Jill on Money with Jill Schlesinger

Episode: Can I Retire in Just Over Two Years?
Date: December 8, 2025
Host: Jill Schlesinger, CFP®

Episode Overview

In this episode, Jill Schlesinger consults with Charles from Rochester, who is considering retirement in about two and a half years at age 62. Charles seeks guidance on whether his current and projected financial situation will allow him to retire comfortably, supporting his desired lifestyle while minimizing tax implications. Jill provides thorough, jargon-free advice on pensions, Social Security strategies, inherited IRA regulations, and prudent cash management, making actionable recommendations tailored to Charles’ scenario.

Key Discussion Points & Insights

1. Charles' Current Situation

• Charles (59), full-time computer programmer.
• Wife (59), retired teacher/vice principal, receiving $80,000/year pension (taxable federally, NY state tax-free).
• Both covered by wife’s health care plan until Medicare at 65.
• Children in their 30s and self-sufficient, though parents provide occasional support.

Memorable Moment:
"Do you guys have kids?"
"We do...they're both in their 30s and fully on their own. But we do, we do help them with stuff."
"They're on their own. Except they're not."
— Jill (05:02)

2. Income, Expenses, and Retirement Needs

• Charles’ current earnings: ~$150,000/year including bonus.
• Estimated retirement living expenses: Started at $7,000/month, Jill recommends planning for $8,000–$9,000 to account for inflation and unforeseen costs.
  "Would you be more comfortable just saying 9,000, just so we have that?" — Jill (05:38)
• Charles will receive a small pension ($7,000/year) upon his retirement.
• Both eligible for Social Security (estimated $32,000/year for Charles at full retirement age; wife’s figure not specified but likely substantial based on her career).

3. Retirement Savings & Assets

• Charles’ Retirement Accounts:
  • IRA with Vanguard: $472,000
  • Roth IRA: $78,000
  • 401(k): $515,000
• Wife’s Retirement Accounts:
  • 403(b): $60,000
  • Inherited IRA: $275,000 (must be distributed within 10 years due to SECURE Act)
• Cash & Non-Retirement Savings:
  • High-yield savings: $20,000
  • Checking: $20,000
  • Emergency fund: $18,000 (Vanguard money market)
  • Company stock plan: $50,000
• Real Estate Holdings:
  • Rochester home: $250,000 (no mortgage)
  • Florida home: $350,000 (no mortgage)
  • Cottage/vacation home: $500,000 (mortgage: $100,000, partial rental covers costs)

4. Jill’s Financial Guidance & Strategies

Social Security & Income Gap

• Delay Social Security: Jill agrees Charles should postpone claiming to maximize benefits.
• Cover the interim (“income gap”):
  • Use inherited IRA withdrawals to bridge the period between Charles’ retirement and when Social Security starts.
  • "Delay taking any money out of the inherited IRA until you stop working, and then...take the money out over those [gap] years..." (13:32)
• Inherited IRA strategy: Wait until Charles stops working to start taking annual withdrawals (~$45,000/year over six years), minimizing tax impact by spreading distributions over lower-income years.

Cash Flow Planning

• Reduce retirement account contributions:
  • Contribute only enough (4%) to get the employer match; redirect additional savings to cash/brokerage.
  • "I would put up to 4% and the rest of the money, I would stop contributing to retirement accounts. I think you should build up your non retirement savings in anticipation of the next three years..." — Jill (10:46)
• Goal:
  • Increase liquid cash reserves to cover unplanned expenses and supplement the gap years.

Tax and Charitable Considerations

• Expect higher future tax brackets: Due to pension and required minimum distributions from retirement accounts.
• Suggestions for the future:
  • Consider "dribbling money out" of the IRAs if giving to children.
  • Use Qualified Charitable Distributions for donations from IRAs once eligible.

5. Estate Planning

• Estate documents: In good order after wife's father’s passing, motivated by the complexity the family faced.
  • “Once you have to go through that yourself, then you’re like, nah, that’s never happening in my life.” — Jill (15:09)

Notable Quotes & Memorable Moments

• “You got no problems, you’re great. This is fantastic... All of this real estate is fabulous.” — Jill, 10:15
• “You can retire in two and a half years. You could probably actually retire before then.” — Jill, 14:26
• “That’s a great plan, thank you very much.” — Charles, 14:42
• “Try to leave. Lift someone up. Change your work, change your wealth, change your life.” — Jill, closing encouragement, 15:51

Important Timestamps

• 03:44 — Charles introduces his situation, expresses retirement goal.
• 04:16 — Wife’s pension and healthcare details.
• 05:02 — “They’re on their own. Except they’re not.” (Humor about financially independent kids)
• 07:12 — Charles and wife detail their retirement assets.
• 09:07 — Description of real estate holdings.
• 10:46 — Jill recommends redirecting savings to build cash position.
• 12:19 — Plan for inherited IRA withdrawals post-retirement.
• 14:28 — Charles expresses gratitude for the clarity and advice.
• 14:49 — Estate planning discussion and motivation.

Summary Table — Jill’s Main Recommendations

| Topic | Jill’s Advice | Timestamp | |----------------------|-------------------------------------------------------------------|------------| | Retirement Plan | You’re ready; timing is a matter of preference, not means | 10:15 | | Inherited IRA | Wait to distribute until working income stops; spread over 6 yrs | 12:19 | | Cash Savings | Halt extra 401(k) savings; grow non-retirement cash for runway | 10:46 | | Tax Planning | Take advantage of lower-income years before Social Security | 13:32 | | Estate Documents | Confirmed, up-to-date; learned from prior family experience | 14:49 |

Conclusion

Jill assures Charles and listeners that his disciplined approach, generous pension benefits, manageable expenses, and diverse assets put him in an excellent position to retire comfortably, even ahead of schedule if he wishes. Her advice is practical, clear, and rooted in maximizing both flexibility and tax efficiency while ensuring peace of mind.

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