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
• LinkedIn: Greg Shepard
• Website: TIAA Simplified
• Website: S&A Financial Services
• LinkedIn: S&A Financial Services, Inc.

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
• LinkedIn: Greg Shepard
• Website: TIAA Simplified
• Website: S&A Financial Services
• LinkedIn: S&A Financial Services, Inc.

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
• LinkedIn: Greg Shepard
• Website: TIAA Simplified
• Website: S&A Financial Services
• LinkedIn: S&A Financial Services, Inc.

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

Connect with Greg Shepard:

• Phone: (913) 521-2381
• Email: greg@shepardfinancial.com
• LinkedIn: Greg Shepard
• Website: TIAA Simplified
• Website: S&A Financial Services
• LinkedIn: S&A Financial Services, Inc.

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!

Connect with Greg Shepard:

• Phone: (913) 521-2381
• Email: greg@shepardfinancial.com
• LinkedIn: Greg Shepard
• Website: TIAA Simplified
• Website: S&A Financial Services
• LinkedIn: S&A Financial Services, Inc.

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!

Connect with Greg Shepard:

• Phone: (913) 521-2381
• Email: greg@shepardfinancial.com
• LinkedIn: Greg Shepard
• Website: TIAA Simplified
• Website: S&A Financial Services
• LinkedIn: S&A Financial Services, Inc.

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!

Connect with Greg Shepard:

• Phone: (913) 521-2381
• Email: greg@shepardfinancial.com
• LinkedIn: Greg Shepard
• Website: TIAA Simplified
• Website: S&A Financial Services
• LinkedIn: S&A Financial Services, Inc.

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.

Greg discusses:

• Why waiting until the last minute can limit your retirement choices
• The role of TIAA Traditional in your income strategy
• How to rebalance your portfolio as you approach retirement
• Common mistakes people make with too much or too little in Traditional
• And more!

Connect with Greg Shepard:

• Phone: (913) 521-2381
• Email: greg@shepardfinancial.com
• LinkedIn: Greg Shepard
• Website: TIAA Simplified
• Website: S&A Financial Services
• LinkedIn: S&A Financial Services, Inc.