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 Berger says if you're worried about all that, it's a sign you're thinking clearly.

Rob Berger is a former securities lawyer, founder of the personal finance site Dough Roller, and host of a nearly 300,000-subscriber YouTube channel on investing and retirement planning. He started writing about money in 2007, just months before the Great Recession.

In this episode, we discuss:

How to tell whether today's high stock prices should change your plan

When to trim a stock that's grown too big, and when to let it ride

Why a booming economy can still leave so many people feeling squeezed

What a looming Social Security shortfall could mean for your retirement

How to cover your basic bills with guaranteed income, whatever markets do

How to ease into retirement instead of going from 40 hours to zero

Why daily spending habits matter more than investing knowledge

Whether you're five years from retirement or five years into your career, this episode will help you separate what's truly changing from what never does.

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