Jill on Money with Jill Schlesinger

Episode: Can We Splurge a Little Bit?
Date: August 27, 2025
Host: Jill Schlesinger, CFP®
Caller: Julie from California

Episode Overview

In this episode, Jill Schlesinger answers a listener’s question about how much she and her husband can safely spend on travel, hobbies, and “play things” during their active years of early retirement. Julie’s detailed financial situation—including significant assets and a $4.5 million rental property—sparks an in-depth conversation about prudent spending, investment strategy, and the value (or lack thereof) in holding underperforming real estate. The episode blends practical advice with friendly, lighthearted banter, resulting in what Jill describes as “as much a therapy session as a finance session” (19:33).

Key Discussion Points & Insights

1. Julie’s Situation and Big Question

Julie, age 63, is retired; her 65-year-old husband still works but may retire in two years. She wonders:

• How much can they “splurge” for travel and hobbies over the next 5–7 years while still being financially responsible?
• She wants a straightforward, jargon-free evaluation: “How much extra money can I spend on play things?” (02:20)

2. Income & Retirement Outlook (03:30–04:47)

• Julie’s husband earns ~$200k/year (salary + consulting), planning to keep consulting for five years post-retirement ($30–50k/year).
• Husband will receive a $70k/year pension (with a survivor benefit, at Jill’s recommendation).
• No pension for Julie.
• Consulting income expected to continue, supplementing the pension.

3. Wealth Snapshot & Asset Breakdown (04:47–07:14)

• Total assets: Approximately $3.4M–$3.5M
  • IRAs (SEP and traditional): ~$1.65M (pre-tax)
  • Taxable brokerage: Above $300K
  • Roth IRA: ~$33K (recently started)
  • Inherited IRA from her mother: ~$867K (Julie takes required minimum distributions)
  • Additional “household” and “charitable” funds among brokerage accounts
• Spending: ~$10,000/month baseline; some years, they spend >$220,000 total (including large travel/hobby years). “But that’s not every year...” (08:03)
• Rental property: Owns half of a residential Silicon Valley asset valued at $4.5M; generates only ~$6,700/month gross rent—split between Julie and her brother (09:33–09:45).

4. Rental Property Dilemma (09:14–18:30)

• Jill is shocked at the low yield: “It should be generating like $20,000 a month at least on that kind of...I mean, it's a $4.5 million asset” (11:02).
• Julie inherited the property via trust; she and her brother are now tenants in common.
• Both siblings are open to selling; even their shared advisor recommends it, but hasn’t pressed the issue (“she...she would love for us to sell the property, but she also likes that we’re diversified,” 10:42).
• Jill pushes hard to sell ASAP, voicing skepticism at holding such an illiquid, poorly performing asset:
  • “Sell it, Sell it.” (09:57)
  • “The only way to use [a ‘real’ asset] is to get it liquid. So why am I waiting to get liquid when I know you’re going to want to spend more money in the next five to seven years?” (17:31–17:44)
  • On timing the market: “Julie’s like timing the market for sure.” (13:42)
  • “Why are we waiting? When you have all this money...it defies any sort of logic to wait five years.” (17:54)

5. Investment Philosophy & Spending Recommendations (13:19–18:37)

• Can they safely spend $220k–$250k/year for the next five to seven years?
  • Jill: “Like there’s no way you’re spending through all this money.” (13:19)
  • Julie’s planner models higher spending every other year with no concerns.
  • Jill (and Mark): There’s plenty of margin even if they “splurge” on travel and hobbies.
• Jill’s suggestion: Sell the rental, invest the proceeds in a balanced, low-fee portfolio aligned to their risk profile and spending needs.
  • “I would take your $2 million and invest it. In a safe way.” (17:52–17:53)
  • “A nice balanced portfolio to suit your, you know, your ages and your lifestyle. You’ll be set. So set. This is such good news. Why are you asking for a problem?” (17:54–18:09)
• Jill’s final advice: Enjoy what they’ve built and don’t be afraid to spend within means—“Otherwise, what are we doing this for? Come on now.” (19:29)

