Retire Sooner with Wes Moss

What if a happier retirement has as much to do with how you spend your time as how you invest your money? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase explore the research behind retirement happiness, answer listener questions on retirement planning, and share how you can pre-order Wes’s new book, The Retire Sooner Method, and unlock exclusive bonuses!

• Discover why core pursuits—the activities that get you excited to start the day—are often linked to greater retirement satisfaction.

• Explore the hobbies, passions, and routines most commonly found among retirees who report higher levels of happiness and fulfillment.

• Review how retirement withdrawal frameworks work, including considerations around cash reserves and 4%+ distribution strategies.

• Compare Equity Indexed Annuities (EIAs), dividend-focused approaches, and pension-versus-lump-sum options when evaluating retirement income choices.

• Consider Roth conversions, required minimum distributions (RMDs), and other tax-planning factors that may influence long-term retirement strategies.

• Evaluate the opportunities and risks that may come with concentrated RSU and company stock positions.

• Understand how FDIC insurance works and what to know about coverage for savings accounts and CD ladders.

Whether you're years from retirement or already there, this episode blends retirement happiness research with practical financial planning conversations. Listen to the Retire Sooner Podcast and subscribe for more discussions about retirement, investing, personal finance, and building a life you look forward to living.

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Retirement planning doesn’t always follow a straight line, and this episode of the Retire Sooner Podcast tackles the pressing money decisions families are talking about. Join Wes Moss and guest host Mallory Boggs for a lively conversation about helping adult children buy homes, Roth conversions, Social Security timing, investing, taxes, and the lifestyle choices often associated with a happy retirement.

• Explore the financial and emotional tradeoffs that may come with helping adult children buy a home while still protecting your own retirement goals.

• Examine how higher home prices, rising mortgage rates, and ongoing family support may help shape retirement planning and financial flexibility.

• Evaluate Roth conversions, Social Security claiming strategies, IRA withdrawals, and HELOC financing through the lens of taxes and long-term retirement income planning.

• Reconsider how spending on travel, family experiences, health, hobbies, and social connections may play a role in retirement satisfaction.

• Assess portfolio diversification considerations beyond concentrated “Magnificent 7” exposure while tackling listener questions on IRAs, emergency funds, taxable accounts, and retirement investing.

Listen and subscribe to the Retire Sooner Podcast for more conversations on retirement planning, investing, taxes, and navigating today’s financial landscape with a practical long-term perspective.

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Retirement rarely goes exactly according to plan—and this episode of the Retire Sooner Podcast tackles the real-life financial curveballs that may affect the timeline. Join Wes Moss and special guest host Mallory Boggs for a fast-moving conversation on early retirement, market volatility, taxes, rollover IRAs, annuities, direct indexing, and diversification strategies.

• Explore why many Americans retire earlier than expected and how health issues, caregiving responsibilities, and job loss may reshape retirement plans.

• Learn how thoughtful retirement income planning, IRA rollover decisions, and mortgage strategies may help create more financial flexibility.

• Compare the pros, cons, and tradeoffs of annuities, direct indexing, tax-loss harvesting, and alternative investment strategies beyond the traditional 60/40 portfolio.

• Understand why unusually fast stock market recoveries have historically been less common, and why long-term investors often focus on perspective over prediction.

• Examine practical planning considerations for high-income earners, looking at tax efficiency, portfolio diversification, and varying levels of investment risk.

Listen and subscribe to the Retire Sooner Podcast for more conversations on retirement planning, investing, taxes, and navigating today’s financial landscape with a clear, practical long-term perspective.

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Retirement planning is about far more than picking investments, and this episode of the Retire Sooner Podcast shows just how many moving pieces may shape your financial life over time. Join Wes Moss and Christa DiBiase for a fast-moving conversation covering retirement income planning, tax strategy, dividend investing, market volatility, and the potential value of working with a fiduciary, fee-only advisor.

• Compare fiduciary advisors and non-fiduciary advisors through a simple “orange pepper” analogy.

• Explore how tax planning, behavioral coaching, retirement forecasting, and portfolio strategy may work together in long-term financial planning.

• Evaluate real estate decisions, business transitions, and career planning during peak earning years and retirement.

• Review dividend investing, ETF selection, cash reserves, and sequence-of-returns risk considerations for retirees and near-retirees.

• Organize retirement rollovers, trusts, pensions, and tax records with greater clarity and flexibility.

Whether you’re building a retirement plan or fine-tuning an existing strategy, this episode delivers practical financial conversations grounded in long-term thinking and real-life investor questions. Listen and subscribe to the Retire Sooner Podcast for more discussions on retirement investing, financial planning, and navigating today’s changing economic landscape.

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Clark Howard joins Wes Moss and Christa DiBiase for a fun, fast-moving Retire Sooner Podcast episode packed with conversations about retirement planning, Roth conversions, HSAs, taxes, investing, and the lifestyle choices that may help to shape financial life. From boats and horse racing to tax strategies and retirement income planning, this episode blends practical financial conversations with the relatable chemistry listeners love.

• Compare **Roth vs. traditional **401(k) contribution approaches as Clark Howard and Wes Moss sort through taxes, future flexibility, and retirement income planning considerations.

• Consider how state income taxes, Roth conversions, required minimum distributions (RMDs), and Medicare IRMAA (Income-Related Monthly Adjustment Amount) surcharges may influence retirement cash flow over time.

• Explore HSA strategies, backdoor Roth IRAs, and mega backdoor Roth opportunities while reviewing contribution rules and planning considerations for higher earners.

• Weigh whether buying a boat aligns with lifestyle goals and retirement spending priorities by comparing personal value and real-world price-per-use scenarios.

• Enjoy Christa DiBiase’s stories about horse racing, sports fandom, and finding balance between financial goals and enjoying life along the way.

Listen and subscribe to the Retire Sooner Podcast to hear Clark Howard, Wes Moss, and Christa DiBiase bring retirement planning and investing conversations to life with humor, perspective, and approachable discussions about financial independence, retirement income, and long-term planning strategies.

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