners can donate to help the victims here:

The Prime Minister Relief Fund: https://pmdrf.nchl.com.np/

Caritas Nepal: https://www.caritasnepal.org/donate-now/

Learn more about the ongoing rescue efforts at https://help.ekantipur.com/

A caller wants to put part of her mom's $80,000 home-sale proceeds into an annuity — and it left her financial-planner co-host doing a double take. Turns out it might be the first caller in the show's history the product was actually built for.

This week's Q&A tackles two retirement questions from listeners: when it makes sense to ease off maxing out a 401k in favor of a more flexible brokerage account, and whether a guaranteed-income annuity is the right move for a retiree who isn't great at managing money on her own.

In this episode, we discuss:

How to know when to stop maxing out your 401k and start filling a taxable brokerage account instead

The real "deal" you're making with the government every time you use a tax-advantaged account

Why an insurance company can keep 100% of the money if the annuity holder dies too soon — and how to avoid it

The one type of person a guaranteed-income annuity is actually built for

A simple daily habit trick for building consistency, borrowed from a world-class choreographer

Why doing everything right doesn't guarantee a good outcome, and what that means for your own decisions

What Nepal's disaster response reveals about the real payoff of economic development

Whether you're mapping out an early-retirement bridge or helping a parent build guardrails around a windfall, this episode will help you think more clearly about the trade-offs each option carries.

🔗 RESOURCES MENTIONED

👉 Not sure which investments belong in your 401k, your Roth, or your taxable account? Grab our free guide to figuring out where each one goes: https://affordanything.com/assetlocation

👉 Morgan Housel on the split-second decision that changed everything: https://affordanything.com/488-gut-instincts-and-big-decisions-with-morgan-housel/

👉 Our interview with retirement researcher Dr. Wade Pfau on annuities and retirement income: https://affordanything.com/271-retirement-planning-in-2020-with-dr-wade-pfau/

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#745: A friend once asked Sahil Bloom how often he saw his parents. About once a year, Sahil said.

How old are they? Mid-60s.

His friend did the math out loud. If they live to 80, you'll see them 15 more times.

Sahil was 30, living in California and making great money at a venture fund. Within 45 days of that conversation, he quit his job, sold his house and moved across the country to be near family.

He's now managing partner of SRB Ventures, an early-stage fund backing more than 60 startups, and he writes The Curiosity Chronicle, a newsletter read by millions. His book, "The 5 Types of Wealth," is a New York Times bestseller.

His framework starts with a scoring problem. Financial wealth gets measured every day. Time, social, mental and physical wealth run in the background, unmeasured, until something forces you to look.

You'll get exercises for each. Build an energy calendar that tracks which activities charge you up and which drain you.

Map your relationships by how healthy and how frequent they are. Ask what your family and your community need from you. Define what "enough" means in dollars, then write the number down.

Sahil also walks through anti-goals — the things you refuse to sacrifice on the way to a goal — and Memento Mori, the Roman habit of keeping your own death in view.

Two questions run underneath all of it. Think about how you spent yesterday. Would your 10-year-old self be impressed? Would your 90-year-old self?

You don't experience all four seasons in a single day. Sahil argues your life runs on seasons too. Some stretches call for financial growth. Others call for family.

Find Sahil at the5typesofwealth.com.
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#744: With about $200 and a crypto exchange, historian Joseph Moore turned himself into a legitimate billionaire — a stunt that says more about how money actually works than most financial advice does. It's also a preview of the 300-year argument he makes in this episode: that almost everything we're told about money is newer, and far less permanent, than we think.Joseph Moore, PhD, is a historian and the national bestselling author of How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn't). His own self-experiments with historical money strategies helped him become financially independent in his mid-40s.

In this episode, we discuss:

How "never save your money" used to be completely reasonable financial advice

Why bonds quietly beat stocks for nearly all of the 1800s

How to spot when today's "obvious" financial rules are about to expire

Why real estate booms always show up right alongside inflation spikes

Why young people's unemployment is outpacing everyone else's — and what history says to do about it

Why economic optimism and economic data have stopped matching up

Why building more housing is the only housing-crisis fix that's ever actually worked

This one's for anyone who feels like the rules of money keep changing under them — because they do, and always have. Understanding that pattern is the first step to building wealth in whatever era you happen to be living in.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(05:18) How a runaway slave built his own legal currency

(06:52) How he legally declared himself a crypto billionaire

(13:22) Why a fifth of the Smithsonian's money collection is fake

(15:52) The bestselling book that told readers to commit fraud

(20:10) The decades when bonds quietly beat stocks

(26:04) How his grandfather secretly became a bond millionaire

(31:09) Why that "$10K in 1929" chart is misleading

(48:02) Why wages are up 50% and nobody believes it

(1:06:39) Why most Americans once owned one shirt

(1:23:48) The rent control law that backfired for renters

🔗 RESOURCES MENTIONED

👉 Build a Life of Financial Freedom with our free workbook: https://affordanything.com/fiire

👉 Joseph Moore's site — his book, essays, and more: https://www.josephmoorebooks.com

👉 Your Money or Your Life by Vicki Robin & Joe Dominguez: https://vickirobin.com/your-money-or-your-life/

👉 The Latte Factor by David Bach: https://www.simonandschuster.com/books/The-Latte-Factor/David-Bach/9781982120245
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