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.

Nicole Giordano spends three months a year living in Europe, owns her home, and works thirty hours a week in a career she loves. She's the founder of Midlife Creative Studio and a long-time online entrepreneur who has spent the last decade designing a life around what actually matters to her, thoughtfully and strategically. In this episode, she sits down with me to break down how she actually affords the lifestyle.

Nicole and I walk through exactly what she spent on her recent three-month stay in Spain, how she and her partner built a life where either of them could afford it on their own, and her best travel hacks for stretching the budget. Plus, she shares the mindset shift that turned three months in Europe from a vacation fantasy into an annual ritual.

Nicole reveals her "enough" philosophy that lets her spend $12,000 on a kitchen renovation instead of $50,000, the mantra she uses to stay the course even when she’s tempted, and the one question she wants us all to ask ourselves to craft and afford our dream lives.

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.

Learn more about The Studio, Nicole’s community for midlifers who want more creative practice in their lives.

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.