Jill on Money with Jill Schlesinger

Episode: If I Retire, Does Our Plan Work?
Date: December 18, 2025
Guest: Joy (Listener, Pacific Northwest)

Overview

In this episode, host Jill Schlesinger takes a call from Joy, a long-term state government employee, to evaluate whether she and her husband can safely retire and maintain their desired lifestyle. Joy seeks reassurance and practical guidance on retiring early, blending pensions, Social Security, personal savings, and rental income to fund the years until both pensions and Social Security fully kick in.

Key Discussion Points & Insights

Joy’s Big Question: Can She Retire Early and Still Afford Her Plans?

• Joy is contemplating retiring after 25 years with the state government, at approximately 54 years old.
• Her husband (65) is already retired, collecting a healthy pension.

Quote (Jill, 08:10):
"Why are you even hesitating about retirement? I don't get it... Are you worried that you can't, or do you actually know that you can and you just need us to give you permission?"

The Financial Snapshot

Income and Spending

• Husband’s Pension: $7,000/month (already started)
• Joy’s Future Pension: ~$5,000/month (available at 65; begins in 10 years)
• Husband’s Social Security: ~$700/month (already started, began early)
• Joy’s Social Security:
  • ~$3,500/month at 65
  • ~$4,000/month at 67
  • ~$5,000/month at 70
• Retirement Savings:
  • Joy: ~$350,000 in 401(a), $200,000 in 457(b), $3,000 in Roth
  • Husband: ~$150,000 in 401(k)
• Health Savings Account (HSA): ~$50,000
• Brokerage (Non-Retirement): ~$100,000
• Cash (Checking + Savings): ~$80,000
• Monthly Spending Estimate: $10,000–$12,000 (includes projected healthcare costs)

Real Estate

• Primary Home: Worth ~$1.2M, $500,000 mortgage at 3%
• Rental Properties:
  • Pacific Northwest: $450-475K value, $260K mortgage (3%), $600/mo net income
  • Two in the South (both paid off):
    • One nets $1,200/mo
    • VRBO nets ~$5,000/year

Assets vs. Anxiety: “I Probably Need More Permission”

Joy felt some unease comparing her non-millionaire portfolio to others' larger retirement balances.

Quote (Joy, 08:10):
"I probably need more permission, even though in my mind, when I think about what people my age have, it's more in the millions rather than hundreds of thousands."

Jill’s Response (08:22):
"Those people don't have two pension checks. You have millions. It's just in the form of pensions... Think of it this way: $12,000 a month coming in from our pensions? That's $144,000 a year. You'd have to have three and a half, four million already saved to generate that."

Filling the 10-Year Income Gap Before Joy’s Pension

• Joy’s pension doesn’t start for 10 years (her at age 65).
• Plan:
  • Rely first on husband's accounts for withdrawals (~$30,000+ per year)
  • Use rental income to supplement pension/withdrawal gaps
  • Once husband’s account is depleted, shift to Joy’s pre-tax accounts, maintaining cash flow until pensions and Social Security kick in.
  • Possible sale of one rental property in the coming years to boost cash if needed.
  • Keeping the primary home is feasible; selling not required.

Jill’s Calculations (14:23):
"I don't think you're going to even need the brokerage... If we did $30 grand a year out of [your husband’s account], and then use that to cover needs... you can wait... and do the same with your accounts between age 60 and 65. When you claim Social Security, you’re basically set!"

Real Estate: Keep, Sell, or Simplify?

• Joy wants to keep the primary home and at least one rental for personal use.
• Jill notes that rental management could become more burdensome with age—eventually selling one makes sense for both cash flow and simplicity.

Quote (Jill, 16:50):
"One of these is probably going to go... and you’re going to have plenty of money. But you don’t need to sell them right now."

Quote (Jill, 20:25):
"To make your life less stressful... one of those properties you’re going to need for cash flow. Unless something weird falls in your lap... But you have it, it’s an asset, so use it."

Health Insurance & Spending

• No retiree health coverage from state, but the $12,000/month spending estimate includes health insurance costs for both Joy and her husband.

Estate Planning

• Wills, trusts, and other estate documents are in place and currently being refreshed due to changing circumstances.

Kids & Other Family Considerations

• Children are grown, self-sufficient; one wrapping up college (fully funded).

Mindset Check: Retiring “For the Money”

• Jill and producer Mark emphasize: Joy shouldn’t stay working out of financial fear, as their plan holds together well.
• Jill gives the green light for retiring on Joy’s target timeline (8-10 months).

Quote (Jill, 20:25):
"Don’t stay for the money, okay? Don’t stay. You have plenty of money."

Notable Quotes & Memorable Moments

• On pension envy:
  Jill (21:24): "Mark, why did we not get pension jobs? What happened to us?"

• On giving permission:
  Jill (08:10): "Are you worried that you can't, or do you actually know that you can and you just need us to give you permission?"

• On comparing assets:
  Jill (08:22): “You have millions. You have a guarantee, and your guarantee comes with an extra benefit… you don’t have to sweat the risk.”

Timestamps for Key Segments

• Meet Joy & Outline of Situation – 03:26–05:20
• Pension, Social Security, and Savings Breakdown – 05:20–07:24
• Asset Comparison & Reassurance – 08:10–09:56
• Primary Home and Mortgage Discussion – 09:56–10:45
• Rental Property Portfolio – 10:47–12:49
• Income Gap, Withdrawal Strategy & Future Planning – 13:36–19:37
• Health Insurance & All-in Spending – 12:49–13:09
• Estate Planning & Family – 17:55–18:09, 19:59–20:09
• Timeline for Retirement & Next Steps – 20:09–20:25

Conclusion & Takeaways

• Joy and her husband have “done everything right” financially.
• Their combined pensions, Social Security, retirement savings, and rental income create a robust, sustainable retirement plan, even if Joy retires well before her pension starts.
• Downsizing rental properties for simplicity and liquidity makes sense, but there’s no urgency to sell.
• Keeping the primary home is sustainable; selling is not required.
• Jill emphatically grants “permission” to retire—reminding listeners that comparing themselves to others without context can be misleading, especially when defined benefit pensions are in play.
• Final takeaway: Joy has plenty of financial security and should feel empowered to transition into retirement on her preferred timeline.

Host: Jill Schlesinger
Guest: Joy (Listener, Pacific Northwest)
Producer: Mark
Podcast: Jill on Money, Audacy