Tag: Relax It’s Retirement
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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Putting Time on Your Side in Retirement (Ep. 68)

Putting Time on Your Side in Retirement (Ep. 68)

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Time can still be on your side even in retirement!

In this episode, Josh dives into the fascinating dynamics of time and retirement planning. You’ll learn how to maximize your retirement years by leveraging the power of compounding interest, making strategic investment decisions, and using financial tools like annuities and HSAs to ensure your money lasts. Join us as we explore practical strategies to make the most of this new chapter in your life.

Josh discusses: 

  • 03:28) The importance and impact of time and compounding interest in retirement
  • (06:07) How to manage finances effectively with Cash, Income, and Growth Buckets
  • (09:18) Utilizing financial tools like HSAs and annuities to maximize benefits
  • (16:57) Adapting to market volatility without making hasty decisions
  • (21:18) Making the most of your newfound time, hobbies, family time, and volunteering
  • And more

Resources:

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6 Ways to Travel on a Budget in Retirement
6 Ways to Travel on a Budget in Retirement (Ep. 67)

6 Ways to Travel on a Budget in Retirement (Ep. 67)

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Ready to make your dream retirement travel a reality without breaking the bank?

In this episode, Josh Leonard guides you through six effective strategies for budget-friendly travel during retirement. Learn why flexibility is crucial, how to use points and miles effectively, and the surprising alternatives to traditional accommodations. This is your roadmap to financially savvy and fulfilling travel adventures, specially crafted for retirees.

Josh discusses: 

  • Flexibility around travel dates to find cheap flights
  • Using credit card points and loyalty programs
  • Considering alternative accommodations such as Airbnbs or house swaps
  • Planning your travel budget, tracking expenses, and taking advantage of discounts
  • And more

 

Resources:

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Overcoming Obstacles With Grit, Endurance & Family Support (Ep. 66)

Overcoming Obstacles With Grit, Endurance & Family Support (Ep. 66)

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Are you ready to hear a story about grit, teamwork, and the unexpected turns that can define your journey, whether it’s a race or your retirement plan?

In this episode, Josh recounts his recent journey of conquering the Leadville MTB 100 in the Colorado Rockies, with the invaluable support of his wife Yana Leonard, CIA, MBA, Director of Finance. Alongside tales of determination and grit, Josh and Yana emphasize the remarkable role family support played in achieving this monumental feat. Packed with real-world lessons, hear how Josh navigated unexpected hurdles and triumphed with one crucial lesson – preparation and a reliable support system can make all the difference. From unexpected flat tires to quick solutions, learn how this endurance race teaches vital lessons for retirement planning and navigating life’s unpredictability. 

Josh and Yana talk about:

  • How Josh overcame unexpected challenges during the race with the help of his wife and community
  • The quick, practical solutions that helped Josh complete the race – a lesson in planning for the unpredictable
  • The crucial role of support systems in achieving big goals, both in sports and financial planning
  • How disciplined training and strategic planning in sports can translate to successful retirement strategies
  • And more

 

Resources:

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Planning for an Early and Intentional Retirement (Ep. 65)

Planning for an Early and Intentional Retirement (Ep. 65)

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What if you could retire earlier than you think?

In this episode, Josh Leonard and Pete Belcastro dive into the concept of early retirement with the FIRE (Financially Independent, Retire Early) movement, a lifestyle choice emphasizing extreme savings and smart investments. They provide information about how adopting frugality and strategic financial planning can help set you on a path to early retirement. Josh and Pete cover practical tips on extreme savings, smart investing, and the importance of a frugal yet fulfilling lifestyle.

Josh and Pete discuss: 

  • Overview of the FIRE movement and its focus on extreme savings and lifestyle choices
  • Challenges and strategies for those aiming to retire in their 30s or 40s versus traditional retirement age
  • Tips for managing finances, including healthcare and penalty-free withdrawals, for those considering early retirement
  • And more

Resources:

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Estate Planning Essentials (Ep. 64)

Estate Planning Essentials (Ep. 64)

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You can protect your loved ones and legacy as you transition into retirement by estate planning.

Today on Relax, It’s Retirement, host Josh Leonard, and Pete Belcastro dive into the often overlooked but crucial aspect of retirement planning: estate planning. They talk about how to effectively prepare your essential estate documents, avoid the drawbacks of probate, leverage trusts for tax planning, and ensure your loved ones are protected. Tune in for some practical tips and advice around estate planning that can give you peace of mind as you plan for your golden years.

Josh and Pete discuss: 

  • Why regularly updating your will and legal documents is important
  • The role of Power of Attorney in managing assets during incapacitation
  • How to use trusts to protect assets and control distributions
  • How you can minimize the impact of estate taxes
  • And more

Resources:

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How to Choose the Best State for Your Retirement (Ep. 63)

How to Choose the Best State for Your Retirement (Ep. 63)

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Where should you retire? Your perfect place could be closer than you think.

Let’s take a look at some factors that could make or break your retirement decision.

Today on Relax, It’s Retirement, Josh Leonard and Pete Belcastro talk about what truly makes a state great for retirement. They dissect a recent study listing the top states for retirement, unpacking factors such as the cost of living, weather, healthcare, and why personal preferences can completely change the ideal location for retirement. 

Tune in to learn how to weigh these factors with your personal priorities and hear insightful anecdotes from Josh’s years of experience.

Josh and Pete discuss: 

  • The top factors that determine the best states to retire in
  • How different states compare
  • The impact of state and local taxes on retirement planning
  • The importance of balancing the cost of living with lifestyle and proximity to family
  • 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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Healthcare Costs in Retirement: Strategies to Manage Your Expenses (Ep. 61)

Healthcare Costs in Retirement: Strategies to Manage Your Expenses (Ep. 61)

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Are you struggling to navigate the maze of Medicare and healthcare costs in retirement?

In this episode, Josh Leonard and Pete Belcastro delve into the complexities of healthcare planning for retirees. They discuss understanding Medicare, evaluating different health plans, and the critical steps to prevent unexpected medical expenses. Josh and Pete share valuable insights into Medicare’s parts, long-term care options, and the magical benefits of a Health Savings Account (HSA).

Josh and Pete discuss: 

  • Understanding the intricacies of Medicare parts A, B, C, and D
  • Evaluating long-term care options and associated costs
  • Strategies for shopping around for prescription drug plans annually
  • The advantages of contributing to and using a Health Savings Account (HSA)
  • And more

 

Resources:

 

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Breaking Financial Rules (Ep. 60)

Breaking Financial Rules (Ep. 60)

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Are you ready to break some financial rules to optimize your retirement planning?

Today, we’re challenging the rules of retirement planning to see when breaking them might actually be in your best interest.

In this episode, Josh Leonard and his partner in crime, Pete Belcastro dive into five conventional financial rules that many believe are set in stone but might be worth reconsidering to better fit individual needs. They discuss why paying off your mortgage before retirement, avoiding credit cards, and rigidly maintaining a budget might not always be the best advice. Instead, they offer nuanced views and actionable insights on when to break these rules to suit individual financial needs and goals better. Join their discussion as they talk about how to achieve a more nuanced and personalized approach to financial planning, ensuring a more robust and flexible retirement strategy for listeners.

Josh and Pete discuss:

  • The true impact of paying off your mortgage before retirement
  • The benefits and drawbacks of using credit cards in retirement
  • How to maintain a realistic budget without sacrificing quality of life
  • The importance of re-evaluating the “100 minus your age” rule in investment strategies
  • And more

 

Resources:

 

Connect with Josh Leonard: 

 

Connect with Pete Belcastro: 

 

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