Tag: Financial Education
You Don’t Know What You Don’t Know About TIAA Retirement Planning (Ep. 10)

You Don’t Know What You Don’t Know About TIAA Retirement Planning (Ep. 10)

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Most people believe they have their retirement plan under control until they get closer to the finish line and realize they are guessing. When it comes to TIAA accounts, guessing can create costly mistakes, stress, and irreversible decisions.

In this episode, Greg Shepard breaks down why DIY retirement planning often falls apart, especially for higher education professionals navigating TIAA’s complex rules. Through real client stories and candid conversations, Greg explains why confidence without clarity can lead to missed opportunities, tax inefficiencies, and unnecessary strain at home.

Key insights covered:

  • Why most pre-retirees underestimate TIAA complexity
  • The risks of relying on call centers, YouTube, or AI for retirement decisions
  • How irreversible paperwork mistakes can derail a retirement plan
    The emotional toll DIY planning can place on couples
  • Why humility and professional guidance can reduce stress and improve outcomes
  • And more!

Connect with Greg Shepard: 

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Meet the Man Behind the Mic: Introduction to TIAA Simplified’s Greg Shepard (Ep. 1)

Meet the Man Behind the Mic: Introduction to TIAA Simplified’s Greg Shepard (Ep. 1)

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Most people believe their retirement plan is on autopilot. But what if the fine print in your TIAA Traditional account could derail everything at the finish line?

In the premiere episode of TIAA Simplified, Greg Shepard shares how helping higher ed professionals navigate their TIAA investments has completely reshaped his approach to advising. 

These aren’t just account balances and allocations. They’re emotional, high-stakes decisions often made without the right information. Greg dives into the real stories of confusion, frustration, and life-altering revelations that sparked his mission to bring clarity to this overlooked topic.

Greg discusses:

  • How years of traditional financial advising felt empty until he began helping TIAA participants with their most pressing questions
  • The overlooked restrictions inside TIAA Traditional and how they catch people off guard near retirement
  • Why even highly intelligent professionals struggle to understand the mechanics of their plan
  • What pushed Greg to start making videos and podcasts that became lifelines for people in need of answers
  • The urgency of asking the right questions well before retirement to avoid irreversible planning mistakes
  • And more!

Connect with Greg Shepard: 

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