Retire Sooner with Wes Moss

The stock market may be hitting all-time highs, but is that a reason to celebrate or worry about what comes next? On the Retire Sooner Podcast, Wes Moss and Christa DiBiase turn current headlines and listener questions into a lively conversation about investing, retirement, Social Security, housing, 55+ communities, healthcare, and more.

·       See what history may tell us about stock market all-time highs, why they have historically arrived in bunches, and how corrections may fit into the picture.

·       Track the S&P 500’s historical performance and put today’s market highs into historical perspective.

·       Ask whether early retirement m...

What does it really take to retire sooner and enjoy the years you’ve worked so hard for? On this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase tackle listener questions about retirement planning, investing, taxes, retirement income, and the pursuit of a happier life after work.

·       Examine the idea of building a retirement life map around what matters most to you.

·       Discover what Aristotle can teach us about retirement happiness, purpose, and fulfillment.

·       Confront spending anxiety and why letting yourself enjoy your savings can be surprisingly difficult.

·       Consider when it might be time for a change o...

When should you claim Social Security? Should you pay off your mortgage before retirement? And how do you balance saving for retirement while helping pay for college? Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they tackle listener questions and explore practical perspectives on retirement planning, retirement income, taxes, pensions, and planning for a more fulfilling retirement.

planning for a more fulfilling retirement

• Compare Social Security claiming approaches and the factors that may influence your decision.

• Consider how health, longevity, your spouse, and taxes may shape your...

Retirement planning isn't just about the numbers—it's also about trying to create a life you'll enjoy living. Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they tackle listener questions, share fresh retirement planning perspectives, and explore the habits that may help shape a more fulfilling future, including sleep!

• Discover The Retire Sooner Method, including the Money & Happiness Green Zones, the Retirement Superpower, and the role Core Pursuits may play in retirement.

• See how sleep, net worth benchmarks, liquid investable assets, income, and mortgage payoff may influence long-term retire...

What does it really take to build a happy retirement? Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they blend retirement planning research with listener questions to explore the financial and lifestyle choices that may help shape life after work.

• Learn how the five-step Retire Sooner Method brings together the financial and personal sides of retirement planning.

• See how retirement "green zones" may help you think about savings, income, liquidity, and mortgage decisions.

• Explore why core pursuits, strong friendships, and even better sleep have been linked to gre...

Retirement is about more than growing your nest egg; it’s also about building friendships, finding purpose, and making informed financial decisions along the way. Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they blend listener questions, new research, and practical conversations about retirement planning, retirement investing, and personal finance.

• Hear an inspiring listener story about trading everyday life for a full-time adventure aboard a sailboat in the Caribbean.

• Discover new research on how long it may take to build close friendships and why those relationships may matter throug...

In this special episode of the Retire Sooner Podcast, Wes Moss shares the story behind The Retire Sooner Method and explores the research on the financial and lifestyle habits associated with greater retirement satisfaction.

• Discover five habits that research has associated with greater retirement satisfaction.

• See how saving a little time today may create more flexibility in retirement.

• Hear the story behind the "Happiest Retiree on the Block" and The Retire Sooner Method.

• Explore how purpose, core pursuits, close friendships, and a written financial plan may support retirement well-being.

• Learn how...

Retirement planning comes with plenty of questions, and this episode of the Retire Sooner Podcast is built around answering them. Join Wes Moss and Christa DiBiase as they tackle listener questions on retirement income, investing, 401(k)s, Roth IRAs, target-date funds, and career changes.

• Compare the bucket strategy with other approaches to generating retirement income.

• Learn how withdrawal guardrails may help shape spending decisions in different market environments.

• Consider 401(k) and Roth IRA options if you're working to build your retirement savings.

• Find out how target-date fund fees and expense ratios really w...

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-pl...

Is retirement just about accumulating assets, or is it also about creating the flexibility to spend your time in ways that matter most to you? Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they explore retirement planning, investor behavior, and the financial decisions that may influence long-term outcomes.

• Discover why building wealth and preserving wealth often involve different financial considerations.

• Examine how emotions, habits, and investor behavior may affect financial decision-making over time.

