Jill on Money with Jill Schlesinger
Episode: Is Our Plan Solid?
Date: November 11, 2025
Host: Jill Schlesinger, CFP® with Executive Producer Mark Tularcio
Episode Overview
In this episode, Jill answers listener questions about retirement planning, asset allocation, tax strategies, and making major life decisions around money. With her signature jargon-free, pragmatic approach—and banter with co-host Mark—Jill provides reassuring, actionable advice to help listeners build financial plans that fit their real lives. The conversation focuses on how to navigate big milestones, manage inheritance windfalls, deal with market uncertainty, and avoid common pitfalls, all while staying grounded and tuned out from financial "noise".
Key Discussion Points & Insights
1. Investing Philosophy & Show Purpose
[02:12]
- Jill stresses the show is about "real life" money decisions, not picking hot stocks or getting rich quick.
- Emphasis on using the resources you have to get where you want to go, with an understanding of available options.
- She reiterates advice shared by David Booth (founder, Dimensional Fund Advisors):
"Tune out the noise. It is really a way for you to remain sane."
(Jill quoting David Booth, 03:10)
2. Listener Question: Managing Retirement Assets & Inheritance (Steve)
[04:04]
- Steve, 67, and his wife, 66, are retired with a paid-off house, no debt, self-sufficient children, and multiple streams of income (Social Security, annuity).
- Assets include $480k in Roths, $1.4M in IRAs, $100k in Chevron stock (inherited), and $600k in CDs (inherited).
- Their expenses are $9,000/month after tax; income (Social Security + annuity) is $6,800/month.
- Steve prefers cash safety in CDs; his advisor recommends municipal bonds or a cash/bond mix, and Roth conversions.
Jill's Take:
- She generally agrees with the advisor that a Roth conversion could be beneficial, especially once business income drops.
- Advocates for stability at this stage:
"...you're at a point in your life where having some stability here is a nice thing."
(Jill, 08:39) - Suggests possible sale of Chevron stock, but cautions against converting too much IRA at once or burning through cash just to pay taxes.
- Reiterates the importance of evaluating municipal bond returns versus CD rates, advising to keep some flexibility.
3. Listener Question: Can I Retire Early & Buy a New Home? (Kathy)
[10:10]
- Kathy (56.5) works part-time; her husband is a professor planning to work until 65.
- They have substantial cash, brokerage, Roth, and traditional retirement assets (totals over $3M).
- They plan on spending $75K–$100K annually and hope to buy a $600–$700K house (current home worth $300K) mortgage-free after her husband retires.
Jill's Advice:
- Kathy can likely retire early ("you've got plenty of money"), but cautions against depleting their savings for a new house purchase.
- Advises waiting until husband's retirement for a home move; if Kathy retires now, she should draw on cash until she's 59.5, then tap pre-tax retirement accounts.
- Emphasizes flexibility and the unpredictable nature of making such big plans years in advance:
"It's very hard to make these decisions when we're looking at, you know, eight years in advance..."
(Jill, 12:10)
4. Listener Question: Roth IRA Rules for Older Savers (Lance)
[12:44]
- A listener misunderstood Jill's stance on Roth IRAs for people over 40.
- Lance inherited $15,000 and wants to start a Roth IRA for himself and his wife (eligible for $8,000/year each).
- He and his wife already have traditional IRAs and $500,000 in a brokerage account.
Jill's Clarification:
- Clarifies she likes Roths for nearly everyone now, not just younger savers.
- Encourages creating additional Roth assets if possible, assuming earned income:
"Having some Roth money—we love having Roth money. It's good."
(Jill, 13:30)
5. Listener Question: Are I Bonds Still a Good Investment?
[13:55]
- Listener asks if there's a rule of thumb for buying I Bonds.
- Jill and Mark reflect on their own I Bond purchases during the high-inflation period ("all the rage" in 2021).
Jill's Take:
- Not a great time for I Bonds due to their inflexibility and lock-in periods.
- Recommends considering alternatives or I Bonds only if inflation protection is a top concern:
"It's just that it's the inflexibility...right now is not like my favorite time to buy an I bond."
(Jill, 14:00)
6. Notable Listener Appreciation
[14:20]
- Alison writes to thank Jill and Mark for their nonjudgmental, supportive approach.
- Jill shares the gratitude with the audience, underscoring the mission of the show:
"It's so good. I'm so, so happy when we do this."
(Jill, 14:32)
Notable Quotes & Memorable Moments
-
On tuning out investing noise:
"Tune out the noise. It is really a way for you to remain sane."
(Jill quoting David Booth, 03:10) -
On the value of stability in retirement:
"You're at a point in your life where having some stability here is a nice thing."
(Jill, 08:39) -
On planning for a future home purchase:
"It's very hard to make these decisions when we're looking at, you know, eight years in advance..."
(Jill, 12:10) -
On Roth IRA relevance at any age:
"Having some Roth money—we love having Roth money. It's good."
(Jill, 13:30) -
On I Bonds in the current market:
"It's just that it's the inflexibility...right now is not like my favorite time to buy an I bond."
(Jill, 14:00) -
Listener appreciation:
"It's so good. I'm so, so happy when we do this."
(Jill, 14:32)
Timestamps for Key Segments
- [02:12] – Jill describes show philosophy and shares David Booth's investing wisdom
- [04:04] – Steve’s retirement portfolio and managing $600K inheritance
- [10:10] – Kathy's question about early retirement and buying a home
- [12:44] – Lance’s Roth IRA query and clarification for older savers
- [13:55] – I Bonds: When are they worth it?
- [14:20] – Listener praise and Jill’s gratitude
Tone and Style
The episode is reassuring, practical, empathetic, and down-to-earth. Jill avoids jargon, encourages listeners to focus on what they can control, and is consistently supportive—providing both technical guidance and psychological reassurance for those facing big or uncertain money decisions.
This summary omits all advertisements, promotional material, intros, and outros to focus solely on the content and advice provided during the episode.