Preparing for travel. 5 Things Families Can Miss When Getting Ready to Worldschool or Travel Full-Time.
- Christina Dargatz
- 1 day ago
- 6 min read
There’s no doubt about it: the most paralyzing thing keeping families from traveling is fear. Fear of the unknown, fear of things not going to plan, fear of losing an income, and the flat-out fear of failing in the eyes of peers and family.
We are culturechalk.org. Our job isn’t just to host families at hubs; we’ve lived this reality. Over five years ago, we sold everything, left Canada, and set off for Guatemala—a country we had never been to and knew relatively little about.
With five children ranging from 11 years old down to just 7 months, we literally bushwhacked along the shores of a small village on Lake Atitlán. We knocked on doors until we found a place to rent for $200 a month. It came with a single bunk bed, so I travelled across the lake to a village famous for weaving grass mats (petates) so we'd have something to sleep on.
We lived like that for our first year while running a children’s program. We hosted beach cleanups with local neighbourhood kids, gathering week after week to pick up trash, wash it, sort it by colour, and turn it into art. We always finished with a big meal, one that eventually attracted a regular attendance of over 50 local children.
“How does this tie into the 5 things families miss when getting ready for full-time travel?”
It’s simple: we did things the hard way. We have a lot of insight, or rather, hindsight, on what we could have done better and what we would do differently if we could turn back the clock.
That early cleanup program eventually evolved into an ecosystem of local families and businesses that continue to support one another today. Now, Culture Chalk functions as a soft landing pad for other families looking to take the leap. We provide the guidance you need to step out of your comfort zone without breaking your back in the process.
Based on our journey, here are five major ways you can get your family prepared for travel.
1. Define Your Purpose and Timeline
For most families, the initial goal looks like “one year of travelling the world.” That is a great starting point for several reasons.
First, it gives your family, friends, and even yourselves an "out" if full-time globetrotting doesn’t pan out as expected. If the journey feels temporary, loved ones will have an easier time letting go, and goodbyes won’t feel so heavy. By framing this journey as an experiment, you eliminate the possibility of failure; you are simply testing different variables to observe the results.
When we started, our family sat down to discuss the core values that would guide our decision-making: generosity, respect, exploration, and commitment. We launched a blog called thegivingexperiment.org and cut all ties to equity and wealth as our bottom line metrics. Truly loving our neighbour as ourselves was at the heart of our experiment.
Everyone will have different reasons for travelling, but having a clear "WHY" is non-negotiable. Your purpose dictates your logistics.
If your goal is to de-stress and take a total break from work, you will look for curated, easy-to-navigate destinations and seamless, pre-booked experiences. We call this Re-Centering Travel.
If your purpose is seeking adrenaline and exploration, you’ll naturally drift toward unpolished itineraries, rugged hikes, and plenty of room for improvisation. This is Adventure Travel.
Then there is Community Travel. If you’re like us, where leaving was driven by a certain disillusionment with the pace of modern Western society, you’ll define your purpose as a search for deep community, aiming to restore your family's faith in humanity.
Point 1 Recap: Define why you want to leave, establish the core values that will serve as your compass, and use them to guide every single decision you make on the road.
2. Learn to Let Go of Control
In Western culture, control is the foundation of everything we do. We work hard to generate income and savings, pay into insurance policies, and meticulously curate schedules and budgets. We do all of this to avoid distress, or at the very least, to minimize it when the unexpected occurs.
Other cultures do not all function this way.
The biggest culture shock Western travellers face is the absolute lack of structure and the casual, dismissive nature toward perceived problems.
The bus didn’t arrive on time? No big deal.
The workshop teacher didn't show up? It’s fine, we’ll postpone.
Safety equipment is missing? That’s okay, we’ll just be careful.
No spare tire when you get a flat? “No problem, you can sit on the side of the road while I hitchhike to the nearest tire shop, buy a replacement, and come back to change it.”
