Episode Summary: "Possible Health Issues, Can I Retire?" – Jill on Money with Jill Schlesinger

In the August 8, 2025 episode of Jill on Money with Jill Schlesinger, host Jill Schlesinger engages in a heartfelt and insightful conversation with Kim from Pennsylvania. Addressing pressing concerns about retirement amidst potential health issues, Kim seeks guidance on navigating her financial landscape to ensure a secure and enjoyable retirement. Co-host Mark Tulaeur also contributes valuable perspectives, making this episode a comprehensive guide for listeners contemplating similar life transitions.

Listener Call: Kim’s Retirement Concerns [02:08 - 16:05]

Introduction to Kim’s Situation [02:08 - 03:14]

Kim initiates the conversation by expressing her and her husband’s plans to retire—she at 61 and him at 59 years old. A significant factor influencing their decision is their familial experience with dementia, as both Kim’s parents are in memory care, highlighting their desire to enjoy life fully should they face similar health challenges.

Kim: "We want to make sure we're able to enjoy life in case one or both of us has dementia in our future." [02:40]

Financial Overview [03:14 - 07:02]

Jill delves into Kim’s financial details, uncovering a robust portfolio comprising various retirement accounts:

• Kim's Accounts:

  • Rollover IRA: $1.7 million
  • Roth IRA: $27,000
  • Self-Employed 401(k): $30,000
  • Previous Employer’s 401(k): $120,000
  • 403(b): $9,700
  • HSA: $7,000

• Husband’s Accounts:

  • SEP IRA: $600,000

Additionally, Kim shares significant liquid assets:

• Safe Money: $355,000
• Stock Account & CDs: $203,000

Jill: "You've done a lot of different things in your life, haven't you?" [03:38]

Kim and her husband also own three rental properties generating a net income of approximately $65,000 to $70,000 annually. Their primary residence is valued at $1.1 million, with plans to downsize in the next five to six years.

Monthly Expenditures and Social Security Planning [07:02 - 12:34]

Kim outlines her monthly expenses at around $11,000, which Jill helps break down to include both fixed bills and variable costs like credit card payments.

Kim: "It's probably closer to like 9 to 10,000. Sorry. That was a big difference. Yeah, let's do 11." [07:35]

Jill and Mark explore the optimal timing for claiming Social Security benefits, suggesting that waiting until age 67 maximizes her monthly benefits.

Jill: "That's really much better to wait until your full retirement age." [08:28]

Bridging the Gap to Social Security [12:34 - 15:35]

Jill assesses the feasibility of Kim’s retirement plan, emphasizing the substantial income generated from rental properties and Social Security. She reassures Kim that her financial setup is robust, particularly highlighting the rental income as a significant contributor toward her monthly expenses.

Jill: "Social Security is really going to get you a lot of the way towards your goal." [10:42]

The discussion shifts to strategies for managing expenses before Social Security kicks in, including the potential use of retirement account withdrawals.

Jill: "What we're really trying to figure out is how do we make it up until you get to your Social Security benefit?" [09:11]

Roth Conversion Considerations [12:49 - 15:02]

Kim inquires about the possibility of Roth conversions, weighing the benefits against the immediate need for funds.

Kim: "I guess Roth Conversion. Should I think about doing any more conversions or just really think about pulling the money out?" [12:49]

Jill and Mark advise against immediate conversions, recommending instead to utilize withdrawals from pre-tax accounts to cover living expenses, thereby preserving safe money and minimizing tax burdens.

Mark: "I think you're better off just getting money out of that IRA that hasn't been taxed yet." [12:55]

Professional Guidance and Final Thoughts [14:32 - 15:35]

Kim shares her past experience with financial advisors, noting a misstep with a previous wealth manager and satisfaction with her current services at Fidelity.

Kim: "We moved over to Fidelity and they've been really good." [14:32]

Jill reinforces the importance of proactive health insurance planning, especially given Kim’s family history with dementia, and commends her for her diligent financial management.

Jill: "From my perspective at least, there is no reason to delay this... Real game changer for you guys." [15:02]

Key Takeaways and Insights

1. Comprehensive Financial Planning is Crucial: Kim’s diverse portfolio, including IRAs, 401(k)s, HSAs, and rental properties, underscores the importance of a multi-faceted approach to retirement savings.

2. Rental Income as a Financial Pillar: The substantial income from rental properties plays a pivotal role in bridging the gap between retirement onset and Social Security benefits, highlighting real estate as a valuable asset class in retirement planning.

3. Strategic Social Security Claiming: Waiting until full retirement age (67) to claim Social Security benefits can significantly enhance monthly income, providing greater financial stability in retirement.

4. Health Insurance Planning: Proactively addressing health insurance needs, especially when anticipating potential cognitive health issues, is essential. Options like COBRA and the Affordable Care Act should be carefully evaluated to manage costs effectively.

5. Cautious Approach to Roth Conversions: In scenarios where immediate funds are required, it may be more beneficial to withdraw from pre-tax accounts rather than pursuing Roth conversions, thereby managing taxable income efficiently.

6. Value of Professional Financial Advice: Leveraging trustworthy financial advisors ensures that retirement plans remain on track and can adapt to changing circumstances or past missteps.

Notable Quotes

• Jill Schlesinger: "Social Security is really going to get you a lot of the way towards your goal." [10:42]

• Mark Tulaeur: "I think you're better off just getting money out of that IRA that hasn't been taxed yet." [12:55]

• Kim: "We moved over to Fidelity and they've been really good." [14:32]

Conclusion

Kim’s comprehensive review of her financial situation, guided by Jill and Mark’s expert advice, exemplifies effective retirement planning amidst potential health uncertainties. By leveraging diverse income streams, optimizing Social Security benefits, and carefully managing withdrawals from retirement accounts, Kim and her husband are well-positioned to enjoy a secure and fulfilling retirement. This episode serves as a valuable resource for listeners facing similar retirement dilemmas, emphasizing the importance of proactive financial management and the benefits of seeking professional guidance.

For more personalized advice or to share your own retirement concerns, visit jillonmoney.com and click the "Contact Us" button to connect with Jill and her team.