Podcast Episode Summary

Podcast: Jill on Money with Jill Schlesinger
Episode: Red Flag Warning
Date: November 13, 2025
Host: Jill Schlesinger, CFP®

Overview

In this episode, Jill Schlesinger addresses a variety of listener questions focused on crucial year-end financial decisions. Topics include warning signs when selecting a financial planner, how conservative investors should handle market volatility, tax implications of retirement account withdrawals, the nuances of pension planning, and the importance of maintaining thoughtful, respectful financial conversations. Jill’s advice is both practical and jargon-free, providing clear guidance and reassurance in what can often be overwhelming territory.

Key Discussion Points & Insights

1. Red Flags When Choosing a Financial Planner

[03:18 – 08:55]

• Listener Scenario: Tammy, age 63, and her husband (60), are considering whether to hire a financial advisor that handled a relative's funds, particularly as a potential inheritance might soon be involved.

  • Tammy is the primary money manager; her husband is less engaged.
  • The prospective advisor charges a 1.5% AUM fee plus high mutual fund fees.
  • The advisor purportedly said they could easily retire without knowing any spending needs.

• Jill’s Take:

  • Jill cautions strongly against hiring this advisor, especially given Tammy’s solid track record as a DIY investor and the high cost of the proposed relationship.
  • Points out that the advisor's promise that they could retire—without any knowledge of their spending—was a "red flag" itself.
  • Urges careful evaluation before transferring assets simply out of convenience or familiarity.
  • On paying advisory fees:

    “Are you really interested in plunking over 15 grand just for a year? Not just now, but every year? This seems a little bit crazy to me. So I think the warning that you’re feeling is basically, well, why would I hire this person?” — Jill [05:57]

  • Suggests staying the course, especially since Tammy’s current conservative, low-cost approach has weathered market downturns well.

2. Retirement Planning and Pensions—"Am I Missing Anything?"

[09:00 – 11:06]

• Listener Scenario: Calvin, 58, educator and military veteran, asks for a financial checkup.

  • Three and a half years from retirement, expects a $5,000/month pension, $4,000/month military pension.
  • Wife, younger by four years, also has a robust pension and significant retirement savings.
  • No debt; home nearly paid off; plans a dream car purchase post-retirement.
  • Saving $60,000/year now, plans to continue.

• Jill’s Verdict:

  • Calvin is in excellent financial health.

    “Are you crazy? You’re in great shape. You literally spend no money. And your full pension in three and a half years is going to be covering most of your expenses, not to mention the military pension.” — Jill [09:44]

  • Advises no change; affirms that their plan is optimal.

3. Handling Market Corrections and Required Minimum Distributions (RMDs)

[11:07 – 12:30]

• Listener Scenario: Steven asks about moving three to four years’ worth of RMDs to cash or money market, as a buffer against market downturns.

• Jill’s Analysis:

  • Two years’ worth of RMDs in cash may be sufficient unless someone is especially risk-averse or simply feels more secure with more liquidity.

    “If you have tons of money and it just makes you feel better, then that’s okay too, I guess.” — Jill [12:20]

  • Both Jill and co-host Mark agree that more than two or three years is generally unnecessary.

4. Using Retirement Savings to Pay Off Debt

[12:31 – 13:32]

• Listener Scenario: Mike, a 60-year-old federal worker, took $45,000 from his Thrift Savings Plan to pay off credit card debt; asks about tax implications.

• Jill’s Thoughts:

  • Not an ideal habitual practice but understandable in specific situations.
    • The outcome depends on current year’s total income/tax situation.

    “First of all, don’t ask me this after the fact. It’s already done....I like the idea of using money that is available to pay down credit card debt, but I don’t want to get in the habit of doing this.” — Jill [12:36]

  • Withholding may or may not fully cover taxes owed.

5. Best Source for Retirement Withdrawals as a Couple

[13:33 – 14:23]

• Listener Scenario: Jan (71) and wife (70) have $1.5M in retirement savings, considering how to balance withdrawals between their accounts as wife’s account is being depleted faster.

• Jill Recommends:

  • Draw from the older spouse’s account first, since their RMDs will be larger.
  • Otherwise, it makes little practical difference, as long as total needs are met.

6. Celebrating Listener Appreciation and Positive Podcasting

[14:24 – 15:02]

• Listener Email: Stephen expresses gratitude for the show’s respectful tone and focus on practical advice, contrasting it with sensationalist financial media.

  “You are a beacon of positivity in a sea of unnecessary drama.” — Stephen [14:40, listener email]

• Jill’s Response:

  • Grateful for the positive feedback; affirms the show’s commitment to removing “the mystery out of your financial lives.”
  • Assures listeners that feedback is valued, and any constructive criticism is welcomed.

Notable Quotes & Memorable Moments

• Red Flag on Advisors:

  “The warning that you’re feeling is basically, well, why would I hire this person?…You’ve been doing such a good job.” — Jill [05:53]

• On Conservative Investing:

  “We haven’t lost huge amounts when the markets crashed over the last 20 years.” — Tammy [04:43, listener email; paraphrased by Jill]

• When You’re Already Doing Well:

  “You’re in great shape, man. I wouldn’t do a thing different.” — Jill [10:00]

• On Cash vs. Investment for RMDs:

  “If you have tons of money and it just makes you feel better, then that’s okay too, I guess.” — Jill [12:20]

• Listener Praise:

  “Your pods have become a staple of my personal finance diet... You are a beacon of positivity in a sea of unnecessary drama.” — Stephen [14:40, email read aloud]

Important Segments and Timestamps

• Red flags with financial advisors: [03:18 – 08:55]
• Retirement check-in for pensions and savings: [09:00 – 11:06]
• Cash vs. market for RMD strategy: [11:07 – 12:30]
• Using retirement funds for debt payoff: [12:31 – 13:32]
• How to balance withdrawals between spouses: [13:33 – 14:23]
• Listener appreciation and show values: [14:24 – 15:02]

Tone & Language

Throughout the episode, Jill maintains a conversational, encouraging, and frank tone. She avoids jargon, explains reasoning clearly, and treats all listener questions with respect—even when delivering tough love or common-sense advice.

Summary for New Listeners

This episode is an excellent snapshot of Jill Schlesinger’s accessible, no-nonsense approach to financial planning. She calls out “red flags” from both advisors and products, reassures listeners when they’re on the right track, and never misses a chance to empower the audience with straightforward, non-judgmental financial guidance. Listeners receive both practical information and a healthy dose of reassurance that “change your work, change your wealth, change your life” is within reach, no matter where they start.