Tag: Greg Shepard
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!

Connect with Greg Shepard: 

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