Me on the Great Ocean Road

How I Can Afford My Life Of Constant Travel

Derek Popular, Work & Travel 1346 Comments

Me on the Great Ocean Road

I’m confused.

I’m simply confused as to how it’s possible that I have so far failed to properly explain how I’ve managed to travel/live/work abroad nonstop for 12 years straight (and counting).

The questions are still pouring in every single day: How do you do it? How is it possible to travel for so long? Where does the money come from?

And while I thoroughly enjoy communicating with readers (I’m being completely serious and encourage you all to continue sending your emails to me as often as you wish), the fact that these very questions are on the minds of so many of you out there has led me to believe that I need to do a better job at providing the answers.

While it’s true that I’ve already written plenty of posts on the matter, clearly all of these posts, even as one collective entity, still fall well short of proving that a life of travel is not some crazy fantasy but a perfectly reasonable and easily attainable lifestyle option instead.

I’ve even referred to other travelers who are out there living a similar nomadic lifestyle, but apparently, that hasn’t been enough either.

So what am I to do?

How do I prove, once and for all, that you do not need $500,000 or even $50,000 in your bank account, that if you are able to scrounge together $500 bucks, there’s little stopping you from becoming a full-time nomad. I’m not joking here. After all, this is exactly what I’ve done myself. Okay, I first left home with $1500 to my name but that’s not exactly a fortune either.

I’m not going to give up trying, so here’s another attempt to show you how I’ve managed to live a life of constant travel.

The following is a brief summary of the past 12 years of my life. It is a timeline of sorts that details where I’ve been, what I’ve been doing and where my money has come from at all times. Ultimately, it shows just how one ordinary person has so far managed to fund 4,195 days straight of traveling and living abroad.

Dead Cities in Syria


December 25, 1999:

  • Left home and flew to Bangkok with $1500 in my bank account
  • Planned to spend 3 months traveling around Southeast Asia

March 2000

  • Decided to officially extend my trip despite having only $500 left to my name
  • Taught English in Chiang Mai, Thailand, earning approximately $150 USD per week (more than enough to live well in this city at the time)

October 2000

  • Returned to the US with $300 in my account (after paying for the flight home)
  • Spent 2 months in Boston working as a high school substitute teacher
  • Saved $2500 during this time

January 2001

  • Returned to Asia and spent 12 months traveling through Thailand, Burma, Indonesia, Singapore, Malaysia and Australia
  • While in India, volunteered as an English teacher for 3 months in exchange for room and board
  • Stayed with friends for 3 months in Thailand and taught English once again in Chiang Mai
  • Lived with friends for 2 months in Australia, which kept my expenses quite low
  • Returned to the US with no money at all

February 2002

  • Through a contact, I applied to work on board cruise ships
  • Landed a job as a Tour Staff with Carnival Cruise Lines
  • Worked on board two different ships during one 8-month contract
  • Saved $8000 during this time and then decided not to return for another contract

November 2002

  • Traveled to Australia for 4 months

February 2003

  • With $4000 in the bank, I spent two months living with a friend in Los Angeles
  • Found a short-term job at an advertising company through a temp agency
  • Worked for two months and left LA with $5000 in the bank

April 2003

  • Traveled to Thailand, Bangladesh and India

Norwegian Cruise Lines

September 2003

  • Landed a job as a Tour Manager for Norwegian Cruise Lines
  • Worked two contracts on board ships located in Hawaii and the South Pacific
  • Traveled to Europe during my 6-week vacation between contracts
  • Saved $20,000 by the end of my second contract

July 2004

  • Spent 7 months traveling to Europe, India, Nepal, Pakistan and Afghanistan

March 2005

  • With $10,000 still in my account, decided to work two more contracts as a Tour Manager for Norwegian Cruise Lines
  • Saved an additional $20,000 during these contracts
  • Traveled to Europe during my 2-month vacation in between contracts

December 2005

  • Traveled for 8 months to South America, Europe and India

La Boca, Buenos Aires

September 2006

  • Was offered a job with Cunard Line (cruise line based out of the UK)
  • Worked as a Tour Manager on board the Queen Mary 2 and Queen Elizabeth 2 ocean liners
  • Spent 18 months with Cunard, saving over $3300 per month
  • Traveled through Europe, Caribbean, Mexico, the Middle East and SE Asia during my vacations in between contracts