You have to let go. Situations like these happen constantly when travelling in developing countries, and the only person who will be stressed or think it's "wrong" is you. Relax, keep a good book handy, maintain a flexible mindset, and embrace the chaos. Those unscripted moments always lead to the absolute best stories.
Point 2 Recap: Full-time travel requires fluidity and flexibility over rigidity. When your environment refuses to bend, your attitude must.
3. Understand That Small, Consistent Steps Get You There
People tend to think that launching a revolutionary lifestyle requires a massive, overnight transformation. The exact opposite is true. Making sudden, monumental changes in a single day is completely unsustainable. It only makes you look inconsistent, sporadic, and downright crazy to your peers when you declare, "I'm gonna do it!"…only to work yourself to exhaustion for two weeks and completely peter out.
The truth is, you don't need to broadcast your big plans and dreams to everyone in your social sphere.
A 180-degree change in direction is only sustainable when built on one or two small daily actions. One baby step a day, maintained over a year, is what actually gets you across the finish line. Make that phone call. Establish that contact. Empty out a single closet. Take one box to Goodwill. You cannot get a house ready to rent, sell, or housesit in a weekend; it takes months. If you approach the process with slow consideration, you will be rewarded.
We knew we were genuinely committed to this path when my wife and I started a nightly ritual. After a long, exhausting day, often when we were already tucked in, one of us would turn to the other and ask:
“What did we do to take a step toward Guatemala today?”
There were countless nights when we would haul ourselves back out of bed, get dressed, go down to the garage, and sort through just one box. We did this over and over and over again. It wasn’t glamorous, but it was the process that made our dream a reality.
Point 3 Recap: You’ll know you truly want this lifestyle when you are willing to put in the quiet, unglamorous daily work required to achieve it.
4. Balance Freedom with the Reality of Loneliness
Remember: you’re simply exchanging old challenges for new ones.
Full-time travel isn't always a bed of roses; it comes with serious trials. One of the biggest realities to accept is that this journey can be a lonely road at times. Both parents and children must frequently say goodbye to new friends, which can quickly drain morale and weigh heavily on the heart.
While hubs, pop-up communities, and expat gatherings are incredibly fun, the best way to build long-lasting relationships is to slow travel. Give your family enough time to truly integrate into local neighbourhoods. Establish real roots with actual neighbours: love them, and let yourself be loved by people who may live very differently than you do. These established, stationary communities are always welcoming places to return to, whereas building a lasting bond with other transient, nomadic families takes a massive amount of time and effort.
While planning trips to cross paths with families you’ve previously clicked with is incredibly special, departures bring a consistent reminder: ultimately, your family is on its own. We are all on our own distinct journeys, and another family's purpose for travel will rarely mirror yours. Furthermore, trying to force intense, compressed friendships on the road can be emotionally draining because time is limited and the fear of missing out (FOMO) is real.
Point 4 Recap: You will be alone a lot with just your immediate family. Lean into those core connections and find a shared focal point within the purpose of your travels. Outside friends are an amazing bonus, but remember: the road changes, people move on, but your family remains your constant.
5. Remember That You Represent Your People
Travellers can quickly forget this in a moment of frustration. When you're dealing with the lack of control mentioned in Point 2: a delayed flight, a missed bus, or a situation that throws your carefully planned week out the window, it's easy to snap.
But don't be a jerk.
Locals don’t always get to interact with people from your culture. If you are packing up your life because you’re disillusioned with your own society, then strive to be the exception you consider yourself to be, even in the tense moments. Fake it if you have to. Be kind, take a deep breath, do what you need to do, but don’t freak out on local staff because things aren’t going your way.
Remember the quiet patience of Point 3, apply it to the chaos, and you can gracefully navigate any travel hiccup.
Point 5 Recap: Travel can be stressful, but you need to realize that the unexpected is your new normal. This lifestyle is a conscious choice you are making for all the good that comes with it, and setbacks are just the cost of admission. Your kids are always watching and learning! You can either reinforce a negative stereotype or change people’s perceptions by representing your home country well.
-Owen D.
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