How to Land Jobs Along the Way While you Travel

by Nora on May 27, 2013


If you’re over the age of 30 (and thus not eligible for working holiday visas), and if you’re not interested in managing an online business while you travel, you might wonder how to make your full-time travel adventures financially sustainable.

Never fear! Where there’s a will, there’s a way.


DeborahI was chatting with Deborah Benbrook, who has been traveling full-time with her husband since early 2011, after taking almost 2 years to sell everything they owned. When they left the UK, they knew they had to stretch their money and would need to work, but they didn’t know where or when that would happen.


They’ve done an amazing job of finding work along the way as they’ve traveled. In this interview with Deborah, I discover just how they do it – right down to the nitty gritty of visas and how they get paid.



Nora: Let’s start with your first gig running a hostel in Chile. What happened?

Deborah: We had no idea where we were going once we landed in Santiago. A few people suggested Pucon – dubbed the Queenstown of Chile – white water rafting, climbing an active volcano etc. So we headed there.

We booked a hostel called El Refugio. We arrived after a night bus and we sat and had a cup of tea with the Dutch couple who were running the hostel on behalf of the owner. They’d been there for a year, but had received some sad news from home and were heading back the following week.

We didn’t have a flight out of South America for 11 months, so we were obviously in no rush to go anywhere. By the end of the first day there, we’d agreed to run the hostel from the following week.




Nora: Had you run hostels before?

Deborah: We had no prior experience and our Spanish was almost nonexistent! We survived 6 weeks and received great reviews on Trip Advisor, Hostelworld and Hostelbookers. Then we set off travelling again.


Nora: Lucky Break! Where did you go after that?

Deborah: We traveled south to Patagonia, then up through Argentina, Bolivia, and Peru, when we got an email from Peter (the guy who owned El Refugio) – he was opening a new hostel and wanted us to return to Pucon and run it for him. We returned to Pucon, but the deal fell through as he couldn’t secure the premises he wanted.

But when we arrived back in Pucon, we were offered 7 different jobs! After some negotiations, we took one of the offers and stayed 5 months.


Nora: What about logistics like visas?

Deborah: In Chile, we had a 90-day tourist visa which we received on arrival. We met so many people who worked with a tourist visa, and no one seemed to worry about it.

We thought we had a 3-month visa for Chile and cut it fine when we did a border run into Argentina. The Chilean visa was in fact for exactly 90 days, and we’d been there for 92 days. We were terrified once we realized whilst stood at the border, watching the guard count the days on a giant calendar.

They wouldn’t allow us to leave Chile, so we had to hitch a lift back to Pucon. The following week we had to travel to Temuco and face immigration.

Thankfully we had a friend who knew someone in the office, so we got away with a written warning. We left via the same border and were told if we tried to re-enter Chile at the same border, they would only ever give us 10 days. So we traveled south through Argentina and re-entered at a different border with out a hitch and walked away with another 90-day visa.


Nora: How did you get paid?

Deborah: Our first job in Chile, we got free accommodation (which wasn’t great), money for food (which wasn’t a lot) and commission on any excursions we sold (which we did very well at). We didn’t spend much for the 6 weeks and we walked away with a bit of money.

When we returned to Pucon and secured a job in another hostel, we negotiated hard and got paid a lot more money.



New Zealand

Nora: You found a neat strategy to hack your way into getting a working visa in New Zealand even though you were too old to qualify for a working holiday visa. How did you do it?

Deborah: A friend helped us find an orchard that was willing to give us a letter saying that they would employ us and then we applied for a waiver to our tourist visa which allowed us to work in the nut and fruit picking industry legally.

NA apples NZ tree 

It was worded quite ambiguously – you could work for each company for 6 weeks for the length of your visa. We worked for the same company for 6 months…but on different contracts; we also extended our visa and stayed in New Zealand for 9 months in the end.




Nora: Okay, back to your blossoming hostel management career. What did you do when you first landed in Thailand?

Deborah: It’s weird how things fall into place. We arrived in Asia in November and my brother said he was coming to Thailand for 2 weeks. We met him on Koh Phangan.

When we arrived we just got chatting to the girl who ran the resort (on behalf of her ageing parents) we were staying at and it came out that we’d run hostels in the past. Next thing she was offering us work over the xmas and new year period.

It was slave labour to be honest, but we didn’t really spend anything over the expensive holiday period and it lead to more work.


Nora: How did it lead to more work?

