Do you dream of spending your afternoons on the beach with your family? Or getting yourself and your family out of the rat race and enjoying life at a slower, more manageable pace?
So did we.
Before starting our journey as digital nomads in 2022, we were filled with doubts. We thought it was for singles in their twenties, not for married 30-year-olds.
We had established careers, a great apartment, and a great group of supportive friends and family. And we were expecting our first child!
Now, two years and one baby later, we can’t imagine living a different lifestyle.
Here, I’ll give you a step-by-step guide to everything we did (and some of our more memorable mistakes) in our four-year journey to freedom. This is a anecdotal step-by-step guide, the exact steps you and your family need to take may be similar or wildly different from how we did it!
Table Of Contents
A Word Of Warning
This blog post is long—it’s too long. But moving your entire family into a nomadic lifestyle is a huge decision that should not be taken lightly. You have to do thousands of things before heading off into the sunset—or to the beach—or the mountains!
That’s why I haven’t shortened this article. If you aren’t interested in personal anecdotes, insider tips, or stories about our journey, check out my Article on How To Become A Digital Nomad Family in a Year. That article has the same links but omitted the anecdotes and personal information.
Each step also has an additional blog article that goes into more detail. Transitioning into a nomadic lifestyle is just as complicated as doing anything else as a family, and we’re learning new tips, hacks, tricks, and mistakes we’ve made every day.
3 Years Before Becoming a Digital Nomad Family
You don’t have to follow our slow pace when making your lifestyle change, but I’ve listed everything we did in chronological order for clarity. You’ll probably notice our skillful procrastination – most tasks were completed in the final two months!
Becoming Digital Nomads: Making The Decision
Deciding to become a digital nomad is a big decision. Leaving everything and everyone you know behind and heading into the unknown is terrifying. For us, the discussions about changing our lives and escaping the 9-5 grind began years before we actually did it.
In 2019, we were living in the city of Hamburg, Germany.
At that time, neither one of us knew about digital nomadism. We just knew we weren’t happy with our lives in the city. It felt like we were stuck on a hamster wheel of work, chores, and more work.
It took a pandemic to show us how to work from home, and once the lockdown was lifted, we began to dream of a life filled with adventure, travel, and freedom.
We spent years discussing our hopes, ambitions, and dreams before plunging into a digital nomad lifestyle. It was worth it.
Step 1: Brainstorming
In 2021, we started talking to our social circle about our dreams of digital nomadism. This networking turned out to be the most critical step—after hearing about my dream of working from abroad, a family I babysat for offered me a position as a content creator for their AI start-up.
Now is a great time to make family and individual bucket lists.
These lists will help your family decide where to go next and keep the excitement levels up as you wade through the bureaucratic nonsense that comes with digital nomad family life.
Try to discuss the goals, hopes, and dreams your family has for their time as digital nomads. Now is the time to figure out how long you’d like to be digital nomads and where you’d like to travel. There are different kinds of nomads; some keep a home to return to, and others travel full-time. Some travel slowly, others switch their location every week or so. Now is a great time to figure out what country (or continent) you’d like to explore.
Decide on universal family goals before beginning the prep work to become a digital nomad family. Why do we want to transition into a nomadic lifestyle? Where would you like to go? How are we going to be able to afford this lifestyle?
2 Years Before Becoming A Digital Nomad Family
Step 2: Practice Run as a Digital Nomad Family
After endless discussions, we decided to go on a practice run. We flew to the Italian island of Lipari in October and lived there as digital nomads. If we hated it, we could return to our old lives with our tails between our legs, but at least we had tried out the nomadic lifestyle.
We loved it. We discovered a previously unknown love of slow travel, living our ordinary, daily lives in a new location, and adapting our routine to fit in with our new home.
We spent our time in Lipari cooking elaborate meals, going for long walks on the beach, and getting engaged!
Our practice run allowed us to test out all the solutions we use today to afford our lifestyle. We left our cat with family friends who still lovingly care for him today. We confirmed that we both wanted digital nomadism and made a shocking discovery.
My husband’s employer was not on board with him working abroad. They were fine with him working from home, but when he mentioned his home being in Italy, they demanded he return to Hamburg – but not to the office! After returning home to Hamburg, we hit the ground running and began researching solutions to this problem. Eventually, we settled on working as self-employed freelancers.
