Jill on Money: "Struggling to Even Think of Retirement"

Date: March 25, 2026
Host: Jill Schlesinger, CFP® with producer Mark
Guest Caller: Kat, from the southern United States

Episode Overview

This episode centers on the anxieties and practical dilemmas faced by a middle-aged working family struggling to imagine a comfortable retirement, despite having assets and good intentions. Listener Kat calls in to get straight answers about her family's future prospects, expressing both stress and confusion about whether they're on track for retirement at age 70—and whether their assets are being managed wisely.

Jill and Mark walk Kat through a candid, methodical review of her financial picture, pausing for tough-love advice and empathetic reassurance. The conversation covers topics like cash flow, real estate decisions, retirement contributions, and why college savings shouldn’t come before securing the parents’ own future. The episode is highly relatable for listeners juggling debts, uncertain plans, and reluctance to let go of assets that aren’t working hard enough.

Key Discussion Points & Insights

1. Introducing Kat’s Situation (03:17–04:54)

• Kat is 44, her husband is 50, they both work full time and have 10-year-old fraternal twins.
• Household take-home pay: about $120,000.
• Both have just recently started contributing to employer retirement plans.

2. The Reality Check — Feeling Strapped (04:54–05:41)

• Despite a reasonable income, Kat describes their finances as "paycheck to paycheck" and "strapped."
• College funding is important to them but not yet financially set aside.

Notable quote:

Kat (03:29): "I sent in a rather panicked email because I feel like, you know, we're middle aged and we're stressed and we don't know if we have enough or even will be on the road to retirement at 70...whether it's yes or no, I just, I feel like I need to know."

3. Breaking Down Assets and Debts (05:41–09:48)

Primary Residence

• Value: ~$410,000
• Mortgage remaining: $79,000 at 3.5%, 4.5 years left
• They love this house

Rental Property (Out-of-State)

• Value: ~$465,000
• Mortgage: $298,000 at 2.875%
• Property is a headache to manage, and currently loses a couple thousand dollars a year
• Required to use a property management firm due to not living nearby

Retirement & Savings

• Kat: $111,000 in tax-deferred account
• Husband: $45,000 in traditional, just started
• No emergency savings (drained for home renovations)
• Additional debt: $11,000 (mostly credit card and personal loan)
• Life insurance: $600,000 (husband), $850,000 (Kat), both term
• No college savings started

4. Rental Property Dilemma (07:34–11:34)

• Jill and Mark dig into why Kat’s family keeps a rental property that consistently produces losses.
• The plan: it's meant to become their retirement home after the kids are in college.
• Jill highlights the emotional and financial tension: would selling ease stress (and why hang on to the low-rate mortgage if it’s a burden?)

Notable exchange:

Mark (07:34): "Why, why are we keeping this? Let's get rid of it."

Kat (07:37): "...This is a home we plan to move into when our boys go off to college."

• Kat is also worried about potentially needing to take on a much larger mortgage if they sold and re-entered the market later at higher interest rates.

5. The Hidden Asset: Primary Home with Rental Potential (13:05–15:51)

• Their current home is a fourplex: 1 apartment rented ($1,250/mo), two more need renovation.
• Cost to renovate both: ~$50,000.
• Jill suggests unlocking more rental income to improve cash flow and overall retirement security.

Notable suggestion:

Jill (15:04): "How would you feel if I took a $25,000 loan from Kat's retirement account to get the work done so I can get some cash flow? ...I think that this may be a chance for you to kind of get out from under."

• Mark (15:08): "I would probably do it."

Risk factors outlined (16:01)

• If you lose your job, a 401(k) loan must be rapidly repaid or it becomes a taxable distribution (with penalty).
• The move is only suggested if Kat feels highly secure in her employment.

