When we sent out a listener survey last fall, one topic seemed to be on everyone’s minds: investing. So many of you told us you don’t feel ready to invest yet.

We relate to this deeply. Even after years of writing about investing professionally, talking to experts, and researching the topic, we still felt that hesitation ourselves. We kept setting what we jokingly call “procrastination goals” — telling ourselves we’d start investing after we saved a little more, paid off one more thing, or learned just a little bit more.

In this episode, we unpack what people often mean when they say “I’m not ready to invest yet.” We walk through the hidden beliefs that keep many of us stuck in that in-between phase — and the signs you might actually be more ready to invest than you think. Finally, we talk about how to overcome the “I’m just not ready” hurdle once and for all. 

If investing has been floating around in the back of your brain for months (or years), this conversation is for you.

Episode Timestamps

• [00:00] The surprisingly common feeling of “I’m not ready to invest” — even among people who know a lot about money
• [03:00] “I don’t have enough money to invest” — when competing financial goals make everything feel tight
• [04:00] When inconsistent income makes investing feel impossible (even though it doesn’t have to be)
• [06:00] When traditional finance advice feels like it wasn’t made for people like you
• [08:00] Why investing feels scary — especially if your first exposure was 2008 crash stories or crypto chaos
• [10:00] The “I need to learn more first” trap (aka procrastinating perfectionism)
• [13:00] The sneaky procrastination mindset: “I still have plenty of time”
• [15:00] Signs you might actually be ready to invest: curiosity, extra money sometimes, and no high-interest debt
• [17:30] The biggest signal of readiness: wanting more freedom in your future
• [18:00] The one thing that actually makes people feel ready to invest — and our live workshop for getting started

Resources:

• Register for our Investing Before You’re Ready Workshop
• Book: The Perfectionist’s Guide to Losing Control by Katherine Morgan Schafler

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This week, we’re talking about the emotional and behavioral side of money with money coach Michelle Malawer. We explore what money coaching actually looks like, how it differs from working with a financial advisor, and why changing your finances often starts with understanding your patterns — not just your numbers.

We also talk about the beliefs and challenges Michelle frequently sees with women around money, from debt shame to undercharging to feeling stuck. Plus, we dig into a surprisingly powerful idea: imagination as a money skill. Once we’re not just trying to survive financially, we can start asking what we actually want our lives to feel like — and how our money can support that.

Episode Timestamps

[02:00] The key differences between money coaches and financial advisors — and when you might want to hire each
[03:00] A real-life example of money coaching in action
[06:00] Common problems people (especially women) bring to money coaching
[08:00] What it means to “taste test” joy and pleasure with spending
[11:00] What’s actually behind feeling stuck with money
[13:00] Why emotions often come before numbers in coaching
[16:00] The surprising insights clients discover about themselves
[17:00] Why fostering your sense of imagination is an underrated money skill
[25:00] Money beliefs that show up often for women
[29:00] Michelle’s experience working with financial therapist

Resources:

• Connect with Michelle on LinkedIn
• Join Michelle’s free money book club for women
• Get Ramit Sethi’s I Will Teach You To Be Rich: The Journal

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Today we’re joined by Sarah Turner — the mentor who brought us together and helped shape the way we think about building businesses, earning more, and how money shows up in our lives.

In this episode, we talk about what it actually looks like to live authentically (especially when “bloom where you’re planted” feels more like rotting in the wrong soil), plus how Sarah’s money story evolved (and how it didn’t) after her income exploded. She explains how and why the old stuff can still show up, even when the numbers change.

If you’ve ever felt guilt about wanting ease, gotten caught in lifestyle creep pressure, or found yourself avoiding your bank account because it spikes your nervous system, Sarah’s been there too — and she’s got wisdom to share. 

