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.