100+ Questions to Ask Before Going Nomad

Deciding to “go nomad” is a big decision that takes lots of planning and soul-searching. We sold all of our stuff in May 2021 and hit the road. But it wasn’t an overnight decision. We kept track of all of our decisions and questions, and we offer 100 of those questions here.

Looking for the answers or insight into these questions? You can find all of these questions and more in our latest book, Two Carry-Ons and a Plan: Retiring as Full-Time Nomads available on Amazon. (Download the Kindle App to read it. You must purchase it from Amazon.com. Sadly, Amazon doesn’t allow you to purchase books through the Kindle app.)

Read our entire story, find the answers, ask more questions, and interact with us here in this blog, on Youtube, or at Instagram.

handsome hiking couple
Nomadlife and happy

We sort out the questions into categories, starting with your vision of your nomad life.

What’s your Vision?

  1. What do you want to see when you travel? Sculpture, the Seven Wonders, canyons, snow, beaches, orchestras, books?
  2. Is there a temperature range you’ll want to stay in? Are you searching for an endless summer?
  3. Will you carry a backpack or check your luggage? Is it important to you that you have the right outfit everytime or can you make a few wardrobe pieces work for all occasions?
  4. Are there particular countries you want to see? Or avoid?
  5. Will you have a “project” to do like genealogy, follow world battles, or find the best wool skeins?
  6. Are you okay with not knowing the language, or do you want to only stay in countries that speak your language?

Need answers? Get our book, Two Carry-Ons and a Plan: Retiring as Full-Time Nomads available on Amazon.

What Are Your Family and Friends’ Concerns

If you’re going to travel with someone, you may have some convincing to do. Or you may have to give your partner some time to digest your idea. You may need to modify and adapt. 

Then, you’ll need to tell your family. Telling your family that you’re retiring is one thing. 

Telling them that you’re selling the house and everything in it, permanently packing, and traveling the world is another. They’ll be worried about three things:

  1. Your safety.
  2. Your connection and obligations to the family.
  3. Your money.

What’s Your Rough Idea of a Plan?

  1. How will you travel? Air, bus, van, plane, train, camel, horse, bike?
  2. Will you limit your geography?
  3. Are you following a hobby?
  4. Are you following a passion?
  5. Do you have a bucket list to complete?
  6. Why are you going?
  7. Are you running away from something?
  8. Have you sorted your End-of-Life arrangements?
  9. When will you return?
  10. Why will you come off the road?
  11. What’s your end plan?

Get items from our travel packing list right here.

How Will You Carry Your Stuff?

Break down your action plan of what to bring by starting with the end in mind. 

  1. How will you carry your stuff?
  2. What type of luggage do you want? Hard side? Soft side? Duffle? Wheeled? Checked or Carry-on? Backpack? Day pack? 
  3. What stuff will you bring? Tents? Clothes? Shoes? Sleeping pads? Yoga mats? Hats? Rain coats? Jackets? Shorts? Sweaters? Pants? Dressy things? Casual things? Socks? Sandals?
  4. Will you sell the house or rent the house?
  5. Will you use a storage unit?
  6. How do you get rid of the rest of your stuff?

Need answers? Get our book, Two Carry-Ons and a Plan: Retiring as Full-Time Nomads available on Amazon.

Will You Use Checked Bags or Carry-on Bags?

Here are some things to consider when deciding on your luggage setup:

  1. Will you check your baggage or carry it on?
  2. If you’ll be flying often, are you prepared to roll your bag many thousands of steps to get it on the plane?
  3. Can you lift your bag?
  4. Even if you check your bag, you’ll have hundreds of staircases and steps to get from the terminal to your hotel. Many places don’t have elevators. Can you manage it yourself? Are you willing to pay for porters?
  5. Do you want to pay for checked bags over and over again?
  6. Do you have large or oversized items?
  7. If your luggage got lost, what would you do?
  8. Do you have cameras and other gear that you can’t or won’t check?
  9. What else do you need to personally carry?

What bag should you get? Read our review about the bags we use.

