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November 12, 2025 19 mins

Show Notes: Worldschooling Q&A – Episode 10

Episode Title: Episode 10: Can I Work Remotely or Take On Temporary Jobs While Traveling?

Hosts: Astrid & Clint, creators of The Wandering Daughter

Episode Summary:

In this episode of Worldschooling Q&A, Astrid and Clint answer a top question for traveling families: Can I work remotely or take temporary jobs while worldschooling?

They share insights from four years of full-time travel, explaining how they balanced freelance work, full-time employment, and entrepreneurship while staying compliant with visa and tax regulations. The hosts also discuss digital nomad visas, ethical work practices abroad, and how to avoid harming local economies.

If you’re dreaming of funding your worldschooling adventures through remote or flexible work, this episode offers practical guidance and real-world advice for families like yours.

 

🎧 Ready to dive in?

 

👉 For full show notes, links to resources, and a breakdown of topics covered, visit:

https://thewanderingdaughter.com/episode-10-working-remotely-while-traveling

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
There are plenty of people that dosell their house and sell everything.
They do have money to go on.
We have friends that have done that.
And there are people that have businesseswho've earned a lot of money
over the years.
On a, the business.
But the business is kind of shuttered.
Or they sold. It.
They sold travel funds for sale.

(00:20):
And while those are all great waysto farm,
grow square, it's not as common to start
talking about getting remoteor taking temporary job or traveling.
It's probably the story.
This is Worldschool and Q&A.
I'm Astrid.
Creator of The Wandering Daughteras a traveling family.

(00:42):
We spent four years traveling full timeto over 18 countries and six continents.
Wherever we go, we try to learn
as much as we canabout the countries and cultures we visit.
While we didn't coined the term,we like to call this world's schooling.
Using the world as our classroom.
Each week, my husband Clint, and I willanswer one question about worldschooling

(01:04):
and share our experiencesof traveling the world with our kids.
Ready to get started?
Great. Let's dive in.
Okay, today's
question is can I work remotely
or take on temporary jobswhile traveling to support work schooling?

(01:29):
This is a very common question,if not the most common question.
Yeah. I think every world's going course.
Everything talks about this or addressesit in some way.
Before we start,I just want to acknowledge
we are not lawyers or accountantsor tax advisors.
So please take what we saylive with a grain of salt.

(01:53):
There is nuance to whatwe're going to talk about.
And there is a certain amount of riskdepending on how risk averse.
Yeah. You are.
So we're speakingfrom our own experiences.
But do not take this as any kind of,like, legal advice
or tax advice or immigration advice,you know.

(02:15):
And our our experience is pretty common
for a lot of digitalnomads and world scores to.
So that's,
just give you a little contextthere as well.
Yeah. Okay.
So I think this is a common question,partially because like, people
just want to be able to payfor travel, to pay for worlds.

(02:37):
And unless you have like hundredsof thousands of dollars
saved up or you sold your houseor something like that, there's not really
like you.
You need to be able to have a wayto sustainably fund your travels.
Yeah. And I guess it's a good point.
I mean, there are plenty of peoplethat do sell their house
and sell everything,and then they do have money to go on.

(03:00):
We have friends that have done that.
And there are people who have businesseswho've earned a lot of money
over the years.
On off of business.
But the business is kind of shuttered.
Or they sold. It or they sold it.
They travelusing the funds from that sale.
And while those are all great ways to fund
worldsgoing, it's not as common of a scenario.

(03:23):
And I think talking about working remoteor taking temporary jobs
while traveling isprobably the more common scenario, right?
And this is this is what we didwhen we were traveling full time
from 2018 to 2022.
We both worked remotelyand, did a combination,

(03:43):
like I did some freelance stuff and I
had, my travel website business.
And then you primarilyworked for a company
and then also had like,I think you did some freelance.
Yeah. That's, zero income. Yeah. Yeah. So,
yeah.

(04:03):
So we, we had multiple ways.
I think the biggest one,
to talk about.
Well, we can talk
we can talk about the employeeand self-employed thing in a second.
I think the biggest thing we need totackle is just
visas.
Like what? What's allowed?
What's not allowed?
Is there wiggle room?

(04:24):
What's the risk?
The short answer tothis is it's going to vastly vary
depending where you're goingand how long you're going for it.
Yeah.
And a lot of what we've noticed,
in some digital nomad circles,they're like, oh, don't worry about it.
Just do it under the table and blah blah,blah.
And like, as long as you're not, you know,

(04:48):
making waves, you'll be okay.
And we kind of
we do want to be cautiousabout things like that
because, you know, it's not just us.
It's traveling.We're traveling with our kids too.
So like, God forbidwe get deported or something like that.
Like we would not want that to happenfor us.
So we do want whenever we travel,we do pay attention to like

(05:12):
the visa rules, like the type of visathat we're getting and whether it's
allowed for us to earn incomewhile we're traveling under that visa.
So the challenge with that, though,having said that,
is a lot of times we do.
There is an ambiguitypurposely written into the visas.

(05:32):
And for example, visa,
a tourist visa to Mexico, for example,
basically says
that you are not allowed to hire
or work with local people
or have clientele that are locals.

