How to Make Money While Traveling Wherever You Want — I’ve Done It for 10 Years

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How to Make Money While Traveling Wherever You Want — I’ve Done It for 10 Years

Scott LiebermanHow to Make Money While Traveling Wherever You Want — I’ve Done It for 10 YearsMillion Mile Secrets Team

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Scott:   I have made money while traveling for the past decade.  Here’s how I’ve done it.  And here are ways people I know have done it.  And I’ll give you other options too.  Don’t worry.  None involve you becoming an Instagram bikini model.

How To Make Money While Traveling
That’s me, Scott, about to indulge on unlimited beach-side cocktails at the all-inclusive Hyatt Zilara in Cancun. I paid $0 by using points from my Chase Sapphire Preferred card. I paid $5 for sunblock on my scalp. It was a good investment.

How to Make Money While Traveling

I’ll start with my personal experience.  Because of the work I’ve done, and with the help of our money-saving travel secrets, I’ve enjoyed:

  • a month living just a 5-minute walk to the beach in Punta Cana, Dominican Republic
  • a 2-week cruise around the UK and Ireland to make my Game of Thrones sightseeing dreams come true
  • summer in Montreal (where I attended the biggest international comedy festival in the world)
  • a month in Portugal (loved Anthony Bourdain’s favorite seafood restaurant and explored amazing hill-top castles)
  • life with Finnish folks in Helsinki (with a side-trip to the must-see Tallinn, Estonia)
  • life with Polish people (where I saw the most amazing man-made creation and then the saddest man-made catastrophe)
  • life with Mexican amigos (where I learned the best small towns outside Cancun for true relaxation and island-style living)

And much more, including months in France eating entire fresh baguettes for breakfast, and weeks at a time in various countries throughout Europe and the Caribbean.

Also, while in Amsterdam — I’m not proud of this, but — I was walking around and nearly got hit by a trolley, car, and bicyclist at the same time.  Definitely look all ways before crossing the street there.  It’s crazy.

I don’t travel all the time.  But I can if I choose.  And to me, that’s the fun part.

OK, OK, Which Jobs Will Allow Me to Travel While Getting Paid?

US-based jobs that allow you to work from anywhere you want…

I edit, write, and do other work remotely for Million Mile Secrets.  But you can apply for jobs with different companies as a:

  • coder
  • online marketer (pay-per-click professional, email marketing expert, social media guru, etc.)
  • graphic designer
  • do you know what a “pivot table” is?  Then you can do stuff with Excel spreadsheets for management types

It’s not just our Million Mile Secrets writers who can work while traveling.  Our digital marketing professional also makes his money while traveling.

How To Make Money While Traveling
I visited Blarney Castle (just outside Cork, Ireland) but REFUSED to wait in the ridiculously long line to kiss the famous Blarney Stone. I’d be that guy who first disinfects it with anti-bacterial wipes anyway. That said, I’d visit again! Not to get the “gift of gab” but because of the gorgeous gardens nearby — they’re some of the most beautiful I’ve ever seen — no offense to New Jersey, “The Garden State.”

US-based businesses you can start so you can make money while traveling…

Instead of being employed by one company, you can BE the company and earn work from various organizations.

The best freelance travel writers form strong relationships with various online publications because of their expertise and work ethic.  They can make 6-figure incomes.

How To Make Money While Traveling
You can get this traditional Lapland treat in Finland. It’s delicious sautéed reindeer with mashed potatoes and lingonberries. I’ve used credit card points to fly non-stop on Finnair.

But you can run other businesses online besides writing for travel blogs or writing your own travel blog.  I worked for myself and wrote about completely different topics before I joined Million Mile Secrets.  I’ve also worked in online marketing.

Some folks start websites to sell products from others companies online.  This is called affiliate marketing.  You are affiliated with those companies and they pay you a percentage of whatever you sell, whether it be clothing, fitness equipment, or memorabilia from the hit TV sitcom ALF.