April 2008

  • Traveled back to India for 3 months

July 2008

  • Worked one final two-month contract for Cunard Line, saving an additional $6000

September 2008

  • Left Cunard (with more than enough money saved up by now) and moved to Australia
  • Spent five months in Melbourne working on creating online streams of income

December 2008

  • Sold my first eBook online
  • Continued working on promoting my eBook while creating a second eBook to sell
  • Began earning some income through affiliate marketing

February 2009

  • Spent six weeks in Thailand
  • Volunteered and traveled in India for six weeks
  • Visited Italy for a few weeks

Tuscany, Italy

June 2009

  • Traveled through Central America and Mexico, finishing the trip by renting an apartment in Sayulita, Mexico
  • Continued working on my online projects
  • Income from my online projects reached $1000 per month for the first time

December 2009

  • Moved to the Caribbean coast of Mexico and rented an apartment in Playa del Carmen, where I spent more time working on my online projects
  • Officially launched

September 2010

  • Spent 6 months traveling around the Middle East, Australia and Southeast Asia

April 2011

  • Returned to Playa del Carmen (where I am currently living) in order to catch up on work
  • Reached $2500+ per month in online income through the sales of three eBooks I’ve authored and through my efforts with affiliate marketing

Right Now

  • Planning some new adventures for later this year, including a most interesting 30 day train challenge for the month of September (more details to come in my next post)
  • Life as a permanent nomad continues

And that’s all there is to it. The truth of the matter is…

$2500 per month, and even $1000 or $1500 per month, is more than sufficient to achieve a lifestyle that involves extensive travel. It really doesn’t take much. Some teaching English here, some cruise ship work there, some internet marketing in your spare time and VOILA!

And this is only a tiny fraction of the opportunities to earn money while traveling that exist out there. Once you realize this, you’ll also realize that luck, miracles and having an overflowing bank account play no role whatsoever in allowing you to achieve your travel goals.

All you need is the courage to take the first step and a mind that is open to trying new experiences!

***If you want to create your own life of travel, you may be interested in my new project – How to Live a Life of Travel.

This one resource will teach you everything you need to know. Be sure to check it out!***

Since 1999 I've been traveling and living around the world nonstop. Sign up below for personal stories, real advice and useful updates from my adventures. Only good stuff, no nonsense.

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Comments 1,346

  1. Henry

    What are your plans for retirement? Do you have any savings for that, or are you planning on working till you drop? What about if something catastrophic healthwise happens?

    1. Post

      Hey Henry – I’ve been saving money whenever I can and since 2009, when I started working online, I’ve saved every month. And I have health insurance in the US in case anything happens. In the end, it’s really no different than any other lifestyle…I work, earn money, save money, have health insurance just like everyone else!

  2. Jaycen Timm

    hi there! I am currently a high school senior and am so undecided on a major for college. I really want to travel. Did you get a college degree?

    1. Post
  3. Jc

    Hi wanderingEarl, I enjoyed reading your blogs/stories about your nomadic lifestyle. Such an inspiration especially to those people like me who wants to travel around the globe. Keep inspiring.God bless!

  4. Kylee from Kylee Cooks

    I always found it hard to explain how I left home in 1999 and returned home-ish, in 2004 when people say “you’re so lucky”

    Well, luck has nothing to do with it. I worked and saved before I left – just to have a cushion. But when I arrived in the UK – I grabbed a temp job. Working hard when there’s work, not being too picky about what you do (it’s pretty easy to stomach handing out flyers for a job while in the Greek Islands), and being open and flexible – and interested in traveling to places that aren’t necessarily on the tourist map. Being open to being a bartender one day, an office temp the next, and then passing out flyers the next.

    Seeing opportunity wherever you go, is key.

    I used to work in London for a little bit as a temp – then disappear for an original intention of being gone for a week, and ending up working in a campground in Oludinez in Turkey for 4 months. It was random, I was like – I like it here, how can I stay and not drain my bank account? So, I just asked “hey, can I work here?” and what do you know? They gave me a job. I spent my time off lazing in the blue lagoon, checking out the rest of the country and having experiences only possible by being at the right place at the right time.