Deborah: During that time, we met an English guy who was building 5-star apartments up the hill. Within minutes of meeting us, he’d offered us a job and here we are! We are planning on staying until November, maybe longer…why not?


Nora: What’s the visa situation?

Deborah: We went to Singapore to get work permits – all paid for by our employer as he wants us to be official.

Thailand is very strict about what a foreigner can and cannot do. We are only allowed to do certain jobs. If a Thai can do it, then we shouldn’t be…such as cleaning the pool, serving food etc.


Nora: How are you paid?

Deborah: We are being paid into our UK bank account and we also negotiated money for food, so we are managing to save money.



Tips on the Lifestyle

Nora: You mentioned to me that you’re learning new skills all the time – most recently it was how to maintain a swimming pool and keep free of biting bugs! What has been the hardest thing to wrap your head around while working on the road?

Deborah: I would say learning a new language whilst learning a new job has been the hardest thing.

Before we left the UK, we’d attended Spanish classes and some of what we’d learnt stuck, but being in a classroom is very different to speaking to the chap who we hired to take guests to the hot springs (who only spoke Chilean Spanish). It was a steep learning curve.


Nora: Do you earn any other money to sustain your travels?

Deborah: I am a travel and landscape photographer and I supply images to lots of stock libraries. The sales from these images have helped us whilst travelling. My brother built me a new site which is more orientated to making me money, with referral links –


Nora: What would you recommend to help other travelers find work along the way as you have done?

Deborah: We would say be yourself and just chat to people – honestly this is how we’ve managed to secure almost all of our work. Be open to any suggestions that come your way…you can always leave if it doesn’t work out.

In New Zealand, we were initially told that we couldn’t work without a working holiday visa as we were too old and neither of us had a skill that was listed on the skills shortage list. We didn’t take no for an answer, and dug deeper and made more phone calls. That’s when we found out about the waiver that we could apply for.


Nora: Thank you, Deborah, for this great interview. I’m really impressed with your resume from the road, and your courage to simultaneously tackle language, culture, and a new profession – and make a spectacular go of traveling full-time in a financially sustainable way. You are an inspiration!


Find out more about Deborah and her travel adventures at DeborahBenbrook, and check out her blog.


Update 2015: I interviewed Deborah at greater length about her uncanny ability to land jobs along the way in my latest book: Working on the Road: The Unconventional Guide to Full-Time Freedom. Check it out!  


{ 25 comments… read them below or add one }

1 Tim Hirtle May 28, 2013 at 2:16 pm

It’s good to hear that someone “old” was still able to get work. Being above 30 is depressing when you start looking at working holiday visas.


2 theprofessionalhobo May 28, 2013 at 3:12 pm

This is why I wanted to publish my conversation with Deborah! She has made a real success of finding jobs along the way – despite the lack of “working holiday” visas.


3 Thomas May 29, 2013 at 5:44 am

This is really an inspirational article in that the “older” traveler, or more “wise” as I like to put it, can still make things work and dodge the bureaucracy trail. Good on you guys.


4 theprofessionalhobo May 29, 2013 at 10:29 am

Hey Thomas – I’m impressed with Deborah’s success too! Very inspirational. 🙂


5 Mike May 30, 2013 at 9:34 am

Wow! This is a true testament that things can work out for good people. I liked your “go with the flow” attitude and how you managed to make it work when once in a lifetime opportunities were presented to you.


6 theprofessionalhobo June 1, 2013 at 7:47 am

Mike: I’m really impressed with how “easily” they found gigs. I’ve been led to believe it’s quite difficult – but then again it all boils down to circumstance, personality, and a dash of serendipity.


7 Cheryl May 31, 2013 at 2:13 pm

Great interview Nora. Nice to hear how the over 30 crowd can manage on the road, and very inspiring to hear about the available work if you’re willing to chat with people. I love that Deborah’s a travel and landscape photographer…thanks for the tips on your site Deb, and I love your work. I’m also a photographer gathering my images for stock, so this will be quite helpful toward my quest of full time travel. Thanks!


8 theprofessionalhobo June 1, 2013 at 7:49 am

Awesome! Happy snapping!
Deborah and her hubby are certainly an inspiration for us all.


