Podcast Summary: Jill on Money – "I Got a Late Start, Am I Okay for Retirement?"

Episode Date: February 11, 2026
Host: Jill Schlesinger, CFP®
Guest Caller: Katherine from Connecticut

Episode Overview

In this episode, Jill Schlesinger takes a listener call from Katherine, a 58-year-old single professional who started investing for retirement late (mid-40s) and seeks reassurance about her financial path. The conversation delves into Katherine’s finances, future plans (including property sale), investment strategy, and lifestyle questions, providing actionable advice and reassurance for late starters to retirement savings.

Key Discussion Points & Insights

1. Katherine’s Financial Snapshot

[03:46–08:08]

• Age & Status: 58, single, no children, happy renter
• Earnings: ~$250,000/year (variable due to self-employment/business moves)
• Retirement Savings:
  • $333,000 in 401(k) (of which $32,000 is Roth)
  • $21,000 in IRA
• Brokerage Account: $1.1 million, mainly in stocks
• High-Yield Savings/CDs: $300,000 (aiming to reduce to $200,000 as not all needed for liquidity)
• Real Estate Outside US: Worth $1.3 million after taxes, to be sold within the year
• Monthly Spending: ~$6,000

Jill [07:06]: “That’s incredible. Good for you. Is it all in stocks? ... All right, so that’s it. So I just want to make sure we got everything.”

2. Retirement Planning & Concerns

[08:42–09:41]

• Katherine says she enjoys her work but has health considerations; she wants to work full-time until 65 and then part-time into her 70s, if possible.
• Her primary worry: Having started retirement savings late, is she truly “okay” for retirement, despite assurances from her financial advisor?

3. Jill and Mark’s Analysis: “This is a Layup”

[09:41–11:19]

• Mark (Producer/Co-host, CFP®): Confirms Katherine is in very strong financial shape, echoing her advisor’s reassurance.
• Jill: Affirms that Katherine’s spending is reasonable and her assets are significant, especially factoring in her brokerage account and upcoming real estate sale.

Jill [09:57]: “The amount of money that you have saved, even though you got a late start, is awesome... You don’t spend a ton of money. So this is a really amazing story. I don’t think there’s any problem with the plan.”

Mark [10:10]: “Is this a slam dunk or a layup, which is easier? I say a layup.”

4. Investment Strategy Going Forward

[11:19–12:25]

• Asset Sale: Jill recommends, when real estate proceeds arrive, that Katherine adjusts to a more diversified (less aggressive) portfolio, adding bonds and dialing back stock exposure.
• Advisory Fee: Jill encourages Katherine to negotiate for a lower advisor fee due to her increased assets.

Jill [11:40]: “You don’t have to be 100% stocks anymore. You’ve already gotten like the greatest benefit... When you add [the] new money, you should get your fee lowered; you should talk to the advisor and say, ‘Okay, I want to take less risk. I want to do something that’s a little bit less edgy, maybe add some bonds…’”

5. Estate Planning & Lifestyle Spending

[12:25–13:15]

• Estate Documents: Thanks to Jill’s prior advice, Katherine has her paperwork in order and will leave her assets to extended family (not just her cat).
• Travel Wishes: Katherine wonders if she can afford to travel more, given her health has prevented it in the past.
• Jill’s Response: Full approval! Even annual $10–15,000 travel is manageable within her plan; “Fly business class!”

Katherine [13:08]: “If I were to spend more money on traveling—”

Jill [13:10]: “Not gonna be a problem... Go business class. Really, come on. I think you’re in great shape.”

6. Encouragement for Late Starters

[13:15–14:00]

• Jill emphasizes that Katherine’s story shows one can get a late start and still end up in a strong position—especially if focused, with modest spending and by making investments work for them.

Jill [13:33]: “Everybody listening, you can get a late start and still be in great shape. So please, go off, enjoy yourself, and don’t worry about retirement.”

Notable Quotes & Memorable Moments

• On Financial Anxiety:

  “Before you start judging yourself, we all have emotions around money and it’s very important to at least just acknowledge that.”
  — Jill [01:07]

• On Late Starts:

  “You can get a late start and still be in great shape... Don’t worry about retirement. Late start, worried about retirement is the name of the [episode]. And she doesn’t even want to retire—she wants to keep working.” — Jill [13:33]

• On Investment Adjustments:

  “You don’t have to be 100% stocks anymore. ... You should talk to the advisor and say, ‘I want to take less risk.’ ... Maybe add some bonds, do something less edgy.” — Jill [11:40]

• On Enjoying Life:

  “Go business class. Really, come on. I think you’re in great shape.”
  — Jill [13:16]

Segment Timestamps

| Segment | Timestamp | |------------------------------------------------------|--------------| | Katherine introduces her financial situation | 03:46–08:08 | | Jill and Mark analyze the financial picture | 08:42–11:19 | | Advice on investment, risk, and advisory fees | 11:19–12:25 | | Discussion of estate planning and travel spending | 12:25–13:15 | | Broader encouragement to late starters | 13:15–14:00 |

Takeaways for Listeners

• Starting late with retirement savings isn’t a dealbreaker—focus, high savings rates, and discipline can yield impressive results even in a compressed timeframe.
• Diversification and risk assessment should be revisited after major liquidity events like property sales.
• Reassess fee structures with your advisor as your assets grow.
• Quality-of-life spending (like travel) can be justified, especially if the plan is solid and well-funded.
• Estate planning isn’t just for the wealthy or for those with children—single individuals need this too.

Tone: Encouraging, affirming, clear, and grounded in actionable guidance—Jill’s signature “no-jargon, all-heart” financial wisdom throughout.