Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Is Retirement in Five Years Possible?
Date: October 9, 2025
Host: Jill Schlesinger, CFP®
Listener Caller: Jim from Connecticut

Episode Overview

In this episode, Jill takes a listener call from Jim, a 55-year-old nurse from Connecticut, who, together with his wife, wants to know if early retirement—in five years—is a feasible goal. Jill dives into the specifics of Jim’s financial situation, discusses the implications of his retirement savings and pension choices, and delivers key strategies for optimizing Social Security and income distributions. The episode is packed with actionable advice for anyone contemplating early retirement.

Key Discussion Points & Insights

1. Current Financial Snapshot

[03:10 – 11:27]

• Ages & Employment:
  Jim (55) and his wife (56) are both nurses, currently working and aiming to retire at age 60.
• Income:
  Combined salary of $315k/year.
• Retirement Contributions:
  • Both are maximizing contributions to their 403(b) plans, including catch-up contributions.
  • Recently began directing new contributions to Roth 403(b)s.
• Retirement Account Balances:
  • Combined Traditional 403(b) balances: $1.9 million.
  • Roth 403(b): $30,000.
  • Roth IRAs (using backdoor method): $300,000.
  • Rollover IRAs from previous jobs: $150,000.
  • Brokerage account: $235,000 (majority in CDs; some individual stocks/mutual funds).
• Savings:
  Checking and savings: $75,000 for a year’s expenses and emergencies.

Notable Moment:
Jill flags a technical issue with backdoor Roth IRAs and rollover IRAs, explaining the “pro rata rule” and suggesting Jim checks whether he can roll over his old IRAs into current 403(b)s before continuing backdoor contributions.

“The old IRAs, they're sitting out there. That should generally prevent you from doing a backdoor Roth because you would be subject to the pro rata rule.” — Jill ([05:43])

2. Living Expenses and Lifestyle

[07:53 – 10:00]

• Current monthly spending: $3,000–$3,500 (low key), possibly $4,500 with increased leisure.
• Jill conservatively pushes the estimate to $5,000/month to “live a little.”

Memorable Quote:

“Wait a minute. I’m gonna give you five grand a month. Come on, live a little.” — Jill ([08:29])

3. Pensions and Homes

[08:29 – 11:27]

• Cash Balance Pension: Each is grandfathered into a “cash account pension plan” (CAP), now stopped but earning interest.
  • Projected value: $250,000 together.
  • Annuity options: $1,200/month (Jim), $900/month (wife); survivor and period-certain options available.
• Real Estate:
  • Connecticut home (plan to sell): ~$425K value.
  • Texas home (currently rented; plan for future residence): ~$450K value.

4. Family Considerations

[11:03 – 11:27]

• Daughter, 28, fully launched and independent.
• Planned $50,000 contribution to her upcoming wedding.

5. Retirement Sustainability Analysis

[11:27 – 14:22]

• Jill models $6,500/month in needed income (including health care costs before Medicare).
• Social Security estimates:
  • Jim: ~$3,400/month at 67.
  • Wife: ~$2,200/month at 62 (but Jill recommends deferring for financial advantage).
• Jill and producer Mark agree that annuitizing pensions makes sense for guaranteed lifetime income.
• Advocates for a “10-year period certain” annuity payout with survivor benefits.

Notable Quotes:

“You’re in very good shape… trying to generate $6,500 a month for the rest of their lives.” — Jill ([13:03])
“I personally would take the $2,000 a month as an annuity. So… they got a good chunk of it.” — Mark ([13:18])

6. Withdrawal and Tax Strategy

[14:22 – 16:00]

• Use early-retirement years (60–70) to strategically withdraw from tax-deferred accounts while in a lower tax bracket.
• Prioritize withdrawals (rather than Roth conversions), especially if relocating to income-tax-free Texas.
• Delay Social Security to age 70 for maximized benefits unless a health situation suggests otherwise.
• If/when Connecticut home is sold, free up additional liquidity for flexible retirement funding.

Notable Quotes:

“From age 60 to age 70, you’re going to pull money out of these traditional accounts… You should be thinking about taking $100,000 a year out of anything that has not yet been taxed from ages 60 to 70.” — Jill ([14:22])
“If you think about it, you could take even more out… and stay in the 22% tax bracket. You’ll be in good shape.” — Jill ([16:00])

Key Takeaways & Actionable Advice

• Backdoor Roths: Check if rollovers can go into active 403(b)s to avoid the pro rata rule; stop backdoors if not possible.
• Expense Planning: Be realistic (and generous) in estimating retirement spending for comfort and flexibility.
• Annuities: Annuitize pensions using survivor or period-certain features, not straight life, to protect both spouses and beneficiaries.
• Withdrawal Timing: Use low-tax years pre-Social Security (ages 60–70) to draw heavily from tax-deferred retirement accounts, especially if living in a state with no income tax like Texas.
• Social Security: Delay claiming until 70 for larger survivor benefit and increased overall lifetime payout.
• Relocation: Strategic state residency (moving from Connecticut to Texas) further optimizes post-retirement finances.
• Stay Flexible: Plans can (and should) change if significant health or family situations arise.

Timestamps for Important Segments

• Listener Financial Picture & Goals: [03:04 – 06:11]
• Backdoor Roth & Pro Rata Rule Discussion: [05:43 – 07:38]
• Brokerage + Homeownership Details: [07:38 – 11:27]
• Social Security & Annuities Analysis: [11:27 – 14:22]
• Withdrawal & Tax Strategies: [14:22 – 16:00]
• Final Advice on Relocation and Flexibility: [16:00 – 18:19]

Most Memorable Quote

“This looks like a good plan to me… When you think about it, you are in the 24% bracket now. You’ll probably go down to 22 and you’re not gonna have to pay state income tax. This looks like a good plan to me, so I hope that that helps.”
— Jill Schlesinger ([16:00])

Overall Tone & Approach

Jill’s style is empathetic, direct, and empowering. She demystifies complex financial rules, nudges listeners to be realistic, and encourages strategic thinking about taxes and retirement. Mark’s supportive commentary adds a layer of confirmation and practical insight.

For those considering early retirement: Even with strong savings, your withdrawal strategy, tax planning, and benefit timing can hugely impact your security and peace of mind. As Jill’s advice shows, personal finance is about customizing the rules to your life’s real contours.