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
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