Beginning Your Digital Nomadic Life – Our 1-Year Checklist

Beginning Your Digital Nomadic Life – Our 1-Year Checklist

As we’ve mentioned, everyone wanting to live the nomadic life is in a different place in their lives. If you already have a good bit of money and a remote job, it may not take a year to become nomadic. If you’re like we were after returning from Jamaica, working crappy jobs and basically broke all the time, it may take a year to prepare for your nomadic life. 

Regardless of where you are in life, the below checklist of tasks is worth going over. Most of the entries in our list are the exact steps we took the year before we left on our latest 10-year adventure living the nomadic life. The below topics that we didn’t do the year prior to our leaving are things, looking back, that would have made our nomadic lifestyle a lot easier (like a virtual mailbox).

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Before We Get Started on our Nomadic Life Checklist

Sadly, most people who read this probably won’t end up living a nomadic life. Not because it’s out of reach for them but because there are a lot of sacrifices that need to be made. Especially in the year prior to leaving.

I promise you, though, it will be worth it. The year we spent sacrificing and saving before our trip put us on the beach in Nicaragua, doing absolutely nothing for the next two years. If you’re serious about traveling and living a nomadic life, this checklist will help get you there.

Starting Your Nomad Life: 1-Year Out

This year is going to go much quicker than you think it will. Getting these little tasks out of the way now will get you in a much better position to living the nomadic life.

1-Year Out – Downsize, Downsize, Downsize

If you’re a hoarder or love collecting things, living a nomadic life will be a difficult transition for you. Most nomads, us included, just don’t own many things. We prefer to collect memories and experiences rather than trinkets and knickknacks. 

As a matter of fact, I know many digital nomads, us included, who own only as much as we can fit into our carry-on suitcases. That may seem odd to people who are used to owning 15 pairs of shoes or a collection of sports memorabilia. 

If your plan is to become nomadic, for the long term, you will need to downsize. And that includes everything:

  • cars, 
  • living arrangements, 
  • clothes, 
  • artwork, 
  • and everything else. 

I know it sounds intimidating to get rid of everything you’ve spent your life collecting, but it will be worth it when you’re lounging on a beach doing nothing while everyone else is at home, admiring all of the things they’ve managed to collect.

Downsizing – Living Arrangements

Living arrangements are what keeps most people from living the life they want as a digital nomad. This is a mindset you may want to get out of. We’ve been on the road for a long time, and we’ve never really had a permanent place to live. Neither do most digital nomads. We travel around from place to place, living where ever we want until we get bored of it. This is the mindset you should be getting in.

A year out is the perfect time to start downsizing your living arrangements. If you have a house or huge apartment, consider renting out rooms or moving to something less expensive. The year before we left, we rented out our extra rooms and our attic space to students from the College of Art in our neighborhood. Much of the money we saved that year was from rent and utilities we charged our roommates.

Anything you can do to save money on your living arrangements over this year will add months or years to your nomadic life.

Downsizing – Vehicles

nomadic life checklist - sell your car

I’m always confused when people say their cars give them freedom. This couldn’t be farther from the truth. We do what we want, where we want, whenever we want, and we haven’t had a car in 15 years. All a car will do is give you added expenses and headaches for the next year.

Think about how much you spend in:

  • Car payments
  • Car insurance
  • Gas
  • Repairs
  • Maintenance
  • Parking
  • Tags and registration, etc.

According to AAA, these expenses cost the average American nearly $10,000 a year. Considering we’ve lived on the beaches of Costa Rica, Panama, Mexico, and Nicaragua for less than $1000 a month, ditching your car a year out could put you on the beach, doing nothing, for up to 10 months.

Why waste all of that money on a car, especially when you could use public transportation, Uber, or ride-share for a fraction of that money? It’s not like you’ll own a car in your nomadic life (unless you’re going for the van-life scenario).

Downsizing – Most of Your Stuff

Again, living a nomad life means not having a lot of crap to carry around from country to country. And a year out is the perfect time to start getting used to it. 

A great place to start would be to sell off everything you haven’t used in the past 3 months. This includes cooking gear, kitchen wares, shoes, clothes, knickknacks, and everything else sitting around gathering dust. Turn those unused things into cash to enjoy your nomadic lifestyle.

