TIAA Simplified

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 intellig...

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 comp...

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, revea...

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...

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...

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:...

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 ne...

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...

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 al...

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...

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 allocatio...

Welcome to TIAA Simplified with Greg Shepard from S&A Financial Services. In this podcast, we help HigherEd professionals overcome the confusion and frustration around managing their TIAA retirement accounts. We do this by breaking down complex rules, hidden risks, and smart strategies into clear, actionable insights. Join us for this journey where we explore how to retire smarter by truly und...