• Explore the transition from asset accumulation to retirement income planning and ri...

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 reti...

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 suppor...

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, co...

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 dec...

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...

Do headlines about AI, jobs, and markets feel overwhelming? Let this episode of the Retire Sooner Podcast help put things into perspective, using real data and relatable scenarios to connect today’s trends with everyday financial decisions.

• Rethink college graduate unemployment and see how AI may be shaping hiring, with recent data pointing to more stability than disruption.

• Put the U.S. job market in context by examining constant turnover, career shifts, and ongoing opportunity.

• Consider what a midlife career change might look like while factoring in updated 529 plan rules that may offer more fle...

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 eval...

On this episode of the Retire Sooner Podcast, step back and reassess your retirement plan as Wes Moss and Christa DiBiase examine what may drive retirement happiness. Connect financial independence, taxes, and today’s economic backdrop into a clearer long-term perspective. See how big decisions, from pensions to property taxes to market uncertainty, may fit together to help evaluate what matters most for your own path.

• Reimagine how achieving financial independence may shift your sense of purpose, and consider ways to redirect that drive toward a more fulfilling retirement.

• Size up how property taxes may shape...

Rethink retirement, and how the financial and lifestyle choices of today may shape tomorrow. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase bring real-world context to retirement planning, housing decisions, investment strategies, and tax considerations.

• Discover how consistent saving and long-term investing have historically supported greater flexibility in retirement, though past performance does not guarantee future results and may not indicate future market direction.

• Picture how your retirement location, cost of living, and closeness to family may shape your day-to-day happiness.

• Use a simple framework to research and test p...

If the financial headlines feel overwhelming, Wes Moss and Christa DiBiase help bring things back into focus. This episode of the Retire Sooner Podcast ties real listener questions to long-term investing principles, offering context to support more informed decision-making.

• Examine why many Americans feel financially behind while weighing the risks often associated with higher-risk areas such as crypto, meme stocks, options trading, and sports betting—and the behavioral pull of comparison-driven investing.

• Evaluate pension choices by comparing lump sum payouts versus lifetime income streams in the context of longevity, income needs, and personal financial goals.

...

Reimagine what retirement could look like with Wes Moss and guest host Mallory Boggs, as they connect today’s biggest financial questions to real-life planning decisions. From new savings strategies to listener-driven scenarios, this episode of the Retire Sooner Podcast delivers timely context to help you think differently about your financial future.

• Discover how “Trump Accounts,” seed funding, and consistent contributions are being discussed as tools for early, tax-advantaged, multigenerational savings.

• Explore how a Year Zero Savings Plan may shape a child’s financial starting point while highlighting the impact of time in long-term investing.

• Eval...

Special guest Clark Howard joins Wes Moss to co-host a standout episode of the Retire Sooner Podcast, exploring how market volatility, energy prices, and global events may intersect with retirement planning considerations. Evaluate how shifting economic forces, from inflation to Federal Reserve policy, may shape investment decisions and long-term financial positioning.

• Explore how rising oil and energy prices may influence gasoline, travel, and everyday consumer costs through petroleum-based dependencies.

• Assess how production levels, demand shifts, and changing consumer behavior may shape economic activity and regional growth.

• Evaluate how international slowdowns and Federal Reserve rate d...

Market volatility, inflation, and rapid technological change are shaping today’s financial landscape, while long-term planning remains an important consideration for many investors. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase share general perspectives on investing, retirement planning, and workplace trends to help inform decision-making within a broader financial context.

• Assess how geopolitical events and oil price volatility may influence inflation, consumer costs, and market performance.

• Understand how energy markets and real-time information flow may contribute to stock market swings and investor sentiment.

• Review historical market behavior following geopolit...

Retirement planning questions often intersect with global markets, tax decisions, and long-term investing strategy. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase examine listener questions while exploring how portfolio diversification, retirement readiness, and disciplined investing may help shape long-term financial planning.

• Evaluate international vs. U.S. stocks when considering portfolio diversification and the potential influence of recency bias in investment decisions.