Can you attract a lot of attention?

If you can get millions of people to watch your videos or listen to your podcast or read your blog, you’ll have an opportunity to sell space on your show or blog to advertisers who want to reach your audience.  But you do not necessarily need millions of people in your audience if your following is of a demographic that particular advertisers are struggling to reach.

You also don’t need millions of fans to sell your OWN products.  Your adoring fans may want to buy your self-published book, enlightening e-course, pay for private consultations, or pay to see you speak in person.

I’ve had friends who were and are performers.  They took gigs as entertainers on cruise ships as a way to make money while traveling.  And they have accepted paid shows overseas and stayed extra to enjoy exploring a new country.  Performers include the obvious like singers, dancers, comedians, and musicians, but there is also money for public speakers who are experts in various topics.

Also, there has yet to be a downturn in the “tourists-who-want-a-photo-with-a-parrot-on-their-shoulder” market.  So if you can train a colorful bird, you’ll always make money wherever you go.  (I knew a guy who did that, too.  Really.)

How To Make Money While Traveling
This is the prettiest boat parking lot I’ve ever photographed. The old harbor in Honfleur, France, with its 16th century townhouses has inspired artists like Claude Monet and Eugène Boudin.

You can pick up jobs in the various places you visit.

This isn’t my style, but I’ve met free spirits who have taken jobs such as:

  • front desk person at a youth hostel so they could live in New York City for a summer
  • cleaning snow off roofs in Helsinki, Finland, was how one Australian young man made money
  • work at a resort during their busy season

Cruise Ship Worker, English Teacher, Landlord, Pet Sitter, and More

I’ve been on a number of cruises, and while many crew workers are NOT traveling for the enjoyment — SOME are.  I got to know a bartender or two or ten during my time on cruises.  And some saw the job as a way to make money and see the world while meeting fascinating customers who speak too loudly while peppering them with questions about why they bartend on a ship.

I have an American friend who taught English in-person in Asia.  There are also jobs where you teach English online.  Teaching any course online could be a good way to make money while traveling.  (There are sites like udemy.com that advertise to gain students and then pay you to teach them a subject.)

How To Make Money While Traveling
Mighty and mysterious prehistoric Stonehenge… no one is certain how it was built. I thought, “Bah, I don’t want to see a bunch of stacked rocks.” But I was wrong! It was really cool and I’m glad I visited.

Sites like upwork.com help you find legitimate online jobs (though use common sense) that include social media management, accounting, virtual assistant work, search engine optimization, research, and website design.

I had a friend who worked as an online day trader and spent half the day on the beach.  He later quit to travel the world.  He used savings and — this part was key — he owned a rental property.  That income funded his travels.

  • If you own a home, you could rent it out while you travel.  Sure, strangers will sleep in your bed and use your toothbrush.  But it’s OK because you’ll probably forget that happened by the time you get back.
  • I’ve met young women who worked as au pairs so they could live in a new country for a time.
  • You may be able to make money while traveling to different spots as a pet sitter or house sitter.  And yes, there are apps for that.

Keys to Making Money While Traveling

You can decide to make just enough to get by.  Or you can really build your business or career by taking your work seriously like I do.

Here’s what I’ve done.  I try to AVOID running around to different places like 2 days here and 2 days there.  That’s too stressful for me.  And I usually don’t enjoy that kind of travel.

I prefer to pick a place and plop down for anywhere from 3 weeks to 3 months.  I work full days or more.  And I use weekends and after-work hours (or before work hours depending on the time zone) to explore.  I usually live like a local in a regular neighborhood Airbnb apartment.  Then I bust out my points for an awesome weekend splurge at an upscale hotel.  And credit card miles help me affordably fly to the places I go.

Do Not Screw This Up If You Want to Work Online While Traveling

When your business is online, you absolutely 100% need reliable internet.  I’ve run into unexpected problems over the last 10 years, but I’ve never been without internet for long.  Because I always have a back-up and a back-up to the back-up.