1-Year Out – Get Into a Money-Saving Mindset

nomadic life checklist - save every penny

Speaking of turning stuff into cash, now is the time to start putting away every penny you can. Every $1 you make selling something or every $1 you save during this year equals about $3-$4 if you’re traveling somewhere south of the border. 

We have a whole section here, for info on how we were able to save up enough money in the year before we left to put us on the beach in Nicaragua, doing nothing, for nearly two years. If we can do it, so can you.

1-Year Out – Stop Buying Things

This goes along with the last few suggestions. Unless it has to do with your trip, stop buying things you’ll eventually just need to get rid of. Do you really need that new $40 t-shirt, or that new $100 kitchen gadget, if you’re going to be living a nomadic lifestyle overseas? That money will go much further after you move.

Think about where you want to be in a year, and ask yourself if this purchase will help you get there. If not, why bother? You’re going to be living a nomadic life soon, you probably won’t need anything new that doesn’t have to do with your trip.

1-Year Out – Drop Unnecessary Expenses

We’ve all heard it before; if you want to save money, drop the unnecessary expenses. Things like eating out all of the time, expensive coffees in the morning, an evening at the movies, etc. 

We’re not saying to deny yourself of the things you love, but all of the money you can save this year will be worth it when you spend it overseas. Again, $1 saved in the US is worth $4-$5 overseas, where the cost of living is lower.

1-Year Out – Time to Find Your Side Hustle

nomadic life checklist - figure out side hustle

If you already have a money-making side hustle you can work remotely, you’re more than halfway to living the nomadic life. For the rest of you, us included when we were a year out, you’ll have to figure out how to make money while you’re on the road. 

We have a whole section here, on how to use your existing skills to make money while traveling. And it’s not nearly as difficult as most people think. There’s no sense in waiting until the last minute, like we did. Get your side hustle in order now, and you’ll hit the ground running when you’re ready to start living nomadically.

1-Year Out – Get Your Business Affairs in Order

What we didn’t realize the first few years as digital nomads was that having a registered business made nomadic life easier and less expensive. Getting your business set up now will make your life much easier once you’re overseas.

The first step will be to set up your LLC. It’s easy and inexpensive, and you can do 100% of it on your own online and for very little money. Once you have an established LLC, you can open up bank accounts for your business. The debit cards attached to these businesses have much lower international ATM fees and have saved us $1000s on these fees over the past 10 years.

1-Year Out – Start House and/or Pet Sitting Locally

nomadic life - pet sitting

House and/or pet sitting is a digital nomad’s little secret to living for free in some amazing places. We’ve lived in Caribbean beach houses for six months at a time, beautiful penthouse apartments, and all-inclusive resorts, all for free, just for looking after some cute pets while their owners were away.

If you plan on living the nomadic life for the long haul, chances are you’ll also be doing some house/pet sitting. Might as well get some clients in the meantime by offering these services close to where you live. By the time you start your nomadic life, you’ll have all of the references you need to land some choice house/pet-sitting gigs.

1-Year Out – Start Researching your First Destination for a Nomadic Life

As a digital nomad, you’re going to be traveling around a lot. That’s the best part about being nomadic. If you’re bored of where you’re living now, you can just pick up and move somewhere new. 

That being said, your first destination really isn’t that important. Your first destination is really more about getting you in the right frame of mind for the rest of your nomadic life, which could last years and cover hundreds of destinations.

Natasha wrote a blog titled, “Choosing Your Initial Destination for a Fully Nomadic Lifestyle”. Now is the time to start thinking about your first trip and where it will be.

1-Year Out – Start Using Social Media to Your Benefit

You’re probably already scrolling through social media. Might as well use that time online to get a head start on your nomadic life. Join some social media groups that have to do with:

  • Living Nomadically – Nomads are a pretty helpful group, for the most part, and love helping aspiring nomads with any questions they may have.
  • Working Remotely – These groups will help you determine if a destination is good for working remotely. If you want to live in a remote beach town, best to get advice from remote workers if it’s feasible.
  • House/Pet-Sitting – If you plan on house/pet sitting while living as a digital nomad, these groups can give you all the information you need to know to do so successfully.
  • Expat Groups – If you already have a destination in mind for your nomadic life, start joining some “Expats of XXX” groups online. These expats are more than willing to answer any questions you might have about your first destination.

