256. Do It Scared: Raising Kids Who Aren’t Afraid to Explore with Raise Her Roaming

What happens when the trip you planned suddenly isn’t the trip you need anymore? Today we’re joined by Rachel and Margaux, the dynamic duo behind Raise Her Roaming, to talk about one of our favorite benefits of points and miles: the freedom to change your mind.We’re talking about traveling with kids, last-minute pivots, rebooking flights and hotels, unexpected family emergencies, and why we never stop checking our reservations even after everything is booked. From a child getting sick on a flight to swapping hotels in Japan and a trip to Santa Fe somehow turning into Portugal, Rachel and Margaux have some incredible stories of plans changing on the fly.But this conversation goes so much deeper than points and miles. We talk about the incredible value of traveling with our kids and what they learn when they see us navigate unfamiliar places, solve problems, change plans, and keep going when things feel uncomfortable. Sometimes we have to “do it scared,” and there’s something really powerful about teaching the next generation that they can do that too.This episode is such a good reminder that points and miles aren’t just about traveling for less. They give our families the flexibility to take more chances, experience more of the world together, and raise kids who know they’re capable of figuring things out—even when the plan completely falls apart.JOIN WONDERLAND BESTIES:Get bonus episodes, ad-free listening, timely points & miles updates, member Q&As, and more with our Wonderland Besties membership!FIND US ONLINE:Mary Ellen | JoannaWonderland on Points Facebook GroupOUR FAVORITE LINKS & DISCOUNTS:Some of the links below are affiliate or referral links, which means we may receive a commission or referral bonus when you use them. Thank you for supporting Wonderland on Points!Our Favorite Credit CardsRakuten — Mary Ellen (Get 5,000 Amex or Bilt Points)Rakuten — Joanna (Get 5,000 Amex or Bilt Points)Mary Ellen’s Fetch — Use code MARYELLENJoanna’s Fetch — Use code JOANNALYNNSeats.AeroCardPointers — Get Our Best PriceHalara — 10% off with code WONDERLANDComfrt — 15% offRove — Get 1,500 Free Miles