Roth Rules, Pension Puzzles, and Real Retirement Stories: Your Questions Answered
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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From FOMO to Focused: Retirement Strategies for Market Volatility and Asset Allocation
In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase explore the role of dry powder assets in retirement planning and revisit “FOMO Freddie”—a cautionary character representing the risks of chasing investment trends without a long-term strategy. 🚀
They discuss why trend-chasing can be detrimental and how aligning with a consistent investment approach may help support long-term outcomes. You’ll hear comparisons of various investment styles—index, value, growth, momentum, and minimum volatility—and the potential drawbacks of “style timing” versus maintaining a steady allocation.
The episode also covers listener questions around portfolio transitions, including strategies for minimizing market disruption when moving IRAs or 401(k)s.
Additional topics include:
• Understanding TreasuryDirect accounts like I Bonds and EE Bonds
• Key risks of Market Linked Notes, including credit and liquidity concerns
• The “three-year dry powder” rule of thumb as a retirement buffer
• Age-based asset allocation considerations, including I Bonds as a potential emergency fund component for younger investors
• Considerations around high-yield municipal bond funds, especially for tax-conscious, high-net-worth retirees
• Factors to weigh when deciding whether to work with a financial advisor, including costs and allocation structure
Looking for help to strengthen your financial plan? Tune in for thoughtful insights to help you navigate market decisions with clarity and caution. For additional resources, visit yourwealth.com.
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Keys to Early Retirement: Rule 72(t), New Research, Investing Insights, and Lasting Happiness
Dreaming about retiring early, but worried you’ll never have enough? On this episode of Retire Sooner with Wes Moss, Wes and Christa DiBiase break down powerful strategies and mindset shifts that could help folks retire sooner and happier, including:
• Tap Your IRA Early—Penalty-Free: Learn how Rule 72(t) and SEPPs can sometimes unlock your IRA before many expect and how that might help customize an early retirement plan.
• Rule of 55 vs. Rule 72(t): Compare two powerful early withdrawal strategies and discover which one could work for your retirement timeline.
• Smart Rollover and Roth Moves: Wes tackles listener questions on IRAs, dry powder strategy, and recovering from past investing mistakes.
• S&P 500 or Total Market Index? Find out which fund could fit your growth goals—and why broad diversification is often a winning strategy.
• The Real Source of Retirement Happiness: New research reveals it’s not just money—core pursuits like travel, hobbies, and connection can fuel lasting joy.
• Annuities & Life Insurance—Worth It? Explore the pros, cons, and ideal timing for annuities and whole life policies in your retirement plan.
Let years of retirement planning, actionable anecdotes, relatable listener questions, and eye-opening research fine-tune your investment and happiness game plan.
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Are Earnings Everything? Plus More Strategies To Boost Long-Term Investing and Retirement Planning
Explore powerful, often-overlooked retirement tactics—like the Rule of 55 and the 62/70 Social Security strategy—and hear listener questions answered by Wes and Christa to help you build an effective, income-focused financial future. 🎯
• Are corporate earnings the #1 financial metric for long-term investors to track when making better investment decisions?
• Learn how to evaluate earnings per share (EPS) and earnings growth when investing in individual stocks or index funds.
• Should retail investors join earnings calls—or is it better to focus on broader S&P 500 earnings trends?
• Understand how proxy voting works and whether your shareholder vote might impact company decisions.
• Get insight on the “62/70” Social Security strategy—why one spouse claiming early while the other waits may optimize retirement income and possibly protect surviving spouses.
• Explore the Rule of 55, which lets you withdraw from your 401(k) without penalties starting at age 55, years earlier than the standard 59½ rule. Learn the critical conditions and employer plan requirements that determine Rule of 55 eligibility.
• Discover how a “reverse rollover,” for those who choose it, could unlock penalty-free access to retirement savings by shifting IRA funds into a qualifying 401(k).
• Understand the pros and cons of rules-based ETFs and factor investing versus traditional low-cost index funds.
• Hear Wes’s take on expense ratios, investment screening methods, and how to align your portfolio with your beliefs, without overpaying on fees.
• Dive into the mechanics of backdoor Roth IRAs and how those who choose to roll over traditional IRAs might be able to simplify the Roth conversion strategy.
• Learn how to optimize Health Savings Accounts (HSAs) and Flexible Spending Accounts (FSAs) when changing jobs or insurance plans.
Start creating your path toward financial freedom and retirement happiness with these topics and more on this episode of the Retire Sooner Podcast!
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From Gold to Growth: Long-Term Retirement Planning in Uncertain Times
Looking for retirement guidance and insights on navigating gold investments, market volatility, and the impact of AI on jobs? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase address essential topics and answer listener questions on financial planning, investment returns, and preparing for the future of work.
• Gold as an Investment: Discuss the pros and cons of investing in gold, including historical performance and volatility. What’s an effective percentage to hold in a portfolio?
• Gold’s Performance Over Time: Gold has shown a respectable average annual return in recent decades; however, can it also be highly volatile?
• Gold in Times of Crisis: How does gold perform during a recession?
• Physical Gold vs. Gold ETFs: Both are options, but which offers greater ease of access and lower logistical risk?
• 401(k) Rollover Strategy: For retirees who choose to rollover 401k assets to an IRA, can dollar-cost averaging reduce emotional stress?
• Seeking Steady 7% Returns: Investors looking for steady 7% returns may be compelled to take on significant risk, such as high-yield junk bonds or illiquid private real estate. Does this make balanced portfolios more strategic long-term options?
• AI’s Impact on White Collar Jobs: Is there credence to the claims that AI could eliminate many entry-level white-collar positions in the next five years? Are there ways to assess job vulnerability and anticipate how new opportunities and industries will emerge in response to technological change?
• Investing in an AI-Transformed World: Rather than chasing individual AI stocks, can broad, diversified index investing capture overall market growth and the success of future industry leaders?
• Weighing Rental Properties vs. Selling: When considering whether to keep or sell a paid-off home, consider balancing the potential for appreciation and rental income against the additional management work and risk.
• Equal Weight vs. Cap Weight Indexes: Is there potential for ETF bubbles due to mega-cap stock concentration? Can equal-weighted ETFs mitigate some risk?
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Wes Moss is on a mission: help at least 1 million Americans of any age retire sooner and find joy along the way. A seasoned finance professional, best-selling author, broadcaster, and teacher, Wes has done extensive research on the habits of the happiest retirees. On this podcast, Wes shares key lifestyle and money habits you can implement now to prepare for a secure future while not depriving yourself of happiness in the present. In addition to leveraging his 20+ years of knowledge as an investment advisor, Wes brings in guests and specialists to teach you how to set and work towards your financial and lifestyle objectives. Refreshingly-free of mind-numbing financial jargon and unrealistic money goals, Retire Sooner with Wes Moss gives listeners the tools on how to retire sooner in the real world.
Listen to Retire Sooner with Wes Moss, Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing) and many other podcasts from around the world with the radio.net app
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