You’ll find many like-minded people online who can help you prepare over the next year for your new nomadic life.

1-Year Out – Get your Passport in Order

nomadic life checklist - get passport

If you don’t already have a passport, get one now. If you have a passport, and it only has a year or two left on it before it expires, consider getting it renewed now. If you have a passport with only a few empty pages left for stamps, consider renewing it.

The last thing you want to do is be a few weeks out from your initial trip only to find out there are issues with your passport that are going to cause issues traveling overseas. Resolve those issues now, and you’ll have fewer things to worry about when it’s time to travel.

1-Year Out – Start Learning a New Language

If you know where you’re traveling, start learning some of the language. Even if it’s only a few words, that will be incredibly helpful. 

We’ve decided that most of the places we want to travel are in Latin America. When we first started traveling, we had zero Spanish. None. And it sucked. Even just knowing pleasantries (hello, good morning, please, thank you, etc) will help you in your travels.

Starting Your Nomad Life: 6-Months Out

When preparing for a nomadic life, most of your major lifestyle changes will happen a year out. This is when you’ll start downsizing everything and, hopefully, getting rid of most of your stuff that you won’t need.

The next six months will be more downsizing and making final arrangements for your new lifestyle. Let’s get into it.

6-months Out – Sell More Stuff

nomadic life checklist - sell everything

When you had a year left before your first trip, we advised you to sell off everything you hadn’t used in the prior three months. We’re advising you to do the same now. 

Again, you can’t take everything with you on your new nomadic life, and storing it isn’t worth the money or headaches involved. Sell even more of your stuff off and put that money away to enjoy during your travels.

6-months Out – Start to Finalize your First Destination

You’ve probably been researching your first nomadic destination of the past six months. Now is the time to start thinking about finalizing these plans. Again, Natasha’s section on choosing your first destination will be helpful.

Just remember, you’re not looking for a place to live long-term. You’re looking for a place to begin your nomadic journey. Find somewhere close-ish to home and cheap to get to. This will give you a good head-start on your nomadic life.

Before our first trip, we found flights from the US to Jamaica for less than $100, so that’s what made our decision. Same with our second trip; we found flights from the US to Costa Rica for less than $100. So we started there and then moved on.

Your first destination isn’t as important as just getting started. Once you’re on the road, if you decide you’re not loving where you are, you can always move. That’s the best part about being nomadic; the freedom to live where you want for as long as you want.

6-months Out – Think About Getting an English-Teaching Certification

Sure, you have your remote job and your side hustle … why not have a fall-back plan as well? We’ve met dozens of digital nomads who fund their travels entirely by teaching English online. Getting this certification now could help you add months or years to your nomadic life.

6-months Out – Start Taking your Side Hustle to the Next Level

nomadic life checklist - take side hustle to next level

Hopefully, you’ve been spending the past six months getting your side hustle figured out. It doesn’t matter what it is; writing, coding, yoga, or marketing. Whatever your side hustle is, it’s time to take it to the next level.

This means marketing your services, creating a website, making a Facebook business page, etc. Get all of this together now, and when you hit the road in six months, your side hustle should be ready to fund your travels.

Starting Your Nomad Life: 3-Months Out

You think the past nine months have flown by? These next three are going to be over before you know it. Now is the time to get everything together and prepare for your new lifestyle. Let’s look at some of the tasks you will want to complete over the next few months.

3-Months Out – Get Virtual Mailbox

Living a fully nomadic lifestyle means you won’t have your own physical address. Sounds kind of intimidating, but you’ll get used to it. We haven’t had a physical address in years, and it’s not a big deal.

So, how do we get all the important info we need from banks, clients, and government entities? We have a virtual mailbox set up through a company in the US. It’s a normal street address, not a P.O. box, which many places won’t ship to. And we couldn’t get along without it.

