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Vanlife Backstory: StrayWith.Me

Hi Friends! I’m Jessie, a 26-year-old writer traveling North America by van with her rowdy German Shepherd, Shasta. I share stories from my travels, advice, and my journey to more sustainable living!


I didn’t know I wasn’t happy until I was three years deep in an extremely unfulfilling superficial job. I sold expensive wine to the wealthy and had to bite my tongue more times than I liked. I met some interesting people, but most were disconnected from issues I was passionate about. I saved money to spend two months of the year traveling to countries I had dreamt of as a young girl only to go back to that soul-sucking job once again.

Being from California, I was exposed to travelers and transplants from all over the country. It was during this time, I learned I loved road trips. The hours of windshield time was relaxing and I started valuing taking the scenic route over the faster highways to get to my destination.

The hashtag “#vanlife” was on my radar for a couple of years but international travel was what led me to this nomadic lifestyle. Having only seen couples traveling together in vans, as a solo woman, I didn’t think I had it in me to travel full time on my own. If I hadn’t traveled alone internationally, I’m not sure I would have learned that I am capable of anything. After navigating the countless scams in India and jumping off bridges in New Zealand, you become pretty brave, I suppose.

Late 2018, I decided to go for it and started hunting for my van. My budget was more focused on saving for being unemployed on the road than on a $60k van build so I narrowed my search to older (and lower profile) RVs, low roof cargo vans, and eventually settled on conversion vans. In the late winter of 2019, I had talked to SO many people on craigslist and Facebook Marketplace but nothing ever panned out. I was hunting for about four months until I finally found my van, Hulk. He’s a 1999 Dodge 1500 conversion van and, although we’ve hit some road bumps (literal and figurative), he’s been the well-loved roof over my head for the past year.

This life is anything but easy. With two bodies to keep hydrated, I need to refill water every three to five days or so. Everything is always dirty. Always. Your house breaks often. You get lonely even if you are surrounded by people. You can’t keep plants alive, or your dog eats them. If you run out of toilet paper in the backcountry, you’re forced to get creative.

If you can’t handle these challenges (and I’ll be honest, there are many more I haven’t mentioned), you won’t be able to enjoy the endless joys of living in a moving home. The amount of sunsets and mountain views are magical and never ending. I’ve met the kindest people and created lifetime memories. My creativity is almost constantly flowing. My depression rarely rears its ugly head anymore. The joy I see in my dog’s face on our daily hikes cannot be replicated. I’ve slept in places people pay thousands of dollars for. Each person I’ve met who lives like this has found their own joy that can’t be taken away. I don’t think I’ve ever met happier or more friendly people.

This lifestyle has allowed me to get the canine companion I had been longing for, for three years, has pushed me out of my comfort zone, and taught me more things about myself than I thought possible. I don’t see an end to this kind of life any time soon and I am savoring each moment. I have made soul connections with people I would go to the ends of the earth for. And maybe we will!

Check out more stories and tips on sustainable living by visiting Jessie’s website, or follow her vanlife adventures on Instagram,

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