6. Making a Plan (17:01–23:10)

• Immediate Priorities:
  • Use a potential loan to pay off high-interest debt, renovate one apartment for added rental income, and keep a little extra as emergency savings.
  • Once additional rental income flows in, avoid lifestyle inflation and direct surplus to catch up on retirement savings for both spouses.
  • Delay college savings until their household is more stable and retirement is on track.

Notable guidance:

Jill (18:18): "...About the kids in college, you really don't need to worry about that right now. We got to get this. We gotta get you guys in a place where you feel like you're not living paycheck to paycheck."

• Long-term:
  • When the primary home’s mortgage is paid off (~4.5 years), funnel mortgage savings and new rental inflows straight into retirement accounts.
  • When the kids leave home, sell the current house to fund retirement, then move to the out-of-state property (if still wanted).

7. On Education Savings – Tough Love (21:11–23:10)

• Jill insists they must "put yourselves first"—college savings are not practical now.
• Kat and her husband will need to have candid talks with their kids about bright-line college boundaries (public school, scholarships).

Notable quote:

Jill (22:15): "You're going to make sure that we have your retirement plans funded. That is the most important thing for you guys. And then... if they go to school, you are going to be pushing them like heck to say like, either get a scholarship or you're going to public school because we cannot afford it."

8. Big Picture and Reassurance (23:10–26:05)

• Kat’s family is not as off-track as her anxieties suggest: they have time, multiple assets, and a clear path if they focus.
• Jill and Mark stress the uniqueness of every caller; advice is always personalized.

Notable exchange:

Kat (25:13): "Because I think my biggest concern or our biggest concern was retirement at 70..."

Mark (25:25): "70 is like, you're so young... You're going to keep working, keep saving. You got two pieces of real estate. You're going to get some rental income going. I don't think 70 is a... You're going to have Social Security down the line. I think they're going to be good."

Kat (26:01): "I am feeling okay. Actually, I feel pretty good."

Notable Quotes & Moments (with Timestamps)

• "I feel like, you know, we're middle aged and we're stressed and we don't know if we have enough...I feel like I need to know." – Kat (03:29)
• "Why are we keeping this? Let's get rid of it." – Mark, regarding the out-of-state rental (07:34)
• "Having this money and doing the work is very important. Like, fourteen hundred dollars a month could be a very big deal for you." – Jill (17:01)
• "You're going to make sure that, that we have your retirement plans funded. That is the most important thing for you guys." – Jill (22:15)
• "You're going to keep working, keep saving. You got two pieces of real estate. You're going to get some rental income going. I don't think 70 is a—You're going to have Social Security down the line. I think they're going to be good." – Mark (25:40)
• "I am feeling okay. Actually, I feel pretty good." – Kat (26:01)

Important Segments & Timestamps

• Listener call begins / Kat’s anxiety: 03:17
• Full financial snapshot: 05:41–10:03
• Discussion of real estate/rental woes: 07:02–11:34
• Plan to unlock rental income with a retirement loan: 15:04–17:01
• Detailed strategy for moving forward: 17:01–23:10
• Minimum viable college funding, prioritizing parents: 21:11–23:10
• Final reassurance and wrap-up: 25:13–26:05

Tone and Closing

Jill and Mark maintain their signature warmth, mix of empathy and candor, and plain-English advice throughout the call. Even potentially risky strategies (like borrowing from a retirement account) are discussed with a sober, facts-driven approach, always keeping Kat’s emotional well-being and family priorities in the foreground.

Listeners in similar situations will find reassurance—and homework—in these themes:

• Face your numbers
• Prioritize your own financial security before college savings
• Don't let low-yield/high-stress assets weigh down your future
• Small, tactical moves to unlock income can change your trajectory—with careful risk management

Bottom Line:
Even families who "feel behind" or who are cash-strapped have options. With focus, targeted asset management, and realistic goals, retirement—even at 70—is not out of reach. As Jill says, "We are here for you...We really have no way of applying what we do for anyone else to you, so...come on the air with us. Let's walk through it." (26:05)