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Can I Call It Quits and Live a Little?

1/20/26: I badly want to take a break from a well paying career, likely with no chance of going back, yet I'm concerned about healthcare until I turn 65.

PodcastsMark TalercioJanuary 20, 2026Jill Schlesinger, Jill on Money, MoneyWatch, retire, retirement, retirement planning, retirement checkup, Roth IRA, early retirement, can I quit?, can I quit my job?, can we retire?, can I retire?
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At What Age Would I Be Able to Retire?

PodcastsMark TalercioJanuary 21, 2026Jill Schlesinger, Jill on Money, MoneyWatch, retire, retirement, retirement planning, retirement checkup, Roth IRA, early retirement, can I quit?, can I quit my job?, can we retire?, can I retire?
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Can I Retire at 62 in 2027?

PodcastsMark TalercioJanuary 19, 2026Jill Schlesinger, Jill on Money, MoneyWatch, retire, retirement, retirement planning, retirement checkup, Roth IRA, early retirement, can I quit?, can I quit my job?, can we retire?, can I retire?
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All opinions expressed by Jill Schlesinger on this website and on the “Jill On Money” radio show are solely Jill Schlesinger’s opinions and do not reflect the opinions of CBS News, its parent and affiliated companies or radio station affiliates. You should not treat any opinion expressed on this website or on the radio show as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of an opinion. Jill Schlesinger, CBS News, its parent and affiliated companies and radio station affiliates make no warranty as to the completeness or accuracy of any opinion expressed on this website or on the radio show, and any opinion expressed on this website or on the radio show should not be relied upon as complete or accurate. Before acting on any information on this website or on the radio show, you should consider whether it is suitable for your particular circumstances and seek advice from your own financial or investment adviser

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