Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Can I Go Part-Time?
Date: November 4, 2025
Host: Jill Schlesinger, CFP®
Guest: Jean, Listener from Texas

Main Theme

This episode centers on listener Jean’s financial crossroads: deciding whether he can afford to go part-time at work while maintaining his family’s security and financial goals. As always, Jill provides direct, jargon-free advice—covering real estate, cash flow, savings, and why sometimes it’s OK to splurge on yourself.

Key Discussion Points & Insights

1. Listener Profile & Financial Overview

• Jean, 43, married two years, father to a 2-year-old
• Both Jean and spouse work full time; combined salary: ~$300,000/year
• Substantial retirement and investment savings
• Owner of multiple properties (4 rentals plus primary home across several states), all with healthy equity and good mortgage rates

2. The Big Questions

• Jean’s Dilemma:
  • Wants to reduce work hours and spend more time with family
  • Unsure if it’s financially safe to step back
  • Hesitant about splurging on business class tickets for an upcoming Asia trip ("I don't know. Because I'm frugal." – Jean, 11:40)

3. Deep Dive: Assets & Cash Flow

• Retirement Savings (Jean Only):
  • Roth IRA: $164K
  • Rollover: $60K
  • Employer plan: $78K
  • Old 401k: $393K
• Spouse's savings: Unknown; Jill and Mark ([producer]) note importance of financial transparency
• Child Savings: Just started a UTMA instead of a 529 account for flexibility—“If she wants to open a business...she has choices.” (Jean, 06:59)
• Properties:
  • 4 Rentals: Seattle condo ($340K; $172K mortgage), Arizona ($450K-500K; $180K mortgage), Texas ($250K; $150K mortgage), Washington ($650-700K; $130K mortgage)
  • Primary Home: ~$400K value, ~$100K remaining mortgage
• Monthly rental cash flow: Net $2K–3K, “Usually I invest them back to stocks or CDs.” (Jean, 10:38)
• Investments/Cash:
  • Brokerage: $10K
  • Money market: $115K
  • Checking: $52K + smaller additional accounts

4. Expenses & Lifestyle

• Household monthly spending: ~$5,000
• No plans for more children
• Both spouses in good positions, but Jean is hesitant about loosening the financial belt

5. Jill’s Advice

• Permission to Reduce Hours & Enjoy Life:
  • “Obviously you can go part time.” (Jill, 13:25)
  • Income would drop, but plenty of savings/cash flow; could supplement by selling underperforming rental(s) for liquidity
  • To feel more confident, consider:
    • Working with a fee-only financial planner for a detailed cash flow analysis
    • Assessing the performance/value of each property (“Look at the expenses and look at the cash flow and see what’s really working, what’s not.” – Jill, 16:03)
• On Business Class Tickets:
  • “Here’s what I do know. No matter what. Jean, you can fly business class.” (Jill, 16:34)
  • It’s OK to enjoy your money when your finances are secure

6. Notable Quotes & Memorable Moments

• Jill on Voting:
  • “You gotta vote no matter what. Even if you have to hold your nose… Not voting. Not good.” (00:32)
• On Family Finances:
  • “How do you not know [what your wife has]? I have every dollar accounted for. I am telling you, I am an animal about that.” (Jill, 06:10)
• On Real Estate Holdings:
  • “You got so much equity, man.” (Jill, 09:37)
• On Splurging:
  • “Maybe you’re frugal. Well, or cheap, maybe.” (Jill, 11:42)
  • “Business class. Yes, I Jane, I just did it. I just flew to China. Business class. I mean, there’s no going back. So just do it…” (Jill, 17:08)
• On Parenting and College Savings:
  • “Why don’t you want her to go to college?”
  • “Well… if she wants to open a business… she has choices.” (Jean & Jill, 06:56–07:08)

7. Family Communications

• Importance of knowing each other's financial details (“They really do need to know what’s going on with each other’s financial lives. This would be a good time for you to, like, share information...” – Jill, 16:57)
• Jill suggests reviewing estate planning and wills

Timestamps for Key Segments

• [04:25] Jean introduces his situation and the part-time question
• [05:09] Family & income details
• [06:01] Discussion of retirement savings
• [06:43] Child’s savings account and approach
• [07:22] Inventory of properties begins
• [10:21] Net monthly rental cash flow calculated
• [11:40] The “too frugal for business class” debate
• [12:09] Jean expresses desire for part-time work
• [13:25] Jill: “Obviously you can go part time.”
• [14:28] “Sell a property if you want more liquidity”
• [15:19] Retirement planning at 55
• [16:03] Analyzing property value and performance
• [16:34] “No matter what… you can fly business class”
• [17:08] Jill: “There’s no going back” after business class
• [17:33] Managing travel with a toddler and business class

Episode Tone

• Warm, humorous, and direct.
• Jill and Mark tease Jean about his frugality, push for more marital financial openness, and emphasize pragmatic permission to optimize both life and finances.

Actionable Takeaways

• It’s OK to reduce work when your finances allow—money is a means to a better life, not just an end.
• Consider rebalancing assets (e.g., selling a rental) to gain liquidity if work slows down.
• Married couples should understand each other’s complete financial picture, including accounts and assets.
• Don’t feel guilty about enjoying some of your resources (e.g., flying business class with your family).
• Consult a fee-only planner if major changes bring uncertainty.

Final Thought:
Jill’s definitive encouragement: “You’re really much, you’re very much on track to do what you want to do. I think the hard part for you, it sounds to me like you are not necessarily giving yourself permission to do it.” (16:44)

For listeners seeking guidance about shifting work or life priorities, Jill’s door is open: submit your questions at jillonmoney.com.