Many people we interview have life changing moments that serve as the catalyst to their new life abroad. For Dalene and Pete Heck it was a series of tragedies including the death of Pete’s mother and Dalene’s sister passing in her early 30’s that prompted the two Alberta, Canada natives that it was time to make the most of the time they had on this planet. They had been avid travelers during the holidays they had taken but their corporate jobs served as a restriction to the real time and energy they wanted to put in.

In 2009 they hit the road starting in Bolivia and covering much of South America. Since then they have built one of the world’s biggest travel brands and work with many media companies helping them use the travel environment and travel bloggers to build awareness online.

You can check out their journey (and Pete’s wonderful pictures) at

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What I learned from speaking with Dalene:

  1. It’s interesting how Pete and Dalene don’t get tied into doing things that might make them more money but they don’t enjoy. They are aware that building their online business and being a travel blogger is a long term journey and that they need to do what is their passion so it doesn’t become a chore.
  2. Like Nat and Jodie these guys are also a fan of Nomador for finding housesitting gigs. They find it more personable and easier to deal with than some of the larger sites where it is harder to get good housesitting gigs. Again it’s about building a reputation and once you have it things get easier.
  3. Travel is about people. Their experience with the locals in Roatan where they were eventually asked to become god-parents to one of the local villagers ? that’s the sort of special experience that money can’t buy. If you want to know more about Roatan check out our interview with Rika Purdey
  4. The world is not what the media portray. Dalene was very passionate about her experiences of countries, particularly Turkey, where the kindness of locals can be vastly different to the way the world is seen in the news. ( For more on Turkey check out Leonard Durso’s interview)

Check out this episode!

If you’re a stressed out business owner working 60-80 hour weeks and dreaming of a life of travel take heart – so was Nicole Connolly. The former Brisbanite ran a successful business but like many we interview, she felt something was missing from her life – mainly travel and the freedom to enjoy herself.

She set out 4 years ago on an adventure with her husband Mike, initially relying on savings but soon built herself an online business helping others – firstly with their social media, but more recently teaching others to build a successful online business like the one she now has.

We caught up with Nicole in the Bahamas where she shares her journey and provides the step by step process to starting an online business yourself.

You can check out Nicole’s story at or find out how to build your own online business at

 Bahamas Barbados

What I learned from Nicole:

  1. Imagine the worst that can happen and if you can handle it then go ahead! In Nicole’s case she always believed that if the travel lifestyle didn’t work out she could always head for home again
  2. You don’t need higher education to be successful. Nicole is proof of that having left secondary school after only two years. She has taught herself through course and learnings what she needs to know rather than relying on “recognized” education.
  3. It’s important to set your goals before deciding what business is right for you. Do you want to be location independent? Is the money important or the lifestyle? Making these decisions can help avoid pain later if you’ve gone down a path that doesn’t match your objectives.

Check out this episode!

So often we see examples of people who don’t travel simply because they wont permit themselves to. In this day and age many people have jobs that will let them hit the road – two such examples are Evo Terra and Sheila Dee. Evo’s work as a digital strategist (and Sheila’s as an instructional designer) gives them complete freedom to work from anywhere, and with their child now of adult age they saw no reason to stay at home.

In January 2015 they headed off covering much of Western Europe before heading down under via Thailand, China and Vietnam. We caught up with them in Australia where they shared their definition of what opportunistic travel is all about. As part of their strategy the two don’t rely on any one source of income, running their own podcast and receiving funds through their crowdfunding site on Patreon where they offer supporters postcards in return for patronage.

You can follow their journey, listen to their podcast and support their postcards at 

Evo and Sheila Terra - Opportunistic Travelers Evo and Sheila Terra - Opportunistic Travelers

What I learned from talking with Evo and Sheila:

  1. They have been inventive with their income sources using crowdfunding site Patreon to offer postcards from their journey in return for a monthly contribution. Although having only started this year they are already achieving over $300 per month from the site – enough to feed them for a month in many countries.
  2. Skyscanner is a big favorite for Sheila’s flight planning and the couple like to specialize in hunting out the flights that others won’t take.
  3. Work like your internet won’t last. Being digitally dependent can cause difficulties if you have tight deadlines and a poor signal. Don’t put yourself in the position of relying on the internet at the last minute.
  4. You really don’t need stuff – as Sheila says why would 2 people need 3 televisions! Cutting things out of your life won’t deprive you of what really matters – the experiences that define your life.
  5. Despite events that have happened overseas – in some cases around the same time that they were visiting the countries, both Evo and Sheila are very conscious of how the media can make events seem bigger and more dangerous than they are. Tragedies do happen, and you need to be wary, but they have not felt unsafe at any stage of their adventures on the road.

