Technology is changing how we approach retirement planning, but are financial professionals embracing these changes or resisting them?

What if there were a tool that could map out your entire retirement strategy from age 30 to 65, including Roth conversions, tax optimization, and withdrawal strategies?

In this episode, Greg Shepard discusses his hands-on experience implementing artificial intelligence tools to help TIAA participants plan their retirement more effectively. He explains how AI can create personalized roadmaps for retirement contributions, tax diversification strategies, and withdrawal planning. Greg also addresses the concerns and opportunities AI presents for financial advisors, and why younger professionals should pay attention to this technology now.

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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.

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Many higher education professionals are missing out on a powerful retirement tool hiding in plain sight within their employer plans.

Are you leaving tax-free money on the table? Do you know the difference between contribution limits and income restrictions across retirement accounts?

In this episode, Greg Shepard breaks down the critical differences between Roth 403(b) and Roth IRA accounts, revealing why so many employees remain unaware of valuable retirement options. Greg explains income limits, withdrawal rules, tax diversification strategies, and when high earners should reconsider their approach.

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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.

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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.

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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.

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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.

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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.

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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.

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Many higher education and medical professionals depend on TIAA for their retirement savings, yet most don’t fully understand the fine print.

From liquidity restrictions to overlooked contract details, the consequences of not asking the right questions can be costly.

This week, Greg Shepard breaks down the most common misunderstandings about TIAA Traditional and explains why a personalized approach is critical.

His mission is clear: simplify the complexities so you can make informed decisions well before retirement.

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