Category: Education
The Retirement Stress Test: What Breaks First in Your Plan? (Ep. 109)

The Retirement Stress Test: What Breaks First in Your Plan? (Ep. 109)

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Most people don’t have a bad retirement plan; they just haven’t tested it yet.

In this episode, Josh Leonard walks through what it really means to pressure-test your retirement plan before you step away from work. Using a real client story, he breaks down how a plan that looks solid on paper can still carry hidden risks if it hasn’t been coordinated across income, taxes, investments, healthcare, and legacy.

Josh shares how small adjustments, like restructuring investments into purpose-driven “buckets,” planning for tax-efficient withdrawals, and reviewing beneficiary designations, can make a meaningful difference over time. He also highlights how overlooking factors like Medicare decisions or account structure can lead to unnecessary costs later.

This conversation is a reminder that retirement isn’t just about how much you’ve saved; it’s about how everything works together when you need it most.

Josh discusses: 

  • Why retirement plans need to be stress tested, not just built
  • The “bucket strategy” for income, cash, and growth
  • How market downturns early in retirement can impact long-term outcomes
  • Hidden tax risks and how to think about withdrawals more intentionally
  • And more!

Resources:

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Staying Invested Through Market Noise with Dominic Pappalardo (Ep. 108)

Staying Invested Through Market Noise with Dominic Pappalardo (Ep. 108)

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Markets move fast, headlines move faster, and emotions often follow.

So how do you stay grounded when uncertainty feels constant and every decision seems urgent?

In this episode, Josh Leonard speaks with Dominic Pappalardo, Chief Wealth Strategist at Morningstar Wealth, about maintaining discipline during volatile markets. They break down a bucket-based investment approach, the importance of long-term thinking, and why reacting to headlines can hurt outcomes. Dominic also shares insights on missing key market days, evaluating AI valuations, and how bonds and sector dispersion are shaping current opportunities.

Key takeaways:

  • Why structuring portfolios into cash, income, and growth buckets helps reduce emotional decisions
  • Missing just a few key trading days can significantly impact long-term returns and outcomes
  • AI growth remains strong, but long-term value depends on real returns from adoption by businesses
  • Bonds now offer better income support compared to prior years due to higher starting yields
  • Market opportunities often come from gaps between pricing and fundamentals across sectors
  • And more!

Resources:

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Connect with Dominic Pappalardo:

About our Guest: 

Dominic Pappalardo is chief multi-asset strategist for Morningstar Wealth. He plays a crucial role as a public-facing ambassador to a variety of media channels. His work ensures that complex asset class views, macroeconomic insights, and portfolio positioning are communicated effectively to a wide range of audiences. Dominic leads the production of insightful commentary and research intended to engage and inform a diverse client base. Acting as a vital link between the investment team and clients, he is instrumental in enhancing visibility and engagement around the firm’s highest conviction ideas. Internally, he collaborates closely with the portfolio management and research teams to maintain cohesion in macroeconomic perspectives and asset class views, delivering a unified narrative to stakeholders. Advisory services under Morningstar Wealth are offered by Morningstar Investment Management LLC, a registered investment adviser and subsidiary of Morningstar, Inc.

Before joining Morningstar in 2020, Pappalardo cultivated nearly two decades of experience managing all facets of fixed income strategies at McDonnell Investment Management, an affiliate of Natixis Investment Managers.

Pappalardo holds a B.B.A. in Finance from Benedictine University. He also holds an M.B.A from The University of Notre Dame’s Mendoza College of Business.

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Spring Tax Cleaning: 3 Hidden Opportunities in Last Year’s Return (Ep. 107)

Spring Tax Cleaning: 3 Hidden Opportunities in Last Year’s Return (Ep. 107)

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A tax return can reveal more than what happened last year; it can point to choices that may help reduce friction and improve retirement income over time.

What hidden issues could be sitting in your paperwork, and what small moves today could help you avoid bigger tax headaches later?

In this episode, Josh Leonard explains how a closer look at your tax return can uncover planning opportunities before they grow into larger retirement issues. He covers phantom gains in taxable accounts, why a 0% tax bill can still create future problems, and how tax bracket planning matters before required distributions begin. Josh also walks through charitable giving strategies, including new 2026 deduction rules and qualified charitable distributions for IRA owners.