(05:54):
Now, beyond that,
it leaves it kind of,a point of contention.
There will be plenty of people that say,
yeah, that means it gives us freeright to work, whatever we want.
And so long as we're working for USbased companies, for example, or us based,
there are plenty of people, though,that say no, it

(06:14):
clearly defines you cannot make moneywhile you're traveling.
Our stances,
we don't know the exactsof that kind of visa
and that in our experience, we havenormally just gone with the tourist visa.
In that case,
and worked.

(06:36):
And we only work for us based.
We earn income US based.
We do not
make money or have clientelethat are Mexico based in that example.
And so,
we generally have found
that there hasn't been an issue.
Now there's a couple variablesto that too.

(06:57):
We only we always stay under six months.
So usually it's a month to a few,
sometimes longer.
Six month is kind of the tipping point,I think, where a lot of governments,
including the US, will start to start tocrack down on tax and that kind of stuff.
We also have a Washington based addressthat is our

(07:21):
that's our constant home address.
That never changes. Yeah.
And so all of our taxes and everything
go through, Washington. Or.
Yeah. Or a US based, address.
I think if you were,
if you did want to do businessin the countries
that you're traveling to, for instance,if you wanted to stay longer.

(07:45):
There are it's it's not like
most countries.
It's not like
the only visa is that you can't work.
I mean, you can stillyou can look into, like,
what are the business piecesthat are allowed there or like long term
residence visas, there are going to bea probably a little bit more expensive.

(08:06):
They're also going to be more involvedin terms of like how to apply for things
some places require like sponsoror things like that.
So you really needto look at the visa rules.
And see what's allowable
in the particular visathat you're applying for.
And this is not a it's not like

(08:28):
this is a not talked about subject.
This is a constantly debated subject.
And that the proof is in all these digitalnomad visas that have sprung up
countries, a lot of local economies
recognize the potential valuefor digital nomads to be in their region.
They don't have to provide jobs,for example.

(08:50):
And they can they can, in theory,help boost the economy.
Yeah.
So there's been a lot of discussion,about digital nomadism in general.
And that's why I thinka lot of governments will generally
turn a blind eye to,
I say this again with alittle grain of salt, and this depends on
how risk averse you are, but they willgenerally turn a blind eye to that.

(09:14):
Case in point.
You go to Mexico
or Indonesia, for example,and there are tons of co-working spaces,
and lots of the co-workingspaces are filled with foreigners.
I can almost guarantee
90% of themdo not have some sort of working visa.
So again,

(09:35):
take it with a grain of saltlike there's risk involved in this.
Yeah.
So one thing you can do is you can
don't make a spectacle of yourself.
I mean, stay under the radar.
Do not tap into local economies.
That'susually where people get into huge trouble
when they try to create a businessthat is selling to local people,

(09:57):
whether it's in Indonesia,what's really popular is like spas
and like spas type of practicesor yoga types of practices.
Like, do not do that.
If even if you are catering to a, sayyou're a US based person,
you travel to Indonesiaand you are selling to US based customers.

(10:18):
Because that transaction
you're doing that transaction in Indonesiathat can throw a flag.
And they are Mexico, Indonesia,both and other
countries have been knownto make examples of people.
So yeah, it's it's one of those thingswhere you don't really
want to test those watersif you can avoid it.
Yeah.
So the other part is like, do you want towork for a company or be self-employed?

(10:44):
And as I mentioned at the beginningof the episode, we've done both,
and we still do both.
Like we have,
both have full time jobswith, companies based in the US.
And then we also are,
we have our own businesses.

(11:04):
We have the card game business,which is primarily like selling our.
I would consider thatlike an e-commerce business, since we're
mainly selling our productonline, on Amazon.
And then,
the other business that
I have is, The Wandering Daughter,which is,

(11:25):
a travel, you know, travelwebsite business.
Yeah. And,
I've made the majority of my income
while traveling by working as an employee.
I did make some money as a side business,
doing some freelance web development work.
The thing employs a great way to go.
A lot of people do this, I believe,and Tim Ferriss book Four Hour Workweek,

(11:50):
he's explicitly talks about, you know,ask your boss if you can work remote.
That's exactly what happened to us.
I just simply asked my my managerif I could go remote
for a few years and travel.
And that was granted.
And granted.
We both changed jobs during that period,as well, when we were initially traveling.

(12:10):
I think the key point with if you're goingto be an employee doing it,
I know there's this
trend or this thing that people do
that's essentially quiet travel or,
quiet vacationing or whatever they may,they call it now,
that's where you're essentially workingremote for a company

(12:31):
while traveling,but not telling your employer.
We do not advocate for that.
Yeah.
We really I mean, we really recommendbeing transparent with your
with your boss,at least with your manager, you know, like
there's one thing about, you know,
you don't really want to brag that.
Oh yeah. SoI'm working with that in Mexico this week.

