5-29-26 Investor Anxiety, Roth Strategies, and Retirement Reality

Investors continue wrestling with uncertainty, frustration, and the fear of making the wrong move in today’s market environment. Jon Penn & Sarah Buenger discuss why waiting for the “perfect” entry point often keeps investors sidelined, how hindsight bias and regret aversion impact decision-making, and why investing does not have to be an all-or-nothing approach Here's a topical rundown of today's show: 0:00 - INTRO 0:20 - We Don't Sleep so You Can 4:11 - World of Roth Preview & Market Summary 10:15 - How to Get Money Into Roth 13:39 -The Back Door Roth 17:21 - IRS Strategies & Prorata Rule 18:23 - Regular Roth Conversions 20:34 - Super-loading Roths 24:49 - 457 Limitations 25:22 - Mega-Backdoor Roths 27:01 - Not Every Employer Plan Includes Roth 31:35 - 529 to Roth Conversions 30:32 - When the IRS is Your "Business Partner" 33:28 - Rules of Roth & Preferred Order 35:28 - Strategies for Spousal Contributions 37:25 - When the Roth Maths don't Math 38:56 - Inheritance Tax Efficiency Considerations 41:17 - Tax Considerations & Implications in Roth Conversions 43:47 - Pre-Tax vs After-Tax considerations Hosted by RIA Advisors Senior Investment Advisor, Jonathan Penn, CFP, w Senior Investment Advisor, Sarah Buenger, CFP Produced by Brent Clanton, Executive Producer ------- Do you enjoy our content? Rate us on Google: https://bit.ly/4b9JtEo ------- Watch Today's Full Video on our YouTube Channel: https://youtube.com/live/ZL8lA-xHlMs ------- Articles Mentioned in Today's Show: "15 Investing Rules To Win The Long-Game" https://realinvestmentadvice.com/resources/blog/15-investing-rules-to-win-the-long-game/ "AI Productivity And Innovation: Prosperity Or Engels Pause?" https://realinvestmentadvice.com/resources/blog/ai-productivity-and-innovation-prosperity-or-engels-pause/ ------- Watch today's "Before the Bell" feature, "Tech Rally Risk Rising," here: https://youtu.be/AVXI7TCayvI ------- Watch our previous show, "Is the Semiconductor Trade Going Too Far," https://youtube.com/live/XB3W7awMDZk ------- Get more info & commentary: https://realinvestmentadvice.com/insights/real-investment-daily/ ------- * REGISTER for our next Dynamic Learning Series presentation, "A SimpleVisor Tutorial," Thursday, June 4, 2025 at Noon: https://streamyard.com/watch/MwairsimgmnS --- Visit our Site: https://www.realinvestmentadvice.com Contact Us: 1-855-RIA-PLAN --- Subscribe to SimpleVisor : https://www.simplevisor.com/register-new --- Connect with us on social: https://twitter.com/RealInvAdvice https://twitter.com/LanceRoberts https://www.facebook.com/RealInvestmentAdvice/ https://www.linkedin.com/in/realinvestmentadvice/ #RetirementPlanning #Investing #RothIRA #FinancialPlanning #StockMarket