Key takeaways:

  • Why phantom gains from mutual funds can create taxable income even when your account balance declines overall
  • How a 0% tax return may hide a future jump into higher brackets once pensions and RMDs begin later on
  • Why reviewing taxable income sources can reveal avoidable drag from dividends, rebalancing, and fund sales
  • How Roth conversions can help spread taxes across retirement years instead of pushing income into later spikes
  • Why charitable gifts may be more effective through new deductions or direct IRA transfers after age 70 and a half
  • And more!

Resources:

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Don’t Let “One More Year” Steal Your Retirement (Ep. 106)

Don’t Let “One More Year” Steal Your Retirement (Ep. 106)

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What if “just one more year” at work costs you more than it gives you?

In this episode, Josh Leonard challenges one of the most common retirement assumptions, the idea that working one more year is always the safer choice. While extra income can feel reassuring, delaying retirement can quietly take time, health, energy, and meaningful experiences you may never get back.

Josh walks through real client stories and practical planning scenarios that show why one more year is often an emotional decision, not a financial one. He introduces a simple trade-off filter to help listeners evaluate whether delaying retirement truly improves their plan or simply postpones living the life they’ve already earned.

Josh discusses:

  • Why being financially ready does not always make retiring emotionally easy
  • How taxes, required distributions, and healthcare can change the math
  • The hidden cost of delaying retirement when time and health are limited
  • A three-question framework to evaluate if one more year actually helps
  • How intentional income planning creates confidence to retire sooner
  • And more!

Resources:

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From Success to Strategy: Planning With Intent for High Earners (Ep. 105)

From Success to Strategy: Planning With Intent for High Earners (Ep. 105)

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If you have ever thought, “I make good money, so why does this still feel complicated?”, you are not alone.

In this episode, Josh Leonard breaks down why higher income often brings more friction, not less, and why success can quietly add complexity to your financial life if it is not coordinated with intention.

In this episode, Josh walks through what he commonly sees with high earners who are capable, driven, and successful, but short on time. As income grows, financial systems tend to layer on bonuses, equity compensation, multiple accounts, real estate, and tax exposure. None of these are mistakes, but without a clear framework, small inefficiencies can build up and slow progress toward retirement.

Josh discusses:

  • Why success rarely simplifies finances on its own
  • How “financial friction” shows up through taxes, concentration risk, and misaligned accounts
  • The role of coordination across investments, taxes, income, healthcare, and estate planning
  • Why having money does not always mean having liquidity
  • How planning with intent helps decisions reinforce each other instead of working against each other
  • And more!

Resources:

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Setting SMART Goals: From New Year’s Resolutions to Real Retirement Readiness (Ep. 104)

Setting SMART Goals: From New Year’s Resolutions to Real Retirement Readiness (Ep. 104)

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Big goals often feel exciting at the start, but how many actually make it past February? What separates the intentions that fade from the habits that last?

In this episode, Josh Leonard breaks down the SMART goal framework and shares his personal goals for the year, from conquering Pittsburgh’s Dirty Dozen bike race to building non-negotiable daily habits. He explains how this same intentional approach applies to retirement planning and why clarity creates confidence when preparing for your next chapter.

Key points:

  • How the SMART framework turns vague resolutions into achievable goals with clear benchmarks and timelines
  • Josh’s three major goals for the year and the specific training, habits, and preparation each requires
  • Why knowing your monthly expenses is the first step in any meaningful retirement plan
  • How hobbies and projects in retirement create purpose beyond simply not working anymore
  • The importance of aiming high and tracking progress, even when life gets in the way
  • And more!

Resources:

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How a 60-Mile Mountain Bike Race Reinforced the Power of Intentional Living (Ep. 103)

How a 60-Mile Mountain Bike Race Reinforced the Power of Intentional Living (Ep. 103)

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Big goals often look simple until you are in the middle of them, tired, uncertain, and second-guessing everything.

How do you stay steady when the plan shifts? How do you prepare for the parts you cannot predict?

In this episode, Josh Leonard shares how a grueling 60-mile mountain bike race deepened his view on preparation, mindset, and the importance of thinking ahead. He talks about the parallels between physical endurance and retirement planning, the value of support systems, and how steady habits create a more intentional life. 

