If Retirement Requires a Side Hustle, Something’s Broken

About this episode

Derrick Caldwell challenges traditional retirement advice and discusses the importance of active management in retirement planning.

What if being told to grab a part-time job in retirement is a sign something went wrong? On this episode, Derrick Caldwell challenges passive retirement advice, unpack active portfolio management, and walk through real-world decisions around Social Security, income timing and longevity. The conversation also explores Roth IRA conversions, tax tradeoffs, and why retirement planning works best when income, risk, and lifestyle are viewed together—without relying on hope as a strategy. Get Your Complimentary Retirement Analysis Social Media:  Facebook | X See omnystudio.com/listener for privacy information.

People in this episode

Host: Steve Hoyl

Guest: Derrick Caldwell

Topics covered

• retirement planning
• active portfolio management
• Social Security
• income timing
• longevity
• tax tradeoffs
• Roth IRA conversions

Keywords

• retirement
• side hustle
• portfolio management
• Social Security
• income timing
• longevity
• Roth IRA
• tax tradeoffs

Mentioned in this episode

Organizations: Social Security, Roth IRA

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