Podcast Summary: "Making Our Next Move"

Podcast: Jill on Money with Jill Schlesinger
Episode Date: October 6, 2025
Host: Jill Schlesinger, CFP®
Guest: Bella, caller from Reno, Nevada

Episode Overview

In this episode, Jill Schlesinger answers listener Bella’s call, diving into the financial considerations for a major life pivot. Bella, a successful entrepreneur and real estate investor in her 40s, is contemplating a significant lifestyle change in six years: traveling the world with her partner and daughter after her child finishes high school. Jill, along with regular contributor Mark, breaks down Bella’s assets, income strategy, and retirement planning—offering tailored, honest advice (and a dose of dream reality-checking) to help Bella (and listeners) understand what it takes, financially and logistically, to make such a big move.

Main Discussion Points and Insights

1. Life Transitions and Financial Planning

• [01:06] Jill emphasizes that big life transitions—like moving, changing careers, retirement, or funding college—are common sources of financial anxiety.
  • “Usually that's when you start kind of freaking out about your money or thinking about your money, maybe not freaking out.” — Jill
• Jill encourages listeners to reach out for guidance during these periods.

2. Bella's Situation: Goals and Assets

• Bella's Background:

  • In her 40s, has a partner and an 11-year-old daughter
  • Self-employed with a business of 13 years
  • Owns primary residence and two rental properties (no mortgage on primary)
  • Desires a lifestyle change in about six years—world travel, making Reno a home base
  • Partner stays at home but has a side hustle and is on company payroll

• Assets & Income Breakdown ([04:01]–[08:25]):

  • Households earnings from work: ~$150,000/year (excludes rental income)
  • Rental Properties:
    • Rental 1: Worth ~$550k, mortgage $154k @ 3.99%
    • Rental 2: Worth ~$400k, mortgage $174k @ 4.5%
    • Combined net rental cash flow: ~$1,500/month after expenses
  • Savings & Investments:
    • Primary residence: $550k, mortgage-free
    • Roth IRAs: $165k (Bella), $93k (partner)
    • SIMPLE IRA: $16k (recently started)
    • Brokerage accounts: $400k managed + $84k “fun money” (stocks)
    • College savings: $18k in 529, $43k in UTMA for daughter

3. Planning the Next Move: Retirement & Income

• Desired lifestyle: Travel for at least a couple years, possibly work abroad; keep Reno as base
• Planned expenses while traveling: ~$6,000/month ([09:09])
• No pension or significant passive income aside from rentals ([09:13])
• Jill’s Core Advice:
  • Stop paying down low-rate mortgages on rental properties.
    • “Do not pay that down. Please stop the insanity.” — Jill, [06:01]
    • Liquidity and flexibility are more important than being debt-free on low-rate rental mortgages
  • Continue maximizing retirement and brokerage contributions.
    • Currently saving ~$50,000/year (max IRAs, SIMPLE, brokerage)
    • With compound growth, could reach $1.3–$1.5 million in six years
  • Rent out the primary residence while traveling for potentially $2,500/month ([13:11]).
    • Combined with rental income, could reach ~$4,000/month passive income toward the $6,000 target
  • Consider income-generating “side gigs” while traveling.
    • Even $1,000–$2,000/mo reduces stress on investment withdrawals

4. “Can We Make the Numbers Work?” ([12:00]–[16:00])

• Mark and Jill run rough numbers:
  • If Bella keeps saving $50k/year, with rental and primary residence income, and supplements with side income while traveling, the plan is feasible but tight (“priced to perfection”).
  • Contingencies: If Bella can sell her business (even with a payout over several years) or finds part-time work abroad, risk drops significantly.
  • Jill recommends: “If between the two of you, you could figure out how to generate one or two grand a month in income, I like the plan a lot better.” ([15:10])

5. Emotional and Practical Considerations

• Bella is not “burned out” but “bored” ([09:55]) and wants purpose along with adventure.
• Jill urges her not to get swept away emotionally—have financial flexibility and a backup plan.
• Jill repeatedly stresses: Don’t kill liquidity by paying off low-rate rental mortgages early.

6. Other Logistics

• Health Insurance: Must be part of their plan while abroad ([16:51])
  • “You need insurance, so you're going to have to investigate that.” — Jill
• Estate Planning: Check wills, POAs, especially for a mobile lifestyle.
• Timeline Cautions: Consider delaying the transition by a year or two for greater security ([17:01])

Notable Quotes & Memorable Moments

• Jill’s Mortgage Advice ([06:01]):
  • “Do not pay that down. Please stop the insanity.”
• On liquidity and planning for the huge pivot ([13:45]):
  • “For you guys to pull this off, let me tell you what's critical. Don't worry about making sure that the mortgages are paid off. It is making sure you have a good handle on the expenses that you're going to incur.” — Jill
• On side income and plan flexibility ([15:10]):
  • “If between the two of you, you could figure out how to generate one or two grand a month in income, I like the plan a lot better. I really do.” — Jill
• On emotional drivers ([09:55]):
  • “I'm just bored. I just want to do something different.” — Bella
• On the dream of working abroad ([10:44]):
  • “If I found some work in a different country, that would be amazing.” — Bella
  • “Yes, it would be. And highly unlikely, but okay, let's see. Let's see if you could.” — Jill
  • Mark: “The dream crusher is here today.” ([10:53])
• On keeping future options open ([16:00]):
  • “Give yourself a little bit of grace and maybe push out a couple of years, the game plan, and still be able to do it, but with a little more security.” — Jill
• Jill’s closing encouragement ([16:59]):
  • “Bella, I feel like Europe awaits you, the world awaits you. So ciao, Bella, as they say.”

Key Segment Timestamps

• [01:06] – Jill introduces the theme: life transitions & financial planning
• [02:29] – Bella introduces her situation and dream for post-high-school travel
• [03:55] – Discussion of Bella’s partner, household structure
• [04:12] – Discussion of plans post-daughter’s graduation
• [04:33]–[08:25] – Asset, income, and investment deep dive
• [09:09] – Expected expenses while traveling ($6,000/mo)
• [09:55] – Emotional drivers behind the change (“just bored”)
• [12:00]–[13:45] – Retirement saving projections & plan feasibility discussion
• [13:45]–[14:35] – Advice against paying off low-rate mortgages; importance of liquidity
• [15:34]–[15:56] – The prospect of selling the business for additional financial cushion
• [16:51]–[17:01] – Risks: health insurance, estate planning, and timeline tweaks
• [17:44] – Jill’s final encouragement and call for similar listener stories

Takeaways for Listeners

• Life transitions require both math and a gut check—plan for financial and emotional flexibility.
• Don’t rush to pay off low-interest debt if it reduces your financial flexibility (liquidity is king for big pivots).
• Rental income can be a critical piece of post-work life—but understand true cash flow after all expenses.
• Maximize retirement and brokerage contributions while you can, especially before a big income change.
• Health insurance and estate planning are essential for globe-trotting families.
• If your “dream move” is tight on paper, even a small amount of supplemental income or delaying the leap can significantly reduce risk.

“Let us know if you want to live vicariously through you!” — Jill ([17:44])

For more financial guidance or to ask your own question, visit jillonmoney.com.