Month: January 2026
You Don’t Know What You Don’t Know About TIAA Retirement Planning (Ep. 10)

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

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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.

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: 

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

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

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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.

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: 

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