EP74 | EDUCATING KIDS ON THE ROAD: What Should You Do About School?

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Episode Description:  

Many of us in the traveling and outdoor adventure community currently parenting or considering becoming parents wonder about this pivotal question:  Can I take my kids out of school to join me on an epic adventure?

To help find the answers, the team at XOVERLAND has brought together three guests to serve as a panel of experts who can share their experiences and know-how when it comes to taking your kid out of a conventional school setting so they can hit the road with you and head out on a great adventure. 

After all, isn’t an overlanding journey a great opportunity to learn? New places, perspectives, cultures, experiences, skills, and knowledge await the traveling adventurer, so why not share that with our children? 

Our first guest is global overland traveler, XOVERLAND Co-Founder and COO, Rachelle Croft. A mother of three boys, Rachelle has experienced the evolution of seeing her and husband, Clay Croft’s, children go from toddlers to world travelers themselves. The Croft boys have accompanied their parents to Alaska, Scandinavia, and now Africa–all while remaining enrolled in their local public school system. We talk to Rachelle to learn more about how to work with your child’s school to take them on massive adventures that may last weeks or even months.

Our second guest, Christine Dehaven of Family.Overland.Adventure, along with her husband Evan DeHaven, has taken her two boys on a three-year full-time overlanding adventure. Taking place at the start of the COVID-19 pandemic, the DeHavens opted for remote learning to keep their kids enrolled in classes and on the path toward a diploma. Christine explains what this option looks like for travelers and how she has refined the approach to suit the personalities and learning styles of her boys.

Finally, we feature Brittany Highland of Hourless Life. Brittany and husband, Eric, have been full-time overlanding since 2014. In 2016, their son, Caspian, was “born to the road” as Brittany describes it. Giving birth in an L.A. hospital, hours later Brittany was back in the family Jeep with Eric and heading toward Mexico to continue on their epic overlanding adventure. Brittany has been teaching Caspian on the road ever since using a unique method of learning known as “Unschooling.” She and Eric plan on continuing along their journey while Caspian grows up and completes the work necessary for his high school diploma.

If this is a topic you’ve been curious about, please join us for this unprecedented conversation. We hope that by the time you wrap up listening to this episode, you will have both the knowledge and confidence to go after your most ambitious traveling and adventure dreams without being hamstrung by “school”!


Part 1 (0:40-4:21) Episode Intro:  Leah and Jimmy introduce this special episode about educating your kids while traveling and going on adventures. Whether you’re heading out for an extended weekend of camping and recreation or setting out on a full-time overlanding adventure around the world, this conversation will help you answer the big questions when it comes to schooling and your kids. Jimmy and Leah explain the focus of the episode and share some details about our chosen guests.

Part 2 (4:21-9:59) We Welcome XOVERLAND’s Rachelle Croft to Discuss Taking Your Kids Out of School for Big Adventures:  The mother of three boys enrolled in the local public school system, Rachelle has had lots of experience working with her local public school district to figure out how to take her kids on XOVERLAND’s epic global adventures. Leah sits down with Rachelle to find out how she does it. In this part of the conversation, Rachelle shares her philosophy when it comes to taking her kids out of school to travel.

Part 3 (10:00-17:26) How do you complete homework and assignments while traveling and how do you communicate with your school and teachers?  Leah asks what it looks like for Rachelle’s boys to be completing schoolwork while traveling so they don’t fall behind. Rachelle shares her answer, noting familiar issues to this task and how she and her kids have addressed them. Rachelle further explains her effective communication strategies to gain the cooperation of their kids’ school and teachers and support for the Croft family’s travels.

Part 4 (17:27-22:42) What about missing out on the social experiences of school like dances, sports, and other significant events? Leah wonders whether missing school has ever been a problem for the Croft boys socially when it comes to missing things like games, dances, and other significant events. Rachelle explains how she and husband, Clay, addressed these concerns by helping their boys develop more agency and independence when it comes to making their own decisions.

Part 5 (22:43-28:40) Rachelle’s Philosophy of “and” as Opposed to “or”:  Rachelle shares her philosophy around the use of the word “and” to deconstruct typical “either-or” black-and-white approaches to thinking. Hear her explain how powerful and helpful the use of the word “and” can be when figuring out one’s approach to life and the experiences we chase within it.

