Tag: Tax Planning
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!

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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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Should You Buy, Lease, or Hold? Car Buying Decisions in Retirement (Ep. 92)

Should You Buy, Lease, or Hold? Car Buying Decisions in Retirement (Ep. 92)

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Buying a car can be exciting, but it can also be financially confusing, especially as you enter retirement.

How do you decide between leasing, buying new, or buying used? What financial factors should retirees consider before making a vehicle purchase?

In this episode, Josh Leonard guides listeners through the key financial and personal considerations when choosing a new vehicle in retirement. He compares leasing with buying, discusses the impact of interest rates, and shares tips to make smarter purchasing choices without breaking the budget.

Josh discusses:

  • The pros and cons of buying new vs. used vehicles
  • Leasing versus purchasing options, highlighting factors like mileage, monthly payments, and long-term costs
  • Financing strategies, including interest rate comparisons, pre-approvals, and the tax implications for retirees
  • The importance of budgeting for car expenses in retirement
  • Personal stories and anecdotes around car buying experiences
  • And more!

Resources:

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Spring Clean Your Finances: 5 Essential Tips for a Fresh Start (Ep. 90)

Spring Clean Your Finances: 5 Essential Tips for a Fresh Start (Ep. 90)

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Are your finances due for a little spring cleaning? Just like airing out your home after winter, it’s time to dust off your financial strategy!

Join Josh Leonard as he dives into five key tips for a fresh start this spring. He explores ways to tidy up old retirement accounts, refresh your financial planning outlook, and manage risk in a market full of surprises.

Josh covers:

  • Consolidating outdated retirement accounts to cut down on fees and overlap
  • Reviewing and updating your financial strategy to ensure income sufficiency
  • Assessing investment risks and considering portfolio adjustments
  • Conducting a tax review to avoid unexpected surprises
  • Strategies for more tax-efficient charitable giving 
  • And more!

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Mastering the Tax Triangle (Ep. 84)

Mastering the Tax Triangle (Ep. 84)

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What do taxes and retirement have in common with your happiest Saturday? 

In this episode of Relax, It’s Retirement, Josh Leonard invites you to unravel the often confusing world of taxes as you approach your golden years. He dives into the “tax triangle” strategy, offering a simplified perspective on how to categorize your assets for better tax efficiency. 

Josh shares tips on navigating taxed always, taxed later, and the coveted taxed never categories, as well as how these can impact your retirement strategy. 

Josh discusses:

  • The Tax Triangle and how it can guide your financial decisions
  • The benefits of tax-advantaged accounts like Roth IRAs
  • Tips for balancing your tax strategy in retirement 
  • Avoiding common tax pitfalls and optimizing for future changes
  • And more!

Resources:

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Setting Goals for a Purposeful Retirement (Ep. 82)

Setting Goals for a Purposeful Retirement (Ep. 82)

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Goal setting isn’t just for your career—it’s essential for creating an intentional and fulfilling retirement.

What goals will keep you engaged, active, and satisfied as you transition to this next chapter? How do you plan for a successful financial and personal journey during retirement?

In this episode, Josh Leonard recaps his personal and professional goals while emphasizing the importance of intentional goal-setting. 

He explores strategies to maintain motivation, improve well-being, and align your finances with your desired lifestyle. By applying the SMART framework, Josh outlines how retirees can structure their aspirations to make retirement a rewarding experience.

Josh discusses:

  • How achieving his goal of completing the Leadville MTB 100 taught him the value of preparation and persistence
  • The importance of using the SMART framework (Specific, Measurable, Achievable, Relevant, Time-Bound) when setting personal and financial goals
  • Examples of how retirees can create income plans, like targeting $6,000 monthly from various sources, to ensure financial stability
  • Strategies for maintaining healthy habits, such as balancing exercise, diet, and reducing phone time with family
  • The psychological and emotional benefits of setting goals, including enhanced focus, time management, and overall happiness in retirement
  • And more!

Resources:

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5 Key Tax Opportunities to Capture Before Year-End! (Ep. 77)

5 Key Tax Opportunities to Capture Before Year-End! (Ep. 77)

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Are you making the most of your year-end tax planning? 