Will You Use Wheeled Backpacks or Non-Wheeled Backpacks

When looking at backpacks, think of these questions:

  1. Do you carry a water bottle?
  2. Do you need lumbar support?
  3. Do you need a waist belt?
  4. Do you need reflective material?
  5. Do you have keys or fobs you need to have quick access to?
  6. Will you carry a computer that needs a padded sleeve?
  7. Should you get a rain cover?
  8. Will your backpack carry all of your stuff or should you go smaller and get a day pack?
  9. Can your back handle up to 50 pounds for an entire day for multiple days?
  10. Can you lift 50 pounds over your head?
  11. Do you want wheels for when you don’t want to carry it?

Should You Sell or Rent Out Your Home?

Work through the following questions about the decision to rent out your home or to sell it without focusing on the financial side of the picture:

  1. Do you like the house?
  2. Do you still need this house?
  3. Do you want to return to where you live?
  4. Do you want to be homeowners?
  5. Is it a good time to sell?
  6. If you do buy another home elsewhere, what are the criteria for that house purchase?

Now add the financial picture into the questioning strategy.

  1. Do you need rental income in your portfolio?
  2. Do you want to manage a house (even with a management company) from afar?
  3. Do you want a reason to return to your city?
  4. Are you prepared for the unexpected expenses of homeownership?
  5. What will you do with the proceeds of the house sale?
  6. Are there tax consequences you’re willing to bear?

Need answers? Get our book, Two Carry-Ons and a Plan: Retiring as Full-Time Nomads available on Amazon.

Should You Get a Storage Unit?

  1. What would you put in it?
  2. Where will it be?
  3. How much will it cost? Quarterly? Annually? Total over time?
  4. If you pay for storage for a year, is the stuff in it worth that amount financially?
  5. Could you replace the contents for less than the price of storage?
  6. If you have heirlooms, do the kids really want them? Have you asked? If they want them later, why not take them now? If they won’t want them, what’s the real reason you’re keeping them?
  7. If your house burnt down, what would you really miss that isn’t replaceable?
  8. Would you rather have new stuff from your new life?
  9. If you’ll eventually settle somewhere, are you willing to pay to have the contents shipped to your new location?
  10. Do you want to worry about the storage unit?
  11. How will you insure the contents? Are you willing to pay this expense too?

We have loads more tips all over this website. Just search “nomad” above or click the Nomad tab.

One Year Before Departure: What’s the Good Stuff?

The “Good Stuff” in your home is the set of items that will be the hardest to let go of and also might be some of the hardest pieces to sell. They’re unique items that require specialized buyers if you want to get the most amount of money for these items. How do you decide what the good stuff is? Ask these questions:

  1. Is it good because it’s expensive or there’s emotional attachment to it?
  2. If it burned in a fire, what would you do?
  3. Are you looking for a good home for it or a good price?
  4. Do you need appraisals to sell it?
  5. Do you have buyers for it?
  6. Do family members want it? Are you sure?
  7. Has a family member asked for it?
  8. Should it be donated to a museum?
  9. What will make you happiest to get rid of it?
  10. Are you willing to deal with picky buyers in order to get a good price for it?
  11. Do you have the time and skills to sell it?

Need answers? Get our book, Two Carry-Ons and a Plan: Retiring as Full-Time Nomads available on Amazon.

Six Months Before Departure: Make a Plan for the “Estate Sale/Garage Sale” Stuff

At six months out, make a plan to get rid of everything you don’t need in the next six months. Your goal here is to get rid of waste, broken items, trash, and excess. What’s left is the “Estate Sale/Garage Sale Stuff.” When going through the remaining stuff in the house, ask yourself these questions:

  1. Do you need twenty cups or just three?
  2. Do you need your winter clothes or can you get rid of them now?
  3. Are you still using it?
  4. Are you waiting for a season or a holiday to pass before disposing of it?
  5. Do you need all of it? All your baking bowls or just one? All five spatulas or can you get by with one?
  6. Do you play all your CDs or just one or two?

Make piles or set aside a room to put these items. Take an honest look at the collective bunch and evaluate your energy levels. How much effort and time do you want to put into getting rid of the next group of stuff? Ask yourself these questions about the “garage sale stuff”:

  1. Are you willing to interact with lots of buyers?
  2. Do you want to list your items for sale in multiple locations?
  3. Are you willing to have a garage sale? Does your HOA even allow it?
  4. Do you want to get rid of stuff or make the most amount of money for it? These are conflicting needs and require different amounts of time and effort.
  5. Do you want someone else to manage the disposal of these items?