Episode Timestamps

• [00:00] Meet Sarah Turner — mentor, entrepreneur, and the woman who brought Cassidy and Emily together
• [03:00] What it looks like to live authentically (and why “bloom where you’re planted” doesn’t work for everyone)
• [05:00] How money changed for Sarah when she went from earning pennies at content mills to building an 8-figure business
• [08:00] Stepping back from work, shifting identities, and the emotions that come up when your partner becomes the breadwinner
• [12:00] A debate about “manufacturing scarcity,” and why Sarah refuses to use stress as a spending strategy
• [15:00] The limiting beliefs that kept money tied to morality, greed, and gender expectations
• [17:00] Defining mindset work in plain language, including what helped Sarah most
• [22:00] Growing up with a frugal financial advisor dad, and the confusing messages that can create
• [31:00] How to build “proof” when you feel overwhelmed, plus the idea of doing money admin with friends
• [39:00] Lifestyle creep, big mortgages, and why feeling calm matters more than looking successful
• [46:00] Finding your values through patterns, discomfort, and a look at what you’re actually spending

Resources:

• Become a TFG Insider 
• Sarah’s website
• Sarah’s book: Bet on Yourself 
• One of Sarah’s favorite books: The Slight Edge by Jeff Olson
  
  

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We love travel — but we do not love unexpected airport chaos.

On a recent work trip to Mexico, we each faced major delays. One of us was marked a no-show while physically inside the airport because we couldn’t get a boarding pass. The other experienced a domino effect — a missing gate agent, de-icing delays, a missed connection, a four-hour crew delay, and a mechanical issue that led to an overnight stay.

Because these disruptions felt largely outside of our control — and, to some extent, within the airline’s — we decided to advocate for ourselves. We requested cash refunds instead of flight credits, submitted reimbursement claims for meals and hotels, explored credit card trip delay protections, and even filed a DOT complaint.

Some of it worked. Some of it didn’t. We’re breaking it all down so you can feel more prepared if this ever happens to you.

Episode Timestamps:

• [03:00] Cassidy’s travel mishap: protests, road closures, and arriving late to a delayed international flight 
• [07:00] Rebooking, overnight hotel, and initial reimbursement request — and the first denial
• [09:00] Follow-up, second denial, and next steps (escalation and credit card coverage)
• [12:00] Emily’s travel mishap: missing gate agent, de-icing delays, and a missed connection
• [14:00] Emily’s backup plan: buying a last-minute ticket, four-hour crew delay, and mechanical issues
• [18:00] Refund strategy: requesting cash instead of flight credit and submitting expense receipts
• [21:00] A $600 airport hotel surprise, credit card dispute, and goodwill compensation request
• [27:00] Our biggest takeaways: knowing your rights, using the DOT dashboard, credit card protections, and documenting everything

Resources:

• Department of Transportation (DOT) Airline Customer Service Dashboard 
• Financial Feminist episode featuring former Transportation Secretary Pete Buttigieg
• How to Win at Travel by Brian Kelly
• Your credit card’s trip delay / travel disruption coverage (check your card’s Guide to Benefits)

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If Valentine’s Day has ever made you feel pressured, behind, or annoyed at how expensive it all seems — it’s not just you. In this episode, we’re unpacking how Valentine’s Day became a multi-billion-dollar industry, why it can feel so loaded emotionally (and financially), and how to opt out of overconsumption without opting out of joy.

We share the surprising history of Valentine’s Day, the real data behind how much people spend, and how social media fuels comparison spirals. Then we get personal — talking through our very different, very intentional approaches to the holiday, whether that looks like a cozy homemade dinner, a box of chocolates we bought ourselves, or planning something meaningful with friends.

This conversation is for anyone who wants Valentine’s Day to feel more aligned — with your values, your budget, and the way you actually experience love. Partnered, single, or somewhere in between, you deserve a version of this holiday that feels good.

Episode Timestamps

[00:00] Why Valentine’s Day feels so commercial — and why that’s not new
[02:00] Social media, comparison spirals, and performance pressure
[03:30] How much Americans actually spend on Valentine’s Day
[06:00] Emily’s low-key, at-home Valentine’s Day tradition
[07:00] Cassidy’s evolving approach — from compromise to self-celebration
[09:00] Making holidays special when no one else does it for you
[14:00] Low-consumption Valentine’s ideas from real people
[20:00] Wallet-friendly and eco-friendly ways to celebrate
[24:00] A simple reflection exercise to redesign Valentine’s Day for you

Resources:

• National Retail Federation Valentine’s Day spending survey
• Substack post on eco-friendly and wallet-friendly Valentine’s Day ideas
• Reflection questions shared in this episode:
  
  
  • What actually makes me feel loved?
  • What kind of Valentine’s Day do I want, even if no one else sees it?
  • Where am I spending money out of expectation instead of meaning?
  • What’s one small thing that would help me feel more connected to my loved ones this Valentine’s Day?