In this episode, Josh Leonard dives into effective year-end tax planning strategies to maximize your savings. Prepare for an insightful discussion on Roth conversions, tax loss harvesting, and charitable giving. 

Learn how to navigate potential tax pitfalls and make informed financial decisions before the calendar flips to a new year.

Josh covers:

  • Roth conversions and their tax advantages
  • Tax loss harvesting to offset gains
  • Charitable giving strategies, including QCDs and donor-advised funds
  • Maximizing deductions for medical expenses
  • Adjusting withholding for accurate tax planning
  • And more!

Resources:

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Capital Loss Harvesting vs. Capital Gain Harvesting: What’s Right for Your Retirement? (Ep. 69)

Capital Loss Harvesting vs. Capital Gain Harvesting: What’s Right for Your Retirement? (Ep. 69)

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Are you maximizing the potential of capital gains and losses in your retirement planning?

This week, Josh Leonard and Pete Belcastro dive into the often-overlooked strategies of capital gain and loss harvesting. You’ll learn the essential differences between capital loss and capital gain harvesting, why timing and tax brackets play a crucial role in your financial planning, and how these strategies can help minimize your tax liability, particularly in retirement. 

Join us for an informative discussion that could significantly influence how you manage your investments for a more secure financial future.

Josh and Pete discuss: 

  • Exploring Capital Loss vs. Capital Gain Harvesting: Understanding the fundamental principles and their implications for your tax strategy
  • Timing is Everything: Why the fourth quarter is critical for reviewing and adjusting your tax planning strategies
  • Tax Brackets: How these affect your decision-making on selling assets and realizing gains or losses
  • Retirement Focus: Tailoring these strategies to optimize tax savings and maintain financial health in your golden years
  • And more!

Resources:

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Navigating RMD Changes for Your Retirement Plan (Ep. 62)

Navigating RMD Changes for Your Retirement Plan (Ep. 62)

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Why does the government force you to take money out of your retirement accounts, even if you don’t need it?

In this episode or Relax, It’s Retirement, Josh Leonard and Pete Belcastro dive  into the intricacies of Required Minimum Distributions (RMDs) and explain why they are a crucial aspect of retirement planning. Together, they cover recent changes in RMD rules, including the impact of the Secure Act and the importance of understanding how these changes affect your retirement and tax planning. 

You’ll learn about the different types of beneficiaries and the rules surrounding inherited IRAs, making this a must-listen for anyone approaching or navigating retirement.

Josh and Pete discuss: 

  • Understanding Required Minimum Distributions (RMDs) and their recent rule changes
  • The implications of inheriting an IRA and the different types of beneficiaries
  • How the Secure Act has changed the way RMDs are calculated and distributed
  • How to navigate these complex rules and avoid potential penalties
  • And more

Resources:

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Longevity in Retirement: Planning for the Long Haul (Ep. 59)

Longevity in Retirement: Planning for the Long Haul (Ep. 59)

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Are you ready to make your retirement last for the long haul?

In this episode of Relax, It’s Retirement, Josh Leonard and Pete Belcastro discuss the importance of longevity in retirement. They cover strategies for structuring your assets to ensure they last, the importance of tax planning, and tips for maintaining an active and fulfilling lifestyle throughout your retirement years. Learn about the three-bucket strategy for managing your funds, the importance of tax-efficient planning, and how staying active and socially engaged can enhance your quality of life. 

This episode is packed with valuable tips and real-world examples to help you navigate your golden years with confidence.

Josh and Pete explain: 

  • How to allocate your retirement savings into short-term, income, and growth buckets for long-term stability
  • Why being tax-efficient now can save you more in the future and ensure your money lasts longer
  • The importance of staying physically active and socially engaged to improve your quality of life in retirement
  • How maintaining a routine and engaging in activities can enhance your happiness and longevity
  • And more

By focusing on longevity, tax efficiency, and staying active in this episode, we want to empower you to make smart decisions for a secure and enjoyable retirement. Listen now and take the first step toward a well-planned future!

 

Resources:

 

Connect with Josh Leonard: 

 

Connect with Pete Belcastro: 

 

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