The Stacking Benjamins Show Episode SB1676: "Retirement Roadblocks & Resilient Planning: The Squirrels Gone Wild Edition"

Release Date: April 30, 2025

Overview

In this engaging episode of The Stacking Benjamins Show, hosts Joe Saul-Sehy and OG delve into the potential pitfalls that can derail retirement plans. Titled "Retirement Roadblocks & Resilient Planning: The Squirrels Gone Wild Edition," the discussion centers around four primary culprits threatening smooth retirements and strategies to mitigate these risks. The conversation is enriched with humor, personal anecdotes, expert insights, and practical financial advice, making complex topics accessible and enjoyable for listeners.

1. Healthy Longevity: The Unseen Risk

One of the foremost roadblocks discussed is the concept of healthy longevity—living longer while maintaining good health. According to the Wealthy Accountant blog, the average age for healthy longevity in the U.S. is around 66 years old. This metric highlights the risk of not being healthy enough to enjoy retirement as planned.

Notable Quote:
OG (09:56): "If you're going to have a ton of money but be wildly unhealthy, none of that's going to matter."

Key Insights:

• Interconnectedness of Health and Finances: Financial security is meaningless without good health. The ability to enjoy retirement activities hinges on maintaining physical and mental well-being.
• Healthcare Spending Transition: Retirement spending shifts from leisure (like travel) to necessities (such as healthcare and charitable donations).

Example:
Len shares a personal story about contemplating long-term healthcare insurance after witnessing his mother-in-law's battle with cancer, emphasizing the high costs and emotional toll of inadequate planning.

Notable Quote:
Len Pzo (10:09): "One of the toughest decisions I ever made was to not get long-term care insurance."

2. Job Loss: An Unexpected Horizon Change

Job loss represents a significant threat to retirement plans, not just because of the immediate loss of income but also due to the cessation of retirement contributions and loss of employer benefits.

Notable Quote:
Joe's Mom's Neighbor Doug (24:28): "If you're 52 and you're like, I got 10 years to go and you get your walking papers at 59 and a half, you know, it's..."

Key Insights:

• Horizon Risk: Changes in career trajectory can abruptly alter retirement timelines and financial stability.
• Age Discrimination: Older workers may face challenges re-entering the workforce, especially in industries favoring younger talent.

Strategies Discussed:

• Enhanced Savings: Increasing retirement contributions as a buffer against unexpected job loss.
• Emergency Funds: Maintaining robust savings to cover expenses during periods of unemployment.

3. Supporting Adult Children: Balancing Generosity and Security

The third roadblock involves the financial strain of assisting adult children, often referred to as "failure to launch." While helping kids can be rewarding, it can significantly impact one's ability to save for retirement.

Notable Quote:
OG (35:08): "It's very difficult. It's family, you know. How is it any different than helping out mom or grandma?"

Key Insights:

• Generational Financial Pressure: Modern economic challenges make it harder for younger generations to achieve financial independence, increasing reliance on parental support.
• Setting Boundaries: The importance of defining clear financial support limits to protect one's retirement goals.

Example:
Len describes his parents allowing him to live at home post-college to save for a house, contrasting it with the current struggles faced by younger generations in affording independent living.

4. Loss of a Spouse or Partner: Navigating Personal Tragedy

The final roadblock addresses the profound impact of losing a spouse or partner during retirement. This loss can lead to emotional distress and significant financial upheaval.

Notable Quote:
OG (44:38): "Having a separate financial plan in the corner in a red binder that says, if he leaves me, this is what I do. No, no, no."

Key Insights:

• Emotional and Financial Duality: The intertwining of personal grief with financial instability requires sensitive and strategic planning.
• Flexibility in Planning: Developing adaptable financial strategies to accommodate unexpected personal losses.

Resilient Planning Strategies

To combat these roadblocks, the hosts emphasize resilient planning through various strategies:

1. What-If Planning: Proactively considering potential adverse scenarios to prepare appropriate responses.

   Notable Quote:
   OG (17:16): "These are all the decisions that you can work on making early on."

2. Risk Management: Assessing and mitigating financial risks through insurance and diversified investments.

   Notable Quote:
   Len Pzo (21:04): "This is risk management. Do I take the risk myself or do I hand it over to a third party?"

3. Long-Term Care Insurance: Evaluating the necessity and affordability of insurance products to cover healthcare costs in retirement.

   Notable Quote:
   OG (18:26): "If you want to retire with someone, it's not just about living expenses; it's about managing healthcare costs as well."

4. Flexible Financial Plans: Designing retirement plans that can adapt to changes in health, employment, and family dynamics.

   Notable Quote:
   Len Pzo (18:35): "You have to think through that exercise while you're of relatively sound mind."

Real-Life Examples and Anecdotes

Throughout the episode, personal stories illustrate the complexities of retirement planning:

• Len's Mother's Illness: Highlighting the exorbitant costs of long-term care and the difficult decisions faced by families.
• Job Loss Scenario: Discussing the challenges of re-entering the workforce at an older age and the importance of having a financial cushion.
• Supporting Adult Children: Contrasting generational approaches to housing and financial independence.
• Grandparents as Caregivers: Exploring the strain on older adults who become primary caregivers for grandchildren, affecting their retirement plans.

Notable Quotes

1. OG (09:56):
   "If you're going to have a ton of money but be wildly unhealthy, none of that's going to matter."

2. Len Pzo (10:09):
   "One of the toughest decisions I ever made was to not get long-term care insurance."

3. Joe's Mom's Neighbor Doug (24:28):
   "If you're 52 and you're like, I got 10 years to go and you get your walking papers at 59 and a half, you know, it's..."

4. OG (35:08):
   "It's very difficult. It's family, you know. How is it any different than helping out mom or grandma?"

5. OG (17:16):
   "These are all the decisions that you can work on making early on."

Conclusion

The Stacking Benjamins Show Episode SB1676 offers a comprehensive exploration of the multifaceted challenges that can impede a secure retirement. By identifying key roadblocks such as healthy longevity, job loss, supporting adult children, and the loss of a spouse or partner, the hosts provide listeners with actionable strategies to build resilient retirement plans. Emphasizing the importance of proactive planning, risk management, and flexibility, Joe and OG empower their audience to navigate the uncertainties of retirement with confidence and foresight.

Additional Resources

• Featured Article: Four Things That Can Derail Your Retirement Plan
• Atlantic Piece: "Grandparents Are Reaching Their Limit" by Faith Hill
• Visit StackingBenjamins.com for show notes, links, and resources discussed in the episode.