Harder Than It Looks: Retirement Planning’s Hidden Challenges How Money Works podcast

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Harder Than It Looks: Retirement Planning’s Hidden Challenges

2d ago 23:57

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Some financial decisions appear simple on the surface until you start working through the details. In this episode, Craig and Jennifer break down common areas of retirement planning that are harder than they look and explain why professional guidance makes all the difference. Each of these areas can feel overwhelming if you’re going it alone, but with the right plan, they don’t have to be.

They start with Social Security, where the choice of when to file isn’t just about picking an age, it’s about understanding penalties, income limits, and how benefits fit into your larger income plan. From there, they explore the real meaning of diversification, showing why simply owning dozens of funds doesn’t guarantee balance. Join us and get better prepared for the road ahead in retirement.

Here’s some of what we discuss in this episode:

🕰️ Social Security timing: Penalties and income rules can surprise you

📈 Real diversification: Beyond the typical pie charts

🔄 401(k) rollovers: Get them right or risk major headaches

🧩 Simple vs. complex: What looks easy can derail without a plan

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