Tag: Income Planning
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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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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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:

Connect with Josh Leonard: 

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