Q&A: Why Do I Still Feel Anxious When I’m Clearly Doing Well?

Q&A: Why Do I Still Feel Anxious When I’m Clearly Doing Well?

#722: Free lesson: affordanything.com/mistakes Ask us a question: affordanything.com/voicemail What happens when your financial plan is technically working — but emotionally, it still doesn’t feel secure? Caitlin and her husband have their core expenses covered, but her side hustle brings in an extra $600 a month. With young kids, daycare costs, and long-term retirement goals all competing for attention, she’s wondering where that extra money should go right now. Anonymous is in a strong financial position for retirement, with a pension, solid investments, and high savings rates—but is still constantly checking accounts, rerunning projections, and struggling to feel at peace with money. Charlotte is calling back several years after asking whether short-term rentals could fund her early retirement. After buying, renovating, and eventually selling two Airbnb properties—just before a devastating hurricane hit the area—she’s reflecting on what she learned about risk, hype, and investing with emotion. Resources mentioned: Charlotte's original call: affordanything.com/episode352 Paula interview on Emma Chamberlain's podcast: youtube.com/watch?v=VOP7S4w8s0I Midterm Rentals with Jeff Hurst: affordanything.com/episode712 Interview with Brad Klontz, Ep127: affordanything.com/episode127 Interview with Brad Klontz and Adrian Brambila, Ep551: affordanything.com/episode551 Share this episode with a friend, colleagues, and your AirBNB tenants: https://affordanything.com/episode722 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Episoder(805)

My Bank Account Hit Zero ... Then I Got Rich -- with Jaspreet Singh of Minority Mindset

My Bank Account Hit Zero ... Then I Got Rich -- with Jaspreet Singh of Minority Mindset

#759: At 19, Jaspreet Singh bought a rental for $8,000. What followed was a nightmare tenant, a lawsuit, and a later house stripped of its copper, and it taught him what the real estate books leave ou...

16 Okt 1h 42min

Q&A: "I’m 26 and No Longer Motivated by Money. Am I Unemployable?”

Q&A: "I’m 26 and No Longer Motivated by Money. Am I Unemployable?”

#758: Joe says that if you tell an employer you’re not motivated by money, you’re unemployable. Paula says that’s exactly the person she wants to hire. Former financial planner Joe Saul-Sehy joins Pa...

13 Okt 1h 12min

Steve Jobs Hated the Name “Genius Bar.” How He Came Around, with Ron Johnson

Steve Jobs Hated the Name “Genius Bar.” How He Came Around, with Ron Johnson

#757: Ron Johnson is the creator of the Apple Stores and former CEO of JCPenney. At age 24 Ron Johnson turned down a $120,000 Goldman Sachs offer to unload trucks for $40,000, and that detour led Stev...

9 Okt 1h 48min

How Losing $500K in ‘08 Led One Trader to a Different Kind of Portfolio, with Jared Dillian

How Losing $500K in ‘08 Led One Trader to a Different Kind of Portfolio, with Jared Dillian

#756: In September 2008, Jared Dillian watched about half a million dollars of Lehman Brothers stock go to zero in a single week. He wasn't allowed to sell any of it. What he built afterward is a port...

6 Okt 52min

First Friday: AI, Debt, and a Social Security Shortfall. Should Your Money Plans Change? With Rob Berger

First Friday: AI, Debt, and a Social Security Shortfall. Should Your Money Plans Change? With Rob Berger

#755: Many retirees fear running out of money more than they fear dying. AI is reshaping the economy, the U.S. now spends over $1 trillion on interest, and Social Security faces a shortfall. Rob Berge...

2 Okt 1h 9min

Q&A: We Have $80K in Cash and Want a 1–2 Year Sabbatical. Is It Enough?

Q&A: We Have $80K in Cash and Want a 1–2 Year Sabbatical. Is It Enough?

#754: Four months of savings in the bank, a goal of eight, and a career break she's excited to fund. Does everything else really have to wait? Paula and Joe's answer: don't turn your emergency fund in...

29 Sep 1h 14min

Why 60,000 New York Apartments Sit Empty in a Housing Crisis, with Kenny Burgos

Why 60,000 New York Apartments Sit Empty in a Housing Crisis, with Kenny Burgos

#753: New York City is short roughly half a million homes, yet at least 60,000 rent-regulated apartments sit empty. Under current rules, many owners lose less money by leaving them vacant than by fixi...

25 Sep 1h 25min

Q&A: I’m Tired of Managing My Rental Property. Should I Sell It?

Q&A: I’m Tired of Managing My Rental Property. Should I Sell It?

#752: A caller's rental is performing fine, but a late-paying tenant and a roof replacement have her ready to sell it before she moves to Madrid for her MBA. Paula argues the real fix isn't selling — ...

22 Sep 1h

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