Burn it to the ground. Jk.
Preparing for remote-work featured travel takes some planning. Especially if you’re digital nomad-ing for consecutive months. There’s a lot more to getting ready for a remote work trip than throwing some trunks and tank tops into a bag and keeping your liquids separate. Things that you deal with only once a year aren’t easy to remember until you’re three months deep in Morocco and realize your prescription is running out. That’s when you realize you’re f*cked.
I’ve gone through this process three times myself—once moving to Korea, once moving to Canada, and now traveling the world for the last 3 years while running Hacker Paradise, a service that organizes remote-work trips for a wide range of location independent professionals. To date, I’ve guided 12 employees and hundreds of Hacker Paradise participants through the process.
We’ve made the mistakes so you don’t have to.
Becoming a digital nomad is an exciting, life-changing adventure. Set yourself up for success by cleaning up your life at home before heading out on that remote-work & travel road.
All the Sh*t You’ve Accumulated
Your house, car, furniture and Star Wars memorabilia. Hopefully, these are the first things you think of. For most of these, you have three choices:
- Sell or rent it
- Put it in storage
- Give it to someone else for safekeeping (hi mom)
You’re not going to want to lug around all that sh*t on the road and storage fees start adding up. Take this opportunity to cleanse. Unless it has irreplaceable value–financial, emotional, or otherwise–it’s gots to go.
While you’re at it, review the electronic subscriptions you’ve accumulated. Best way is to review your credit card statement for the last several months. That gym membership isn’t going to do much for you on the road. Neither are most of the TV streaming plans unless you have a plan to use VPN with it. Make a list and pause or cancel them.
Don’t forget about the people in your life—you’ve accumulated them over the years too! Start with acquaintances. What professional obligations do you have that need to be taken care of before you leave? Any professional organizations you need to notify?
Most importantly, make a plan for maintaining relationships with your close friends and family. Take it from us–they start to panic if they don’t know when they will see you again.
Clearly communicate the following:
- How they can get a hold of you
- How often they should expect to hear from you
- The time difference between you and them (your future sleep schedule will thank me)
- When they should plan on seeing you next
Hopefully, they’ll take advantage of the opportunity to come visit you on the road.
The Boring Bureaucratic Stuff
Get that passport checked. Nothing cuts your plans short like having to go home to renew your passport prematurely. If you are planning extensive travel, make sure you have enough pages for all the stamps. I made it by the skin of my teeth once with two spots left for stamps before going home to get a new passport.
Passport control in most countries want to see that you have two years left on your passport.
Double check those visa requirements before you begin your trip. While you can sometimes apply for visas on the road, some have to be taken care of in advance.
Make sure you have proof of onward travel, lodging reservations, and potentially bank statements on hand as you travel to a new country. You won’t always get asked for them but you will be grateful you have them for the couple of times they are useful. I’ve had both the check-in counter and passport control ask for all of these at some point–with THOU SHALT NOT PASS punishments if I wasn’t able to produce them.
All the Feels
Preparing for proper physical and mental health on the road is critical. Before you leave, go to the doctor, visit the dentist, and get any other regular checkups you might need over the course of the year. Make sure your shots are up-to-date and check to see if you need any new vaccinations based on where you are going.
Pack all the medications and contacts you will need or have a strategy for getting more while on the road.
You’ll also want to make sure you have a travel medical insurance in place in case you have any emergencies. Trust us.
Don’t overlook your mental health. The top issue digital nomads suffer from is loneliness. It’s one of the reasons Hacker Paradise was created and is successful—people crave to be part of a supportive community of their peers. Make sure you have a plan to join a community wherever you go.
Know what you need to feel stable and ‘at home’ even though your life might be more dynamic and transient than it ever has before. Understand what you need to relax and how to handle stress.
Talk to Me
It’s hard to remember how we lived before cell phones. You will have a quick reminder of how hard it is in our modern world if you don’t figure out your cell phone plan before you leave. Many of us use international plans (Google Fi for the win) while other people purchase a local SIM card when they land. Make sure your phone is unlocked and able to accept foreign SIMs.
Also, make sure you have a tool to pop open your SIM cartridge. If you don’t have the tool, sometimes a paperclip or an earring will do the job.