After you’ve decided to become a digital nomad family, try going on a practice run together. This allows you to test some of the solutions you will use in your new nomadic lives – before becoming technically homeless.
1 Year Before Becoming Digital Nomads
Step 3: Get Inspired (and Excited!)
Remember those goals and bucket lists you wrote? Well, now is the time for you to hang them up somewhere public in your home. Your lives are about to get very stressful. These next few steps are all about getting your family out of their daily grind and into the digital nomad life.
We created Excel Spreadsheets with our goals and countries we’d like to visit. I love a good research project, and these sheets gave us the perfect excuse to go on a research deep-dive. Our lists were a combination of inspiration, motivation, and cold, hard, facts. Here are some of the questions we asked ourselves:
- Visa Requirements
- Language Spoken
- Average Cost of Living
- Taxation Policy (Territorial or Not)
- Activities in the Region
- Hotels, Hostels, or VRBOs
- Experiences you’d like to have
Another way we got excited was by browsing NomadList, Reddit/DigitalNomad, and consuming hours of YouTube from other digital nomad families. If you need more inspiration, here’s our favorite digital nomad families list!
Keeping yourselves inspired and excited about the upcoming changes will help you conquer the challenges headed your way.
Step 4: Paying for Your Lives As A Digital Nomad Family
It doesn’t matter how you and your family are going to finance their trip, whether that be through savings, remote work, working while traveling, or applying for a nomadic job, you’re one year away from the big change.
Now is the time to start taking your career change seriously.
Work From Anywhere
We both had remote jobs before leaving home – we started working remotely in 2021 and left in 2022.
I recommend transitioning into remote work around a year before setting off into the world. This gives you time to build up a client base and trust before changing time zones.
For my husband and I, strong relationships with our employers and coworkers, and clients were essential. We were working 5 hours ahead of them, meaning we stopped working after their lunch break.
If you’re interested in remote career options, check out our blog that lists the best websites for careers for digital nomads – and freelancers!
Savings
Another way some families support themselves while traveling is through their savings. Even if you plan on working while traveling, it’s important to have enough money saved up for emergencies.
Our goal was enough money to last us a year – I recommend saving up at least enough money for emergency flights home, plus hotel stays. Saving this money was easier than we thought – we stopped eating out, stopped going to the movie theater, and invited our friends to our home for drinks instead of drinking at a bar.
We’ve met families who began traveling with far less, and far more than us in their bank accounts. Some families sell their homes and use that money to finance their travels, while others count on cheaper costs of living abroad to help them bolster their savings.
Housesitting
Rent/Accommodation remains our most significant expense while traveling—one creative way to save money while traveling is house-sitting. While you won’t be able to earn money by house-sitting, you should save hundreds, if not thousands, of dollars a month by not paying rent.
Our first month in Thailand was spent as housesitters on the island of Koh Tao. Through house-sitting, we’re able to dive into a local lifestyle, use a fully furnished kitchen, and sleep in someone else’s comfy bed. As an added bonus, we get to cuddle adorable animals while traveling!
We have yet to use our account on Trusted Housesitters, as our very destructive baby would probably demolish the lovely homes advertised there. For now, we find houses through Facebook Groups and by talking to our friends.
Work and Travel
Other families finance their lives by picking up odd jobs, or seasonal work, while traveling. My parents regaled my brother and I with stories about a friend’s cousin – this person lived with their husband in a van and travelled full-time, working as a crop-picker whenever they needed money.
Just be aware – while some countries like Australia and New Zealand have Work and Travel Visas, these rarely allow travelers dependants, meaning you can’t bring your kids with you. Some countries, including Australia, Fiji, and New Zealand, have a dramatic labor shortage in certain sectors. Qualified immigrants are allowed to bring their families with them. While it’s not life as a digital nomad, it is a way for you and your family to travel the world while earning money. There are career paths that allow you to travel while working – no laptop required.
We’ve heard a couple of podcasts about families who pay their way by fixing iPhone screens, cleaning people’s laptops, shooting drone footage for hotels, giving massages, yoga lessons, life coaching, haircuts, or personal training sessions. If you have a physical skill that earns you money at home, it can earn you money abroad.
