Tag: Lifetime Income
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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TIAA vs Fidelity: HigherEd Retirement Plan Showdown (Ep. 6)

TIAA vs Fidelity: HigherEd Retirement Plan Showdown (Ep. 6)

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When it comes to retirement planning in higher ed, two names dominate the conversation: TIAA and Fidelity. 

But how different are they really, and how should you choose between them?

Greg Shepard pulls back the curtain on what sets each apart, where they overlap, and how risk tolerance, investment options, and lifetime income strategies all play a role in making the right decision.

What to expect:

  • Why fees are lower today than they were just a decade ago
  • How to think about TIAA’s traditional account versus Fidelity’s equity platform
  • The pros and cons of brokerage link accounts
  • What questions you should ask before picking a provider
  • And more!

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TIAA Traditional: How Can I Balance Annuitization with Other Income Strategies? (Ep. 5)

TIAA Traditional: How Can I Balance Annuitization with Other Income Strategies? (Ep. 5)

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For many, the word “annuitization” can feel confusing or intimidating. But understanding it can unlock powerful retirement income strategies.

In this episode, Greg Shepard explains what annuitization really means, who it’s best for, and the key benefits and risks to be aware of. He also breaks down how it works within TIAA plans, when to consider it, and the hidden tax and inflation factors you need to keep in mind.

Key takeaways:

  • What annuitization means and how TIAA provides fixed lifetime income
  • How to combine annuitized income with flexible sources like rollover IRAs and Social Security
  • Why annuitization may benefit people who are less comfortable with managing money
  • The estate planning pitfalls of annuities and what beneficiaries need to know
  • The impact of inflation on annuities and why delaying annuitization may be more advantageous
  • And more!

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Top 5 Questions You Should Ask Your TIAA Wealth Advisor (Ep. 4)

Top 5 Questions You Should Ask Your TIAA Wealth Advisor (Ep. 4)

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Retirement planning can feel overwhelming, especially when faced with complex products and advice that may not always align with your best interests.

In this episode, Greg Shepard breaks down five essential questions every TIAA participant should ask their advisor. He explains how to spot hidden fees, evaluate income strategies, and make informed choices that keep your money working for you. Greg also stresses the importance of education, transparency, and staying proactive about your retirement plan.

Key takeaways:

  • The importance of clarifying an advisor’s true investment philosophy and whether it aligns with your goals
  • Why relying solely on lifetime income could expose you to inflation risk
  • What to know about advisor fees, expense ratios, and trading costs
  • How to prepare for income changes in evolving interest rate environments
  • Tax efficiency strategies, including Roth conversions and planning for withdrawals
  • And more!

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