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Parenthood has a way of turning even the most detailed budgeter into a “good enough and moving on” budgeter — and honestly, that’s not a personal failure. It’s reality. In this episode, we’re joined by Taylor Nelson (accredited financial counselor and the voice behind The Financial Planner Substack) to talk about what the “cost of kids” actually looks like in real life — and why it’s not just diapers and strollers. 

We get into the biggest surprise costs (spoiler: it’s often the income hit more than the baby gear), how to think about childcare and leave before your baby arrives, and why the retirement vs. college savings debate is rarely as black-and-white as the internet makes it seem.

If you’ve ever thought, “I’ll have kids when I feel financially ready,” Taylor offers a grounding perspective: most people don’t feel perfectly ready — they just build flexibility, make the best decision they can, and keep going.

Episode Timestamps

• [03:00] How becoming a parent changes budgeting — less line-by-line, more “one-number” simplicity
• [07:00] The costs that surprise people most: Childcare, and the income hit from parental leave, or career pauses
• [12:00] When you think you’ll go back to work… then you meet your baby and everything shifts
• [14:00] What to do before baby arrives: Health insurance math, hospital indemnity insurance, and childcare waitlists
  [16:00] “Order of operations” for saving when kids are in the future (and money is tight)
• [20:00] How to prioritize retirement vs. college savings — and why it’s rarely all-or-nothing
• [25:00] The tax benefit people mess up: Dependent care FSA rules and childcare “under the table”
  [29:00] What parents who feel behind need to hear — kids want attention, not perfection
• [33:00] How Taylor talks about money with young kids (and why grocery store trips count)
• [37:00] One small step that makes everything easier: More cash savings for flexibility and peace of mind

Resources:

• Taylor’s website: tailoredfinancialplans.com
• Taylor’s Substack: The Financial Planner
  
  

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What if knowing your worth intellectually isn’t enough — and the real work has to happen in your body, your nervous system, and your everyday actions? In this episode, we’re joined by Claire Wasserman, founder of Ladies Get Paid, career coach, and writer who offers tactical advice and deep emotional insight in a way that feels grounding, honest, and actually doable.

This conversation felt like part therapy session, part masterclass in self-trust. Claire shares why so many of us still tie our value to our paycheck (even when we know better), how to identify the core money beliefs driving our anxiety, and why asking for more money builds self-advocacy far beyond your bank account.

We also talk candidly about shame — from food stamps to inner critics — and why transparency can be a powerful tool for healing, resilience, and reinvention. 

Confidence doesn’t start with earning more, and this episode explains why.

Episode timestamps

• [00:02:00] Why self-worth vs. net worth can’t be solved intellectually
• [00:03:00] The “downward arrow” exercise to uncover core money beliefs
• [00:06:00] The “joy antidote”: taking action to counter anxiety and self-doubt
• [00:08:00] Patterns Claire sees in how women hold themselves back with money
• [00:15:00] Why asking for more money builds self-advocacy (not just income)
• [00:22:00] How to frame raises and rate increases around business value
• [00:28:00] Shame, food stamps, and why transparency matters
• [00:38:00] Resilience, reinvention, and expanding your window of tolerance
• [00:40:00] Expanding your worth “inside and out” through practice
• [00:45:00] Rewiring the inner critic: “I’ll earn more when…”
  
  
  

Resources:

• Coachmeclaire.com (site for coaching + updates)
• Thepracticecards.com (daily 10-min practice tool)
• Work in Progress (Claire’s Substack)
• Instagram: @clairegetspaid and @ladiesgetpaid

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