Podcast Summary: Jill on Money – "Can I Move Up My Retirement Age?"

Host: Jill Schlesinger, CFP®
Guest: Phil from Minneapolis (listener call)
Date: February 9, 2026
Episode Theme:
Exploring the financial, emotional, and practical realities behind moving retirement up several years earlier than originally planned. Jill walks a listener through his changed circumstances and whether his new retirement goal—leaving work at 65 instead of 67—is feasible.

Main Theme Overview

In this episode, Jill Schlesinger answers a listener question about accelerating retirement. Phil from Minneapolis had planned to retire at 67 but, after significant financial changes and family events, is considering leaving the workforce at 65. The discussion focuses on evaluating Phil's assets, income, and readiness for this earlier retirement, emphasizing both practical numbers and deeper personal motivations.

Key Discussion Points & Insights

1. Phil’s New Retirement Reality (02:49–04:19)

• Phil, 64, wants to retire at 65, moving up his target from 67.
• Recent life events drove this:
  • Eight years prior, Phil faced a layoff but landed a better job and paid off debts.
  • Inheritance after both parents’ passing significantly changed his finances.
  • Personal motivation: "I realized I don’t have any time for myself anymore. So I need to do something to take care of me, because that’s basically what killed my father, is taking care of my mother. And he was the healthy one. He died first. So I don’t want that to happen. So I gotta do something different." (Phil, 03:50)
• Phil and his wife both work as personal care attendants for their disabled daughter.

2. Family and Financial Situation Deep Dive (04:19–09:15)

• Healthcare for Phil and his wife is secure (both turning 65 this year).
• Daughter (38), disabled, receives SSI and has a Supplemental Needs Trust, funded by Phil and his late parents.
• Three other daughters are financially independent.
• Home: worth $675,000, with $290,000 left on a 2.75% mortgage.
• Asset Breakdown:
  • Cash: $70,000 (Phil), $3,000 (wife)
  • Brokerage accounts: $402,000 (Phil), $33,000 (wife)
  • Phil’s Retirement:
    • Traditional IRA: $514,000
    • Roth IRA: $6,400
    • 401(k): $234,000 (Traditional), $232,000 (Roth)
    • Inherited IRAs: $165,000 & $162,000
  • Health Savings Account (HSA): $120,000
  • Wife's Retirement: 401(k): $35,000 (Trad), $3,800 (Roth), Roth IRA: $5,700
• Small pensions from Phil’s jobs; options for annuity or lump sum under review.
• Estimated annual household spending: $11,000/month ($132,000/year), described as “conservative.”

3. Social Security & Projected Income Streams (09:21–10:24)

• At 70: Phil estimates $5,000/month, wife $2,200/month in Social Security.
• Potential lump sum pension withdrawals being considered to simplify finances (07:45–08:00).

4. Retirement Strategy: Bridging the Gap (10:27–13:25)

• Phil and wife earn ~$85,000/year as paid personal care attendants for their daughter, non-taxable due to IRS rules.
• Plan to use inherited IRAs to supplement expenses for next 2–3 years before Social Security kicks in.
• Phil’s concern: best sequence to withdraw funds while minimizing taxes.
• Jill’s guidance:
  • For the next 2 years, split inherited IRA distributions and use the attendant earnings to stockpile cash.
  • "If you pulled the inherited IRA out and you have the 85 grand a year and you pile it all together, you probably will be net savers." (Jill, 12:06)
  • After inherited IRA depletion, gradually draw from traditional retirement accounts and wait for Social Security.
  • Build cash reserves for flexibility as circumstances change.

5. Overlooked Asset & Additional Confidence (13:25–14:22)

• Phil then remembers an additional $211,000 in a savings plan accessible at age 70.
• Jill: “That’s a big ‘forgot!’... I think you’re right, that you can retire this year. We now have a tiered strategy.” (Jill, 13:46)

6. Portfolio Management and Practical Steps (14:22–16:40)

• Jill cautions to watch for capital gains when accessing the brokerage account.
• Encourages consolidating assets for easier management as Phil ages.
• Reiterates the need for clear communication about finances and asset locations so his wife is equipped if circumstances change: “One of the best things you can do... is consolidate, get this all in one place. Make sure if something happened to you, your wife would know what to do and where everything was.” (Jill, 16:15)
• Compliments Phil’s handling of special needs estate planning for his daughter.

Notable Quotes & Memorable Moments

• “Phil, you can do this. Sounds like you have all of your estate stuff taken care of because I know you have the special needs trust. So that’s very important.” – Jill Schlesinger (15:45)
• “Taking care of my mother is what killed my father, and he was the healthy one. He died first. So I don’t want that to happen.” – Phil (03:50)
• “Just be careful that you're not creating too much tax liability there, you know.” – Jill, on the brokerage account (14:22)
• “If you are like Phil and real life has called you and said, hey, let's alter the previous game plan, get in touch with us.” – Jill, encouraging listener engagement (16:40)

Timestamps for Important Segments

• 02:49: Phil introduces his situation and motivation for retiring earlier
• 04:19: Family health and caregiving background
• 05:59: Detailed rundown of assets (cash, brokerage, retirement)
• 09:21: Spending needs and Social Security estimates
• 10:27: Discussion of how to bridge income gap pre-Social Security
• 13:25: Discovery of additional $211K savings plan
• 14:22: Advice on sequence of withdrawals and managing taxes
• 16:15: Crucial advice on asset consolidation and family communication

Tone and Language

Jill maintains her signature practical, friendly, and encouraging manner, blending empathy for Phil’s caregiving stresses with clear, actionable financial advice. The conversation is frank, jargon-free, and occasionally laced with light humor ("That's a big ‘forgot!’"). Phil is open, methodical, and candid about both his emotional motivations and his diligent financial planning.

Takeaway for Listeners

• Significant life events can shift retirement timelines, and it’s valid to revisit your plan when circumstances change.
• Asset consolidation and clear family communication become more crucial as you approach and enter retirement.
• Special situations (like care for a disabled dependent) require careful planning but can fit into a secure retirement with the right strategies.
• Ensuring both partners understand where assets are located and how to access them is essential.

If you’re considering a major shift in your own retirement plans, Jill recommends consulting with a financial professional and, if willing, sharing your situation for guidance on the show.