Podcast Summary: Jill on Money – Can I Retire in Two Years?

Host: Jill Schlesinger
Guest: Mary from Northern California (Caller)
Date: December 15, 2025
Key Theme:
Jill advises Mary, a high-earning widow with teenage twins and several properties, on whether she can realistically retire in two to three years while funding her daughters’ college educations and maintaining her desired lifestyle.

1. Overview of Episode Theme

In this listener call-in episode, Jill Schlesinger discusses the complexities of transitioning to retirement for someone with significant assets and expenses. Mary, the caller, wants to know if she’s financially positioned to retire in two or three years, balancing college costs for her twins, supporting elderly parents, and managing multiple properties. The conversation covers optimizing retirement drawdown strategies, handling investment risk, and making pivotal real estate decisions.

2. Key Discussion Points and Insights

Jill’s Return and Personal Update

• Jill opens with stories from her recent trip to India, remarking on sensory overload, local quirks (“honk please” signs), intense air pollution, and vibrant culture.
  • Notable quote: “It’s an assault of the senses... It’s so noisy, the trucks have huge block letters: ‘honk please.’ There’s so much honking I cannot even tell you.” (03:13)

Mary’s Situation & Goals

• 61-year-old widow, wants to retire at 63–64 (~2028).
• Twin daughters turning 18; both entering college soon.
• Recently started listening to Jill’s podcast.
• Wants to focus on herself after years of caregiving (“I want to start living for me.” 07:57).

College Funding Plans

• $200k saved for daughters’ college; expects to spend ~$80k/year total.
• State universities likely, but open to private; doesn’t qualify for financial aid due to high income ($400k+ in sales).
• Preference is to pay 100% of undergrad costs to keep daughters debt-free:
  • “With AI and the world changing, I don’t know how long it will be before they find a way [to support themselves financially].” (10:14)

Financial Snapshot

• Brokerage account: $740k (to be reduced to $600k after college expenses)
• Retirement accounts: $2.35M in 401(k), all traditional (pre-tax)
• Savings/Emergency funds: $130k cash
• Pension: ~$800/month at 65
• Social Security estimate at 70: ~$4,856/month

Real Estate Portfolio

• Primary residence: $1M value; $740k mortgage at 4.5%.
• Rental #1 (Condo): $365k value; $154k mortgage at 3.8%; cash flows at break-even, high HOA.
• Rental #2 (House): $875k value; $490k mortgage at 2.8%; also just covers costs, high HOA.
• Both rentals contribute little to cash flow due to costs/fees.

Retirement Expenses

• Current monthly spend: ~$13k (includes support for parents).
• $4,800 of this is the primary home mortgage.

Key Concerns Raised

• Should Mary keep or sell her rentals in light of weak cash flow but low mortgage rates?
• What’s the best strategy for handling investment risk so close to retirement (currently 100% equities)?
• Is her current savings and property structure aligned with her retirement goals?

3. Notable Quotes & Memorable Moments

• Mary on starting a new phase:

  • “I want to start living for me.” (07:57)

• Jill’s perspective on real estate:

  • “Forget about the low mortgage interest rate... these are not properties that are really kicking tush. The best days may be behind you.” (19:40)
  • “It works a lot better if you sell both of these properties earlier in your retirement.” (20:35)

• Mary’s portfolio risk:

  • Mary: “Most of my assets are in very aggressive stocks.”
  • Jill: “Stop taking so much risk... Bulls and bears make money, and pigs get slaughtered!” (23:29)
  • “If you’re really aggressive, it would behoove you to make some changes.” (24:16)

• Jill on retirement readiness:

  • “You and your husband did a really good job of accumulating these assets. Now we’re just trying to figure out how to get you there most efficiently.” (26:56)

4. Timestamps for Major Segments

| Timestamp | Segment | |---------------|--------------------------------------------------------------------------------------------------------| | 02:39 | Travel talk: Jill recounts her India trip, culture, air quality, and contrasts with New York. | | 06:21 | Introduction of Mary from Northern California. | | 07:32 | Mary’s age, family, and retirement timeline. | | 08:46 | College funding, daughters’ plans, expected expenses. | | 09:48 | Household income and decision to fully fund daughters’ education. | | 10:42 | Breakdown of brokerage and retirement accounts. | | 12:17 | Real estate and mortgage details for each property. | | 14:12 | Discussion about rentals’ profitability and HOAs eating up profits. | | 15:21 | Monthly spend and inclusion of support for parents. | | 16:00 | Discussion of possible timelines for retiring, healthcare transitions, and future plans. | | 17:15 | Social Security and pension estimates. | | 19:11 | Mark and Jill debate the benefits of offloading rental properties before or in early retirement. | | 22:44 | Tax implications of selling real estate, step-up in basis after spouse’s death. | | 23:17 | Discussion about investment risk and the need to dial back aggressive stock positions. | | 25:18 | Estate planning – are documents ready for adult children? | | 26:56 | Jill summarizes: Mary is generally on-track, just needs to tweak property and risk strategies. |

5. Key Takeaways and Recommendations

Retirement Feasibility

• Mary can retire in about two years—but only if she:
  • Sells both rental properties upon, or shortly after, retiring. This generates liquid assets to support her withdrawal needs and reduces the risk of real estate underperformance.
  • Moderates her spending if keeping both rentals; $13k per month is a stretch unless more cash is freed up.

College Funding

• Her daughters’ education is secure, but funding it means reducing her brokerage holdings from $740k to $600k. She should continue to reserve retirement account funds primarily for her own benefit.

Investment Strategy

• Mary is overexposed to equities (almost 100% stock). Jill strongly recommends reallocating to reduce risk as retirement approaches.
  • “It would behoove you to make some changes... You may be feeling a little bit of anxiety because you’ve taken all this risk.” (24:16)
• Take advantage of the ability to rebalance within her 401(k) without tax consequences.

Real Estate Optimization

• Both rentals have little net cash flow and rising expenses (HOA, insurance, taxes).
• Low interest rates tempt her to keep them, but the downsides (no cash flow, hassle, uncertain appreciation) outweigh the benefits as she enters retirement.
• Jill and Mark both recommend selling both or at least one property to increase financial flexibility and reduce risk.

Next Steps

• Begin preparing for the real estate sale, consult a tax advisor, and potentially a financial planner for full retirement planning.
• Revisit the investment allocation and dial down risk.
• Finalize estate planning now that children are turning 18.
• Continue employment at least until college funding is certain and lifestyle post-children becomes clear.
  • “It gives you a little bit more comfort with a little more knowledge.” (26:56)

6. Closing Guidance

Mary is generally in excellent financial shape—thanks to high earnings and disciplined saving. Jill affirms her path is workable with modifications: freeing up more liquid wealth from real estate, reducing investment risk, and seeking professional guidance on taxes and estate planning.

Memorable Closing Quote:
“You and your husband did a really good job of accumulating these assets. Now we’re just trying to figure out how to get you there most efficiently.” (26:56)