Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Managing the Moving Parts
Air Date: January 12, 2026
Host: Jill Schlesinger, CFP®
Guests: Jane and Pat, listeners from Chicago

Episode Overview

In this episode, Jill Schlesinger assists Jane and Pat, a couple from Chicago navigating the complexities of approaching retirement while addressing ongoing family responsibilities, particularly for their younger son with special needs. The discussion centers on financial reassurance, strategic retirement withdrawals, estate planning, and handling emotional aspects of this major life transition.

Key Discussion Points & Insights

1. Family Background & Context

• Jane (61, stay-at-home mom) and Pat (64, local government worker) have two children:
  • 28-year-old, fully independent
  • 17-year-old, junior in high school with lifelong special needs requiring continued support (05:12)
• Pat continues to work full-time; Jane manages household and caregiving (05:53)

2. Current Financial Snapshot

• Income:
  • Pat earns $13,900/month gross (06:09)
  • Receives a pension: $7,850/month, guaranteed for his and Jane's lifetime; possibly transferable to their youngest son with special needs (06:47; 06:59)
  • Expecting a second pension: $49,000/year after full retirement (09:04)
• Savings & Investments:
  • Brokerage accounts: $55,000 (07:28)
  • HSA/HRA: $150,000 (07:29)
  • Pre-tax retirement savings: $1.9 million (07:53)
  • Roth retirement: $1.37 million (08:09)
  • Inherited IRA: $280,000, subject to lifetime distribution (08:23)
• Monthly Living Expenses: Approximately $15,000, possibly rising to $17,000 due to healthcare costs (08:38; 10:01)

3. Housing & Real Estate

• Current home value: $800,000 with $108,000 remaining on a 3.3% mortgage (11:01; 24:00)
• No additional properties
• Flexibility to relocate depending on youngest child's future education or the older child’s location (11:14)

4. Retirement & Income Planning

• Planned retirement age for Pat: Possibly 65, but open-ended; Pat expressed difficulty envisioning retirement after working since age 14 (10:18; 10:21)
• Combined pensions will generate ~$143,000/year gross (09:17 onward)
• Jane and Pat anticipate Social Security benefits ($3,000/month for Jane and $2,600/month for Pat at 67) (12:58–13:13)
• Strategy: Supplement any income gap with pre-tax retirement account withdrawals, rather than solely relying on pension/Social Security (14:18–18:27)
• Quote:
  • Jill: “One of the funny things is that you have all this money in pre tax retirement, right?... Maybe one of the things that we really decide to do is that... you start taking some money out of that pre tax retirement account and using that to supplement whatever you need.” (14:18)

5. Special Needs & Estate Planning

• Special needs trust in place and being actively updated; attorney involved (11:33–11:45)
• Main goal is to ensure lifetime support for their younger son; considering optimal estate and tax strategies for this outcome (10:52; 14:54)
• Quote:
  • Jane: “Probably [inheritance] would go mostly to the 17-year-old, but certainly the other one will, you know, will be considered as well.” (14:54)

6. Roth Conversions and Tax Strategy

• Debate on whether to convert pre-tax retirement funds to Roth now
• Mark (producer): Pulling from pre-tax accounts preferable to conversion at this stage, due to limited brokerage cash (15:19–15:25; 20:04–23:09)
• Consider withdrawing to the top of the 24% tax bracket annually for tax efficiency (21:43; 23:08)
• Quote:
  • Jill: “If you even thought to yourself, the most important thing that we can do is take as much money out of our pre tax retirement accounts to keep us in the 24% bracket, that is truly the best you can do, I think.” (23:09)

7. Mortgage and Home Equity

• Advised against paying off remaining low-interest mortgage given favorable rate and current cash needs (24:00–24:14)
• Quote:
  • Jill: “You should not [pay off the mortgage]. Do not pay off the mortgage. That's not a good place to use your cash.” (24:08–24:10)

8. Emotional Aspects of Retirement

• Pat admitted being a “workaholic” and struggling with the idea of stopping work; Jill acknowledged the emotional shift for long-time workers (10:21; 18:29)
• Jill’s reassurance: Financially, they’re in strong shape, need to give themselves permission to change their routine and approach retirement with confidence (18:29; 19:09)
• Quote:
  • Jill: “...At some point, you have to give yourself permission to not do that or to say, okay, you know what I'm going to do, I'm going to be a volunteeraholic or whatever you decide you want to do. Like you're going to use your time differently.” (18:29)

9. Takeaways and Final Reassurances

• Jill and Mark both strongly reassured Jane and Pat they’re well-positioned for a secure retirement, even under conservative spending assumptions (19:19–19:38)
• Encourage annual withdrawal strategy, consult with a CPA for evolving tax planning, and avoid impulsive Roth conversions (20:11; 21:43)
• Stay flexible for future changes in family or living situations (24:15)

Notable Quotes & Memorable Moments

• On work & retirement:

  • Pat: “I'm a workaholic. I work, work, work. I've been working since I was 14. But the end is near...” (10:21)
  • Jill: “At some point you have to give yourself permission to not do that...” (18:29)

• On financial security:

  • Jill: “You’re not going to run out of money. I can tell you that right now...” (18:29)

• On estate planning:

  • Jane: “We have a special needs trust…but it’s being updated. You know, it’s constantly an updated type situation...” (11:43)

• On tax strategy:

  • Jill: “If you even thought to yourself, the most important thing…is take as much money out of our pre tax retirement accounts to keep us in the 24% bracket, that is truly the best you can do, I think.” (23:09)

• On mortgage payoff:

  • Jill: “Do not pay off the mortgage. That's not a good place to use your cash.” (24:10)

• Summing up reassurance:

  • Jill: “I don’t see any, I don’t really see any problem here.” (19:09)
  • Mark: “Zero problems. They got this huge income from the pensions...” (19:19)

Important Timestamps

• 04:23–05:11 – Introduction to Jane & Pat and their situation
• 06:00–07:13 – Discussion of Pat’s income, pensions, and employment
• 07:28–08:23 – Review of savings and investment accounts
• 08:38–10:01 – Current and projected expenses, including healthcare
• 11:01–11:39 – Housing value, mortgage, estate planning
• 12:49–14:18 – Social Security and income strategy
• 14:54–15:25 – Legacy wishes for children, Roth conversion debate
• 18:29–19:09 – Emotional side of retirement, Jill’s major reassurance
• 20:04–23:09 – Tax strategies for retirement withdrawals
• 24:00–24:14 – Mortgage payoff advice
• 24:22–24:33 – Final reassurances and encouragement for retirement

Conclusion

Jill on Money’s “Managing the Moving Parts” offers an in-depth, supportive session guiding a couple through the overlapping financial and emotional decisions of retirement—while planning for unique family needs and managing substantial resources. Jill and Mark provide clear, actionable advice, a strong sense of reassurance, and encourage seeking professional tax help as their situation evolves. Listeners in similar situations will find both the practical financial strategies and the compassionate approach to life’s transitions invaluable.