HerMoney with Jean Chatzky – Mailbag: Taboo Money Questions with Gretchen Rubin

Date: December 12, 2025
Guest: Gretchen Rubin, happiness expert and co-host of "Since You Asked"

Episode Overview

In this special "Mailbag" episode, host Jean Chatzky and returning guest Gretchen Rubin tackle listeners’ most taboo and tricky money questions. The conversation ranges from asking for employer sponsorship in a beauty pageant, to the anxiety and confusion of having a long-standing bank account abruptly closed, and finally, navigating the fraught topic of pay disparities in the workplace. The tone is practical, empathetic, and often amusing—true to the spirit of HerMoney—while offering genuinely actionable advice for women facing financial quandaries that are rarely discussed out loud.

Key Discussion Points & Insights

1. Gretchen Rubin on Collaboration and New Podcast (since you asked)

• Gretchen shares the inspiration behind her new advice podcast "Since You Asked," co-hosted with Lori Gottlieb.
• She highlights the universal appeal of advice podcasts, comparing them to procedural TV shows:
  • "I think there's sort of limitless interest in it... you just want more and more and more." (Gretchen, 06:05)
• Most listener questions for their show are about relationships—family, friends, and sometimes neighbors.

Timestamps:
05:15 – 06:24: Gretchen on working with Lori and the appeal of advice formats.

2. Asking Your Employer to Sponsor a Beauty Pageant

Listener Question:

A woman working at a large insurance company wants advice on asking her employer to sponsor her entry into a state pageant without sounding unprofessional.

Key Advice:

• Gretchen Rubin:
  Advocates a light-hearted, positive approach emphasizing opportunity for company visibility rather than a hard sell.
  • "Ask in a light-hearted way... I would love to represent the company and not ask in kind of an earnest way." (Gretchen, 07:48)
• Jean Chatzky:
  Suggests creating a sense of exclusivity:
  • "Before I go out and ask anybody else, I thought, boy, maybe I should ask you because I don't want you to feel as if I didn't give you the opportunity." (Jean, 08:48)
• Lori Gottlieb:
  Recommends framing the sponsorship as a chance for the employer to be the first to say yes, not as a favor.

Notable Quotes:

• "No one has an opinion till someone else has an opinion." (Gretchen relaying her sister’s Hollywood wisdom, 09:09)

Timestamps:
07:33 – 09:41: Conversation about company sponsorship, tone, and strategy.

3. Bank Account Closed Without Warning

Listener Question:

A long-time customer at a major bank received a sudden (and unexplained) account closure, followed by a report to ChexSystems and Early Warning Services, making her feel anxious and embarrassed.

Key Advice:

• Jean Chatzky:
  Notes that this is not uncommon and can happen for various reasons, including profitability or policy, but worries about possible fraud or identity theft.
  • Urges freezing credit immediately:
    • "If there's fraud... you gotta get your credit frozen, and you have to do it really, really quickly." (Jean, 11:06)
  • Recommends opening a new account at a credit union with a more personal touch.
• Gretchen Rubin:
  Advocates advocating for oneself, not letting embarrassment or confusion prevent you from seeking answers:
  • "Go to this bank, get all your papers in hand... I really need to understand why you took the action that you took." (Gretchen, 12:36)
  • Reassures listeners that money triggers deep emotions, especially anxiety and shame.
  • Suggests requesting records from both banks and reporting agencies.
• Jean Chatzky (continued):
  Offers to help the listener as part of her AARP column, if the listener is willing to go public.
• Discussion:
  The hosts agree it's essential to investigate possible identity theft, emphasizing that freezing credit is a critical, immediate step.

Notable Quotes:

• “...all the emotions around money and how scary it is... it just feels awful.” (Gretchen, 12:36)
• “Freezing your credit, not just putting a fraud alert... but actually freezing your accounts with all three of the major credit bureaus is something you should do now.” (Jean, 15:38)

Timestamps:
09:41 – 16:00: Detailed breakdown of the situation, practical action steps, and empathy for the emotional toll.

4. Pay Disparities & How to Ask for a Raise

Listener Question:

A public school administrator learns a newly hired colleague with less experience makes $20,000 more, despite them having similar roles and reporting lines. She seeks advice and even a script for addressing this discrepancy, noting her own discomfort with confrontation.

Key Advice:

• Lori Gottlieb & Gretchen Rubin: Both recommend a face-to-face meeting, not email.
  • Frame the conversation around curiosity and seeking understanding, not accusation or anger.
  • “It's very tempting to go in and be angry... but when people are on the defensive, they tend to want to defend their positions and argue why they're right and you really want them to see that a mistake has been made and needs to be fixed.” (Lori, 21:11)
  • Tone should be firm but not apologetic—don't act like you're asking a favor; you are clarifying a potential error.
• Jean Chatzky:
  • "She expects to get an answer, but she's expecting to at least be brought up to the same level. And I think it's okay to be clear about that." (Jean, 22:35)
  • Cautions about possible outcomes (systemic error vs. individual error), and recommends gathering as much information as possible (e.g., salary tier data of colleagues).
  • Advises starting with one's direct supervisor before escalating to HR or higher administration.
• On Transparency:
  • The hosts praise colleagues being open about their salaries—citing it as key to challenging inequity—and note generational differences in willingness to discuss pay.
  • "People just don't do it. But younger women do it. My daughter knows what all of her friends make." (Jean, 26:29)

Notable Quotes:

• "Use a tone of like, this doesn't make sense to me... I wanted to just talk it through with you." (Lori, 21:11)
• "This information came to light, and it just… it just doesn't add up to me." (Gretchen, 21:12)

Timestamps:
20:58 – 27:26: Analysis of pay discrepancy, advice on approach, and comments on salary transparency.

Memorable Moments & Timestamps

• Advice as a format: 06:02–06:24
  “Advice... you just want more and more and more.” (Gretchen)
• How to ask for pageant sponsorship: 07:48–09:09
  “Ask in a light-hearted way… not in an earnest way.” (Gretchen)
• Emotional impact of banking issues: 12:36–13:20
  “We feel extremely sheepish and reluctant to press our claim...” (Gretchen)
• How to approach a salary discrepancy: 21:11–21:12
  “Go in with a tone of curiosity and dispassion, but also expecting a real answer.” (Lori/Gretchen)
• Power of salary transparency: 26:29
  “My daughter knows what all of her friends make.” (Jean)

Summary Table of Main Listeners' Questions

| Time | Topic | Core Advice | |---------|---------------------------------------------------|----------------------------------------------| | 07:33 | Asking for pageant sponsorship | Be light-hearted, present as a fun opp. | | 09:41 | Sudden bank account closure | Investigate; freeze credit; advocate | | 20:58 | Addressing pay disparity in the workplace | Face-to-face convo, curious and firm tone |

Podcast Tone and Takeaways

The hosts offer not just practical guidance but a sense of solidarity and empathy, recognizing the emotional weight women often carry around money matters. They emphasize the value of transparency, community, and direct advocacy—reminding listeners that speaking up, even on taboo topics, is key to financial empowerment.