    Back then, internet marketing wasn’t so huge – and I WISH I had had the resources we do now. I’m now older, married, and have children – but I’m SO glad that I had the life changing experiences in my 20s that allow me to BE settled now.

    It’s about the life experience….. right?

  5. Gary Gilbert

    Hi Earl,

    Nice write up, we have “only” been on the road for a little over two years, though in our Landrover Defender. What is interesting to see it that you are not travelling with your own vehicle but you have projected similar costs as we have experienced with our own vehicle. I guess the costs of travelling by bus and staying in youth hostels or similar evens out the costs of camping, fuel and repair expenses.

  6. Katie - Round the World Magazine

    What a brilliant, inspirational way to live. We hope to live the same life and we’re just starting out. Thanks for the tips.
    Can’t wait to hear about the 30 day train challenge!

  7. Maya

    I am in your shoes now have $1,500 to my name and I want to go back to travel. I just came back from a trip I feel like I want to go back on the road. The thought of getting a “job” here just depletes my soul.

  8. Raymond Carroll

    Hi Earl, I just ‘StumbledUpon’ this post, it’s a great read (even although it’s a few years old). First time I was in Thailand was in 1999. I went there to manage a bar on Koh Samet – bar thing didn’t work out but I stayed for 3 months and met a girl, before traveling to Nepal, and then back to Thailand. Found out that my Thai girlfriend was pregnant, returned to the UK to make some money and then went back to Thailand in 2000-2001 (for 6 months) to visit my girlfriend and daughter. Returned to Thailand and stayed in Bangkok, Pattaya, Phuket, & Taiwan (2 years this time, 2002 -2004, doing mostly sales jobs); returned to the UK with my girlfriend and daughter because my girlfriend was pregnant at the time with our second child (my son – now 12 years old in 2017).

    Prior to going to Thailand in 1999, I had lived and worked in Jersey in the Channel Islands (2 years), Canada (18 months), California (1 year), Egypt (6 months), and London UK (15 months); I am originally from Glasgow, Scotland.

    Kids put paid to the more or less constant traveling, but I have no regrets – my kids are my best pals; luckily I am self-employed back in Scotland so still get to travel more than most. Off to Barcelona in April, trekking in Nepal in October this year also. I also have some online interests – a novel I have written set in Thailand, and I own and operate a Thailand Travel Blog, and make some money with that through affiliate marketing.

    How are you these days? Still on the road? Hope all is well and wish you good luck for the future.


  9. chip ruckgaber

    So my question is did you have health insurance? If yes how did you pay for it? If no what was your plan if you got real sick or injured?
    I hope you did not expect that you would just go to the hospital and the rest of society would pay your bill.

    1. Post

      Hey Chip – Yes, I usually had travel insurance and I’ve also had private health insurance in the US. But the couple of times I got sick or injured while traveling, it was usually cheaper to just pay at the hospital and not go through my insurance. When I busted my toes in Thailand, I had extensive care in the hospital and it cost $30.

  10. Omar

    Inspirational! I aspire to live the nomadic lifestyle in the near future, but until then, I guess my “work to live” philosophy will have to do. I consider myself somewhat of a “part time nomad”, makes little sense I know, but I’ve explained it in an article I wrote entitled “living to work, why I refuse”

    I think a big part of the problem is that many of us find ourselves tied down with well paid jobs, mortgages and children, which isn’t the best starting point when wanting to be nomadic!

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  12. Maartje

    That’s amazing! You are a great inspiration! I’ve been on the road for 4 years now reading your blogs frequently. Travelling long term is possible, for the right people of course. I think it’s great that you show others that it’s possible.

  13. ajay

    Nicely done.. i noticed that you travvelled to india quite a few times. just wondering what was the attraction and what parts have you travelled there?

    1. Post

      Hey Ajay – I just find India to be one of those countries where, every time I visit, I have a completely different experience. Also, it’s so large and diverse that I can always find something that interests me. I’ve actually be to India 23 times now and have pretty much explored most of the country 🙂

  14. Ayush

    Thank-you so much for this inspiration..i just can’t wait to take full control of my life. Once i do, I’ll start travelling and never stop

  15. Shana Jones

    Great post, Earl, and very very motivating! I guess anything is possible if you remove the barriers and personal hangups. Thanks!