We met a couple of nomads in Thailand who worked as assistants for different AirBnBs in the area. They could stay for free and earn a small percentage from every house they rented. Many travelers also work for free accommodation on farms, hostels, and hotels. These jobs sometimes require little to no skills (besides speaking English). A word of caution here – working while traveling on a tourist visa is illegal.
Further Financial Tasks
This is not financial advice; it reflects what we do. I am not qualified to give financial advice.
Retirement Policy
One of the most difficult parts about transitioning into a Digital Nomad Family life as 30-year-olds is that we are aware of the importance of financial planning. While 23-year-old Caitlin didn’t care about her retirement policy, 32-year-old Caitlin is well aware of the need for proper financial planning.
We don’t pay into a retirement policy, but we are planning financially for retirement. We have life insurance policies and are investing our leftover income broadly to ensure we won’t have to work forever.
Taxes
I could write thousands of words on taxation policies – these vary based on your home country, country of birth, and passport status.
If you’re serious about digital nomad family life, research the taxation policy of your home country before leaving. In Germany, for example, residents have to deregister to avoid paying income tax. In the USA, this is not possible; taxes are unavoidable.
To avoid paying high fees or getting arrested for tax fraud, check your country’s policies and hire a tax consultant or accountant if you have any additional questions. Our friends in Thailand spoke to a consultant and saved tens of thousands of Euros a year.
Life as a digital nomad family isn’t just sunsets and margaritas. It’s important to make sound financial decisions that won’t negatively impact you or your children’s future—even when traveling. Before hitting the road, figure out how you’re going to work, plan for retirement, and continue saving while traveling.
6 Months Before Becoming A Digital Nomad Family
Everyone’s a Critic
If you build it they will come. This saying applies to critics as well! As you begin to build up your digital nomad lifestyle, the critics will appear out of nowhere.
We knew our friends would miss us, and our family worried about us starting our family entirely alone in a foreign country.
We didn’t know how many strangers would have an opinion on our upcoming lifestyle change.
My favorite piece of unwarranted critique? A woman who lived in the apartment below us was shocked when she heard our plans.
Although we had talked with her maybe a total of five times in the four years we lived above her, she criticized the flightiness of today’s generation, the irresponsible parenting choices we were making, and the fact that we weren’t going to let her babysit.
You’ll have to find your own way to deal with the critics. One thing I like to remind myself of is this:
Once you have kids, you’re going to get criticized by strangers anyway.
Step 5: Housing
If you’re renting, now is the time to talk to your landlord. Do you want to sublet first? Ask them. Are you quitting your lease entirely? Tell your landlords about your upcoming travel plans. Our landlords found tenants needing furniture who liked how we painted our apartment, meaning we could move out without repainting and without selling most of our larger furniture pieces.
Six months before we were due to leave Germany, we called our landlord and requested to sublet our home for a year, allowing us a chance to travel for a year and return in 2024. This request was denied.
So, we quit our lease.
Quitting our lease was the single best decision we made that year. It gave us a deadline.
At the time, it felt like the riskiest move we had ever taken. We were shaking when I sent in the letter!
If you’re a homeowner, you can decide what suits you and your family.
We’ve met families who rent out their homes while traveling, some of whom are able to make a small profit through long-term or short-term rentals. We’ve also met families who don’t rent out their homes, preferring to have a safe space to return to. We’ve even met families who sold their homes and are using the money from the sale to fund their travel lifestyle. There’s no right answer here, just what suits your family.
Renters need to talk to their landlords about upcoming travel plans. Ask about subletting or renting to people who need (or want) to purchase your furniture to make moving out easier. Homeowners can decide what to do with their homes; they can rent it, Airbnb it, sell it, or keep it. It’s up to you to figure out what’s best.
Step 6: Getting Rid of Your Belongings
If I could go back in time, I would start getting rid of our belongings SO MUCH EARLIER! Here’s how we got rid of (almost) everything we owned. I will only go into a little detail here, but if you’re stuck on this step, check out our blog on Getting Rid of Everything You Own: The Ultimate Guide.
Get rid of at least one item a day. If you see something you don’t need, snap a picture and load it on your local secondhand site instead of walking past. In Hamburg, this is Ebay Kleinanzeigen, but Facebook Marketplace works well in most parts of the world.
