Tag: Leonard Advisory Group
Can I Retire This Year? (Ep. 93)

Can I Retire This Year? (Ep. 93)

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Market swings, inflation, and shifting headlines can make retiring this year feel uncertain.

But with the right plan, you don’t need to delay your goals — even in a tough market. Are you prepared financially and mentally for what comes next?

In this episode, Josh Leonard shares how to build a flexible retirement strategy that can weather short-term challenges while aligning with your values and lifestyle. He covers tax-efficient tactics, managing income, and finding purpose beyond work.

Josh discusses:

  • How the three-bucket system helps reduce stress about timing your retirement
  • Why proper planning should account for market downturns before they happen
  • The benefits of tax strategies like Roth conversions during lower market years
  • How to prepare mentally and emotionally for the shift from saving to spending
  • Why retirement should be built around purpose, not just portfolios
  • 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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Retirement Resilience: How to Protect Your Plan in a Volatile Market (Ep. 91)

Retirement Resilience: How to Protect Your Plan in a Volatile Market (Ep. 91)

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Worried about market volatility and what it means for your retirement? 

You’re not alone. Many people get anxious when their retirement accounts seem to shrink after years of growth.

In this episode, Josh Leonard discusses market volatility and strategies to remain patient. Josh explains what market corrections are, why they happen, and how to prepare for them. He also details the bucket strategy, a method to help individuals handle financial uncertainties without making rash decisions.

Josh discusses:

  • Navigating market volatility with long-term plans
  • Understanding market corrections and identifying opportunities
  • The importance of cash and retirement buckets for stability
  • Evaluating risks and rebalancing your portfolio
  • 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!

Resources:

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Avoiding the Good Saver Tax Problem with Proactive Planning (Ep. 89)

Avoiding the Good Saver Tax Problem with Proactive Planning (Ep. 89)

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Could saving smart lead to a tax nightmare? 

Join Josh Leonard as he unravels the unexpected “Good Saver Tax Problem” that even the most prepared might face.

Josh explores strategies to sidestep surprise tax burdens during retirement. Dive into proactive approaches like phase-based tax stacking and unravel the complexities of Roth conversions, Required Minimum Distributions (RMDs), and the interplay between social security and taxes.

Through real-life scenarios, gain clarity on navigating these financial challenges.

Josh discusses:

  • The phases of the “Good Saver Tax Problem”
  • How tax stacking can unexpectedly raise brackets
  • The importance of incremental tax strategies
  • Options for those in the required distribution stage
  • Future tax landscape insights
  • And more!

Resources:

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Unpacking Social Security Changes (Ep. 88)

Unpacking Social Security Changes (Ep. 88)

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Social Security remains a critical foundation for retirement, but recent changes bring new opportunities and challenges for retirees.

What strategies can maximize your Social Security benefits? How do recent legislative changes impact your retirement income plan?

In this episode, Josh Leonard explains the updates to Social Security regulations, including the removal of provisions like WEP and GPO, and their potential impact on retirees. He also shares actionable strategies to optimize benefits and maintain a stable financial future.

Josh discusses: 

  • How Social Security benefits are calculated and ways to maximize them based on retirement age and income
  • The removal of WEP (Windfall Elimination Provision) and GPO (Government Pension Offset) under the Social Security Fairness Act of 2025
  • The potential implications of retroactive payments and strategies to manage tax liabilities from lump sums
  • The importance of evaluating spousal and survivor benefits to enhance financial security for couples
  • Balancing Social Security with other income sources, such as 401(k)s and pensions, to create a comprehensive retirement plan
  • And more!

Resources:

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Planning Ahead for Retirement (Ep. 87)

Planning Ahead for Retirement (Ep. 87)

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Retirement should be a time of fulfillment, not financial stress, yet many retirees face unexpected challenges.

How can you make decisions today that your future self will thank you for? What steps can you take to avoid common retirement regrets and financial pitfalls?

In this episode, Josh Leonard and Pete Belcastro discuss essential retirement planning strategies, from managing healthcare costs to optimizing tax efficiency. They emphasize the importance of flexibility, debt management, and long-term financial preparedness to ensure a comfortable and intentional retirement.

Josh and Pete discuss:

  • The top financial concerns of retirees, including the fear of outliving savings and rising healthcare expenses
  • How to strategically plan for major purchases and avoid tax pitfalls in retirement
  • The impact of debt in retirement, including the pros and cons of using 401(k) loans and different debt repayment methods
  • The importance of financial flexibility, including maintaining an emergency fund and planning for unexpected family support needs
  • Common retirement regrets, such as not diversifying investments early enough or failing to plan for long-term financial security
  • And more!

Resources:

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Conquering Retirement Fears with Confidence (Ep. 86)

Conquering Retirement Fears with Confidence (Ep. 86)

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Retirement is a time for celebration, but it often brings up important concerns about money, health, and purpose. 

How can you prepare to enjoy this new chapter with peace of mind?

In this episode, Josh Leonard and Pete Belcastro discuss actionable steps to overcome common retirement fears, from financial security to finding joy and meaning beyond work. Whether it’s optimizing Social Security, managing healthcare costs, or staying socially connected, this episode provides key strategies for a rewarding retirement.

Josh and Pete discuss:

  • How to overcome the fear of running out of savings with practical financial planning
  • Strategic approaches to maximize Social Security benefits for long-term security
  • The importance of maintaining purpose and emotional fulfillment after retirement
  • Tips for managing healthcare costs and understanding Medicare options
  • Lifestyle considerations like downsizing or relocating to meet personal and financial goals
  • And more!

Resources:

Connect with Josh Leonard: 

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The Diversification Dilemma: Are Your Investments Really Safe? (Ep. 85)

The Diversification Dilemma: Are Your Investments Really Safe? (Ep. 85)

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Diversification isn’t just a buzzword—it’s a critical tool for protecting your retirement savings and future security.

This week, Josh Leonard and Pete Belcastro tackle common misconceptions about diversification and share actionable insights on creating a retirement plan that minimizes risk and maximizes opportunities. From portfolio strategies to tax diversification and financial tools, this episode has everything you need to feel confident about your golden years.

Josh and Pete discuss:

  • Why holding accounts at different firms doesn’t guarantee diversification and how to avoid overlapping investments
  • How to spread investments across sectors, regions, and company sizes to minimize risks
  • The importance of tax diversification through tools like Roth IRAs and taxable accounts for greater financial flexibility
  • How annuities, life insurance, and other financial tools can secure income and simplify legacy planning
  • Strategies to avoid over-concentration in employer-linked investments and protect both your career and portfolio
  • And more!

Resources:

Connect with Josh Leonard: 

Connect with Pete Belcastro: 

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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:

Connect with Josh Leonard: 

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