Category: Business
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:

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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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Turning High Income Into Lasting Wealth (Ep. 99)

Turning High Income Into Lasting Wealth (Ep. 99)

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Earning a high income doesn’t automatically translate to lasting wealth. The real challenge is how to transform those peak earning years into a retirement filled with stability and freedom.

In this episode, Josh Leonard shares three practical strategies to reduce taxes now and build wealth for the long term. From maxing out tax-advantaged accounts to using charitable giving vehicles and understanding capital gains planning, Josh explains how intentional decisions today can lead to a more tax-efficient retirement tomorrow.

Key takeaways:

  • The importance of converting “rich” (high income) into true wealth 
  • Maxing out 401(k), IRA, Roth, and HSA contributions to take advantage of tax benefits 
  • How donor-advised funds can amplify charitable giving while reducing taxes
  • Using deferred compensation and capital gains strategies for long-term efficiency
  • Why proactive retirement planning makes the transition smoother and more intentional
  • And more!

Resources:

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6 Tax-Smart Takeaways from the One Big Beautiful Bill Act (Ep. 98)

6 Tax-Smart Takeaways from the One Big Beautiful Bill Act (Ep. 98)

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Tax law changes are here, some good, some complicated. 

But one thing’s for sure: now is the time to adjust your plan.

In this episode, Josh Leonard breaks down the One Big Beautiful Bill Act and what it means for those nearing or entering retirement. From enhanced deductions to planning around RMDs and Social Security, he outlines six crucial areas that deserve your attention now.

Josh covers:

  • How slightly wider tax brackets may still trigger more taxable income due to Social Security inclusion
  • A new $1,000 charitable deduction for non-itemizers starting in 2026, and how to strategize around it
  • The $6,000 senior deduction and how to layer it with other tactics like Roth conversions
  • SALT cap increases and strategies for households earning $500–600K to reduce taxable income
  • The time-sensitive nature of these changes and how intentional planning can help offset future burdens
  • And more!

Resources:

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