We should have started this process sooner – because we rented a 5×5 meter storage locker in Hamburg, and it is filled to the brim! We’ve been traveling for two years and have only needed the winter boots and coats from that locker – nothing else.
The fact that we’re paying 1500 euros a year to keep junk safe keeps me up at night.
Step 7: Become a Legal Family
One of our main issues before starting our lives as digital nomads was our marital status. We got engaged on Lipari, and wanted to marry before traveling. While we wed out of love, our main motivation for this was to clear up our relationship status.
My husband and I have two different nationalities, and we knew that having a baby together would be a beaurocratic nightmare – and that was before we wanted to have a baby in Thailand!
Another reason to get married before becoming digital nomads? Married couples can claim the other as a dependent when applying visas or residency.
We married in Jamaica 3 months before starting our world trip. This wedding (and the honeymoon) gave us a much-needed breather before cleaning out our chaotic Hamburg apartment.
Clear up any legal questions about your family before traveling. This means having a clear will in your home country, discussing estate planning with a close relative, and clearing up any custody issues with partners – before boarding a flight.
Step 8: Quit Those Contracts
Oh – the Contracts. The closer our departure date came, the more contracts we discovered— and I quit my fitness studio four months after leaving Germany! We had contracts with fitness studios, cell phone providers, internet, electricity, water, gas, public transportation, health insurance, accident insurance, legal insurance, and a meal delivery service, to name a few.
We were shocked at how much money we spent monthly on contracts! Our total monthly fees totaled over 800 Euros—that’s how much we spent on rent in Thailand.
Notifying your School, Daycare, or Childcare
This didn’t apply to us, as we didn’t have any children yet – but if you’re setting out into the world with your children, notify their school, daycare, or nanny well in advance.
Leaving an official school system without a set destination can be difficult, so it’s better to leave your family time to figure out a solution well in advance. Plus, daycares and nannies depend on your child for their income; it’s polite to give them advance notice.
Step 9: Get Health and Travel Insurance
Do NOT start traveling without health insurance!
If you’re planning on being a stationary nomad, meaning you’ll spend at least six months in one specific country, you may want to look into insurance in that specific country.
As digital nomads, we frequently change countries; even when we’re based in one country, we travel. We’re insured through Genki, a health insurance company created for digital nomads.
Although Genki ended up not covering the costs of my C-Section and subsequent hospital stay, we knew about this before we began traveling.
Genki had multiple internal meetings to discuss our case, lengthy phone calls with myself and my husband, and answered all of our questions clearly and kindly.
Step 10: Bank Accounts
This is your time to begin researching the banking solution for your family. You may need to open an account with a new bank, open a travel credit card, or inform your bank of upcoming travel plans. Ensure you clear these issues before boarding the flight – you want to arrive at your destination with access to funds!
We’ve always had a complicated relationship with banks. As a US citizen, I have a bank account in the US. I also had a local bank account in Germany and a joint account with my husband, who had two additional accounts in his name. Life as digital nomads has yet to make our banking situation any less complicated!
Our local bank in Germany had horrible exchange rates and high foreign transaction fees, and the ATM card only worked in the EU. So, we closed our accounts and transferred our funds to Wise, as well as opened a Chase Bank Account for the Credit Card with Points. These points add up quickly—we go on a “free” month-long trip to the Caribbean every year.
2 Months Before Becoming Digital Nomads
Step 11: Final Preparations
This is your last chance to clear up anything left on your To-Do list. We found keeping a running list of Short, Medium, and Long tasks helpful. Each of us was responsible for a Short Task a day, two medium and one long task a week. Prioritize Tasks that have to be done in person, as you won’t be there for much longer!
Applying for Visas
You may need to apply for visas depending on your family’s citizenship, how slow you intend to travel, and what work you’ll be doing while traveling. While most countries have tourist visas for members of the privileged Passport Club (EU, USA, CA, AUS, and NZ) on arrival, some countries may require you to apply for a visa in advance.
In many countries, you cannot work while on a tourist visa. There are ways to avoid falling into this trap – none technically legal.
First, refrain from mentioning that you intend to work on the application. Also, don’t mention your work when asked at immigration. If you’re entering a country on a tourist visa, you say you’re there as a tourist. Not as a digital nomad.
