Surviving Your First 100 Days on the Road
Search “vanlife,” “nomad,” or “travel” on any social platform and your feed will quickly flood with glowing golden-hour sprinter vans, usually inhabited by couples who match their “glamorous but just dusty enough” vibe. Yes, you can go see those priceless sun-soaked vistas, and yes, the sprinter vans will be there—but that’s just the tip of the iceberg when it comes to living full-time on the road.
Don’t get me wrong: if I could afford a sprinter van, I’d buy one in a heartbeat. I simply can’t. And if you’re reading this, chances are, you can’t either.
I’ve been living on the road for the past 100 days, and I want to show you the scrappier side of being a nomad—trust funds and sprinter vans optional.
Let’s be real. I know I’m not breaking new ground here—there’s a whole corner of the “campfluencer” community dedicated to pulling back the curtain… or, well, the bug screen… to show a more honest look at this lifestyle. I’m only here to add my voice to the campfire chat. Just don’t expect a curated day-in-the-life reel with a promo code for mushroom coffee in the description anytime soon.
That’s because I’m not here to sell you a lifestyle—I’m here to show you that with some zip ties, duct tape, and a little grit, you can build your own.
Step 1 — You Have to Go
The first step to becoming a nomad is incredibly simple. But just because something is simple doesn’t mean it’s easy, right?
You have to go.
You have to forgo the comfort of what feels familiar, throw caution to the wind, and do something that is inherently against human nature: leave everything you know behind.
As someone who planned my lifestyle change over the course of a few years, I know how easy it is to get stuck in planning mode.
Sure, you could leave tomorrow… but maybe you need just one more piece of gear. Or wait a few more weeks to save a little more cash. Or wait for cooler weather. Suddenly, it’s never the right time.
Sound familiar? Even if you’re not debating vanlife vs. apartment life, I bet there’s something else you’ve been on the fence about—quitting that job, leaving that toxic relationship, or joining that gym you drive past every day.
The truth is, there’s no perfect time. You just have to start.
In a past life, I worked for a giant (green) financial firm whose name will not be mentioned. One of their favorite corporate buzz phrases was “pace over perfection,” and as much as I grit my teeth saying this… they were right.
So take it from me—even if we’ve never met—there will never be a more perfect time than right now. So just go.
Step 2 — Lean on Your People
Okay, so you’ve made it on the road. Now what?
First, you’ve got to find a place to sleep (hopefully free). Then you’re probably going to want food. Then a shower.
Do that for a few days and suddenly you’re running low on gas, the first campsite is full, and the second one is an hour away. You’re tired, hangry, and mentally fried… and then something breaks.
Now you’re stressed, overwhelmed, and questioning your choices.
This is when Step 2 kicks in: lean on your people.
We all have someone in our lives who wants to see us succeed. Even if that person is only you—or someone you’ve lost—find ways to connect. Call home. Write postcards. Send voice memos.
If talking openly about your experience feels awkward, 1) get a journal, and 2) get better friends (kidding… kind of).
If you’ve heard people recommend journaling, it’s because it works. Start with: “How am I feeling today?” and let it flow.
Whether it’s journaling, a daily walk, or a scheduled call with someone you trust, don’t underestimate the power of rituals.
It won’t fix everything, but it’ll help you weather nearly any storm in those first 100 days.
Step 3 — Pack Less Than You Think
So, you’re settling in. You’ve proven you can survive, even thrive, on your own terms. You’ve got a rhythm, a routine, and a few good stories under your belt.
But everything is a mess.
Your car is cluttered. Your gear’s in disarray. And you probably packed way more than you need.
When you live on the road, every cubic inch matters.
I get it. We all have our non-negotiables. For me, it was gym shoes and button-downs. I wanted to hit the gym and take myself to dinner now and then.
We all bring things we think we’ll need “just in case.” But here’s my rule: if your ‘what if’ scenario doesn’t involve literal survival, leave it behind.
Sell it, donate it, or store it—but challenge yourself to strip back. You’ll be surprised how free you feel without all that weight.
And hey—if you make it past your first 100 days and still miss it? You’ll find a way to get it back.
Making it through your first 100 days is the threshold. You’ll face challenges you couldn’t have predicted and overcome them with a resilience you didn’t know you had.
None of us are here forever. We’re just visitors.
I hope this first edition of Tails from the Trails gives you the courage to start.
Because adventure? It’s for all of us.
If you liked this piece, follow my journey @4WDrew on all socials.
Want to go deeper? Book a free 1:1 consult and let’s talk about what’s holding you back.
Stay scrappy, friends.