What’s the one retirement question you’re afraid to ask and could the answer change everything? In this episode, Gary Garland explores the questions many retirees never ask, from whether they’re truly on track for retirement to understanding fees, fiduciary responsibilities, investment strategies, and estate planning decisions. Gary explains why asking better questions often leads to better outcomes and why a good advisor should be willing to say, “I don’t know, let me find out.” The conversation also covers common misconceptions, family legacy concerns, and the importance of having a plan that reflects what matters most to you. The quality of your retirement planning is often tied to the quality of the questions you ask.

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