6. Advisor Relationship & Fees (18:37–19:20)

• Jill questions the fee structure as the advisor would get more to manage if they sell the property.
  • “Don’t forget to tell your advisor you want a cheaper fee when you give her the extra 2 million bucks.” (18:35)
  • Julie admits she doesn’t know the fee—Jill encourages clarity: “Come on. ...Let us know what you’re paying.” (18:43–18:50)
  • Advisor is “inherited,” having previously worked with Julie’s father.

Notable Quotes & Memorable Moments

• On rental property performance:

  “It should be generating like $20,000 a month at least on that kind of...I mean, it’s a $4.5 million asset.”
  — Jill, (11:02)

• On market timing and real estate:

  “Julie’s like timing the market for sure. ...If you really believe, like, the economy’s going into the tank, why would real estate do better then?”
  — Jill, (13:42–15:13)

• On selling and investing proceeds:

  “I would take your $2 million and invest it. In a safe way.”
  — Jill, (17:52)

  “A nice balanced portfolio to suit your, you know, your ages and your lifestyle. You’ll be set. So set.”
  — Jill, (17:53–18:09)

• On enjoying wealth:

  “We absolutely encourage you to get your money and spend your money.”
  — Jill, (19:21)

  “Otherwise, what are we doing this for? Come on now.”
  — Jill, (19:29)

• On the therapeutic value of good financial advice:

  “I feel this was as much a therapy session as a finance [session].”
  — Julie, (19:33)
  “That is what we do. Dr. Mark and Dr. Jill are in practice.”
  — Jill, (19:37)

Important Timestamps

• 02:20: Julie introduces her central question about discretionary spending.
• 03:00–04:47: Breakdown of retirement status, income, and pension.
• 04:47–07:14: Detailed asset/investment review.
• 08:00–08:23: Discussion of actual and aspirational annual spending.
• 09:14–13:31: The $4.5M rental property—questions, income, and selling debate.
• 13:19–18:37: Discussion of spending safety, motivations for asset liquidation, investment planning, and risk.
• 18:37–19:20: Advisor management and fee awareness.
• 19:33–19:39: “Therapy session” exchange bringing humor and humanity to personal finance.

Summary Table: Julie’s Financial Landscape

| Asset/Income | Amount | Notes | |-------------------------|-----------------------------------|----------------------------------------------------| | Husband’s salary | $150–200k/year (pre-retirement) | Plus $30–50k/yr consulting through retirement | | Husband’s pension | $70k/year | Survivor benefit selected | | Retirement accounts | ~$1.65M (pre-tax IRAs) | | | Taxable brokerage | ~$300k+ | | | Roth IRA | $33k | Newly established | | Inherited IRA | ~$867k | RMDs: ~$36k/year | | Own home | ~$2.2M | Fully owned | | Rental property | $4.5M (own half) | ~$6,700/month total rent, split with brother | | Annual spending target | $220k–$250k for travel/hobbies | For next 5–7 years | | Advisor fee | Unknown—needs clarification | Jill urges getting a lower rate upon more assets |

Tone and Takeaways

Jill’s signature mix of empathy and blunt financial wisdom shines throughout—she roots for Julie’s happiness and security, provides clear explanations without jargon, but doesn’t shy away from calling out logical missteps (“Why are you asking for a problem? ...You’re in great shape,” 18:09). The episode encourages listeners to balance prudent stewardship of wealth with joy in spending on what matters most during the “active years”—and, above all, to demystify their own finances so they can act with confidence.

Bottom Line:
Julie (and households like hers) can “splurge a little—or a lot—without sacrificing long-term security,” so long as big illiquid, underperforming assets like the Silicon Valley rental aren’t left dragging down the overall plan.

For more details or to ask your own question, visit jillonmoney.com!