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When people imagine full-time travel, they often focus on destinations, vehicles, or how they’ll fund it. Those things matter, but they’re rarely where plans succeed or fail.
If we were starting again, the questions we’d ask ourselves wouldn’t be about where to go first or what setup to choose. They’d be about sustainability, trade-offs, and how this life would actually work once the novelty wore off.
These are the kinds of questions that only really surface after you’ve been living this way for a while.
If you’re thinking about full-time travel or nomadic life, this post walks through the questions we’d now ask ourselves before starting again, based on years of living on the road.
It covers sustainability, money, decision-making, and the trade-offs that matter once the initial excitement wears off.
This isn’t a checklist or a blueprint; it’s a way to think more clearly before making big, hard-to-reverse decisions.
What are we trying to change, and what are we trying to keep?
This sounds obvious, but it’s one of the most commonly skipped steps.
Are you trying to escape a job, a routine, a location, or a pace of life? And just as importantly, what do you want to keep: stability, relationships, certain comforts, a sense of progress?
Full-time travel tends to amplify whatever is already present. If you don’t know what you’re moving away from and what you’re trying to protect, it’s very easy to design a life that solves one problem and creates three others.
How do we want our days to feel, not just our travels to look?
Most people plan around movement. Fewer plan around ordinary days.
How much time do you actually want to spend driving, navigating, fixing things, or planning the next step? How much routine do you need to feel settled rather than restless? How do you recharge when everything around you keeps changing?
These aren’t abstract questions. They shape decisions about pace, locations, vehicle choice, accommodation, and how long this lifestyle remains enjoyable rather than draining.
What does “enough money” actually mean for us?
A lot of plans collapse because “financial freedom” stays vague.
Are you trying to minimise spending, maintain a certain standard of living, or buy yourself flexibility and time? Do you want income that’s predictable, or are you comfortable with variability? How much uncertainty can you tolerate before it starts to affect how you travel?
Without clear answers here, it’s easy to either overspend early on or undercut your own sense of security.
What are we assuming will be easy that probably won’t be?
Every plan contains blind spots.
Sometimes it’s underestimating how tiring constant decision-making can be. Sometimes it’s assuming you’ll work more easily on the road than you actually do. Sometimes it’s believing that a particular vehicle or setup will remove friction, when in reality it just changes the type of friction you deal with.
Surfacing assumptions early doesn’t make plans pessimistic. It makes them more robust.
How reversible are the decisions we’re making?
This is a big one.
Some choices are easy to change later. Others quietly lock you in for years.
Buying a vehicle, committing to a build, selling property, or relying on a single income stream can all be hard to undo once you’re in motion. Knowing which decisions carry the most inertia helps you slow down where it matters and stay flexible where you can.
Looking back, some decisions we thought were temporary ended up shaping years of travel. Changing them later was possible, but far more costly and disruptive than we’d expected at the outset. It’s why we later wrote about what to sense-check before making irreversible full-time travel decisions.
What would make us stop, slow down, or change direction?
Most people plan how to start. Fewer plan how to adapt.
What would tell you that this lifestyle needs adjusting? Burnout, financial pressure, loss of enjoyment, relationship strain? And what would you do if that happened?
Having exit ramps doesn’t mean you expect failure. It means you’ve thought about sustainability beyond the first year.
Are we designing our version of this life, or copying someone else’s?
It’s very easy to borrow someone else’s setup, route, or income model and assume it will translate.
But circumstances, energy levels, responsibilities, and priorities differ far more than social media suggests. The more closely you copy someone else’s version of nomadic life, the less likely it is to fit comfortably.
The real work is in adapting ideas to your own constraints and preferences.
Why these questions matter
None of these questions have universal answers. What works brilliantly for one person can feel completely wrong for another.
But taking the time to work through them properly often reveals where plans need adjusting before big, hard-to-reverse decisions are made.
It’s also where a lot of people realise they don’t need more information. They need clearer thinking.
If you’re at this stage
We now offer private, one-to-one strategy sessions built around these kinds of questions.
They’re designed for people who want to talk things through properly, sense-check plans, and think realistically about what would work for them, based on lived experience rather than templates or hype.
If that feels useful, you can find more details and book a strategy session with us.
