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AirBNB and the ultimate in hybrid Sydney living

What if you lived in a city without ever putting down roots? One professional couple made AirBNB part of their weekly routine and experienced Sydney more deeply than almost anyone alive.
A truck backs up to a home, dropping off a giant load of moving boxes for the inhabitants. It’s a suburban scene like any other. Except this wasn’t a family moving in. This was an AirBNB.

For Trevor and Gisèle Woods (@WoodsAusCan), this was the first time they’d seen their belongings in two years. After over 100 AirBNBs and similar short-stay homes since the end of 2019, living out of a suitcase of clothes and a few essentials, it was decision time. Which physical objects, all of which seemed so important before this journey began, even matter anymore?

AirBNB CEO Brian Chesky has himself spent a lot of time travelling and living in houses available through the platform he co-founded. For him, it works on many levels. It’s good business tactics. It’s clever PR. And when you’re worth $10 billion you could buy houses wherever you like anytime you want. There’s no real risk for Chesky to live the AirBNB life.

But what about for people with a job based in one location? People who need to make the dollars spent on accommodation deliver real value for their monthly housing budget? People who aren’t on a mission to live the life of a ‘digital nomad’?

“I wasn’t the kind of guy who would do this,” says Trevor. “I like stability. I like order and to plan things to a tee. We really pushed ourselves to even attempt this idea for a few weeks let alone how it has all unfolded.”

At the end of 2019, the couple was moving from Melbourne to Sydney where Trevor would take up an executive role at one of Australia’s top universities. Their children had all just moved out of home so this was a new phase of life for the pair.

“We had thought about just quitting and taking a year off to travel the world,” says Trevor. “When the opportunity arose in Sydney we decided to make that move to coincide with the family changes and downsizing from our family home in Melbourne.”

“The notion of living out of our suitcase for a little while seemed palatable at the time because it was temporary,” says Gisèle . “It was only for a few months. It was a fun little adventure! In the end we really have had some phenomenal adventures.”

On return from a Christmas trip back to Canada, a few more AirBNBs got them back on the ground ahead of deciding where to stop. But then March 2020 arrived, and the uncertainty of a pandemic made AirBNB seem like the smart choice instead of investing in a purchase or long lease.

Optimising the AirBNB lifestyle

Those first months played out the way most of us probably approach booking AirBNBs. Trevor, ever the efficient executive , was eager to optimise every choice.

“When we were planning holidays with the kids I would plan the heck out of it,” says Trevor. “I would know everything we were doing, and when. So at first there were weeks of being very stressed about not knowing where we were going to live in the coming weeks.”

“At first it was very strategic. Trevor would have a dozen tabs open with a bunch of potential places for different weeks,” says Gisèle . “He would try to coordinate this, that and the other. But by the time a few months had kicked in we got comfortable with the routine . Then we’d ask ‘So where are we moving in two days, or tomorrow?!’”

“Without a family to manage, if Saturday comes and goes without making a booking we finally convinced ourselves that we could always just check into a hotel,” says Trevor.

In fact, the process of living this nomadic lifestyle entirely in and around a single city offered some fascinating lessons in what really matters to live a functional home life. Through that first year, a number of important realisations occurred. One was finding the optimal time to stay in any given home.

“We tried five days, three days, two weeks, and we really quickly settled into one week,” says Trevor. “It was short enough that if the bed was uncomfortable or it was noisy you knew there were only a few more days to suffer but it was long enough to feel like we’ve really given a place a try. There was almost always an option to return in the future, we sometimes did.”

From bad beds and showers to noisy ‘Eastern European mobster’ neighbours and cockroach infested terraces, the Woods had their fair share of tricky stops along the way. As time progressed, travelling as far south as Jervis Bay all the way through to the Central Coast and beyond, they came up with their methods for how to pick a good short-term stay .

One was picking the right keywords to search on guest reviews. Testing both the positives and negatives – quiet and noise, comfortable and uncomfortable – to find the concepts you wanted to hear about. The other was visiting an area to get a better sense of what a place would really be like to live in.

“Staying within Sydney meant you could scout out a neighbourhood and see if it is as good as it sounds,” says Trevor. “Is there construction next door? What are we not seeing in the pictures? There’s a lot of places we didn’t end up going because we figured out where the property was, walked around and thought ‘Oh, forget that.’”

Other lessons were about what you needed to secure your sense of comfort in whatever house you found yourself in.

“Jumping around, you’re at the mercy of the place you’re staying this week,” says Trevor. “Like dull knives. We bought ourselves two good knives to take the edge off that problem. And then I also like having fresh mint in a drink, so we started buying a few small fresh herbs from Bunnings. Mint, basil and chives. They cost a few dollars and we can easily replace them at the next place for less money than buying them cut at the grocery store .”

On a tech level, living in the era of high-powered laptops clearly makes the entire concept possible. Sit down at any table and you have yourself a workspace, and Trevor found his MacBook Air, iPad mini and iPhone the ideal combination to meet all needs. Plus an Apple TV that does more than just make it easy to log into all your favourite TV streamers.