Part 6 (28:41-36:35) We welcome our 2nd Guest, Christine DeHaven, of Family.Overland.Adventure on to the podcast to discuss remote learning for kids while full-time traveling:  Christine and husband, Evan, DeHaven, left the fast lane of L.A. during the time Covid was in full-force to pursue a life of full-time overlanding with their young two sons (4th & 6th Grade). Christine shares how she set up a mobile remote-learning platform out of their restored Ford Bronco and the challenges of teaching her kids on the road.

Part 7 (36:35-41:30) Remote Learning Limitations:  Can you take your kids to Baja? It’s one thing to travel to Baja as a childless couple in your twenties with plans to go overlanding and camp on remote beaches; it’s another to take your school-age kids with you with a requirement to keep them remotely enrolled in a charter school. Christine explains what it’s like to teach your kids via a remote learning platform in Baja.

Part 8 (41:30-47:35) What’s it like to go from remote learning to being back to school in person? Christian explains what the transition looked like for her kids to go from a remote learning platform as a family of overlanders on the road for three years to being back to school in person.

Part 9 (47:36-54:57) Utilizing Starlink and Hiring Tutors for Your Kids Schooling While Overlanding: Are you prepared to teach your child how to read? Do algebra? What about learning to write well and learning chemistry? Enter the private tutor! Christine shares how she and her husband were able to utilize SpaceX’s Starlink system to hire and work with tutors to assist them in teaching their kids the more difficult subjects.

Part 10 (54:58-1:01:35) What is “World Schooling”? What is “Unschooling”? Our third and final guest on this episode, Brittany Highland of @Hourlesslife, has the answers!  Brittany and her husband, Eric, have been overlanding full-time for over ten years. (Follow them on all socials @hourlesslife and on their website:  hourlesslife.com) Their son, Caspian, was “born to the road” as Brittany puts it, and has never known anything else in his six years of life but overland travel. How does he keep up with school? Brittany has your answers!

Part 11 (1:01:36-1:05:04) Overcoming Common Fears When It Comes to Homeschooling and Teaching Your Kids While Traveling: Brittany and Jimmy look at the parallels between homeschooling and teaching your kids while on the road traveling. Brittany examines common objections to her “Unschooling” approach and ways of pivoting to incorporate a more structured approach to learning. 

Part 12 (1:05:05-1:15:03) Is homeschooling legal? Taking into account a global perspective and a global audience, Brittany examines the legalities of homeschooling and teaching your kids on the road and explains how to ensure your child will be able to obtain a valid diploma upon completing his or her K-12 coursework. 

Part 13 (1:15:04-1:15:03) What are the Benefits of Teaching Your Kids While Traveling? Brittany shares how, in her experience, teaching her son while overland traveling has inspired a love of learning in him along with the skills he needs to continue learning throughout his life. She also explains the many less tangible aspects of learning while engaged in overland travel, like communication and critical thinking skills along with social skills and discovering new languages and cultures.

Part 14 (1:15:04-1:23:23) What are the Benefits of Teaching Your Kids While Traveling? Brittany shares how in her experience, teaching her son while overland traveling has inspired a love of learning in him along with the skills he needs to continue learning throughout his life. She also explains the many less tangible aspects of learning while engaged in overland travel, like communication and critical thinking skills along with social skills and discovering new languages and cultures.

Part 15 (1:23:24-1:31:03) What have been the outcomes of Brittany’s approach to Teaching? Brittany has been teaching her son, Caspian, for six years while full-time overlanding. What are the results? How is her “Unschooling” approach working? What have been her greatest challenges so far? Where is he thriving and where is he struggling? Brittany shares the details of Caspian’s accomplishments and obstacles as a learner so far.

Part 16 (1:31:03-1:36:27) Will my kid get accepted into college if we do “school” while overlanding? Brittany says that the biggest objection she hears to “Unschooling” and to homeschooling in general, whether you be full-time traveling or living in a conventional homelife environment is the fear that your child will not be admitted into universities and colleges. Brittany explains why this fear is unwarranted and how you can address these concerns as a homeschooling/traveling parent.

  • Reach out to Brittany with all of your questions and concerns about educating and schooling your child while traveling overland at her website:  Hourlesslife.com 

Part 17 (1:36:28-End) Outro and Reflection:  Leah & Jimmy reflect on the episode and their respective conversations with our guests, sharing their thoughts, insights, and what they’ve learned.

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