  16. Orange

    To begin with, you are very fortunate be a national coming from a 1st world country as your passport does not require you to get visa approval in major countries.
    And yes, I sadly envy you as I have been wanting to travel and see the sun and moon from other side of the world.
    Hope I could bump into you someday and will certainly be happy to hear from you directly your crazy topsy turvy journey=)

  17. harambee

    Hey WEarl, Do U Know transports from Islands like Bahamas to Cuba to Jamaica or Turks. Trying to see if I can fly from Florida & hit several islands inexpensively. URock & Thanks!

    1. Post

      There’s really no way to do that inexpensively unfortunately. Stopping in the islands along the way always adds a lot of money to the total cost.

  18. Sandra Muller

    Thanks for sharing your journey. I’ve just moved to Vietnam to give the digital nomad thing a go for a few months – I work as a copywriter. Turns out I’m not much of a digital nomad, so I’ve taken the ‘nomad’ out of being a digital nomad and instead, I’ve set up a kind of home base in Nha Trang. I lived and worked abroad for a few years back in the early 200s, but this time has been more challenging as now I have a husband and three-year-old in tow!

  19. Cindy Coco Follonier

    Love this post and laughed a bit because my friends always think that I spend my life traveling and that money falls from the sky. I mean if it would we would know it right?! I think it’s great that you explained it all and that hopefully people who think we need lots of money to travel the world will understand the tips & tricks and will get inspired. 🙂 On a personal note, I believe that if people were less materialistic, they would suddenly figure out that their money can be spent on amazing experiences around the globe rather than on a new car or pair or shoes they don’t need…

  20. Gessell

    What an amazing journey. It makes me think of what I could have accomplished years ago if I set out to try to do it then. Now I have a baby to support which makes the budget traveling a bit more difficult. I recently wrote a family travel guide to Amsterdam, where we’re living as American expats. Hope to make a series out of that and pursue traveling more often. Here’s hoping!

  21. Paul

    Very interesting reading.

    My question is about your business and where you have set it up?
    I guess you have to pay tax somewhere?

    1. Post
  22. Namastegypsy

    Hey Earl!

    Thanks so much for posting this.

    I’m a junior traveller with aspirations to one day travel close to full time. It’s great seeing your break down with the timeline and it shows me, and I’m sure your other readers, that you have to think outside the box to make the lifestyle work. There are also far more ways to earn enough coin to keep on the road that what most people imagine.

    Thanks again and I look forward to more articles!


  23. Ep

    The people I’ve known with nomadic travelling lifestyles all had favorabke life situations and opportunities that enabled them to take on such lifestyles.

    They were all university grads/students with supportive well-to-do families and/or friends they could fall back on ( if things went wrong) They didn’t have to bunker down in unfavorable dead end jobs just to make ends meet…

    What I’m trying to say is, the opprtunies described in the article are not available to everyone who would like to embark on such a journey.

    1. Wandering Earl

      Hey Ep – I can say that after meeting thousands of people over the past 16 years of travel, I’ve met plenty of travelers who don’t fit into that category you describe. So I’d have to disagree with that statement that it’s not open to everyone as I’ve heard incredible stories, over and over again, from those who did not have university degrees, who didn’t have supportive families, who had nothing to fall back on…and yet they used their determination to make it happen!

      1. Ivan the Intrepid

        I agree! I’ve met travelers from all different walks of life. You meet people from less than fortunate backgrounds especially in cheap travel places. In my opinion, the only real excuse is being from a country that is unstable, has a week currency, and/or a restricted passport. If you are from Europe, the US, Canada, Australia, etc., then really the only thing holding you back is you. That’s not to say it isn’t easier for some than others and it’s not to down play the obstacles that poverty and rough family backgrounds creates. But I don’t believe for a second that, with the right mindset, those are things that can prevent you from traveling the world. Thanks for the post!

  24. Tristian

    Very interesting Diary ;), I have found especially interesting working on Cruise ships ;). I was wondering, your online income comes mostly from sales (your products) and affiliate sales, yes ?

