Tag: TIAA Traditional
TIAA Traditional: Which Contracts do I Annuitize First? (Ep. 8)

TIAA Traditional: Which Contracts do I Annuitize First? (Ep. 8)

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If you’ve ever wondered whether you’re making the most of your TIAA Traditional account, this episode is a must-listen. Greg Shepard breaks down the five essential questions every TIAA participant should ask, whether you’re ten years from retirement or just starting your career.

In this episode, Greg explains how to think strategically about your TIAA Traditional contracts, plan ahead for lifetime income options, and avoid common mistakes that can limit flexibility later. He shares real-world insights on how early preparation can help you retire with confidence and clarity.

Greg discusses:

  • What key actions to take ten years before retirement
  • How to rebalance your portfolio as you approach retirement
  • The most common mistakes people make when planning
  • How to model future income and healthcare costs
  • What to know before choosing an annuitization strategy
  • And more!

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TIAA Traditional Lifetime Income Pros vs Cons (Ep. 7)

TIAA Traditional Lifetime Income Pros vs Cons (Ep. 7)

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Retirement income decisions can be overwhelming, especially when converting TIAA Traditional balances into lifetime income.

In this episode, Greg Shepard breaks down one of his most frequently asked questions: “Should I choose lifetime income, and how much?” Greg shares real client stories and explains the pros, cons, and emotional factors behind this important decision. He also explains how TIAA lifetime income works, when it makes sense, and how to avoid costly mistakes when selecting it.

Greg shares:

  • The key differences between lifetime income and maintaining liquidity
  • The ideal scenarios where lifetime income might make sense
  • The 40% guideline for transitioning to lifetime income
  • Emotional and behavioral factors that influence retirement decisions
  • The importance of asking the right questions before locking in your plan
  • And more!

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Why 10 Years Out Matters for Your TIAA Plan (Ep. 3)

Why 10 Years Out Matters for Your TIAA Plan (Ep. 3)

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Ten. It is a simple number, but when it comes to your TIAA retirement plan, it can make all the difference.

In this episode of TIAA Simplified, Greg Shepard shares why preparing at least ten years before retirement is critical for higher-ed professionals with TIAA accounts. Through real client stories and clear explanations, Greg breaks down the importance of understanding liquidity, portfolio allocation, and the unique rules around TIAA Traditional.

Greg discusses:

  • Why waiting until the last minute can limit your retirement choices
  • The role of TIAA Traditional in your income strategy
  • How to rebalance your portfolio as you approach retirement
  • Common mistakes people make with too much or too little in Traditional
  • And more!

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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!

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