Check out this episode!

In today’s interview we catch up with Sean and Jen Boyle who left the sunny San Diego area in early 2014 to hit the road. They’ve have since covered much of Central America and Southern Europe and have recently arrived in Thailand. They don’t believe in roughing it but have comfortably kept to an annual budget of around $US40-$US50000 during the last 12 months.

We caught up with them to discuss Air BNB (where they book 80% of their accommodation) and the pros and cons of house-swapping.

You can follow their journey (and try some of the delicious recipes they have included) at their blog

Sean and Jen Boyle - Venturists Sean and Jen Boyle - Venturists

What I learned from speaking with Sean and Jen:

  1. Sean and Jen like to spend a short while in each place they visit and have recognized that staying for a month not only gives them a good look around but helps them keep their accommodation costs to a minimum. Air BNB offers a better rate when staying for 30 days but they can often negotiate the rate down to 22/25 days with the renter while keeping their daily costs the same.
  2. Renting out a property versus house swap is always a debate for travelers with a property. If your own property is in a place where higher net rents can be achieved over where you’re staying then you may be best to rent your own place rather than swap. Do consider tax with this though – you might want to talk to your accountant about whether it will be deemed as income.
  3. Although the Boyles are comfortably within their budget and have stopped monitoring their costs to the same extent they do recommend recording costs in the first year so you can keep a handle on spending.
  4. Although their blog includes food they have added recipes from the countries they visit which helps attract a whole new audience of readers.

Check out this episode!

If the harsh Minnesota winters get a little too much for you after a while there is always an alternative. Betsy and Pete Wuebker were ordinary 50 somethings living a suburban lifestyle and working the corporate job – in Pete’s case in a stressful marketing position. Deciding they needed to supplement their income with retirement on the horizon they took to online marketing as a means of building a business and soon realized after a period of time that they were doing well enough to throw in their day jobs.

With freedom now an option they moved to Hawaii, a place still dear to their heart, but after a trip to the Winter Olympics in Sochi, Russia in 2014 they decided that a life of travel was what they needed most.

They’ve been on the road since last year using housesitting as one of their primary means of reducing costs while their online income from various sources keeps them in the manner to which they are accustomed.

You can check out their blog at

Betsy and Pete Betsy and Peter Wuebker Peter and Betsy Wuebker

What I learned from Betsy and Pete:

  1. You’re never too late to start an online business. These guys were into their 50’s before they started to learn how to make money online. From a standing start they’ve built a thriving little business that enables them to live their travel lifestyle on their terms.
  2. Have a plan and a vision for your online income. They treat it as a serious business and regularly hold meetings to plan and strategize. Like many others they don’t rely on one income but they do like to bring traffic back through their blog – a central spot where they can build a good following before sending people out to their various income methods.
  3. Their secret to picking up housesitting gigs is to build a good rapport with the home owner. They let their seniority work in their favor – showing themselves as the ideal prospects to look after anyone’s home. They have followed Nat and Jodie’s recipe at the Housesitting Academy which has helped them get more housesits than they might have otherwise.

Check out this episode!

If you are a digital expert who talks to their clients about being location independent it certainly helps if you can show them by example! That’s precisely what Michelle Frost and her husband Simon did when they embarked on a long term trip around the world with their 3 teenage children.

The Frosts left Australia just over 12 months ago and have traveled through Asia and Europe spending long periods of time in different locations living much like the locals. They have successfully home schooled their children with the support of their school back home who felt the children would be richer for the experiences they would encounter.

We caught up with the Frosts in their current location of Formello, Italy where they had just spent the day delivering the olives they had picked to the factory to be pressed – ah the joys of travel!

