Podcast Summary: The Money with Katie Show

Episode Title: Why We Judge Women’s Spending, What We Hide, & What We’re Afraid to Admit
Host: Katie Gatti Tassin
Guest: Lindsey Stanberry (founding editor of Money Diaries, founder of The Purse)
Release Date: December 17, 2025

Episode Overview

This episode features a deeply personal and insightful conversation between Katie and Lindsey Stanberry, focusing on how women's spending is judged, what we hide about money, and what we're afraid to admit. They dive into the origins of the viral Money Diaries series, explore themes from anonymity to vulnerability, and reflect on cultural as well as economic shifts affecting women's financial lives. Katie and Lindsey also discuss the pressures, tradeoffs, and evolving definitions of financial success, both from their own lived experience and through the stories they've shared with and from others.

Key Discussion Points & Insights

1. Origin of Money Diaries and the Power of Financial Disclosure

• The Viral Start:
  Lindsey recounts the surprisingly scandalous and honest first Money Diary entry, which included a line item for cocaine—a moment that set an unsanitized, confessional tone for the series.
  • Quote (Lindsey):
    "There was a line item at the end of the date and it said, my date and I did cocaine, but he paid for it. And I don't know what it costs... That was the first one that set the tone." [04:16]
• Confessional Content:
  Katie and Lindsey discuss how authentic, raw admissions (even anonymously) create instant connections and community, highlighting the difference between sanitized social media and true disclosure.
  • Quote (Katie):
    "There's always that undertone of this has been sanitized... but it's still kind of shocking when you see someone admit to something like that." [05:05]

2. Why Do We Judge Women's Spending?

• Comment Section Reactions:
  Both discuss the often “judgmental” and intense reactions from readers, especially around certain topics (e.g., parental support, high earners, luxury spending).
  • Quote (Lindsey):
    “For better or worse, the Money Diary comment section was a place where people could go and sort of vent.” [07:33]
  • Examples:
    • Diaries from women with family assistance (e.g., high allowances, subsidized rent) sparked accusations of the stories being out of touch or misleading.
    • Judgement came from women as well, showing internalized societal expectations.
  • The deeper question: judgments often reflect internal uncertainties, jealousy, or relief (I’m not alone / I’m normal).

3. Anonymity as an Enabler for Vulnerability

• A Cloak for Honesty:
  Anonymity allows women to open up about their finances in a way that's often not possible in personal circles.
  • Quote (Lindsey):
    “People are desperate, desperate to talk about money… this is really like a cloak of anonymity.” [14:24]

4. Changing Trends in Women’s Financial Lives (2016–2025)

• Greater Financial Literacy:
  More participants now understand and optimize their financial basics (retirement accounts, savings), but emotional drivers and life phases (childcare, breadwinner status, job insecurity, FIRE movement) are more pronounced and nuanced.
  • Quote (Lindsey):
    “There is more financial fluency in the last five years... but it's the feelings behind it that become really interesting.” [18:48]
• Evolving Priorities:
  Decisions about spending are increasingly value-driven, especially around childcare (often more expensive than mortgages) and career flexibility.

5. On FIRE (Financial Independence, Retire Early) and Security

• Why FIRE Resonates:
  For many, especially women, FIRE signals a desire for insurance against job insecurity and burnout—less about leaving work and more about having options.
  • Quote (Katie):
    "I think that so quickly after I started working, I started to feel that sense of claustrophobia or insecurity, and it felt like a way out. It felt like an insurance policy." [28:50]
• Need for a Reframe:
  Lindsey argues for a new take—pausing work in short retirement bursts, especially for caregiving phases—rather than a single focus on early retirement.
  • Quote (Lindsey):
    "Fire drives me crazy... I almost feel like it could use a reframe—the retire often idea, take short retirements more frequently." [30:36]

6. Balancing Work, Family, and Self—(Im)possibility of "Having It All"

• Universal Struggle:
  Katie shares a listener’s message about the impossibility of keeping up with work, family, and self, sparking a frank talk on guilt, perfectionism, and letting go.
  • Quote (Lindsey):
    "Time is… is all of it. That's the thing." [24:35]
• Lowering Expectations and Avoiding Perfectionism:
  Both agree that sometimes you have to accept disappointing someone to be at peace with your own limits.
  • Quote (Katie):
    "Maybe we all, like, lower our expectations a little bit." [24:35]
• Advice vs. Disclosure:
  Lindsey stresses the value of sharing stories over prescribing advice, making room for readers to draw their own lessons.
  • Quote (Lindsey):
    “I really don't like giving advice... So I've sort of tried to reframe it more as, like you said, disclosure.” [28:23]

