The Holidays, Transitions, and Giving Ourselves Permission in Vanlife

In our last Adventure Together call, we set out to talk about the holidays in vanlife — but what unfolded was something deeper.

We found ourselves talking about transitions — retirement, loss, empty nests, moving, selling homes, or simply closing one chapter and beginning another.

Vanlife, in many ways, is a vehicle for transition. It gives us the ability to change our surroundings, step into new environments, and open ourselves to fresh experiences, routines, and traditions. Sometimes that’s freeing. Sometimes it stirs up grief for what we’ve left behind — or what has left us without our choosing.

The holidays can amplify those feelings. They often bring a swirl of shoulds — how we “should” celebrate, what family “should” look like, or how we “should” feel. But in truth, there’s no one right way. Whether your circle includes work family, chosen family, bio family, or no family at all — the holidays are yours to shape.

Our group shared beautiful new traditions:
• Mac and cheese from Chick-fil-A
• One-pot meals cooked on the road
• Heading to Baja or spending time with friends

Some of the best holidays are the ones spent on the road — simple, nourishing, and different.

And yes, sometimes loneliness surfaces. That’s part of the human experience too. You might embrace it, or shift your plans. Maybe you take yourself on a hike. Maybe you spend a quiet afternoon in the library — surrounded by people, yet with no pressure to speak.

For those newly retired or stepping into vanlife, it’s easy to think we “should” feel excited by all the freedom. But an unstructured schedule can feel disorienting after years of routine. Maybe you feel like you should be exploring, meeting new people, or doing something “productive.” Yet sometimes all you want is to crawl into your van with a blanket and your favorite game.

And that’s okay.

Doing something just for yourself isn’t selfish — it’s self-care.
Take the expectations off your plate. Be patient with yourself. Everyone’s timeline is different.

Holiday or no holiday, this is your journey.


We ended our conversation with these words from Michell C. Clark’s Eyes on the Road:

“Keep living. Keep healing. Keep pouring into yourself — not only for yourself, but also for the people who need the version of yourself that you’re growing into. You are needed. You are necessary.”


Adventure In,


Amy & Marcy

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The Emotional Side of Vanlife: Fear, Loneliness, Excitement, and Everything in Between