(12:51):
Oh that I have that meetingsometimes. But,
you know,
your boss should knowwhere you're working from
just so that, like,
in case something happens,in case there's an emergency, that
you need to be contacted,
then they'll be able to know,
you know, you're not going toyou're not in your home,

(13:13):
your regular home.
You're somewhere else.
Yeah.
I think they also they want to knowif like, equipment gets stolen
or something like that.That's all critical stuff.
I think the other aspect too is,
they need to knowbecause they need to know on their end
if there's going to be tax implicationsor things that they're worried about.
And we havewe have experience with some companies

(13:34):
who are not comfortablewith us working remote,
because of potentiallike tax implications.
Yeah, yeah.
And then also like the trust aspect,you know, you part of
being an employee for a companyis having them be able to trust you.
And so that's a big thing. Yeah.

(13:55):
There was something we do you know,
I have also in the past,like taking on temporary jobs.
There's we did
teaching or not teaching, but,
do I did English tutoring,
for, Chinese like, language company.

(14:17):
And so that's kind ofsome people do that of like,
some kind of like tutoringor courses or things, and that allows for
some flexibility in your work hours and,and your schedule and location.
And then I've, I've done
jobs like temporary jobs with like,

(14:39):
like companies
doing, you know, a social media managementor something like that.
So, yeah, there's be open like there's,
there's places that you can find,
remote first jobs.
In the past I've used a website called
Flex Jobs where, you could find,you can, like, search up

(15:00):
like 100% remote hybrid,all sorts of different, industries.
They there's definitely jobs out therethat they hire.
They're okay with hiring remote workers.
Yeah.
And companies like Airbnb, for example,if you're if you're lucky enough
to be able to work in a company like that,they exclude is explicitly allow,

(15:25):
working from anywhere in the worldfor certain periods of time.
As long as you have manager approval.
So there are companies supporting it.
I know in the news there's a lot of remotejobs are disappearing.
And yes,the landscape is kind of evening out
a little bit since the pandemic, but,there's still plenty available.
Still plenty of companies
that are remote first or at least remoteis a big portion of their their business.

(15:47):
I think the other thing I want to talkabout with temporary jobs is that,
we've seen
this when we've travel,we've seen in the digital nomad community.
But, getting temporary jobsor doing things
that can have an ill effecton the local economy.
Yeah.

(16:08):
And I think that's somethingto be really cautious.
We're huge advocates for responsibleand ethical travel.
And I think if you're
potentially taking a job away, maybe it'seven just a volunteer opportunity.
Yeah.
If you're potentially taking a job awayfrom someone local,

(16:31):
that is both
not ethical in our eyes, but also, that'sthe kind of stuff that raises red flags
and potentially gets you reported,to immigration.
Yeah.
So just really be mindful,that the work that you're doing
while you're traveling is not,negatively impacting
the local economy in any way.

(16:52):
And that that's truewith even the digital nomad visas.
I mean, the zoom digitalnomad visas are meant that you are earning
income from outside the country and you'reyou're inputting money into the economy.
Yeah.
So you're not hurting the local economy.
If anything, the idea is to try to boostlocal economy.
Yeah, yeah. Anything else?

(17:13):
No, I think that's it.
I mean, we've covered a lot of good topicsrelated to like working remotely and.
Oh, I guess one thing to add, if you'regoing to be self-employed, think about,
where your
business will be located.
Because that's also going to impact,you know,

(17:33):
the taxes that you pay and stuff.
Our businessesare, are on paper based in the US.
And so we are paying like federal,
federal taxes, on those businesses.
And all the other potential feesand employment taxes and all that
that might come with it.
I think the only thing else I wanted toplug was we've mentioned her

(17:55):
multiple times, but, our friendLiz Queen actually
has a really exhaustive listof how I think over 100 different hours.
I think. It's like almost 200.
Almost 200, of ways you can earn incomewhile traveling full time.
Yeah.
And she's a great resourceto reach out to,
like it through some program or email,sign up or something.

(18:16):
I can check out, Trailblazing Families.
There's Facebook group.
And then she also has a website.
Okay, okay, okay.
Well, that's all for today.
Thank you for joining us
on this episode of Worldschooling Q&Awith Astrid and Clint.
Be sure to check out the show notesfor any links we mentioned in the episode,

(18:38):
and visit my website,
The Wandering Daughter.com, to dive deeperinto worldschooling and family travel.
If you like what you hear,
please consider supporting The WanderingDaughter on Patreon.
It really helps us outand keeps the show going.
You'll also get exclusiveperks like episode transcripts,
additional resources, accessto office hours with us, and more.
You can find us on Spotifyor the podcast app of your choice.

(19:00):
If you're listening to this on Spotify,you can tap the bell icon to get notified
when new episodes come out.
And if you like this episode,please give us a five star review.
It really helps new people find our show.
If you're watching this on YouTube, don'tforget to like
and subscribe and tap the bellicon to get notified of new episodes.
You can follow me on Instagram
at Wander Daughter or follow The WanderingDaughter on Facebook.

(19:24):
Links to these are also in the show notes.
If you have any worldschooling questionsyou'd like us to answer for future
episodes, feel free to throw themin the comments or send us a message
at The Wandering daughter.com/podcast.
Until next time, happy travels. Bye.
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