Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Should I Tap a CD or My Roth?
Date: April 7, 2026
Host: Jill Schlesinger, CFP® (A)
Executive Producer/Co-host: Mark (B)

Main Theme

In this episode, Jill Schlesinger and her producer Mark answer financial questions from listeners via email, focusing on common dilemmas around college savings, handling rental property, navigating pension and retirement choices, and making smart withdrawal decisions between CDs and Roth IRAs. The hosts offer accessible, jargon-free advice informed by practical experience, tailored to real listener scenarios.

Key Discussion Points & Insights

1. 529 Plans & Grandparent Contributions (02:00–03:30)

• Listener Lisa’s Question: Is a traditional 529 plan disadvantageous for college savings for grandchildren because it will adversely affect their FAFSA? She seeks advice on tax-free ways to save for kids' college.
• Mark’s Update (02:55):
  "Very recently they changed this. When it comes to accounts owned by the grandparents, as long as the grandparent is the owner and the child is listed as the beneficiary, it is not reported on the FAFSA. So that was a change."
  • Key Insight: Grandparent-owned 529s are not reported on the FAFSA due to a recent rules update effective 2024-25.
• Jill’s Additional Tips (03:21):
  • If grandparents want to help but are concerned about gifting rules or taxes, they can write a check directly to the institution to avoid gift tax implications.
  • Consider whether retirement assets or Roth IRAs could be used creatively for education funding.

2. Rental Property: Pay Off Mortgage vs. Reinvest (04:20–06:20)

• Listener Russell’s Scenario: Owns a fully depreciated rental property that breaks even, still owes $50,000 at a 6% variable rate. He’s now required to take RMDs and wonders if he should pay off the mortgage or reinvest the funds.
• Jill’s Analysis (05:11):
  "If it's not making any money, I might sell it. But you have to then...maybe you do a like-kind exchange—that 1031 exchange."
  • Key Insight: If the property isn’t profitable, consider selling and using a 1031 exchange to defer taxes; paying off the mortgage may not be best. More info needed about Russell’s big-picture goals.

3. Withdrawing from a CD vs. Roth IRA (06:21–06:40)

• Listener Lisa’s Dilemma: Needs to withdraw funds for a car purchase; deciding between breaking a 24-month CD (recently renewed) or taking money from her Roth IRA.
• Mark’s Take (06:21):
  "I'm going to assume that the CD is not her emergency reserve. If that's the case, I would tap the CD."
• Jill’s Nuance:
  • If the CD is the emergency reserve, check for other sources (traditional IRA or brokerage) before invading retirement accounts.
  • It’s better to use regular funds over retirement assets due to tax consequences and future RMDs.

4. Pension Lump Sum vs. Monthly Payout—And Gifting to Family (06:41–08:32)

• Listener Susan’s Query: At 66, holds a $220,000 pension (option for $1,300/month or lump sum), has $2 million in other retirement savings, and considers taking the lump sum to help her son buy a house.
• Jill’s Concern (08:08):
  "I don't see why you wouldn't just roll this $220k over and not take this huge tax hit on $200,000."
  • Key Insight: Taking a lump sum now incurs significant taxes and potential higher bracket; rolling over defers taxes and keeps more money invested. More info about her son’s house purchase needed.

5. Retirement Timing & Social Security Claims (08:33–10:35)

• Listener Stephanie: Retiring at 62, solid savings across brokerage and retirement accounts; her broker advises taking Social Security immediately for a ~$1,950/month benefit.
• Jill’s Rebuttal (09:50):
  "There doesn't seem to me to be a real need for you to take Social Security now...has this person, your quote, unquote broker, advisor, have they run a retirement planning scenario for you?"
  • Key Insight: Without knowing Stephanie’s spending, proper advisement isn’t possible. Delaying Social Security may offer higher payouts and overall stability. Financial advisors must provide holistic retirement planning, not just product-focused advice.

6. Listener Success Story: CFP Exam Motivation (10:45–13:14)

• Drake’s Email:
  Inspired by Jill on Money to take and pass the CFP exam after years in the financial industry:
  "Mark made the comment, 'this would be like a case study every day for someone prepping for the exam.' At that point I thought, gosh darn it...let's go for it. While studying the past few months, there were so many times that things I had learned on your show came into play. Mark was right. I passed." (12:15)
• Mark’s Reply (13:09):
  "Yeah, sure, I have no problem. Let's go. Beer and tennis. What could be better?"
• Jill’s Reflection:
  • The show helps industry professionals understand the real concerns and questions of everyday clients—an “on the ground floor” perspective.
  • Call to listeners in the industry: “If anybody out there is listening in the industry, pass it along. Come on, tell us your story.”

Notable Quotes

• Jill (03:21):
  "So what's important there, I think from Lisa's perspective, is when you have this money and it's owned by the grandparent, him or herself, then it's fine."
• Jill (05:11):
  "If it's not making any money, I might sell it...Maybe you do a like-kind exchange...I'd love it if you could make this property a better working property."
• Jill (08:08):
  "I don't see why you wouldn't just roll this $220k over and not take this huge tax hit on $200,000."
• Jill (09:50):
  "If you don't tell us how much you spend, it's hard for us to make a recommendation to you...If this person has not created a retirement planning scenario for you, then I would not plan on retiring."
• Drake (12:15):
  "While studying the past few months, there were so many times that things I had learned on your show came into play. Mark was right. I passed [the CFP exam]."

Timestamps for Important Segments

• 02:00 – 529 Plans and FAFSA changes
• 04:20 – Rental property analysis and depreciation
• 06:21 – CD vs. Roth IRA withdrawal for car purchase
• 06:41 – Lump sum pension, gifting strategy, and tax implications
• 08:33 – Retirement timing, Social Security strategy, and advisor criticism
• 10:45 – Listener success story: Passing the CFP exam
• 13:14 – Closing thoughts; advice for financial industry professionals

Episode Tone & Final Advice

Jill combines warmth, humor, and straight talk—encouraging listeners to give detailed financial info, especially about spending, for better advice. She emphasizes practical planning over quick fixes or tax-heavy moves, and the importance of advisors who actually run holistic retirement scenarios. The show is equally relevant for consumers and industry professionals who want to understand real-world financial issues.

Final Words (paraphrased, 14:35):
If you write in for advice, give full details, especially about what you spend. "It’s the most important piece of information for these mini-plans."