Doing Everything Right…So Why Am I Still Afraid to Retire?

If you’ve been doing all the “right” things with your money—saving, contributing to your 401(k), staying afloat—yet still quietly wonder, “What if I run out of money when I retire?”…this episode is for you.In this Sock Drawer Podcast conversation, Lisa sits down with Derek Mazzarella, CFP®, author of Just Retire Already, to talk about the fears people rarely admit out loud: tax anxiety, stock plan confusion, information overload, and the emotional shift of life after work.Derek breaks down why taxes are one of the most underestimated retirement risks, how “whack-a-mole finances” keep people stuck, and why company stock can either trap you in a job you’ve outgrown—or give you the freedom to step into your next chapter with confidence.This isn’t a Wall Street lecture. It’s a kitchen-table conversation about clarity, confidence, and designing a life you’re excited to wake up to—one small, intentional step at a time.