S&A Financial Services – TIAA Simplified

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

By TIAASimplified | December 24, 2025

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)

By TIAASimplified | December 3, 2025

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!