Roth Rules, Pension Puzzles, and Real Retirement Stories: Your Questions Answered

Retire Sooner with Wes Moss

In this episode of the Retire Sooner podcast, Wes Moss and Christa DiBiase respond to listener questions and explore practical approaches to navigating retirement, investing, and financial planning.

• Discover a common Roth IRA misstep that can lead to unexpected taxes in retirement and learn how to approach it with more clarity.

• Explore the process of rolling over a Roth 401(k) into a Roth IRA and how the five-year rule of thumb might impact your withdrawal timeline.

• Hear real-world scenarios that highlight different outcomes based on how long your Roth accounts have been in place.

• Understand how to approach IRA rebalancing, including what to consider when dealing with concentrated stock positions and market changes.

• Compare Social Security and police pension benefits while examining updates to the Social Security Fairness Act and what it could mean for spousal coverage.

• Consider the use of retirement income projection tools and how applying more conservative assumptions may help you plan with greater confidence.

• Reflect on a “retirement love letter” that reveals three powerful themes behind a fulfilling retirement: financial flexibility, lifestyle design, and intentional planning.

• Follow the story of a couple who built a $6 million net worth, established six income streams, and prioritized meaningful pursuits and family in retirement.

• Explore why consistent movement and a sense of adventure are strongly connected to retirement satisfaction—and how shared community living can sometimes support both.

• Examine how changing family dynamics may shift your highest spending years later in life and why it matters for long-term planning.

• Get a clearer understanding of buffered index-linked notes, including their structure, potential costs, and how they differ from ETFs and other options.

• Learn how to calculate the present value of a pension using basic inputs such as years of service and average salary.

• Hear answers to more listener questions, including how stay-at-home spouses may qualify for Social Security and what pensions might mean for younger professionals.

Listen now to explore thoughtful planning strategies, real retirement stories, and insights that can help you design a future with more purpose and peace of mind.

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