Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Taking Advantage of a Unique Year

Date: December 26, 2025
Host: Jill Schlesinger
Producer/Contributor: Mark
Caller/Guest: Jennifer (Washington, D.C.)

Overview

Main Theme:
Jill Schlesinger helps caller Jennifer navigate the financial decisions stemming from an unusual year in her life—one with a dramatic drop in income due to a planned career break—by exploring strategies like Roth conversions, donor-advised funds, retirement contributions, and tax planning. The episode is a masterclass in using transitional years for unique tax and investment opportunities, all discussed in Jill's engaging, practical, and approachable style.

Key Discussion Points and Insights

1. Jennifer’s Unique Year: The Backstory

• Situation: Jennifer, aged 54, is a former high earner who left her job in August 2024 after 17 years, lived entirely off savings in 2025 (only $40K earned via consulting), and only recently re-entered the workforce with a new (lower, but comfortable) salary.
• Quote:

  “I feel like I have an opportunity to do something with the uniqueness of the year, and I wanted to consult some experts before I do anything stupid.” — Jennifer, [03:30]

2. Career, Income, and Mindful Downsizing

• Previous income: $235,000 base + 25% incentive
• Current income: $190,000 base + 5% incentive (approx. $200K total)
• Marital/family status: Single, no kids, no pets; self-sufficient father; sister recently deceased

3. Living Without a Paycheck

• Used planned savings—no financial stress, enjoyed time off (mahjong, volunteering, hiking, travel).
• Emotional and physical recovery emphasized.
• Quote:

  “It really wasn’t until probably 10 months later that I was really in a place where I thought, okay, I’m ready to go back to work.” — Jennifer, [06:28]

4. Current Financial Landscape

• Retirement savings:
  • 401(k): $940,000 (pre-tax)
  • 457(b): $150,000
• Brokerage: $810,000
• Cash/High-yield savings: $150,000
• I Bonds: $23,000
• Loose cash: $50,000
• Home equity:
  • Value: ~$610,000
  • Mortgage: $210,000 @ 2.99%
• Annual spending (incl. travel): ~$8,500/month (was $9,500 with COBRA)

5. Retirement Contributions & Planning

• Plans to prioritize Roth 401(k) contributions at new job to maximize employer match (8%).
• Has 10-year work horizon; open to longer if feasible.
• Quote:

  “I think another decade of work is probably doable. I like to work. There’s no reason that I need to stop early.” — Jennifer, [10:07]

Strategic Financial Moves: Jill’s & Mark’s Guidance

6. Roth Conversions: Seizing a Low-Income Year

• Jill identifies the gap year as a rare opportunity to move pre-tax dollars into a Roth account at a lower tax rate.
• Suggests converting the entire 457(b) ($150K) in 2025, paying the tax from cash savings.
• Recommends that Jennifer remains in the 24% tax bracket.
• Quote:

  “My inclination is to try to convert a bunch of this... If we could convert you and stay in the 24% bracket would be very interesting to me.” — Jill, [11:06]

7. Practical Steps for Conversions & Rollovers

• Roll the 457(b) to Vanguard (where her brokerage is), then convert to a Roth IRA.
• Emphasizes urgency to complete this before year-end.
• Quote:

  “Like today. So here’s what’s going to happen... Let’s get this done.” — Jill, [13:56]

• Mark clarifies the mechanics:

  “Yeah, she’s got to roll Lincoln into Vanguard. And once it’s in Vanguard, you’ll see the option to convert that traditional IRA into a Roth IRA.” — Mark, [14:01]

8. Donor-Advised Fund (DAF) & Charitable Giving

• For future years (when income is higher), suggests creating a DAF funded with appreciated assets from the brokerage to optimize charitable deductions and allow for incremental Roth conversions.
• Guidance to gift $20,000/year to DAF, matching Jennifer’s past giving patterns.
• Quote:

  “Maybe you just do like 20 grand a year into your donor-advised fund and that’ll give you a little bit of room to convert because you’re going to take that money off the top.” — Jill, [15:47]

9. Estate Planning: The Emotional Dimension

• Jennifer faced the recent loss of her sister (one of her executors); needs to update estate documents to appoint her niece.
• Jill highlights importance of keeping estate documents current.
• Offers empathy for sibling loss, reminding listeners of the often-overlooked emotional toll.

Notable Quotes & Emotional Highlights

• On the emotional impact of a career break:

  “It took much longer to get my body to agree to that. It really wasn't until probably 10 months later that I was really in a place where I thought, ‘Okay, I’m ready to go back to work.’” — Jennifer, [06:28]

• On financial security:

  “If I hear you correctly, I’m not gonna become a homeless bag lady?” — Jennifer, [18:02]
  “I’m going to say state affirmatively, there’s no freaking way.” — Jill, [18:11]

• On the privilege and cost of taking a break:

  “Listen, it takes longer to recover from these high stress jobs.” — Jill, [18:38]

Important Timestamps

• Jennifer’s situation and motivations: [03:26]–[04:56]
• Asset and spending overview: [07:07]–[08:41]
• Discussion of Roth vs. pre-tax strategy: [10:16]–[11:32]
• Roth conversion plan explained and confirmed: [13:00]–[14:13]
• Donor-advised fund discussion: [15:35]–[16:51]
• Estate planning and personal reflection: [17:07]–[18:11]
• Affirmation of Jennifer’s secure future: [18:11]–[18:38]

Tone & Style

The episode is warm, practical, and occasionally humorous. Jill and Mark are empathetic, candid, and jargon-free, always focused on actionable, savvy advice. The rapport with Jennifer is collegial, supportive, and sensitive to both her financial and emotional journey.

Conclusion & Takeaways

• Use temporary drops in income as opportunities for strategic Roth conversions.
• Keep retirement and charitable contributions optimized for both current and future tax savings.
• Don’t neglect estate planning, especially after significant life changes.
• Emotional well-being is as important as financial health—take time to recover from big changes.
• With strong savings and discipline, career breaks can be both financially and personally rewarding.

Quote to Remember:

“You’re going to be in great shape. Okay.” — Jill, [18:23]

Jennifer departs reassured, with clear next steps and the confidence to act on what Jill calls “a unique year”—a message relevant to anyone experiencing big changes or contemplating a reset.

For More

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