OMG, daddy/daughter Van-Life Adventure II with Olive was pure heartfelt magic. Two years ago, we explored the Big Island of Hawaii; this time, Maui.
Olive knows what I do for work at The Transformational Travel Council, but she doesn't recognize how much thought and care I put into designing the adventure, helping her embrace a challenge mindset, 'Traveling with H.E.A.R.T,' and preparing for the unknown.
In the prep phase, I asked her what her intention was, and she said, "to get a tan." So that was a primary focus, which was okay with me! I never thought I'd learn so much about UVA Rays and Index. There was one moment when the UV was perfect and we had to urgently find a beach to lie in the sun. And as any good dad does, I said, "Okay, find the closest one and LET'S GO!"
My intentions included just loving her, being present with her, having long conversations, disconnecting from our screens and social media, and connecting with ourselves, our bond, and nature. I also made a point to frame it all around the importance of self-esteem and self-worth in this current, crazy, and confusing world.
We talked about how healthy self-esteem involves not only liking yourself but also having an overall feeling that you are beautiful, bright, compassionate, and capable of overcoming obstacles and achieving goals.
We also talked about mean girls (unfortunately, it's a real thing) and how many of them may have lower self-esteem, and how to approach some of those uncomfortable dynamics, and help them feel better about themselves, when possible.
Between the negative impacts of social media, screen time, the rigors of school, life, and the chaos so many of us live in, it is so important for parents, grandparents, aunts and uncles, friends to take the younger generation on trips, not just any trip, but more intentional ones that increase awareness, give space and grace for reflection, help them feel alive, and connected to something bigger. You can find some great TTC Ally Members on our website who can help guide and coach you on such a precious adventure.
We did 4 nights in a Campervan and then finished with one night at the Four Seasons Hotels and Resorts for a little luxury (White Lotus Season 1 if you're wondering). I thought it was important to give her the contrast of experiences and help open her mind and her heart to all the people and places we visited, and expose her to different travel styles, budgets, and the value of diverse experiences.
My personal highlight was when I convinced her to snorkel instead of shop and when we were out there, we found a sea turtle and she spent minutes swimming around it, gazing, talking to her, and appreciating her ... She named her, "Tammy the Turtle."
Tammy, I am so grateful to you! Seeing Olive nurture her relationship with nature stokes her sense of stewardship and is exactly what makes me feel alive!
Enjoy the photos, I am happy to share our itinerary if anyone feels inspired.
Journey on,
Jake and Olive









This is so beautiful!!! I gotta admit, I my 16 year old self relates to “get a tan!” Did we understand UV waves yet? No. As a teen, I planned my mom & brother’s April trip to Hewaii. And what I worried about most was not having tan lines given my upcoming junior prom. And yet, this was an experience that changed my mindset. What a great trip you had!!