9 George June 1, 2013 at 2:13 am

Wow this is a reat story I’m glad you didnt give up 🙂


10 theprofessionalhobo June 1, 2013 at 7:49 am

Amen! 🙂


11 Adam - Tropical Nomad June 1, 2013 at 3:09 am

Hi guys,
Great to see you didn’t take no for an answer when it came to New Zealand.. Currently in Queenstown on a WHV and loving it 🙂


12 theprofessionalhobo June 1, 2013 at 7:49 am

I love NZ….what are you doing in Queenstown? (Besides probably just about any adventure activity you can get your hands on…) 🙂


13 Amber June 2, 2013 at 5:00 am

These are great stories, although some it seems like right place, right time, I am sure it is the immediate connections you make with people that make it possible! Congrats.


14 theprofessionalhobo June 2, 2013 at 8:23 am

Amber – There is a lot of serendipity and “right place right time” happening in Deb’s story, for sure. But then again, I’ve had similar (and unexpected) opportunities present themselves in my own travels; it’s about keeping your eyes open and being ready to walk through new doors as they open. Anything’s possible…. 🙂


15 Raul (@ilivetotravel) June 3, 2013 at 9:39 pm

Very insightfull! I love the creativity and persistence! And having worked in Chile for a year, I liked the story about exceeding the visa by 2 days and being made to jump through hoops to recover from the violation 🙂


16 Deborah Benbrook June 5, 2013 at 9:20 am

Hello – this is Deborah, featured in the above article. Thanks for all your comments and feedback.

Tim – thanks for your reply. Yes we were a little depressed when we realised we were too old for a working holiday visa….but age is just a number and most obstacles can be overcome…or gone around via a different route 🙂

Thomas – thanks for the feedback. Great to hear that you found our interview inspirational.

Mike – thanks 🙂 I truly believe that if you are open and willing to give anything a go then the opportunities will present themselves one way or another. I’d worked in an office all my working life and then I was picking apples! You can’t get much different to that.

Cheryl – thanks for taking the time to look at my photography website and that you like what you see 🙂 More tips will be added over the coming weeks, so please keep checking back. Good luck with the stock, if you need any advice, drop me a line via my website.

George – I’m not the type to give up. I’m a stubborn Yorkshire lass.

Adam – New Zealand was a tough nut to crack but we got there. Jealous you are in QT. I’m guessing you have some snow at the mo. Enjoy.

Amber – I agree our very first job was lucky – right place, right time. But we could have said no. Instead we decided to throw caution to the wind and give it a go. In doing so has opened up so many more opportunities. My advice is: say no to nothing (well almost) and give it a go. If it isn’t for you, leave. Life is too short. That’s the motto I live my life by now 🙂


17 lauren June 12, 2013 at 1:12 pm

wonderful article deb and darren! great to hear about all your adventures after we met you in pucon!!!!


18 Vicky June 14, 2013 at 5:47 pm

Great interview. Gives hope to the older travelers. I wish there were more of us. I get tired of traveling solo. The most successful, older traveler I know is my friend, Rita, the female nomad. She was traveling the world before it was cool to do.
I look for new adventures but will be the first to admit, the older I get the scarier it is to go it alone and not know there is a job waiting on the other end.
Experiencing new cultures is amazing..and so worth taking the risk.


19 theprofessionalhobo June 15, 2013 at 12:03 pm

Hey Vicky – I remember reading Rita’s book (Tales of a Female Nomad) shortly after I started traveling myself; what a great and inspirational read!

And you’re right….it’s scary to take that leap and not know if you have a job or opportunities awaiting….I wrote a bit about that here:


20 Kim Law September 12, 2013 at 1:26 pm

wow thank you for posting, gives me some hope as I have been stressing to the max saving and trying to earn extra cash before I leave next April.


21 theprofessionalhobo September 13, 2013 at 2:07 pm

Hey Kim – Where there’s a will, there’s usually a way! The road can reveal many opportunities for those with transferrable skills and networking capabilities. Happy (upcoming) travels!


22 rebecca June 9, 2014 at 4:55 pm

very inspirational read. It really is funny how things just fall into place


23 Nora Dunn June 10, 2014 at 10:17 am

Rebecca – Indeed….with a dose of faith and serendipity/opportunity, things tend to work out. (Oh yeah, and a little hard work never hurt either). 😉


24 Steph August 29, 2014 at 7:45 am

Thank you for posting this article! I am over 30 and this gives me positivity to make some bold moves I keep putting to one side due to fear of travel and working!


25 Nora Dunn August 29, 2014 at 3:30 pm

That’s great, Steph! I too was really impressed with how they’ve managed on the road….where there’s a will, there’s a way. 🙂


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