How To Make Money While Traveling
Making a new friend in Mexico… He taught me how he drinks mezcal. 1. You drink the smooth but very strong liquor (similar to tequila but better) 2. You bite into the orange slice that’s coated with sal de gusano (worm salt) 3. Wash it down with beer. 4. You blurt out, “Guácala! … Que Rico!!” Translation: “Disgusting! (then when it hits you) “Delicious!!”

Do not assume a great hotel has great internet.  And do not assume the Airbnb that bills itself as having “fast Wi-Fi” will have reliable internet.  Here’s what to do if your work life depends on internet:

I usually rent an apartment on Airbnb and earn travel points by paying with my Chase Sapphire Preferred.  I used to just ask the host to take a screenshot of speedtest.net from their apartment.  For the work I do, 10 Mb download and 2 Mb upload is the minimum I need.  But beware!

I’ve learned it’s NOT merely the speed that matters when you are relying on internet for important work phone calls.  The connection must be steady.  Some internet works in spurts.  It’s 10 Mb one second and .1 the next!  Do you ever get that “buffering” message while watching a video?

That’s fine because you can pause and it’ll catch up.  But that doesn’t work when you’re trying to have a live conversation.

So if I’m staying somewhere a relatively long time, I try to get the Airbnb host to video call me on Skype for 5 minutes to give me a visual tour of the place.  I want to be sure the conversation isn’t “choppy.”

The host is often willing to do this because you’re paying a fair amount of local currency when you book someone’s place for a month or more.

Note:   Renting an Airbnb is a great way to use your Capital One Venture Rewards Credit Card miles instead of money!

How To Make Money While Traveling
“Ironborn! Behold House Greyjoy!” Ruined medieval Dunluce Castle in Northern Ireland is one of the impressive settings in the epic Game of Thrones series. I greatly subsidized this trip thanks to credit card points. And I had time to go because I work online.

My back-up is to know exactly where the local shops are that have good internet.  If I had to, I could work from there.  So I make sure to know their hours.

My other back-up is T-Mobile.  While traveling the US, Mexico, and Canada, I’ve been able to connect my computer to my phone’s internet and it’s been reliable.  In other countries, T-Mobile doesn’t let you do that.  But the included international 2G or 3G on your T-Mobile phone (check your plan) may be just enough to make phone calls over Wi-Fi.  (You can call 800 numbers for free on Skype.  And you can call any US number for free using Google Hangouts.)

How to Stretch Your Money While Working and Traveling

I keep my ongoing expenses pretty low.  My US apartment is modest.  At times I’ve lived with roommates to keep costs down.  My car is very impressive to ladies who admire a budget-savvy man.  I am VERY fortunate to be in good health, so I don’t have those bills to pay at the moment.

While living abroad, I do NOT eat at fancy restaurants all the time.  Sure, I pick the best places for date night or to splurge.  But day-to-day I live more like a local.

How To Make Money While Traveling
Worth the price! This is the most delicious seafood I’ve ever had. This is a place called Matt the Thresher in Dublin. And you know I earned 2X points by paying with my Chase Sapphire Preferred. 🙂

I go to the supermarket and cook at home.  I always use credit cards with no foreign transaction fees, like my trusty Chase Sapphire Preferred.  I use credit cards to earn miles and points whenever possible.  I research tourist-type deals in each place.  But I also try to meet local people and learn their insider secrets.  You can read forums all day but talking to a few people might net you better advice if you come to trust them.

For instance, when I lived in New York City, tourists who befriended me would get this suggestion from me, “Skip the long line and expense of going to the observation deck of The Empire State Building.  Because you can’t see the iconic Empire State Building from inside itself!  Instead, there’s free admission to 230 Fifth Rooftop Bar.  There you’ll witness a stunning view of Gotham’s famous 102-story Art Deco skyscraper.”

