Episode Summary: At What Age Would I Be Able to Retire?

Podcast: Jill on Money with Jill Schlesinger
Date: January 21, 2026
Host: Jill Schlesinger, CFP®
Producer: Mark
Theme: Real listener questions about retirement age, investing strategies, and financial advisor fees, with practical, jargon-free guidance.

Main Theme & Purpose

In this episode, Jill Schlesinger and her producer Mark dive into listener emails, focusing on retirement readiness—especially around the question: “At what age would I be able to retire?” Jill parses the financials, asks the tough follow-ups, and gives actionable advice on everything from target retirement age to questions about long-term care, advisor fees, and pension decisions. The tone is empathetic, direct, and reliably irreverent, cutting through complexity to help listeners take practical steps with their money.

Key Discussion Points & Insights

1. Case Study: Katherine’s Retirement Readiness

[03:30 – 09:30]

Background:
Katherine, 52, married with 2 teens, wants to know when she can feasibly retire. She earns $195k/yr, has $851k (mostly pre-tax) in retirement, $227k in joint taxable investments, and hefty emergency savings, but no pension or property. Monthly expenses are $10–12k (with $6k rent in NYC), and college savings are solid at $342k (529 plans). She’s not planning to retire in the next 10 years.

Key Considerations & Jill’s Analysis:

• Retirement Accounts & Savings Rate:

  • Contributes 14% of salary plus $31k (catch-up) annually.
  • Large chunk in traditional pre-tax accounts; some Roth, healthy liquidity.
  • No pension; has a 414(h)—a little-known public sector retirement plan.

• Household Expenses:

  • Unusual division—husband covers rent, Katherine covers all other expenses.
  • “His situation is more unpredictable. He owns his own business.” (06:33)

• Katherine’s Central Question:

  • Should she plan for retirement at 65, 67, or 70+?
  • Wonders if expenses will drop in retirement.
  • Concerned about long-term care insurance and not burdening her kids.

Jill’s Candid Take:

“I think you should target 67. You got to get these kids through school, right?...Then you'll use some pre-tax money for the few years in between and then you’ll get this big chunk of [Social Security].” (09:08)

• On Expecting Lower Expenses in Retirement:

  • “I doubt that. I would never just—everyone listening—don’t presume that unless you are paying for something like out-of-pocket, that definitely will go down. I think we should always presume you’ll spend exactly what you’re spending today.” (07:06)

• On Social Security Timing:

  • Advises deferring until 70 if possible for higher benefits.

Mark’s Observations:

• Wishes Katherine joined on-air for more details, especially about her husband’s finances since the marital finances seem so separate.

  • “Is she asking us will she have enough to cover her expenses or the whole thing?” (08:43)

• Even with incomplete info, Mark estimates:

  • “She’s going to have around $3 million when she’s 64...Yeah, that'll probably get her to what she needs.” (08:50)

Open Questions Jill Wants Answered:

• Why do Katherine and her husband file taxes separately?
• What’s behind their financial separation?
• “Katherine, get back in touch with us.” (09:08)

2. Financial Advisor Fees: Are You Paying Too Much?

[10:30 – 12:30]

Melinda, retired with $330k, wonders about an advisor fee of 1.25% (about $4,000/year), versus the 0.75% internal fees she’s currently paying on her funds (all at Fidelity).

Jill’s Blunt Ruling:

“The acceptable fee is zero if all they’re doing is actually managing money. That’s my feeling.” (11:00)

• For standard asset allocation, Jill says Melinda should stick with index funds (even suggests the Fidelity Go robo-advisor at 0.3%) if she wants hands-off help.

• “No, you don’t [need someone moving money around].” (11:22)

• Mark interjects:

  “Gotta be actively managed because I have one of those same funds, and it’s basically free.” (11:14)

• Jill:

  “They're not gonna be able to find the top and the bottom of the market—nobody can.” (12:18)

3. Should I Use RSUs to Buy Rental Real Estate?

[12:31 – 13:30]

John, 56, is tech-rich in restricted stock units (RSUs) and wondering if he should sell some for a $1M rental property to diversify away from stocks/bonds.

Jill’s Take:
Focus on liquidation and diversification—but a $1M rental is a major commitment. Instead, she recommends:

• “Maybe you sell the RSUs anyway and just like peel off some of that consolidated position.”
• “If you want liquidity, you could certainly sell RSUs to get that big bet off the table.”
• Not enough info on John’s full circumstances:

  “I don't know anything about you. So if you want liquidity...” (13:24)

4. Should I Elect a Pension Annuity or Lump-Sum Rollover?

[13:40 – 15:40]

Jeff has a defined contribution pension, 401k, and brokerage account. Should he take an annuity for guaranteed lifetime income or roll the pension to an IRA? He’s confused why Jill warns about annuities, yet loves pensions.

Jill Distinguishes:

• Pensions often provide lifetime income with low costs.
• Retail annuities usually come with high annual fees (2–3% or more).

“Here’s the question...if you had a million dollars in your 401k and you say, ‘I want to take half of it, buy an annuity, lose the access to the money...Would you pay 2.5% a year for that? I wouldn’t. And that’s what a lot of annuities cost.’” (14:30)

• Each tool can work, but cost matters:

  “It's very important that we would look at the cost of what that annuity is and what your alternatives are.” (15:24)

Memorable Quotes

• On Retirement Planning Realism:

  “Don’t presume [expenses will go down], unless you are paying for something that definitely will. I think we should always presume you’ll spend exactly what you’re spending today.” (07:06, Jill)

• On Financial Advisor Value:

  “The acceptable fee is zero if all they’re doing is actually managing money.” (11:00, Jill)

• On Annuity Fees:

  “Would you pay 2.5% a year for that? I wouldn’t. And that’s what a lot of annuities cost.” (14:30, Jill)

Notable Moments & Recommendations

• Jill and Mark’s candid banter about financial plans that seem “very separate,” highlighting missing info in listener scenarios. (08:21–08:49)
• Jill’s recurring plea for listeners to come on-air for deeper, more helpful conversations.
• Mark’s technical contributions and quick clarifications, such as on 414(h) plans and Fidelity fund fees.

Timestamps for Important Segments

• Listener Katherine’s Retirement Scenario: 03:30 – 09:30
• Advisor Fees and Value: 10:30 – 12:30
• RSUs for Rental Property Decision: 12:31 – 13:30
• Pension Lump Sum vs. Annuity Buy: 13:40 – 15:40

Final Thoughts

This episode is a masterclass in honest, practical financial advice. Jill and Mark walk through complicated family, career, and retirement decisions, always emphasizing the need to ask tougher questions, keep costs low, and make only the moves that serve your specific circumstances. If you want actionable guidance with no sugarcoating, this episode delivers.