What if being told to grab a part-time job in retirement is a sign something went wrong? On this episode, Derrek 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.

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What if being told to grab a part-time job in retirement is a sign something went wrong? On this episode, Derrek 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&mdash;without relying on hope as a strategy.
Get Your Complimentary Retirement Analysis
Social Media:&nbsp;<a href="https://www.facebook.com/HoylFinancialLLC">Facebook</a> | <a href="https://x.com/HoylFinanacial">X</a>

Steve Hoyl and Derrik Caldwell have worked tirelessly to craft personalized, high-quality financial services to a diverse group of clients at all income levels. As a lifelong resident of the Texas Panhandle, Steve has a unique insight into the passions, motivations and concerns of his client. It’s this connection with community — alongside more than three decades of industry experience — that allows Steve and Derrik to create retirement strategies that are as unique as the clients they serve and the places they live.

Learn more about Steve, Derrik and the rest of the team here.

Don't miss an episode. Subscribe or follow wherever you get your favorite podcasts!

For more helpful insights follow on social media: Facebook and X

Steve Hoyl and Derrik Caldwell have worked tirelessly to craft personalized, high-quality financial services to a diverse group of clients at all income levels. As a lifelong resident of the Texas Panhandle, Steve has a unique insight into the passions, motivations and concerns of his client. It’s this connection with community — alongside more than three decades of industry experience — that allows Steve and Derrik to create retirement strategies that are as unique as the clients they serve and the places they live.
Learn more about Steve, Derrik and the rest of the team <a href="https://hoylfinancialgroup.com/podcast/">here</a>.
Don't miss an episode. Subscribe or follow wherever you get your favorite podcasts!
For more helpful insights follow on social media: <a href="https://www.facebook.com/HoylFinancialLLC">Facebook </a>and <a href="https://twitter.com/HoylFinanacial">X</a>

Retire Texas Style!

For over 30 years, Steve has worked tirelessly to craft personalized, high-quality financial services to a diverse group of clients at all income levels. As a lifelong resident of the Texas Panhandle, Steve has a unique insight into the passions, motivations and concerns of his client. It’s this connection with his community — alongside more than three decades of industry experience — that allows Steve to create retirement strategies that are as unique as his clients and the place they live.