Podcast Summary: "Buy a Home or Invest Instead?"
Podcast: Jill on Money with Jill Schlesinger
Airdate: October 31, 2025

Overview

In this episode, Jill Schlesinger and producer Mark Telercio dedicate the show to answering a backlog of listener emails, focusing on key personal finance dilemmas: how to approach retirement withdrawals, portfolio management, college savings, mortgage decisions, and—central to the episode—whether to buy a home or continue investing, especially when income is unpredictable. True to Jill’s style, the conversation is accessible, practical, and sometimes blunt, with a sprinkle of light-hearted banter.

Key Discussion Points and Insights

1. Strategic Year-End Financial Planning

[03:00 - 05:00]

• Jill emphasizes the importance of using the last two months of the year to make "tax and financial planning moves," especially before holiday distractions set in.
• She promotes the upcoming "Jill on Money Live" webinar for more targeted year-end strategies.
• Insight: "If you are really considering what kind of tax and financial planning moves to make before the end of the calendar year, ... there are a lot of moves you may want to consider before the end of the year." — Jill [03:22]

2. Email Q&A Segment

a. Withdrawing from Retirement Accounts: Rachel’s Dilemma

[05:40 - 09:12]

• Situation: Rachel, recently retired at 60, enjoys a strong federal pension, owns her home (with mortgage), and has $1.3M in her Thrift Savings Plan (TSP).
• Questions: Does she need to do Roth IRA conversions? What withdrawal strategy should she use?
• Jill and Mark’s Advice:
  • Roth conversions are not necessary; withdrawals are preferable.
  • Consider withdrawing more than $25k/year—possibly $40–50k—to have available cash and reduce future required minimum distributions (RMDs).
  • Delay Social Security to age 70 if healthy ("unless you are not in good health, I would think about 70." — Jill [08:18]).
  • Gradually shift asset allocation toward a more balanced stocks/bonds mix.
  • Open a taxable brokerage for surplus withdrawn funds; no need for an annuity.
  • Memorable Quote: "No annuity. N A, no annuity." — Jill [09:12]

b. Should I Consolidate My IRAs? Lily’s Question

[09:12 - 10:40]

• Situation: Lily has IRAs at T. Rowe Price (stocks, unmanaged) and Charles Schwab (bonds, managed).
• Question: Should she combine accounts?
• Advice: Not necessary unless it simplifies her life and she’s comfortable with fees for managed assets. Keeping both is fine if she’s organized.
• Quote: "We always say combine because it's easier to manage. ... But if you're just fine managing it separately, then that doesn't seem like a bad thing at all." — Jill [09:56]

c. Early Retirement and Funding Priorities: Thomas’ Scenario

[10:40 - 13:40]

• Situation: Thomas (41) and spouse (38) have strong retirement and savings, two kids, and want flexibility to retire in 15 years.
• Questions: Are they on track? Should they contribute to Roth 401(k)? How to balance mortgage prepayments, brokerage investments, college savings?
• Advice:
  • Divert savings into 529 college plans if funding education is a true goal.
  • Stop extra mortgage payments; invest those funds instead.
  • Strongly consider switching to Roth 401(k) contributions for tax diversification.
  • They’re doing well but may be on the "borderline" for their $10K/month early retirement target due to variables ("So much for someone who is 38 and 41 ... could change in 15 years." — Jill [13:22]).
  • Mark’s Take: "That's a given." (on Roth 401(k)) [13:01]
  • More info needed; they’re encouraged to come on air for deeper analysis.

d. Buy a Home or Continue Renting/Investing with Unpredictable Income: Samantha’s Choice

[13:40 - 17:30]

• Situation: Samantha, 27, works in 100% commission-based sales, has high (but irregular) annual income, healthy investments, and is considering buying a home versus continuing to invest.
• Questions: How to set a responsible home budget with fluctuating pay? Should she buy or keep renting and investing?
• Advice:
  • Lean towards renting and building investment accounts until income stabilizes or life circumstances change.
  • If she buys, lenders will average her last three years of income.
  • If determined to purchase, ensure a year’s worth of mortgage and expenses are saved in cash reserves.
  • No rush: "You’re a single person. ... Your life could change a lot over the next few years. ... Get back in touch with us." — Jill [16:40, 17:22]
• Mark’s Note: "I have a feeling that she can [buy], I mean, I know her income is ... what she calls inconsistent, but she's consistently bringing in at least five grand every single month." [16:58]
• Jill and Mark invite Samantha back for a more detailed discussion.

Notable Quotes & Memorable Moments

• On Roth Conversions vs. Withdrawals:
  "Do I really need to do Roth conversions? ... I don't think so." — Jill [07:11]
• Annuity Skepticism:
  "No annuity. N A, no annuity." — Jill [09:12]
• On College Savings Priority:
  "What about these 529s? These kids are not so young anymore at 7 and 5. If you really want to fund their education ... get cranking on those." — Jill [12:44]
• Early Retirement Reality:
  "Is that going to generate $10,000 a month? In 15 years? Borderline, yeah. I'm not sure." — Jill [13:33]
• Irregular Income Advisory (Samantha):
  "I love that you're channeling all this cash flow into the markets and being able to invest and be really prepared to buy when things settle in." — Jill [15:50]

Recurring Themes & Tone

• Accessible, Jargon-Free Guidance: Jill’s style is approachable, mixing financial expertise with humor and directness.
• Personalization: Answers are always customized, never one-size-fits-all; Jill invites listeners to come on air for deeper dives.
• Skepticism of Financial Sales Pitches: Frequent reminders to avoid unnecessary fees, annuities, and to keep control of one’s money.
• Encouragement for Ongoing Learning: Regular plugs for the podcast’s website and special webinars underline the importance of financial education.

Timestamps for Important Segments

• [03:00] Year-end financial planning moves
• [05:40] Rachel’s retirement withdrawal strategy
• [09:12] IRA consolidation with Lily
• [10:40] Thomas’ early retirement and college savings strategy
• [13:40] Samantha’s rent vs. buy dilemma with fluctuating income

If you haven’t listened to this episode, the key takeaway is Jill and Mark’s practical, cautionary approach to major financial decisions: Ask what truly serves your long-term goals, walk away from unnecessary complexity, and keep your options open—especially when life is likely to change.