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  26. Serhat Engul

    Sometimes I feel like leaving everything and set out for a long term journey. This is a lifetime dream. I travelled across Europe and India with my backpack but I never dare to leave my settled life for a long time. Actually I did not even know how to do it!
    Now I have the clues. Thank you for sharing secret of your 13 year journey. That is amazing! This is not related to money and time only, but the power of your mind and spirit. I congratulate you my friend. Cheers.

  27. nomadnaturally

    I agree, it can be hard for some people to understand how this digital nomad lifestyle works. It’s hard to get that you don’t need to HAVE that much money to travel everywhere. Usually, most people think of travel in terms of a vacation, which can be expensive, because of course you want to splurge and enjoy and relax since you’re away from home. But traveling as a lifestyle, which I’ve done for over 5 years—that requires a much smaller budget, much less expenses. Even as I write that, it sounds sort of hard to believe 🙂 so I get how it’s confusing. I’ve been trying to explain the way I work and travel on my blog, and recently tried to break down the very specific steps of how to get into travel writing (, although you really have to be motivated, because travel writing alone won’t support long term travels from my own experience–other kinds of freelance writing will, however. In the end, you’ve just got to be persistent and flexible, no matter what kind of jobs you pursue to support your travels.

  28. Jonathan Chin

    This is an extraordinary journey – great stuff. I recently left Australia to work as an Au Pair in Spain for the next 6 months. I’m not planning on coming back home anytime soon, and this has given me just a tad more confidence 🙂

  29. Emma

    I’m returning to this post after being away for (so far) six months. I now feel a lot more confident in being able to manage long term travel. Thank you so much being a motivator in my trip!

  30. Daniel

    I am about to graduate with a PR degree and I am very proficient in video production and have been reading all I can on living and traveling. Do you typically find jobs before you travel to the next location or do find them there? If yes, what means of finding jobs do you utilize. Additionally, how were living conditions? I’m the kind of person who doesn’t mind sleeping outside, or anywhere for that matter.

  31. M

    The fact that you had degree to teach English, contacts for cruise ship work and friends to stay with abroad on multiple occasions in your timeline, every two month period of working while back in the US you managed too save a few thousand is why your able to live a traveling lifestyle. As well as good fortune to have gotten hired abroad and back in the US when you needed too, unemployment is not exactly mythical issue in any country. It’s getting tired how nomadic blogs like this push “anyone” can accomplish this lifestyle, yet successful examples have very particular details that made it possible. Bottom line is if you have money in the bank you can use said funds to pay for as much travel as you can afford. If you don’t you have to figure out continued income or you just vacationing. Being conservative in spending is neither “creative” nor “clever” its common sense, if your bad with your money traveling on a dime isn’t going to workout for you.

    1. Nick Omeara

      Correct; I think Earl is also very lucky man.. beside being smart.. To get jobs like the manager of Norwegian lines is like vinning the lottery … And “living with friends” for months… hmmm .. not everyone’s cup of tea .. ?

      1. Ep

        Exactly… Not everyone can be so lucky to find themselves in life situations that allow for such opportunities.
        It would be disingenuous to assume everyone have those options…

  32. Christopher

    Hey there wandering Earl, I was wondering do you have to have a degree in order to teach english in a foreign country? I know different countries have different requirements.

  33. Kerry-Anne Rowe

    What about black people? Can blacks travel as well without fear of skin color? Because I am from Jamaica and i want to travel soon and i am doing a degree in management studies.

    1. Thomas

      Don’t get caught up in all of that nonsense. Everywhere you go there are some black people. i lived in japan for 6 years with dark skinned African American friends and als Jamaican people that I know are still there. there is always people who may or may not be weary of you but if you approach life with an infectious msile and good cheer, you will have great experiences that far outweigh the negative. I travelled troughout Thailand and Vietnam with my dark skinned canadian friend and we had a blast. he further travelled at least 10 European countries and had 99% positive experiences. He told me there were a few times he new he was being judged but nothing stopped home from enjoying himself and coming home safe. I have also been to Cambodia, Hong Kong, Singapore, Mexico, and Canada. There were always at least some people of brown or black color. Forget all of that and enjoy life!

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