Key points:

  • Planning missteps that made the Austin race tougher, and why preparation shapes outcomes
  • How heat, hydration, and equipment choices influenced the long ride and its lessons
  • Why support systems matter when facing difficult moments or big goals
  • How intentional preparation mirrors the steps needed for retirement planning
  • The value of seeking growth at every stage of life and staying engaged
  • And more!

Resources:

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When Should High-Net-Worth Retirees Take Social Security? (Ep. 102)

When Should High-Net-Worth Retirees Take Social Security? (Ep. 102)

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Planning for retirement comes with many choices that can shape long-term comfort and confidence.

Small shifts in timing, taxes, and income strategy can influence how well your resources support the life you want to enjoy.

In this episode, Josh Leonard breaks down how Social Security fits into a broader retirement plan for high-net-worth individuals, explaining how timing, tax brackets, portfolio design, and future goals work together. He highlights why delaying benefits can reduce risk, how tax planning affects income decisions, and why Social Security should be coordinated with the full financial picture.

Key Insights:

  • Why higher savings create more flexibility around Social Security timing
  • How IRMAA can affect Medicare costs when income rises unexpectedly
  • How delaying benefits can lower long-term risk and support lifetime income
  • How portfolio restructuring reduces unnecessary taxes from mutual fund gains
  • Why Social Security choices must connect with tax, investment, and legacy planning
  • And more!

Resources:

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Taxes, Timing, and the End of the Year: What You Can Still Control (Ep. 101)

Taxes, Timing, and the End of the Year: What You Can Still Control (Ep. 101)

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The end of the year can bring financial stress, but it’s also a valuable time to take control of your retirement strategy.

In this episode of Relax, It’s Retirement, Josh Leonard walks through year-end tax planning steps that can make a real difference for retirees. From RMDs and charitable giving to Roth conversions and managing Medicare costs, Josh highlights how intentional planning today can lead to more confidence tomorrow.

Josh shares:

  • Why year-end tax planning matters and how deadlines impact your financial picture
  • How to use Qualified Charitable Distributions (QCDs) to meet RMD requirements while supporting meaningful causes
  • What to do if you face the “good saver tax problem” and want to pass wealth efficiently to the next generation
  • How Roth conversions and new senior deductions can help balance taxes in retirement
  • Why managing IRMAA limits can prevent unexpected Medicare cost increases
  • And more!

Resources:

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Episode 100 – A Legacy of Intent (Ep. 100)

Episode 100 – A Legacy of Intent (Ep. 100)

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When you hit a milestone, you pause to reflect.

In this special 100th episode, Josh Leonard is joined by his father, Bill Leonard, whose work laid the foundation of what is now the Leonard Advisory Group. Together, they revisit the firm’s humble beginnings, envelopes licked in a basement, meetings around kitchen tables, and the evolution into a practice that now helps hundreds of families retire with clarity and confidence.

Key takeaways:

  • How Bill transitioned from architecture to financial advising
  • Family lessons that shaped Leonard Advisory Group’s mission
  • Stories of clients whose planning ensured lasting comfort
  • The importance of foresight over hindsight in retirement
  • And more!

Resources:

Connect with Josh Leonard: 

Connect with Bill Leonard:

About our Guest: 

William Leonard laid the foundation for  the  Leonard Advisory Group to fill in the gaps he saw when helping his mother plan for retirement. Bill focused much of his career on the insurance and annuity industry. As an independent advisor, he helped thousands of retirees and pre-retirees face the financial challenges that lie ahead with confidence. Since 1996, Bill has worked in a variety of capacities, gaining valuable experience with insurance. In 2007, he became an independent consultant, focusing on income protection and retirement planning. Bill was an honorary host of the “Protecting Your Profits” radio show on 94.5 3WS Pittsburgh and a weekly guest on the national broadcast “Financial Safari” radio show heard locally on NewsTalk 104.7 FM. He has also been featured on WISR 680 AM and WORD FM. In his free time, Bill enjoys traveling, boating, skiing, hiking, biking, restoring antique vehicles, and spending quality time with family, friends, and clients. He has been married to his wife, Cindy, for almost 40 years. They have three children: Zach, Josh, and Zoey, as well as a crazy border collie named Sweep. After over 25 years assisting families transition into retirement Bill transitioned himself into retirement at the end of 2022.

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