• Assess global market trends and examine how diversified asset allocation may support a long-term retirement investing strategy.

• Clarify narratives about the U.S. dollar’s global reserve status a...

Retirement planning is often shaped by disciplined decisions, market realities, and investor behavior. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase address timely retirement investing questions and frame them within a long-term, evidence-based approach designed to inform—not predict—financial outcomes.

• Compare dollar-cost averaging versus lump-sum investing and evaluate how investor psychology may influence portfolio results.

• Reassess what it means to feel behind on retirement savings and explore catch-up strategies, contribution limits, and long-term discipline.

• Evaluate how to handle windfalls, consolidate retirement accounts, and apply the Rule of 55 guideline...

Inflation, record market highs, early retirement dreams, and complex estate questions—retirement planning doesn’t happen in isolation. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase translate timely headlines and listener scenarios into thoughtful, long-term financial planning considerations.

• Assess how rising grocery and beef prices reflect inflation and evaluate ways to think about purchasing power over time.

• Review stock market all-time highs alongside historical correction patterns to frame risk within a diversified allocation.

• Examine what retiring in your 40s may require, including savings rates, spending assumptions, and trade-offs.

• St...

Retirement decisions don’t often happen in isolation—they’re shaped by markets, policy shifts, career trends, and personal trade-offs. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase translate timely financial headlines into practical retirement planning considerations.

• Assess cash-flow strategies for small business owners, including how Roth IRA contribution rules may create flexibility.

• Interpret the latest U.S. jobs report and education-level unemployment trends to help frame portfolio and career decisions.

• Evaluate small-cap and value stock performance after years of lagging returns within a diversified allocation.

• Examine why sa...

Inflation is back in focus—and it’s reshaping how many people think about retirement decisions. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase answer listener questions while providing clear context around markets, portfolios, and long-term planning trade-offs.

• Explore how inflation cycles have historically resurfaced and how price shocks may influence spending and wage conversations.

• Compare growth and value stocks using simple analogies that help clarify their role in retirement portfolios.

• Break down how retirement withdrawals and tax planning are commonly coordinated, including Roth conversions and differ...

Concerned about retirement planning in a market full of uncertainty and noise? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase bring practical context to today’s financial headlines and common retirement questions.

• Analyze movements in gold prices and the U.S. dollar to clarify what currency shifts may indicate for markets and everyday economic conversations.

• Explain why a modestly weaker dollar is not inherently negative and how it can affect U.S. company competitiveness.

• Break down how the 4% retirement withdrawal rule of thumb is commonly discusse...

Is the American middle class actually shrinking, or evolving? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase offer educational context on widely discussed economic, investing, and retirement planning topics shaping today’s financial conversations.

Listen as long-term data, market history, and household-level considerations are used to frame—not forecast—how these issues connect.

• Examine why the U.S. middle class is often described as shrinking and how income mobility, inflation-adjusted thresholds, and household dynamics influence that narrative.

• Review how artificial intelligence is commonly discussed in relation to productivity, workforce...

Gain clear, educational context on today’s investing and retirement planning topics with the Retire Sooner Podcast, hosted by Wes Moss and Christa DiBiase. This episode places market trends, investor behavior, and retirement account considerations into long-term perspective using historical data and widely referenced research.

In this episode, you’ll hear discussions that:

• Define the differences between small-cap, mid-cap, and large-cap stocks and explain how market-capitalization classifications are commonly discussed in retirement planning.

• Examine why individual investors have historically experienced returns that differ from market benchmarks, referencing behavioral research frequently cited by DALBAR.

• ...

The Retire Sooner Podcast welcomes Clark Howard alongside Wes Moss and Christa DiBiase for a special episode focused on market history, long-term investing principles, and today’s most talked-about financial transitions. The conversation emphasizes context over commentary and highlights how investors often think through uncertainty, change, and market structure.

• Highlight Clark Howard’s perspective on Warren Buffett stepping down as CEO of Berkshire Hathaway at age 95 and the transition to Greg Abel.

• Review Berkshire Hathaway’s long-term role in markets and why its history is frequently referenced alongside the S&P 500.

