Retire Sooner with Wes Moss

Cut through noisy financial headlines on this episode of the Retire Sooner Podcast with Wes Moss and Christa DiBiase as they seek to make retirement planning less overwhelming. Explore retirement income, investing, taxes, Social Security, insurance, and the potential trade-offs behind major financial decisions.   ·       Decode what “high yield” means, its risks, and where it may fit within a retirement portfolio. ·       Compare stock dividends and bond yields as potential income sources with added context from Wes’s Forbes article, “5 Keys to Happy Investing and Retiring Sooner.” ·       Visualize your income sources with a yield ladder as interest rates evolve. ·       Assess early retirement readiness by considering spending, interest income, and the path to Social Security. ·       Explore the roles stocks, bonds, and TIPS (Treasury Inflation-Protected Securities) may play in a diversified portfolio, and read “How to Protect Your Retirement Savings From Inflation” for additional perspective. ·       Weigh pension lump sums against annuities while accounting for payouts, liquidity, longevity, costs, and personal circumstances. ·       Consider long-term HSA investing and qualified medical-expense receipt tracking. ·       Examine how HIFO, FIFO, and other cost-basis methods may affect investment taxes. ·       Uncover the possible costs, restrictions, liquidity concerns, and market-exposure limitations of fixed indexed annuities. ·       Evaluate whether term life insurance may still help address a surviving spouse’s income needs after retirement. ·       Explore how multiple income sources may work together in “8 Planning Strategies That Can Help Address Retirement Money Fears.” ·       Hear additional listener questions about portfolio construction and retirement income planning.   Listen and subscribe to this episode of the Retire Sooner Podcast for an educational look at financial choices and retirement-planning conversations with Wes Moss and Christa DiBiase. Learn more about your ad choices. Visit megaphone.fm/adchoices

Could you be spending more in retirement than you think? On this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase dig into new research on retiree spending, a possible comeback for pensions, and a wide-ranging batch of listener questions about saving, investing, and planning for the future.   ·       Explore research suggesting many retirees may underspend, and why money that arrives as an income stream may feel easier to spend than money pulled from savings. ·       Climb the "yield ladder" and see how dividends and interest from different types of investments may factor into retirement income. ·       Examine why more employers seem to be offering pensions again, and how cash balance plans may differ from traditional pensions. ·       Unpack where extra cash flow may go once the mortgage is paid off, from Roth 401(k) catch-up contributions to brokerage accounts. ·       Learn when a 529 plan may be "enough," and how Trump accounts and future Roth conversions may fit into a child's long-term savings. ·       Review how withdrawals from a 403(b) with both pretax and Roth money may be taxed. ·       Compare investing a lump sum all at once versus dollar-cost averaging over time. ·       Follow how the U.S. government and Federal Reserve may add money to the system, and what that may have meant for post-COVID inflation. ·       Discover options for people aging alone, including financial powers of attorney, professional fiduciaries, and trust companies.   From Jean Chatzky’s new book on retiree spending and pensions to 529s, Roth conversions, and estate planning, Wes and Christa take on some of the money questions many listeners may be facing. Listen and subscribe to the Retire Sooner Podcast for more educational conversations about retirement planning, investing, and financial independence. Learn more about your ad choices. Visit megaphone.fm/adchoices

What might everyday millionaires, Coast FI, and skilled trades teach us about building wealth and planning for retirement? On this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase explore the money decisions, tradeoffs, and strategies that may help shape the road to financial independence. ·       Discover how “everywhere millionaires” are building wealth through hands-on businesses far beyond the Silicon Valley spotlight. ·       Explore the appeal of Coast FI and why life’s financial curveballs may complicate even a carefully designed plan. ·       Examine how skilled trades such as plumbing and electrical work may fit into the conversation around careers, income, and wealth building. ·       Assess how risk tolerance, time horizon, and market swings may help shape a retirement investment mix. ·       Consider how young, high-earning professionals might weigh taxes, student loans, and workplace retirement plansas their incomes grow. ·       Compare lump-sum and monthly pension options while factoring in inflation, COLAs, longevity, and income needs. ·       Evaluate securities-backed lines of credit, including their potential benefits and risks, and how they differ from traditional mortgages. ·       Learn how realizing investment gains may affect reportable income and eligibility for ACA health insurance subsidies. ·       Understand the tax and eligibility considerations surrounding custodial accounts and Roth IRAs for young adults. ·       Explore Wes’s new book, The Retire Sooner Method, and the research behind his approach to the financial and lifestyle characteristics associated with a happier retirement. Listen and subscribe to the Retire Sooner Podcast for more conversations about retirement planning, investing, financial independence, building wealth, and the financial and lifestyle decisions that may come into play on the road to financial independence. Learn more about your ad choices. Visit megaphone.fm/adchoices

Consumer advocate Clark Howard joins Wes Moss and Christa DiBiase for a special Retire Sooner Podcast episode packed with listener questions, thoughtful debate, and real-world financial scenarios. From retirement planning and investing to tax considerations and the pursuit of a more fulfilling retirement, this conversation explores a wide range of topics through the lens of everyday decisions. • Explore how technology stocks, index funds, IPOs, and diversification continue to shape the current investing landscape. • Examine retirement timing, market volatility, and the role consistent investing may play over time. • Consider mortgage, refinancing, capital gains, and tax-planning questions raised by listeners navigating major financial decisions. • Compare Target Date Funds and ETF portfolios while weighing different approaches to diversification and risk. • Evaluate the tradeoffs of selling versus renting a home before an extended move overseas. • Explore the role core pursuits, purpose, and meaningful activities may play in discussions about retirement satisfaction. • Learn about the **pre-sale of Wes Moss's new book, **The Retire Sooner Method, including available bonuses and how to reserve a copy. Whether you're thinking about your portfolio, your next chapter, or both, this episode offers plenty to consider. Listen and subscribe to the Retire Sooner Podcast for more conversations about retirement planning, investing, and the financial and lifestyle decisions that may shape life after work. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

Take a step back and get a clearer view of your retirement plan in this episode of the Retire Sooner Podcast with Wes Moss and Christa DiBiase. Enjoy a practical, easy-to-follow conversation that connects real data, real questions, and real-life planning: offering perspective to help guide decisions. • Explore why retirement confidence may be slipping, using insights from the Employee Benefit Research Institute and the University of Michigan, and see how inflation and oil prices have historically been associated with changing outlooks. • Break down the difference between fiduciary and non-fiduciary advisors to provide a backdrop when evaluating who you trust with your financial picture. • Walk through listener questions on 457(b) vs. 401(k) plans, Roth vs. traditional strategies, and how early retirement access rules actually work. • Get more clarity on VEBA HRA accounts vs. HSAs, and consider what may be affecting Roth IRA growth—including allocation choices and tools used. • Think through when a trust might make sense and how savings accounts, money markets, and bonds may play different roles as interest rates shift. • Consider ways to prepare for long-term care costs, including self-insuring concepts that tie into income planning and HSA savings over time. Looking to explore big picture retirement planning without getting lost in the weeds? This episode is a great place to start. Listen and subscribe to the Retire Sooner Podcast! Learn more about your ad choices. Visit megaphone.fm/adchoices