You Don’t Know What You Don’t Know About TIAA Retirement Planning (Ep. 10)

How AI is Transforming TIAA Retirement Planning (Ep. 11)

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. Greg discusses: * The comparison between AI’s current stage and early internet technology like AOL dial-up * How AI tools can create comprehensive retirement roadmaps that offer a different level of detail than some traditional planning tools * The resistance and fear within the financial advisory industry regarding AI implementation * Teaching AI platforms to understand complex TIAA retirement plans and contract structures * Why generalist advisors should be concerned while specialized advisors can leverage AI to enhance their services * And more! Connect with Greg Shepard:  * Phone: (913) 521-2381 * Email: greg@shepardfinancial.com [greg@shepardfinancial.com]  * LinkedIn: Greg Shepard [https://www.linkedin.com/in/gregshepardsafinancial/] * Website: TIAA Simplified [https://tiaasimplified.com/] * Website: S&A Financial Services [https://www.safinancialservices.com/] * LinkedIn: S&A Financial Services, Inc. [https://www.linkedin.com/company/s-a-financial-services-inc/]

You Don’t Know What You Don’t Know About TIAA Retirement Planning (Ep. 10)

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. Key insights covered: * Why most pre-retirees underestimate TIAA complexity * The risks of relying on call centers, YouTube, or AI for retirement decisions * How irreversible paperwork mistakes can derail a retirement plan The emotional toll DIY planning can place on couples * Why humility and professional guidance can reduce stress and improve outcomes * And more! Connect with Greg Shepard:  * Phone: (913) 521-2381 * Email: greg@shepardfinancial.com [greg@shepardfinancial.com]  * LinkedIn: Greg Shepard [https://www.linkedin.com/in/gregshepardsafinancial/] * Website: TIAA Simplified [https://tiaasimplified.com/] * Website: S&A Financial Services [https://www.safinancialservices.com/] * LinkedIn: S&A Financial Services, Inc. [https://www.linkedin.com/company/s-a-financial-services-inc/]

Roth IRA or Roth 403(b): Which Should I Do? (Ep. 9)

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. Key insights covered: * The widespread lack of awareness about Roth 403(b) options among higher education and medical professionals * No income limits on Roth 403(b) contributions versus strict Roth IRA income restrictions * Tax-free withdrawal benefits and the five-year holding requirement for Roth accounts * Custom tool development for calculating optimal pre-tax versus post-tax contribution strategies * Tax diversification strategies for retirement planning and why employers should mandate education sessions * And more! Connect with Greg Shepard:  * Phone: (913) 521-2381 * Email: greg@shepardfinancial.com [greg@shepardfinancial.com]  * LinkedIn: Greg Shepard [https://www.linkedin.com/in/gregshepardsafinancial/] * Website: TIAA Simplified [https://tiaasimplified.com/] * Website: S&A Financial Services [https://www.safinancialservices.com/] * LinkedIn: S&A Financial Services, Inc. [https://www.linkedin.com/company/s-a-financial-services-inc/]

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

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! Connect with Greg Shepard:  * Phone: (913) 521-2381 * Email: greg@shepardfinancial.com [greg@shepardfinancial.com]  * LinkedIn: Greg Shepard [https://www.linkedin.com/in/gregshepardsafinancial/] * Website: TIAA Simplified [https://tiaasimplified.com/] * Website: S&A Financial Services [https://www.safinancialservices.com/] * LinkedIn: S&A Financial Services, Inc. [https://www.linkedin.com/company/s-a-financial-services-inc/]

TIAA Traditional Lifetime Income Pros vs Cons (Ep. 7)

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! Resources: * TIAA Lifetime Income Strategy [https://youtu.be/Pl1A6gCJ_AA] Connect with Greg Shepard:  * Phone: (913) 521-2381 * Email: greg@shepardfinancial.com [greg@shepardfinancial.com]  * LinkedIn: Greg Shepard [https://www.linkedin.com/in/gregshepardsafinancial/] * Website: TIAA Simplified [https://tiaasimplified.com/] * Website: S&A Financial Services [https://www.safinancialservices.com/] * LinkedIn: S&A Financial Services, Inc. [https://www.linkedin.com/company/s-a-financial-services-inc/]