Why Successful People Struggle With Retirement & What’s Going On With the Economy?

In this episode, Wes tackles the psychological hurdle that many high-achievers face when they finally reach the "Retirement Green Zone." After decades of using hard work, discipline, and ambition to build a nest egg, it can be incredibly difficult to simply turn that drive off. Wes discusses the "ambition guilt" that many retirees feel when they pursue creative hobbies or passions that don’t generate a paycheck. Rather than viewing this transition as "lowering" your ambition, Wes argues that the key to a happy retirement is rechanneling that legendary work ethic into areas that feed your soul instead of your bank account. Also, it can feel like we’re in a confusing state of the 2026 economy, where record-breaking corporate data seems at odds with the reality on the ground. While U.S. company profits soared by 26% in late 2025 and nominal GDP has grown significantly since 2019, many consumers are still feeling the weight of high prices. Wes explains how we are living in a "K-shaped" economy and breaks down what these disparities mean for your wallet and how to navigate an environment where productivity is higher than ever, but the benefits aren't being shared equally.

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Plus, Christa shares your #AskWes questions and Wes gives his take. All this and more on the April 21, 2026, Ask an Advisor episode of the Clark Howard podcast.  Submit your questions at clark.com/ask.

We hope you enjoy our weekly Ask An Advisor episodes.  Let us know what you think in the comments!

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