If you’re switching in a new SIM, you’ll get a new, local phone number. That can really f*ck with any two-factor authentication setup you have tied to the phone number you are retiring. Before I got Google Fi, I switched my old phone number tied to all of my two-factor authentication setup to Google Voice and had that forwarded to my local number. Worked like a charm.
You should cancel your cell plan from back home if you aren’t planning on using it. Install apps that you can use to communicate while abroad, regardless of the SIM card plugged into your phone. WhatsApp is a godsend that everyone should install.
Still have snail mail that comes to the house? Cancel them or switch them to email delivery. For those items that you can’t (I’m looking at you, jury summons and IRS notifications), make sure they are going to a real address where someone can alert you. My important mail goes to my sister who opens it and sends me a picture. Other people use a mail receiving service that scans it to you.
Dat Cash Flow
If you were dozing off, this is the time to wake up. Mess this one up and you won’t be traveling for long.
You’re going to need a strategy to manage all your money without ever setting foot in a bank. Start by making sure you can access all your accounts online. Get debit cards with no ATM withdrawal fees (Charles Schwab for Americans, Revolut is good for Europeans).
Make sure your credit card has no international transaction fees. Have a service like TransferWise so you can convert currencies and make international bank transfers without paying an arm and a leg.
Alert your banks that you are going abroad so your cards don’t get flagged. You’ll want to make sure you have more than one credit and debit card in case one is frozen, flagged, or stolen.
Assuming you’ll be hanging out with people, set up money transfer platforms like Paypal or Venmo. Being able to transfer money electronically between your peers will save you a lot of headache.
Don’t forget about taxes! Your tax situation will vary based on your home country, what type of work you do, and how much time you spend abroad. Many countries have clauses that let you pay significantly fewer taxes if you are out of your home country to months on end. Check out regulations for your country, and consult an accountant if necessary.
Things You Can’t Live Without
Pack your bag with what you think you will need. Now eliminate half of it. I’m serious.
There hasn’t been anything I left behind that I wished I had. On the contrary, I keep slimming down on every stop. Things I thought I couldn’t live without have been binned. Everyone that travels will say the same.
Packing light doesn’t mean being unprepared. You learn that you can buy things along the way that you might need and then leave them behind if you don’t need them at your next location.
Compact packable light jackets can be great even for times when the AC is on too high in warm places. Packing cubes and extra bags (yes, I pack bags within bags) are lifesavers. You will probably want a separate work backpack, travel backpack, and small packable backpack for day trips.
Invest in a good suitcase and travel backpack. Nothing is worse than seeing your suitcase break open on the streets of Buenos Aires and scatter your precious belongings everywhere.
I highly recommend looking into a good pair of earplugs and a sleeping face mask if you are a light sleeper. You never know what you’ll encounter as you travel – street noise, overly-romantic neighbors, an air conditioning unit with a fluorescent green screen that floods your room with light. Assume control over these situations by being prepared.
That Sweet Tech
Mark my words, you will live and die by your laptop. You will not regret investing money in an upgrade before you go abroad. For what it is worth, almost all the digital nomads you will see travel with a Macbook.
Then comes the accessories. Make sure you have all the cords you need and make sure they plug into all the things you need them to. Universal adapters are notoriously shitty. Take some time to investigate one that will work well for you.
Think if you want to bring a backup of something. Many people bring a backup charger, an old cell phone, or sometimes a second laptop. Weigh up how important something is to you by seeing how long you could go without it. If your computer broke, could you survive five days without it?
You aren’t going to want to weigh yourself down with extras of everything so think through it carefully. Many generalized replacements you can easily buy abroad–specialized tech will be harder.
Think about your work setup and ergonomics. Laptops are not designed for good posture. Consider using a laptop stand + a wireless keyboard to reduce the strain on your neck.
Finally, you’re going to want to have a good camera to share your experiences with those back at home. New phone cameras are plenty good these days. Just don’t expect to capture the majesty of Machu Picchu with that flip phone from 10 years ago.
Wrapping it Up
You’re about to have the time of your life! Taking the right steps before you go ensures that you are able to have the best time while you are traveling. If you thought cutting your packing in half was a challenge, wait until you see what awaits you out on the road.