How Will You Get Rid of the Last Few Items

  1. Will you throw it all in the city trash?
  2. Will the city trash pick up your stuff?
  3. Do you need to make arrangements to take stuff to the dump?
  4. Should you have an open house for the remaining items?
  5. Should you pay someone to clean out the last of the last items?

Where Will You Domicile/Get Mail/Vote?

  1. Will you keep your current address for voting and mail?
  2. Is your current state tax friendly to your new life style?
  3. Do you need to move to a different state?
  4. Have you signed up for a mail service?
  5. Who will get your mail?
  6. Where will you vote?
  7. How will you get absentee ballots?

Need answers? Get our book, Two Carry-Ons and a Plan: Retiring as Full-Time Nomads available on Amazon.

How Will You Insure Yourself?/Medical Care

  1. Do you need medical insurance?
  2. Does your medical insurance need to cover you in the US?
  3. Do you have pre-existing conditions that will affect your medical coverage?
  4. Do you have prescriptions?
  5. Will your doctor write year-long prescriptions for you?
  6. Where will you get medical care?
  7. Will you come back to the States for routine care?
  8. Can you get the care you need while on the road?

How Will You Bank/Pay/Credit Cards?

  1. How will you get cash on the road?
  2. How will you pay bills?
  3. Do you have good travel credit cards?
  4. What if your credit cards go fraud?
  5. What if your ATM card gets stolen?
  6. How will you manage your portfolio?
  7. How will you pay and file taxes?

Which credit cards to we have? We answer all of that in our book.

How Will You Communicate/Cell Phone/Apps/Computers?

  1. What cell phone will you use?
  2. How will you make phone calls?
  3. How will you use data?
  4. What data plan will you use?
  5. What apps do you need to install?
  6. How will you carry a computer safely?

Need answers? Get our book, Two Carry-Ons and a Plan: Retiring as Full-Time Nomads available on Amazon.

What Other Devices Do You Need?

  1. Will you get a VPN?
  2. Will you use a router?
  3. Do you need camera/video equipment?
  4. How will you insure these devices?
  5. How will you prevent theft?
  6. What if these devices break? How will you replace?

We used to use Google Fi, but we got fired. What happened? Read about it here.

What Documents Do You Need to Bring With You?

  1. Is your passport up to date?
  2. Does your passport have enough pages?
  3. Do you need any visas?
  4. Do you have copies of your passport in the cloud?
  5. Do you have your Covid vaccination card (and others)?
  6. What other papers do you need to bring?

Where Will You Stay?

  1. Will you stay in Airnbs? VRBOs?
  2. Will you stay in hotels?
  3. Will you couch surf?
  4. Do you have minimum criteria for your nightly accomodation?

What Will You Wear?

  1. Do you need clothes for all seasons?
  2. Are you willing to replace clothes on the road?
  3. Will you shop at second-hand/charity shops?
  4. Do you need special gear/clothing?
  5. What shoes will you bring?
  6. Can you ship yourself stuff seasonally?

Need answers? Get our book, Two Carry-Ons and a Plan: Retiring as Full-Time Nomads available on Amazon.

What about Beauty and Self-Care?

  1. Do you need to carry special products with you?
  2. Can you easily replace those products?
  3. Do you have a haircut or color you want to maintain?
  4. Where will you get massages? Nails done? Hair removed?
  5. Can you meditate anywhere?
  6. Where will you work out?
  7. How will you exercise?
  8. Are you fit enough for the daily step count and luggage lift of nomad life?

Work Them One at a Time

These are a lot of questions. Don’t let them get you down or overwhelm you. Set a time line (we had two years) and work backward. Put things on the calendar and cross them off as you go. You can do this. We did, and we’ve yet to look back. Enjoy!

Need motivation or inspiration. Get our book, Two Carry-Ons and a Plan: Retiring as Full-Time Nomads available on Amazon. We answer all of these questions, lay out real time lines, real costs, and real obstacles. Our story is your story. Have a blast.

2 Comments

  1. Paula Kiger

    Well thought through. Thanks for sharing.

    Reply
    • EatWalkLearn

      thank you so much. Are you planning a similar adventure?

      Reply

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handsome hiking couple

Chris and Steve, the empty-nesting nomads, travel the world, one month at a time, housesitting and Airbnbing along the way. We uncover urban walks, great hikes, and vegan/vegetarian eats that other guide books miss. And we throw in a bit about Forex trading along the way.

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