You can find out more about them and their journey via their blog at or get their tips and advice on being a digital nomad and building your audience at and

Cannes Frost family near Rome

What I learned from speaking with Michelle and Simon:

  1. We’ve said it before when we interviewed the Curtis’s but kids really are a reason to travel. Their relationship has strengthened as a result of spending quality time together and creating memories that they will never forget. Like the Morgan family they found their children were richer for the experience of traveling as a family.
  2. I liked Simons take on safety – as he says everyone basically wants to be happy so why would they gain from hurting you? You still need to be wary for the 0.0001% who aren’t but most people you pass are just like you
  3. I didn’t realize the reciprocal medical benefits between Australia and the UK and Italy meaning your medicare card in Australia can be used for healthcare in these countries – that’s definitely a benefit
  4. If you plan on transitioning back to normal life (even if temporarily as the Frosts are) then you need to rebuild your income stream for the higher costs of living you might encounter back home. They have spent the last couple of months building up their digital business so they can recommit to it more fully when they return.

Check out this episode!

Ever heard of Wwoofing? No it doesn’t involve howling at the moon! Wwoof is a means of swapping work for travel where you trade a couple of hours per day in return for accommodation and meals on an organic farm. Today’s guests have successfully wwoofed their way around the world in a variety of countries but in recent years as their desire to live a backpacking life has diminished they have switched to housesitting as a means of reducing their travel costs.

Cheryl MacDonald and Lisa Chavis spend around 8 months of the year overseas while still generating income online working in their respective areas of expertise. For the four months back home they up the rate of earnings and plan their next adventure. Their lifestyle has enabled them to see much of the globe while controlling their living costs and topping up their income during the months they are back in the US.

We spoke with Cheryl and Lisa where they shared their experiences of Wwoofing and talked about the perceived boundaries that make people stop living the type of lifestyle they now have. You can find out more about their adventures on their website

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What I learned from talking to Cheryl and Lisa:

  1. Wwoof provides an opportunity to swap work for travel in over 100 countries worldwide. You can choose your destination and generally only have to give up a few hours per day of your time – but it’s not luxury living and suits the backpack fraternity best. As 40 somethings however they enjoyed the experience and didn’t feel out of place with the younger travelers they encountered.
  2. Earning from your old skills is always an option. Who would have thought a pharmacist could still make money while traveling? For Lisa she is able to top up her income checking medical records and doing some medical writing p roving that almost any skill or career can provide you with money while you travel.
  3. Ask the right questions. These two are a glass half full couple! They ask how they can do things not complain about why they can’t and it has opened many doors for them.

Check out this episode!

Sometimes good things can come from bad experiences and you can look back and be grateful for what went wrong. For Nat Smith and Jodie Thompson a failed business deal in Dubai left them with two choices – head home to Australia with their tails between their legs or embark on something new. Deciding that Europe was closer than Australia they made their mind up – but with only a few hundred dollars to their name how were they going to survive?

That’s when they discovered housesitting and its ability to not only provide a free roof over your head but the opportunity to experience a community in a unique way other accommodation just couldn’t provide.

Several house sits later having enjoyed the experiences of Britain, Europe, Central and North America they found people beginning to ask them what their secret was to finding good housesits on a regular basis – and from that House Sitting World was born – their online resource which provides forums, books, magazines and online training for the new and experienced housesitter to learn and share from.

If you’re interested in housesitting then you’re going to live this interview. Nat and Jodie generously share their top 8 tips on what you need to do if you want to get into housesitting.  Check out the academy here


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Here’s Nat and Jodie’s 8 Tips to Becoming an Effective Housesitter:

  1. Ask yourself WHY do you want to house sit? This exercise is really important and is clearly outlined in both their book and online course – and while it may seem like a silly question… go beyond the surface of “I want to travel or I want free accommodation”
  2. Prepare your being of service mindset– house sitting is far from a ‘Free holiday’ – it comes with responsibilities, not just while on the sit, but also before and after. And ask yourself honestly – can I feel comfortable in someone else’s space and respect their rules and way of living?
  3. Start gathering references asap– again, checklists & templates are in the academy, but try to get your written references stating the skill sets important to house & pet sitting
  4. Brush up on your skill sets– if you haven’t cleaned a pool before, don’t have a green thumb, would feel more confident with knowing pet first aid – get some hands-on experience in the areas that can help you be a great sitter
  5. Sign up to platform like House Carers or Nomador if you are looking for international gigs. Academy members get discounts for both.  Start searching the sites that offer listings in the areas you are seeking – there are Country/region specific sites as well. Don’t fall for the marketing of the largest site (TrustedHouseSitters) thinking they are the best, while they have the biggest marketing budget, in our opinion, it’s a very overcrowded and competitive site now with many members not getting value for their membership fee and making it harder for newbies to get a look in.
  6. Write a great profile/resume– keep in mind what the owner is looking for, they don’t care if you have traveled the world, they want to know that you can lovingly care for their prized possessions – pets & home.
  7. SECRET TIP (no-one else ever suggests this, yet this was the first thing they took advantage of themselves) – use your current or former profession in your headline, don’t be like the thousands of ‘loving, caring, trustworthy, honest, reliable blah, blah adjectives… a trade, professional, job paints a real picture
  8. Do what 90% of people don’t do – record a video & include it on your profile – it’s the key to start getting the best gigs available – guaranteed!

