Jill on Money with Jill Schlesinger — Episode Summary

Episode: “Help for Mom and Me”

Date: November 18, 2025
Host: Jill Schlesinger, CFP®
Show Description: Jill answers listener emails on complex, often sensitive financial topics with her trademark jargon-free, practical approach—aimed at helping listeners make the most of their money.

Overview

In this listener-focused episode, Jill Schlesinger addresses a range of nuanced financial dilemmas sent in by listeners. Topics include pension decisions, Roth conversions, managing family real estate, coping with changing retirement plans, and strategies for multi-generational caregiving and wealth management. Jill emphasizes practical, emotionally intelligent financial advice, especially when personal circumstances intersect with major money decisions.

Key Topics and Insights

1. Pension Decisions & Lump Sums (Ann’s Question)

[03:15–07:40]

• Listener Profile: Ann (61, retired) and husband (54, working). Twins in high school. Ann has two pensions, large retirement savings, and substantial non-retirement investments.
• Main Issue: How to select between lump sum or monthly pension payouts, and whether to do Roth conversions.
• Details:
  • First Pension: Lump sum $220k or $1,226/month with 75% survivor benefit (available at 65)
  • Second Pension: Lump sum $125k or $650/month with 100% survivor (available now)
  • Combined retirement and non-retirement assets exceed $7 million. Twins still in high school.
• Jill’s Take:
  • “It seems to me like they’re in great shape. I’m leaning towards taking the lump sum also… you can put those into your retirement accounts.” – Jill ([05:10])
  • “If you spend a ton of money, we’d have maybe a different conversation.” – Jill ([06:05])
• Roth Conversions:
  • Depends on spending patterns and future tax brackets. Worth considering, but only with clarity on expenses.
• Finding a Fee-Only Advisor:
  • Tip: Visit NAPFA (National Association of Personal Financial Advisors) for referrals ([06:35])
  • Local Referrals: Jill offers to recommend local advisors based on Ann’s location.
• Memorable: Jill and Mark note an uptick in emails from late-50s/early-60s parents of teens—calling it “a lot of complications, man, it’s crazy.” ([04:00])

2. Managing a Family Rental Property (Christina’s Question)

[07:41–10:25]

• Listener Profile: Christina and her siblings manage their dad’s rental; planning for inheritance and property transition.
• Main Issue: Should they pay down the remaining $85k mortgage (6.8% variable) faster, or keep cash available for maintenance?
• Details:
  • $3k/mo rent; $2k in maintenance fund; adjustable mortgage rate (down from 8%)
  • Considering upping mortgage payments from $1,300 to $2,000 monthly
• Jill’s Take:
  • “6.8 is a real number… that high interest rate, boy, it does sort of like blink a blaring red light of, like, pay me down.” ([09:30])
  • Ultimate decision hinges on whether the family needs the cash flow or prefers to minimize interest.
  • Mark agrees, provided Christina can cover emergency expenses if needed.
• Memorable: “It’s kinda up to you and the siblings as to whether or not this makes a ton of sense. But I get it.” – Jill ([09:45])

3. Bond Fund Choice and Mortgage Payoff (Holly’s Question)

[10:26–12:40]

• Listener Profile: Holly (nearly 70, recently retired for health reasons), ~$1m portfolio, just moved and took out a $20k mortgage at 6.4%
• Main Issue: Seeks a U.S. bond fund recommendation (no international), and advice on using Roth conversions and withdrawals to pay down mortgage.
• Jill’s Take:
  • Recommends a “boring intermediate-term bond fund index” ([11:45])
  • Approves strategy to pay down mortgage using Roth IRA conversions, provided she sets aside money for taxes
  • “When that mortgage is all paid off, you’re going to be so happy and you’ll have your cash flow…” ([12:25])

4. Navigating Caregiving & Retirement in Crisis (Mary’s Story)

[12:41–16:05]

• Listener Profile: Mary (68, still working, planning to retire at 70); husband (83, terminal illness); sole caretaker for elderly mom (93)
• Main Issues: Managing mom’s trust ($1m) and pension ($3k/mo) to cover senior facility ($7k/mo); planning widowhood and a possible move to care for both self and mom
• Details:
  • All mom’s assets in safe instruments at the local credit union (CD avg 3.6%)
  • Mary’s investments managed by Vanguard, 70/30 allocation; owns home outright, plans to downsize after husband’s passing
  • Personal spend: ~$6k/month
• Jill’s Take:
  • Approves conservative approach for mom, suggests inquiring at credit union for possible longer-term CDs or other low-risk options
  • “Liquity, access to the money is really important and you’re going to have to spend this down.” ([14:45])
  • Mary is financially stable enough for her plan to work, provided home downsizing yields anticipated equity
  • “Sometimes life will dictate something that is much more important than maximizing your finances.” ([15:50])
• Memorable: Jill expresses deep empathy for Mary’s family situation—“This is so sad, Mark. Oh my God.” ([13:05])

5. Using 529 Plans While Kids Are in College (Joe’s Question)

[16:06–16:45]

• Listener Profile: Joe, two children in college, cash-flowing expenses, wants to preserve/use 529 plans as gifts after graduation.
• Main Issue: Should he use 529 funds now or save them for gifting later?
• Jill’s Take:
  • “Yes, you should use your 529… that money is there for them, which is why you saved it in the first place.” ([16:20])
  • Suggests possibly leaving a portion to roll into Roth IRAs later, but primary strategy should be using the savings to cover current college expenses

Notable Quotes & Memorable Moments

• On Year-End Planning:
  • “I love the year-end planning. I feel so… like, it’s like crossing things off on my list. I love doing it.” – Jill ([01:20])
• On Defining Goals:
  • “Sometimes life will dictate something that is much more important than maximizing your finances.” – Jill ([15:50])
• Wry Humor:
  • “Mark and I were just laughing because we seem to be getting a flurry of messages from people… who have kids in high school [in] their late 50s and 60s. A lot of complications, man—it’s crazy.” ([04:00])
• Empathy in Difficult Circumstances:
  • “This is so sad, Mark. Oh my God.” – Jill ([13:05])

Important Timestamps

• 03:15 – 07:40: Ann’s comprehensive pension strategy and advisor search
• 07:41 – 10:25: Christina’s family rental property paydown
• 10:26 – 12:40: Holly’s bond fund and mortgage/Roth dilemma
• 12:41 – 16:05: Mary’s caregiving, retirement planning, and tough family transitions
• 16:06 – 16:45: Joe’s 529 utilization advice

Tone & Style

Jill provides concise, jargon-free explanations, always returning to each listener’s real-life context. The show’s tone is warm, supportive, and occasionally laced with humor to balance heavier subjects. Jill’s responses exhibit empathy—particularly for those facing family stress, health challenges, or the complexities of intergenerational wealth transitions.

Final Thoughts

This episode underscores Jill’s commitment to practical, emotionally intelligent money advice—always putting listeners’ whole lives, not just their accounts, front and center on the path to financial health.