• Frame why long-term ma...

Start the year with structured context around today’s most frequently discussed retirement planning questions on the Retire Sooner Podcast, hosted by Wes Moss and Christa DiBiase. This episode presents an educational review of real listener scenarios, placing retirement, investing, and planning topics within a long-term analytical framework.

• Review current U.S. wealth statistics by discussing commonly cited data on net worth, retirement account balances, and generational financial trends.

• Outline household risk considerations by examining how families often think about emergency savings, retirement contributions, and income stability.

• Discuss real estate planning considerations by evaluati...

What actually shapes life in retirement—your finances, your relationships, or both? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase walk through new research on happiness in retirement and unpack several financial and economic topics that often come up in retirement planning conversations.

• Share findings from a 2025 Money and Happiness in America study that looks at how social connection is commonly linked to reported retirement satisfaction.

• Talk through research showing how the number of close personal relationships is often discussed when measuring happiness among retirees.

• Reflect on how American...

Looking for clear context around today’s most talked-about retirement planning issues? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase present an educational discussion covering healthcare planning, retirement income considerations, Social Security decisions, and how current economic conditions are commonly framed in retirement conversations.

• Review current healthcare enrollment periods, including Affordable Care Act considerations, and why coverage timing is often discussed by early retirees.

• Illustrate a real-world healthcare planning example that examines estimating and managing medical costs before age 65 using publicly available comparison tools.

• Explain recent healthcare policy changes...

Looking for an educational overview of today’s most commonly searched retirement planning topics? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase provide context around retirement income planning, tax considerations, and widely referenced financial frameworks, helping listeners better understand how these concepts are typically discussed.

• Review how Roth IRA conversions are generally evaluated and why converting an entire retirement account balance in a single tax year can materially affect taxable income calculations.

• Explain how marginal tax brackets apply to large conversions and why simplified terms like “tax bomb” may not fully refl...

Gain a grounded, research-informed perspective on retirement planning in this episode of the Retire Sooner Podcast, where Wes Moss and Christa DiBiase examine the emotional, behavioral, and organizational factors that often influence how individuals approach life after work. This conversation highlights commonly referenced frameworks and planning considerations, offering context for listeners seeking to better understand the many moving parts of a thoughtful retirement process.

• Explore the behavioral and psychological dynamics behind transitioning from a saver mindset to a spending mindset in retirement, including the frequently cited “millionaire’s paradox.”

• Understand how creating a written retirement plan may h...

Stay informed about today’s highly-searched retirement and financial planning topics in this new episode of the Retire Sooner Podcast with Wes Moss and Christa DiBiase. Gain clear, accessible context on economic trends, retirement rules, portfolio structures, and planning conversations that are shaping long-term decision-making discussions.

• Explore how the proposed 50-year mortgage is influencing conversations around affordability, home-equity timelines, and shifting real estate structures.

• Recognize how the K-shaped economy reflects differing financial experiences across households and shapes discussions about consumer sentiment and wealth-building patterns.

• Clarify how mortgage leverage and ultra-long terms relate to borrowin...

Are you prepared for the major life catalysts that may influence your retirement planning and long-term lifestyle? In this episode of the Retire Sooner Podcast, Wes Moss and Producer Mallory highlight key moments that can shape financial decisions, expectations, and overall well-being.

• Explore how the “Retire Sooner Richter Scale” frames the relative influence of major life catalysts on retirement planning.

• Recognize how family transitions—college milestones, caring for aging parents, or losing a spouse—may shift emotional, logistical, and financial considerations.

• Consider how relationship changes, such as marriage, remarriage, or divorce, may alter household fina...

Ready to explore the real questions shaping today’s retirement conversations? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase respond to listener scenarios on family financial decisions, workplace retirement plans, and the changing job landscape—offering context to help listeners better understand the factors involved in long-term planning.

In this episode, you’ll:

• Explore how non-monetary inheritance can influence family values, expectations, and financial communication across generations.

• Review key considerations when evaluating whether to help adult children with debt while maintaining alignment with your own financial priorities.

• Unders...