Check out other housesitting interviews we’ve done with Michael and Yvonne Bauche , Jason and Deidre Mize and how Laura and Tanbay can live in Europe for less than $1000 per month.

Check out this episode!

How does 12 months traveling the world with 4 children sound? What if you had to spend 10 of those weeks together in a combi van? For some people this would be too much of a challenge – for the Morgan Family; Jarred, Iri and their four children aged 5 – 13 years it’s been the making of them as a family.

The Morgan’s left Perth, Australia in December 2014 on a one year journey around the world, starting in Bali, heading up through most of Asia, then heading to Europe and Great Britain before leaping across the ditch to Canada and the United States where we caught up with them visiting family in Wisconsin.

The catalyst for their journey was the death of a young relative with leukemia. On the way to the funeral they discussed their own future and the opportunities they could give their children to live life to the fullest – and an adventure was born.

You’ll love this interview about how a normal family were able to transform their experiences and relationship with each other while on the move.

To follow their journey make sure you catch their blog at

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What I learned from speaking with Jarred and Iri:

  1. Google flights are a good option for seeking out airfare deals. The Morgan’s found some cheap deals looking at smaller airlines heading out of smaller destinations including a cheap flight from Ireland to Canada. All up they have spent around $US5000-$7000 getting their family of 6 from A to B during the 12 months.
  2. If you’re thinking of a long sabbatical like theirs they recommend doing it in steps. A weekend away, then maybe a week to an established holiday destination before you commit to being a family crammed in a small space for a period of time. Small irritations can become bigger when you’re on the road.
  3. The benefits for children are every bit as good as for adults. The Morgan’s have home schooled and have been able to provide their children with many real life examples during the journey. More formal learning can be accessed online

Check out this episode!

Feeling jealous about your children enjoying a gap year overseas? So were Duncan and Jane Dempster-Smith until they asked the question “Why can’t we have a 12 month overseas escape too?” They failed to come up with a good reason why not, and in 2013 headed away on a 12 month sabbatical with the goal of seeing the world and living on $A185 per day – the target for what it would have cost them to have stayed at home.

Experiment over, they decided on their return that it was possible to gear themselves for a more permanent travel experience and, after a short period of housesitting, they embarked on a more permanent overseas lifestyle with the goal of living on the equivalent of the Australian pension of $A92 per day, around $US63.

Well into their experiment the Dempster-Smiths are hitting their expense goals while having a ball traveling the world. In our interview with them they talk through the process of planning, how to ask the right questions before you start and how to keep your travels to an unbelievably affordable budget

You can check out their blog and investigate how to get started on your own adventure with their handy resources at

MarseillesThe View from Mirador Y Monumento Al Pipila

What I learned from speaking with Duncan and Jane:

  1. If the children are keeping you from going then clarify why. When Duncan and Jane established their children were seeking financial rather than emotional support it made it easier to make provision and not let guilt stand in the road of their adventure.
  2. Ask good questions. Don’t assume something is impossible, instead ask how it can be done. Their expectations of the budget they could live on was higher than it needed to be until they encountered the experiences of others who were doing it for less.
  3. Slow your travel down. The cost of relocation is significantly reduced on a daily basis the longer you stay in one spot – and you get a truer experience of what a place is like if you can stop to smell the roses.
  4. Again they emphasized the benefits of housesitting as a means of reducing costs. They got a few housesits under their belt at home in Australia before they embarked.
  5. If relocating don’t just consider airlines. Permanent travelers like Duncan and Jane, and the Mundells are increasingly using cruises as a cheap way to get from A to B. Cruise relocations such as their Miami to Barcelona sailing cost $800 for 14 nights – an average of $57 per day including accommodation, all meals, transport and entertainment. Try matching that on an airline!

Check out this episode!