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A 41-year-old guest on Jill Schlesinger’s show Money Moves told her he felt like a loser. His parents bought their first home at 28, his grandparents at 23, and he was still renting, even though he likely had more saved for retirement than either of them did at his age. His finances were fine; his money anxiety wasn’t.
Jill, a certified financial planner and CBS News business analyst, sees that gap everywhere. Inflation left a lasting scar, social media keeps picking at it, and people whose money anxiety tells them they’re hopelessly behind are more likely to take a flyer on sports betting, meme stocks, or a TikTok guru’s passive-income pitch.
Jill first joined the show in 2019 to talk about the dumb things smart people do with their money. Her take now: the mistakes haven’t changed, only the vehicles have — and the friction that used to slow people down is gone.
She came back to talk about why money anxiety lingers even when the economic data looks strong, how a good financial planner turns emotion into priorities, and what to weigh before making a midlife career change.
Key Takeaways
The biggest ideas from the conversation
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- Feeling behind doesn’t mean you are behind: Many people in their 30s and 40s measure themselves against their parents’ milestones, like owning a home by 28. Jill points out that they often have more invested than their parents did at the same age. Money anxiety often reflects comparison, not actual financial position.
- Feeling hopeless can push people toward risky bets: When people feel they’ll never get ahead, they’re more likely to take a flyer on sports betting, meme stocks, or other get-rich-quick schemes. Low-friction apps make these bets instant, and the dopamine hit makes them feel like a shortcut around slow, boring investing.
- Inflation leaves a lasting scar on the psyche: Even after inflation cooled from its 9% peak in 2022, prices stayed elevated and wages haven’t fully caught up in people’s minds. Like graduating into a recession, that scar can linger for years, and social media keeps feeding the money anxiety.
- Financial planning turns emotions into concrete priorities: About 75% of a planner’s job, Jill says, is managing clients’ emotions. Mapping out what’s coming in and going out reveals the real source of worry — an emergency fund gap, rent that’s too high — and turns it into an action you can take.
- Index funds work, even if they feel boring: Passive investing was born from research showing active managers couldn’t consistently beat the market. Yet many investors still trade their index funds instead of holding them. Jill’s challenge to hedge fund friends: explain why people shouldn’t just buy four or five index funds and leave them alone.
- Run the numbers before a career reset: Leaving a job to work for yourself means giving up the 401(k) match, health insurance, and disability coverage. Jill, who left financial planning for media, says even if you don’t make the leap, analyzing it can clarify things — and a side hustle might deliver the change with less risk.
Resources
Links, tools and references mentioned
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Jill on Money
Jill’s website and where to send her your money questions:
jillonmoney.com
Money Moves with Jill Schlesinger
Watch or listen to Money Moves with Jill Schlesinger:
cbsnews.com
The Great Money Reset
Jill’s book on making a big life or career change, The Great Money Reset:
jillonmoney.com/the-great-money-reset
Chapters
Jump to a specific part of the conversation
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Note: Timestamps are approximate and may vary across listening platforms due to dynamically inserted ads.
| 03:04 |
Why sports betting is the same old money mistake |
| 06:04 |
Why big-picture money advice rarely fits your life |
| 12:38 |
How feeling stuck pushes people toward risky bets |
| 17:36 |
Why a 41-year-old renter isn’t actually behind |
| 21:00 |
Why social media comparison hits harder than TV did |
| 30:57 |
Why good economic data still feels so bad |
| 50:18 |
How a financial plan quiets money anxiety |
| 52:13 |
The guardian fight that almost sank an estate plan |
| 1:04:00 |
Take risks in your career, not your portfolio |
| 1:07:14 |
What “work for yourself” videos leave out |
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