This virtual mailbox collects all of our mail, opens it, and scans it electronically for us to read. It will also forward mail and packages anywhere in the world. We didn’t have this virtual address for the first two years of our travels, which was a huge pain. This is something we strongly suggest having.

3-Months Out – Change your Address

Now that you have your virtual address, it’s time to change your address. This is easier said than done. The USPS won’t just do a change of address to a P.O. box or a virtual address. This means it’ll have to be done manually.

Contact all of your bank accounts, online accounts, and any other entity that mails you something and change your address to your new virtual address. This will save you many headaches in your new nomadic life. 

This is something we neglected to do when we first started, and it caused numerous problems. Best to take care of this now.

Starting Your Nomad Life: 1-Month Out

Day Trip from Cancun to Chichen Itza - Paul and Natasha

You’re so close! By now, you’re probably living in a nearly empty apartment, excited to get started on your new nomadic life. Just a few more things to take care of. 

1-Month Out – Sell Everything

Time to sell everything else off. You won’t need it, and storing it is too much of a hassle. Take the money you make on selling the rest of this off and put it towards your trip.

1-Month Out – Get Nomadic Insurance

Shit happens, and it’s best to be prepared. There’s nothing worse than getting injured overseas and not having insurance. We use SafetyWing insurance, which is specifically tailored to digital nomads.

It will cover nearly any medical bill you could imagine encountering while you travel. Having insurance like this could mean the difference between ending your nomadic journey early due to hospital bills or being able to afford to continue traveling.

1-Month Out – Finalize your Travel Plans

Hopefully, you’ve decided where your first nomadic destination in your nomadic life will be. Now’s the time to purchase your flights and figure out your living arrangements. 

1-Month Out – Give Notice to Work

Don’t do this until you’re two weeks out. Natasha and I each tried to give our work more than two weeks’ notice, and it came back to bite both of us. I was fired immediately after giving a month’s notice, and all of Natasha’s money-making bartending shifts were given to “more loyal” employees.

Starting Your Nomad Life: 1-Week Out

Only a week left! Time to start getting really excited about your new nomadic life. It’s been a year of scrimping, saving, and making some serious changes. Now it’s all about to pay off. In a week or so, you’ll be living the life you’ve always dreamed of for yourself. 

Just a few more things to take care of.

1-Week Out – Notify Financial Institutes

There is nothing worse than going to an ATM only to have it reject your out-of-country ATM card. Or, worse, suspecting fraud and having the ATM machine confiscate your card. It’s happened to us … more than a few times.

Avoid these financial hassles before you get on the road. Call up all of your banks and let them know you’re moving out of the country, and they will start seeing many transactions from many different countries. I promise you this will save you a lot of headaches.

1-Week Out – Print Proof of Onward Travel

As a digital nomad, tickets for roundtrip flights are rarely a concern. It’s very unlikely you’ll ever want to buy return tickets because, as digital nomads, we rarely know what country we will be in next. Life as a digital nomad is just a series of one-way tickets to the next place we want to live, without much thought about what we’ll be doing after that.

Unfortunately, neither customs agents, nor the people working at the airline ticket counters, understand this lifestyle. And both will give you grief if you show up in front of them with nothing but a one-way ticket in your hand. Trust me, we know this from first-hand experience.

Without having proof of onward travel, one of two things could happen:

  1. Your gate agent at the airport will deny you the ability to board your flight. It’s happened to us, and we’ve seen countless … countless travelers stranded at the airport, unable to board their flight because of this.
  2. Customs in the country you’re traveling to may not let you enter the country with proof of onward travel. Again, we know this from firsthand experience. Being stuck in limbo because of an over-zealous customs agent is the absolute worst.

Neither of these are situations you want to find yourself in, especially for your first trip as a digital nomad. Get yourself proof of onward travel, make sure it’s dated at least a week before your tourist visa expires, and print it off before your trip.

Now, booking onward travel whenever you want to move to a new country can be a bit of a drag. What if your plans change? And, trust me, as a digital nomad, plans always change. Still, it has to be done.

