Stefanie O'Connell is an award-winning journalist and the author of The Ambition Penalty. She has run her own business for a decade, and is now doing it while raising a toddler in NYC. But this episode is a little different, because Stefanie isn't here to say she has it all figured out. She sits down with me to break down how she is affording a season where she deliberately stepped back from earning to write her book and be present for her daughter.

We walk through her whole money trajectory, from $450 a week on a Broadway tour to a business pulling in around $300,000 in revenue. Then the part most people never say out loud: how she set aside more than $100,000 as a runway, watched her revenue fall almost 90% last year, and has been spending down that cushion ever since. Plus the data behind the book, including the half-million-dollar lifetime cost of the motherhood penalty.

Stefanie also gets honest about the power dynamics inside households and her own marriage, what she hopes her daughter learns by watching how responsibility gets shared at home, and her reframe of money as seasons instead of a straight line. And of course, what she is working to afford next.

Download Ashley’s free “Get Paid What You’re Worth” negotiation guide (https://www.thefiscalfemme.com/get-paid).

Get Stefanie's book, The Ambition Penalty (https://www.hachettebookgroup.com/titles/stefanie-oconnell/the-ambition-penalty/9781541705210/).

Subscribe to Stefanie's newsletter, Too Ambitious, and follow her on Instagram @stefanieoconnell.

Check out Ashley’s Money Club (https://www.thefiscalfemme.com/money-club) to join a community of women unabashedly going after their money goals.

Take this quiz to get a personalized Wealth Building Blueprint (https://bit.ly/4v94g2C)

Rachel Lipson takes 12 to 15 trips a year with her family of four, her kids have visited 25 countries and they haven’t even finished elementary school, and she lives in one of the most expensive zip codes in the country. She’s the founder of The Point, a best-selling Substack and consulting business that teaches families how to travel using credit card points and the founder of Blue Balloon Songwriting for Small People, a 17-year-old music school for kids that now runs mostly without her. In this episode, she sits down with me to break down how she actually affords the lifestyle.

Rachel and I walk through how she redeemed over $143,000 in points last year, the specifics of her recent three-week family trip across Milan, Athens, and Malta, and the home-swapping strategy that has gotten her family into beautiful homes around the world for free. Plus, she shares her top three points strategies and the simple first step for anyone who feels overwhelmed by the points game.

Rachel reveals the times even she doesn't get the points game perfectly right, the multiple income streams that fund her family's life in Brooklyn, and the surprising childhood backstory that drives her family's travel obsession.

Get Ashley’s travel budget template (https://www.thefiscalfemme.com/travel-budget) where you can estimate trip costs, compare options and plan in advance so that all you have left to do is enjoy your trip, financially stress free.

Subscribe to Rachel’s substack (thepoint.substack.com). Get a Wallet Edit (https://thepointedit.com/wallet-edit-phone-session) for tips on how to leverage spending to earn points for travel!

Check out Ashley’s Money Club (https://www.thefiscalfemme.com/money-club) to join a community of women unabashedly going after their money goals.

Take this quiz to get a personalized Wealth Building Blueprint (https://bit.ly/4v94g2C)

Ashley Torres spends three months per year in a new country with her family, takes five other trips a year, salsas with her friends one to three times a week, and runs multiple businesses. She's been a full-time content creator for over 15 years, writes about her family’s travels on Substack, is the co-founder of LA Girl Dinner Club, and wants us all to live life to the fullest. In this episode, she breaks down how she actually affords the lifestyle.

Ashley walks through exactly what her recent three-month stay in Uruguay actually cost, the surprising income streams that offset the costs, and the trade-offs she makes that make it all work. Plus, she shares her salsa-at-10pm hack that fuels her energy and the worldview that drives her whole approach.

Ashley also reveals how she and her husband Andy navigated combining finances after years of keeping them separate, what she's teaching her daughter about money and gratitude, and where her clothes-and-decor budget actually goes.

Get Ashley’s travel budget template where you can estimate trip costs, compare options and plan in advance so that all you have left to do is enjoy your trip, financially stress free.

Connect with Ashley on Instagram at @everydaypursuits and her family travel Substack.

Check out Ashley’s Money Club to join a community of women unabashedly going after their money goals.

Take this quiz to get a personalized Wealth Building Blueprint.