Second of all, don’t be stupid! Are you being sponsored by a hotel chain to visit a specific country? Make sure you publish the videos after leaving the country. Don’t brag about your high income to locals, and don’t apply for jobs that won’t qualify you for a visa.
If the country you want to visit doesn’t have a visa or residency permit that works for your family, or you feel uncomfortable lying about your employment status, skip it for now and come back later. Applying for visas gets easier with practice.
Here, I think it’s important to mention that I am not a lawyer, immigration specialist, or consultant. So take my advice as anecdotal. We travel and work, and have thus far avoided getting into legal trouble. If you have specific questions, talk to a qualified consultant.
Booking Tickets
By now, you will know where your first destination will be. It’s time to start booking!
We booked our one-way tickets to Thailand three days before our departure date. Why? Because we are pure chaos.
We booked our first week’s accommodation and left the rest up to chance.
One thing to think about? If you’re flying into a country on a tourist visa with a one-way ticket, you will need proof of onward travel. We use the service Onward Ticket – they purchase a real flight reservation for you that will be automatically canceled, for 16$.
A South-East Asia-specific option is to book a bus ticket on 12Go. We arrived in Phuket, claiming to be headed to Laos with a Mini-Bus in one month. The officer knew we were lying, but at least our money went to a Thai Mini-Bus driver when we didn’t use the ticket.
Gathering Documents
Life as a Digital Nomad is a bureaucratic nightmare. We travel with a Binder full of documents everywhere we go. As some countries require your documents to be recent, now is a good time to make sure you have the essentials. These are:
Birth Certificates
Marriage Certificate
Background Checks
Immunization Records
Recent Health Documents
Proof of Income
Proof of Insurance
International Driver’s License
Another thing you may want to do (especially if you are planning on getting married or giving birth abroad, is to have all your documents translated and authenticated. We have copies of our school records and translations of essential documents into German, English, and Spanish – just in case.
Some countries, like Germany, only accept translations from official, authenticated sources. If in doubt, e-mail the consulate’s office and ask for a list of acceptable translators.
Let Your Bank Know
If you haven’t already done so, now is the time to inform your bank about your upcoming travels. My bank allows me to complete a form online with my expected travel dates and locations. This keeps my bank card working and allows me to access my money worldwide.
Undercover Address
Life without a permanent address isn’t possible in today’s world. To get around this issue, we send our mail to my husband’s mother’s house in Germany, and my parent’s house in the US. Legally, those are our two addresses.
Ask a friend or relative about using their address for mail, bills, and visa applications. Make sure you trust this person – if a letter comes, they’re going to be the ones to open them for you!
1 Week Before Becoming Digital Nomads
Step 12: Packing
It’s time to pack up your belongings! And then unpack them because you have too much, before repacking them again!
If you’re looking for tips on packing lightly, check out my blog on Two Suitcases – How We Travel Light.
Even though this is your last chance to go shopping in your home country, it might be better to wait on certain items and purchase them abroad. Clothing in SEA is far better for the extreme heat than the clothing we brought with us from Europe.
Another reason to wait on certain purchases? You’re starting a new life. You may not need everything you think you will.
We lugged hiking poles with us to three different countries before finally getting rid of them in Madeira.
Step 13: Saying Goodbye
The hardest part of your family’s digital nomad journey is here—the Good-Bye Week. We spent as much time with our family and friends as possible before leaving Hamburg, but it will never be enough. There were tears, hugs, and more tears for our entire last month.
One way I like to rationalize the tears is mathematical. Now, we spend 3-5 weeks traveling with our families. That’s, hour per hour, more time spent together than if we lived nearby and had dinner once a month.
I want to say it gets easier, but it doesn’t. Saying goodbye to those you love is the price we pay for our lifestyle. We’ve been doing this for two years, and it’s still hard. But so worth it.
Be Digital Nomads.
You did it!
You waded through the financial, legal, and bureaucratic minefield that laid before you, packed all your belongings into suitcases, and got on the plane! It’s time to sit back, enjoy a well-earned beverage, and get excited about the beautiful life coming your way.
Digital Nomad life is all about relaxing, adapting, and figuring out how to enjoy the finer things in life. Since becoming digital nomads, we’ve switched continents three times, and we’re about to move again this year. It’s essential to keep up with your legal status, relationships, and documentation while traveling – so check out these articles for more tips on life as a digital nomad family.
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