Here are the steps we take to deal with the hassles of proving onward travel out of a country before our visa expires. We usually start this process a week before we travel to a new country:

  1. Find out the exact date our tourist visa expires. It’s different for most cities and usually ranges from 30-180 days.
  2. Pick a date one week before our tourist visa expires, and start looking for one-way flights out of the country we’re about to travel to.
  3. Get on one of the many online flight aggregator websites (Expedia, Priceline, etc) and search for flights out of the country you’re about to travel to. Make sure the flights leave before your tourist visa expires. Make sure the flight is on a different airline than the one you’re about to fly on. And make sure this flight is 100% refundable within 24 hours.
  4. Book the flight, print off the confirmation, and cancel that flight.

It sucks to have to do this, but as of now, we haven’t figured out another way, short of actually planning ahead, to get around the issues with onward travel.

1-Week Out – Print Proof of Lodging

AirBnb vs hotel

This falls under the same category of the proof of onward travel we just discussed. If you’re traveling somewhere on a one-way ticket, even with proof of onward travel, both the airlines and customs want to know that you won’t be living on the streets. 

At some point in your travels, you will be asked for proof of lodging while you’re in the country, whether it’s an AirBnB receipt, confirmation from a hotel, or a confirmation email. We’ve been asked to provide this proof numerous times by customs agents and airline gate agents. We don’t even travel internationally anymore without it. And neither should you.

On our last trip to Mexico, flying in from Colombia, we were asked for onward flights out of Mexico and proof of living arrangements while in Mexico. And the customs agent wanted to see proof for each and every day we were in the country, all the way up to the night before our onward ticket was booked. 

Save yourself the headaches and figure out a way to show proof of where you’ll be living.

1-Week Out – Print Proof of Financial Stability

This isn’t nearly as common as the proof of onward travel and proof of lodging we just discussed. Still, we’ve been asked to prove, mostly in Mexico, that we have the funds to live in a country for the length of time we’ll be there.

Now, customs agents aren’t going around asking every family that flies into Cancun if they can afford to vacation there. We’re not coming in for 7-10 days, though. We’re telling a customs agent (and they will ask in Mexico) for a tourist visa lasting 180 days. They will want to know you have the funds to live there that long. Don’t give them a reason to deny your entry into the country.

Digital Nomad Tip:

While we’re discussing customs agents, this is a good time for a very important tip to always keep in mind: 

No matter what, you will always tell a customs agent you’re in the country for TOURISM.

That’s it. Nothing else. Not that you’re working abroad. Not that you’re house/pet sitting. Not that you’re a digital nomad. And definitely not that you’re living in the country for a while. 


Nothing more. Answering any differently, especially if you’re there on a tourist visa, is the best way to get denied entry into the country.

1-Week Out – Get out as Much Cash as You’re Comfortable Carrying

nomadic life checklist - get cash out

As a digital nomad, cash is almost always king. Especially if you’re traveling to developing nations. We’ve lived on islands before where there wasn’t a single ATM machine or credit card scanner on the whole island or even on the mainland. 

At least for your first few trips as a digital nomad, ensure you have enough cash on hand when you land in a new country to get from the airport to where you’re going and for a few nights’ lodging. You won’t regret it.

1-Week Out – Check your Luggage Size and Weight

I can’t even believe I have to add this section. Sadly, I have seen so many people either denied boarding or forced to pay a ridiculous amount of money to get their oversized bags on their flights. 

On my last trip out of Colombia, I had to throw out my book-bag-sized backpack and all of its contents because replacing it was cheaper than paying the oversized luggage fees. We see this happening all of the time. Especially on the discount airlines that are so common with digital nomads.

Gate agents, especially these days, are not messing around. Try complaining about having to pay the oversize/overweight baggage fees, and you may find yourself denied boarding. We’ve seen it happen. Many times. For a smooth first outing as a digital nomad, don’t overlook this ridiculous restriction. It could cost you. A lot.

It’s Time to Begin your Nomadic Life!

Natasha in Oaxaca
Natasha in Oaxaca

I know this checklist seems a bit of an inconvenience. I promise you, though, once you’re living the nomadic life, you’ll wish you would have made these sacrifices earlier. Again, you don’t have to follow each item on this checklist for a successful first trip as a digital nomad. If you do though, you can be assured of a successful transition from a 9-5 worker bee to living an awesome life as a digital nomad.

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