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

Page: https://stenobird.com/podcast/the-real-investment-show-full-show-1123656/5-29-26-investor-anxiety-roth-strategies-and-retirement-reality
Text version: https://stenobird.com/podcast/the-real-investment-show-full-show-1123656/5-29-26-investor-anxiety-roth-strategies-and-retirement-reality.md
Podcast: [The Real Investment Show (Full Show)](https://stenobird.com/podcast/the-real-investment-show-full-show-1123656)
Published: 2026-05-29T16:03:46+00:00
Episode link: https://soundcloud.com/user-949311744/5-29-26-investor-anxiety-roth
Audio file: https://feeds.soundcloud.com/stream/2329732190-user-949311744-5-29-26-investor-anxiety-roth.mp3
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JSON: https://stenobird.com/v1/public/podcasts/the-real-investment-show-full-show-1123656/episodes/5-29-26-investor-anxiety-roth-strategies-and-retirement-reality
Duration seconds: 2799

## Resource

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/ ----…

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