7. Entrepreneurship and the Trade-Offs of Creative Freedom

• Sacrificing Financial for Emotional Security:
  Lindsey opens up about leaving Fortune to found The Purse—gaining autonomy and creative fulfillment, but losing a steady paycheck and financial security (enabled by prior savings).
  • Quote (Lindsey):
    "Right now I'm sacrificing financial security for emotional security." [37:34]
• Redefining Success:
  Both Katie and Lindsey agree that after years of optimizing for money/status, autonomy/fulfillment turns out to hold more value—and that “optimize everything” thinking has limits.
  • Quote (Lindsey):
    “You can sort of optimize your way out of having a rich life.” [43:45]
  • Quote (Katie):
    “What if the things that like, take up the time and energy that don't make money are good actually?" [44:28]

8. Diversity in Money Stories & Limitations

• Who Gets to Tell Their Stories:
  There’s a lack of first-person stories from people in real poverty or living paycheck-to-paycheck—a function of audience, free time, and digital access, not lack of interest from editors.
  • Quote (Lindsey):
    "If you're like trying to figure out how to make ends meet, you don't have time to sit down and write a home economics entry." [51:39]
• Engaged Niches vs. Big Media:
  Subscription-funded, niche platforms (like The Purse or independent Substacks) allow for more genuine, focused storytelling, unconstrained by click-chasing incentives.

9. Self-Reflection: Katie’s Own Life Shift

• Facing Uncertainty:
  Katie shares her own fears and anticipation about leaving Morning Brew to run her own business—a future that promises autonomy but comes with unknowns.
  • Quote (Katie):
    "I think what feels risky is... I don't know how it's gonna feel... what if the things that make me unhappy are still there?" [53:44]
  • Lindsey offers support, emphasizing excitement, learning, and the value of pursuing challenging things.

Notable Quotes & Memorable Moments (with Timestamps)

• “[Money Diaries]...that was the first one that set the tone.” — Lindsey [04:16]
• “People are desperate, desperate to talk about money… this is really like a cloak of anonymity.” — Lindsey [14:24]
• “Advice vs. disclosure: I really don't like giving advice… So I've sort of tried to reframe it more as… disclosure.” — Lindsey [28:23]
• “You can sort of optimize your way out of having a rich life.” — Lindsey [43:45]
• "What if the things that like, take up the time and energy that don't make money are good actually?" — Katie [44:28]
• "I want to be here. I want to be squeezing every minute out of every day." — Lindsey [43:59]
• “Right now I’m sacrificing financial security for emotional security.” — Lindsey [37:34]

Timestamps for Key Segments

• 03:00 – Money Diaries’ origin, cocaine anecdote, impact of honesty
• 07:33 – Why we judge women’s spending, comment section analysis
• 09:58 – Viral Money Diary entries & public blowback
• 14:23 – The contradiction: afraid to talk about money, yet desperate to share
• 18:48 – Societal changes reflected in women’s finances
• 24:35 – The time vs. money struggle for parents
• 30:36 – FIRE movement, work insecurity, reframing retirement
• 37:34 – Entrepreneurship: trading security for autonomy/meaning
• 43:45 – On optimizing life vs. embracing messiness and fulfillment
• 44:28 – The value of hard, 'unproductive' things
• 51:39 – Why stories of poverty are underrepresented
• 53:43–55:55 – Katie’s anxieties and hopes for self-employment

Tone & Language

The conversation is honest, introspective, often vulnerable, and deeply empathetic. Katie and Lindsey balance humor and candor, speak plainly about anxieties and successes, and encourage reflection more than prescription. The tone remains inviting and relatable throughout, appealing to anyone interested in the “why” behind financial choices and the human realities that underpin them.

Takeaways for Listeners

• Financial conversations expose not just individual budgets, but the cultural baggage and emotions attached to money—especially for women.
• Authentic, unsanitized storytelling about money remains a radical, connective act.
• Everyone is searching for balance, autonomy, and meaning—money is a tool, but time and fulfillment are the ultimate currencies.
• There’s value in reflection, in doing hard things, and in embracing seasons of life where money isn’t the sole focus.
• If you’re feeling alone in your financial struggles or anxieties, these stories prove you are far from it.