Podcast Summary:

Jill on Money with Jill Schlesinger
Episode Drop: “What Should I Do With My Money?” from Morgan Stanley
Date: October 1, 2025
Theme: Exploring the intersection of money, motherhood, and menopause, and how emotions and personal history influence financial decision-making for women in midlife.

Episode Overview

This episode is a crossover featuring Morgan Stanley's “What Should I Do With My Money?”, centering on Kristin—a successful real estate agent and mother navigating rising anxiety around finances as she enters perimenopause. The show lays bare how career, wellness, emotional state, and financial planning intertwine, especially for women in their late 40s and 50s. Host Jamie Rowe introduces a real, in-depth conversation between Kristin and her financial advisor (and friend), Sarah, with expert context from Dr. Kim Henderson, Morgan Stanley’s associate medical director.

Key Discussion Points & Insights

1. Kristin’s Financial Anxiety and Aspirations

• Kristin shares longstanding discomfort discussing money, despite her strong planning instincts.
• Her priority: building a secure financial future for her two daughters, offering them the same advantages she received (“downfield blocks” for college, weddings, home down payments).

  “I want to do that for my kids...any downfield block we can give them, I want to be able to do.” — Kristin [01:18]

• Despite having a plan in place with financial advisor Sarah, persistent anxiety remains about college costs, weddings, and unforeseen needs.

2. Motherhood, Menopause, and Money Stress

• Kristin reflects on perimenopause as triggering heightened emotions and life questioning, which bleed into money worries and career thoughts.

  “I just feel like a wackadoo half the time...Does that lead to my anxiety about whether it’s finance or life or children?” — Kristin [02:20]

• Sarah notes this pattern in many female clients: as they approach menopause, concerns about work-life balance, retirement, and physical well-being rise sharply.

  “If you don’t feel great physically...it makes you question life decisions. Am I gonna have a hot flash in the middle of a presentation?...It’s super stressful.” — Sarah [07:02]

3. Women, Confidence, and Financial Conversations

• Sarah identifies a “crisis of confidence” in women regarding finances, despite being over half the population.

  “The difference between women and men...tends to be a crisis of confidence...Let’s figure out where you are today, and...move forward.” — Sarah [05:30]

• The power of having a relatable, female financial advisor: Kristin went from feeling sidelined to becoming an active participant in her family’s financial planning.

  “I was finally part of the conversation...I actually felt comfortable from the get-go.” — Kristin [03:27]

4. Teaching Kids About Values and Money

• Kristin struggles with how to impart fiscal values to her children, feeling unsure how she was taught them herself.

  “That whole thing sounds awful to me...I hate even talking about that...” — Kristin [10:34]

• Sarah reassures her: values are often passed on through lived example, not formal lectures.

  “You’re probably doing a way better job than you even realize.” — Sarah [11:24]

5. Money, Health, and Permission to Prioritize Well-being

• Dr. Kim Henderson joins to explain the “perfect storm”: menopause brings new anxieties about the future, physical symptoms, and often financial worries, all compounding.

  “There is no separation between physical health and wellness, mental health and wellness, and financial health and wellness. It is all in the same stew.” — Dr. Kim Henderson [15:59]

• Sarah observes many women don’t “give themselves permission” to spend on health needs, like trainers or therapy, and sometimes just need external validation that it’s responsible to do so.

6. Retirement and Long-Term Security Concerns

• Kristin is unsure she’ll ever fully retire, but worries about having “enough” and how to plan for unknowns and potential health crises (e.g., paying for long-term care or assisted living).

  “How do you know when enough is enough?...How many more years do we need to keep working?” — Kristin [17:19]

• Sarah emphasizes the plan incorporates flexible math and scenario modeling, including long-term care insurance and bucketed healthcare savings. She walks Kristin through the practical mechanics—and emotional comfort—of having contingencies.

7. Estate Planning, Trusts, and Protection

• Kristin is comfortable with estate discussion (“That doesn’t make me uncomfortable at all, actually”). She wants safeguards that align with her values and avoids just giving lump sums to her kids.
• Sarah outlines the basics: beneficiary structures, inheritance timelines, preventing common issues (like assets passing to a second spouse), and recommends a guided template for conversations with lawyers.

  “We will...synthesize the legal documents...in a summary...with any questions that we have to make sure...did we cover this?” — Sarah [24:30]

Notable Quotes & Memorable Moments

• Kristin’s vulnerability & humor:

  “I just feel like a wackadoo half the time and thank God I have friends that are willing to talk about it.” [02:20]
  “We do not want the young, hot second wife getting everything I worked for.” [23:26]

• The “aha moment” about self-care:

  “I don’t need to have this guilt over spending money that I wanna spend on myself...That really clicked for me.” — Kristin [27:30]

• Reassurance and gratitude:

  “I cried last time you came over because you made me feel better about our future.” — Kristin [26:49]

Important Timestamps

• 00:52 | Kristin introduces herself and discusses anxiety around money
• 02:20 | Kristin connects perimenopause to increased anxiety
• 05:30 | Sarah discusses women and confidence in financial matters
• 07:02 | The impact of physical wellness on financial decisions
• 10:34 | Kristin’s discomfort with discussing money values with kids
• 11:24 | Sarah’s reassurance about values being passed on
• 14:47 | Dr. Kim Henderson on menopause, anxiety, and money
• 17:19 | Kristin expresses fear about never having “enough”
• 18:21 | Kristin’s aversion to financial lingo; desire for clear answers
• 21:06 | Sarah explains long-term care insurance
• 23:26 | Estate planning details and the “young, hot second wife” bit
• 27:30 | Kristin’s “aha moment” regarding guilt-free self-spending

Episode Tone and Takeaways

The episode blends candid, often humorous admissions of discomfort with deeply practical financial advice. The tone is supportive, gentle, and empathetic: Kristin’s honesty about her unease, Sarah’s warmth and clarity as an advisor, and Dr. Kim’s integration of physical, mental, and financial health contribute to both reassurance and actionable planning.

Key takeaways:

• Financial plans must address not only the numbers, but evolving emotional and physical needs—especially for women in midlife.
• It’s normal for women to feel anxiety and uncertainty as they balance family, health, and finances.
• Talking openly, asking questions, and using trusted professionals can provide both action steps and critical peace of mind.
• Estate planning and long-term care are essential—and not just about what happens at death, but about protecting values and ensuring comfort for future generations.