Then the tourist-person would reply, “Thanks Mister-who-speaks-like-a-travel-writer!”

How To Make Money While Traveling
This is February in the Bahamas. The sand is soft and white. This was a cruise ship stop. You can fly nearly free to the departure port city with airline miles you earn from credit card sign-up bonuses!

The best city tours I’ve ever done were free walking tours where the guides worked for tips.  You can find these on TripAdvisor.  I had great experiences with free walking tours in Budapest, Warsaw, and more.  When I want to see an important or fun tourist site that’s outside the city, I don’t take a cab.  I take an arranged bus trip to save money.

I’m not a fan of city buses and trolleys but I’ll do it if it’s a lot cheaper than a taxi.  It depends on the day and whether I’m valuing money or time.  Either way, I pay with my Chase Sapphire Preferred to earn 2X points per dollar on travel expenses.  And those points discount my next trip!

Do things that are awesome but happen to be cheap where you are

But don’t be so cheap as to miss out on once-in-a-lifetime experiences!  To me it’s all about value – not whether it’s cheap or not.  For example, I treasure a quality back massage.  (Dear Professional Massage Artists, thank you.  I am completely convinced we’d have world peace if every angry ranting dictator would just sit down for a good neck and shoulder rub.)  So if a massage happens to be a good deal where I’m living/visiting, I’ll go for it!  This was the case in both Poland and on the beach in the Dominican Republic.

I can’t remember the price of summer strawberries in Finland — but they were the best I’ve ever tasted.  So it was worth it.  And Fazer chocolate bars in Finland are the best big name chocolate I’ve ever had.  And just about every home has a sauna.  So I enjoy that and do less of things that are expensive there, like drinking in bars.

Bottom Line

My name is Scott, and I look forward to helping you travel while making money and sharing my secrets and tricks for Big Travel!

To earn money while seeing the world, you might consider working for a company that allows you to travel, starting your own location-independent business, working on a cruise ship, or gaining temporary employment at the places you go.

Here’s how I do it:  I secured a work-from-home job based on my previous education and self-made experience.  I mainly use airline miles to fly to Europe and the Caribbean.  This has saved me many thousands of dollars.  I prefer long stays in neighborhood Airbnb apartments.  Then I use hotel points for luxury weekend hotel stays that would cost ~$500 per night.

My favorite credit card is my Chase Sapphire Preferred.  The sign-up bonus is terrific, because depending on how you use it, you can get $625 worth of travel with no blackout dates through their portal OR $1,000+ worth of travel when you transfer to their top-notch airline and hotel partners.

And my favorite part about working at Million Mile Secrets is when you guys send us your amazing success stories and photos!  I get a rush seeing all the different ways you choose to travel with your miles!

If you liked this post, why don’t you join the 25,000+ readers who have signed-up to receive free blog posts via email (only 1 email per day!) or in an RSS reader …because then you’ll never miss another update!

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  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
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Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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That’s what I want to do when I grow up!

I’m a 76 years old retired physician.

I love going to an area for 2-3 months and spending 2-4 weeks in an area, just walking around and eating local. I don’t need to earn money, but don’t spend a lot and have close to 5 million miles to squander.

It’s also nice to have a loved one to travel with!

J R

Author
Scott Lieberman

Agreed!

Spread the word to your fellow retired folks who want to travel spending miles, NOT money! 🙂

Great article! Loved the idea of the free walking tours. Use WhatsApp for free calls, texts, photos on WiFi or data, anywhere. When working from your computer, don’t some countries require a work permit? Taxes? Thanks!

Author
Scott Lieberman

Thanks, Karey! Free walking tours can be a fun way to meet fellow travelers, too.

Good tip about WhatsApp!

Definitely follow the work rules wherever you go.

Enjoy your travels and I’m looking forward to your upcoming Success Story! 🙂