Jill on Money with Jill Schlesinger
Episode: Is a Market Crash Coming?
Date: October 29, 2025

Episode Overview

In this episode of "Jill on Money," Jill Schlesinger, CFP®, answers listener questions centered around managing spending, early retirement planning strategies, investment allocations, and the age-old question: “Is a market crash coming?” The show focuses on practical financial decision-making, addressing both the numbers and the anxieties behind them. Jill provides direct, jargon-free advice, with input from producer and fellow CFP Mark, prioritizing actionable steps and financial wellbeing over market predictions.

Key Topics & Discussions

1. Managing Travel Spending and Marital Finances

[01:18 - 04:44]

• Listener Ellie is in her mid-50s, handling frequent, costly trips to Europe with her husband to visit his ailing parents. She recounts the financial and emotional strain resulting from these trips while managing household and college expenses, and expresses concern about being asked to dip into her own inherited savings.
• Jill’s advice:
  • Strongly recommends working with a fee-only financial planner, emphasizing the importance of being on the same financial page as a couple.
  • Points out the risk of separate financial lives and urges open communication.
  • Suggests seeking professional help immediately, especially given the complexities and potential disagreements about money.
• Notable Quote:
  “Right now I am getting a really massive vibe that you guys are not on the same page. ... It is time to hire a professional, as in right now.” — Jill [04:44]

2. Should I Convert My Traditional IRA or SEP to Roth?

[04:56 - 06:30]

• Listener Christine (67): Considers converting her traditional IRA/SEP to a Roth while her income is lower.
• Jill breaks down the decision:
  • Conversion can be wise if you’re in a lower tax bracket and are able to pay taxes due from non-retirement funds.
  • Notes the strategic benefit of a Roth conversion before the government enforces required minimum distributions at age 75.
• Advice: Christine should follow up with more details for tailored guidance.

3. Are Online-Only CDs Safe?

[06:30 - 08:00]

• Listener Mary: Hesitant about moving $20,000–$40,000 into an online-only bank CD for the higher rates.
• Jill’s reassurance:
  • As long as the bank is FDIC-insured, online CDs are perfectly safe.
  • Suggests using reputable aggregation sites like DepositAccounts.com or Bankrate.com, and double-checking for FDIC insurance.
• Notable Quote:
  “If you have FDIC insurance and then you should be fine. You really should be.” — Jill [07:38]

4. Early Retirement: Brokerage Account vs. Roth Thrift Savings Plan

[08:00 - 10:50]

• Listener Keith (35): Federal worker, saving aggressively and weighing whether to use a taxable brokerage account or a Roth component of his Thrift Savings Plan to support a possible early retirement.
• Discussion Points:
  • Mark notes a brokerage account is useful for penalty-free access to funds before traditional retirement age, in case of retiring as early as 51.
  • Jill suggests a blended approach: “Why don’t we do both? Put a little in both and build that up.”
  • Both reiterate the advantages of TSP, Roth, and flexibility with account choice for early access goals.

5. Is a Market Crash Coming?

[10:50 - 13:34]

• Listener John: Nervous about an impending market crash. Wants to know Jill's opinion.
• Jill’s direct response:
  • No one can reliably predict a market crash; even she doesn’t know, “and nobody does.”
  • The best protection is to ensure proper emergency reserves (especially if retired: 1–2 years of expenses), and an asset allocation aligned with your risk tolerance.
  • Reminds listeners of market volatility and the importance of a long-term perspective.
  • Encourages listeners to reach out for a risk review if they’re anxious about their exposure.
• Notable Quotes:
  • “Could the market crash? Absolutely. Do I know for sure when it will happen? No, I don't.” — Jill [11:14]
  • “If you stay invested over the long term, you’re probably, probably going to be okay.” — Jill [12:24]
  • “Market crash, all caps. Take a deep breath and get in touch with us.” — Jill [12:53]

6. Listener Thank You & Reflections on 10 Years

[13:34 - 14:44]

• Listener Tracy: Shares a heartfelt thank you for the show’s guidance through her and her husband’s retirement and improved financial habits.
• Jill and Mark reflect on nearly 10 years of the podcast and the impact of such messages.
• Memorable Moment: A nod to the deep connection with their audience, evidenced by Tracy’s personal update and the “cute doggie” photo she sent.

Notable Quotes & Timestamps

• “It is time to hire a professional, as in right now.” — Jill [04:44]
• “As long as the bank is FDIC-insured, you should be fine.” — Jill [07:38]
• “Why don’t we do both? Put a little in both and build that up.” — Jill [10:27]
• “Do I know for sure when [a market crash] will happen? No, I don’t.” — Jill [11:14]
• “If you stay invested over the long term, you’re probably going to be okay.” — Jill [12:24]
• “Market crash, all caps. Take a deep breath and get in touch with us.” — Jill [12:53]
• “This is why we do what we do.” — Jill [14:42]

Key Takeaways

• Financial Planning is as emotional as it is logical. Seek professional guidance if there’s marital tension or complexity.
• Roth conversions are strategic, but individual circumstances and tax planning matter most.
• FDIC insurance is the critical factor for online bank safety.
• Early retirees should prioritize flexibility—considered use of both retirement and taxable accounts.
• No one can predict market crashes. The focus should be on preparation, proper allocation, and long-term resilience.
• Listener stories remind everyone of the journey: Financial education and advice can lead to long-term confidence and success.

For more detailed advice and to ask your own question, visit jillonmoney.com.