“I love that Trevor takes lots of photos,” says Gisèle . “I like being in the moment, but I trust he’s capturing the memories to back it up. Having the Apple TV just scroll through our photos is something we enjoy a lot.”

“By travelling with our Apple TV, we would get a little taste of home everywhere we stay. Just plug into the TV’s HDMI and we have our family photo gallery cycling on the screen,” says Trevor. “In a sense, those possessions that make us right at home are more digital now.”

Reaping the benefits

High flexibility in a time of uncertainty can be a significant victory in any scenario. But there were many other benefits that emerged during the process for the couple they would never have thought of ahead of time.

“On one hand, you don’t own anything. But on the other hand, you don’t have to worry about anything,” says Trevor. “All the overhead of life was gone. Cleaning and so many things that take time out of life just disappeared, like changing burnt out light bulbs.”

The other comes back to those knives and herbs. The Woods found this lifestyle changed their shopping habits significantly, leading to a far healthier approach to movement and eating than in their family home.

“W e’d walk everywhere instead of getting in the car, and we lived more simply in terms of food, only buying what we needed for the next meal so we wouldn’t have to pack any food up and move it to the next place” says Trevor. “Only f resh vegetables, fruit, meat, and we’d only use salt and pepper. No BBQ sauce, no ketchup, nothing out of a package. And we’re not eating out either. We’ve actually been for routine blood tests recently and our doctors says we have blood like people in their 20s; they wonder what we’ve been doing! ”

Meeting a city

Thinking back to that first reason for spending a few months in AirBNBs around Sydney – to explore and learn where they might like to live permanently – it’s hard to imagine anyone alive has experienced Sydney to the degree the Woods have.

“When you’re actually walking the streets of this city you realise how close everything actually can be to each other,” says Gisèle . “It’s so interconnected. You can lose yourself but never really be lost.”

“We experienced so many different things,” says Trevor. “We lived near the zoo, at Balmoral Beach, and at Circular Quay looking right at the harbour and the daily swapping of cruise ships. We watched the whales passing by from Vaucluse. We got to ask ourselves if these places were how we wanted to live or not?”

Across their 100+ stays, many were repeat visits to suburbs or properties they were growing to love. Each time a new perspective on the streets, views and neighbours. They found they didn’t care much for Bondi, but would live in Walsh Bay if they were to settle somewhere on the harbour.

“There was always something positive anywhere we stayed,” says Gisèle . “Maybe we didn’t get a lot of sleep in one place but we were right on the cliffs looking at the open ocean. Or we met a lovely neighbour. There was never a truly horrible experience.”

They found a deep love for Sydney as a city, but during the pandemic lockdowns – when they could live further away from Trevor’s workplace – they stayed further afield, as far as Noosa on occasion, and they built a particular affinity for Pearl Beach. They stayed in many houses in that area over the three years, and in recent times have opted for extended stays in homes they have spent time in in the past as their love for specific areas grew.

“Of all the places that we’ve lived in life – and I’ve lived in some places for 10+ years – I don’t know that I’ve known where I lived better,” says Gisèle . “I sincerely mean that. I love Melbourne, but I only knew the little quarter where I lived. In Sydney, I can have a conversation with somebody about a place and I know it, I’ve walked those streets. This part of Australia has become pretty special because I really know it.”

Meeting a budget

Of all the potential counterpoints to this concept, maintaining a reasonable accommodation budget seems like the least plausible part of the journey. For a couple that includes a C-level executive, their typical housing budget would be more than many but could still be stretched by just paying for hotel rooms at hundreds of dollars per night.

“We figured out what we spent per week in Melbourne on the house, the mortgage, the taxes, the heating bill, and all of that and we came up with a number,” says Trevor. “And that was around one to two thousand a week. We then knew this was the average we were aiming for. That gave us the opportunity to try places that were over and under that number and to explore and optimise. It turns out there are a lot of other hidden expenses to a household that just dropped away too. When there is no space, a lot less is purchased!”

Some of the added cost benefit here was the blending of house and holiday budgets. When you’re living this short style lifestyle, a decision to take a weekend getaway to the Blue Mountains is using the same budget as your housing – there’s no rent or mortgage to pay on a house you’re not living in at the same time.

“We realised we were way under budget and two of our kids had come back to live with us for a few months during COVID, so we decided to enjoy our time together and rent some larger places, including some really nice penthouses in the city,” says Trevor. “ Things got complicated with more people and more bags and needing Uber XLs – it felt like the old days of being travel logistics Dad again. But it was a lot of fun.”

The couple also found that being good guests translated into opportunities for discounts. With such an extensive history on AirBNB and other short-stay digital services, you build a network of contacts to negotiate with. The Woods could ask an owner if they could stay during a quiet period at a discount rate – a booking is better than none.

“It’s like flying with only cabin baggage. You can change flights with no dramas,” says Trevor. “Being able to offer to leave quickly (with only a few hours notice) meant we could get great discounts on some long stays.”

“Ratings are reciprocal,” says Gisèle . “We’re nice, we’re clean, we’re not party animals, we didn’t destroy any places, and if we broke a glass or something we always offered to pay. So we have fabulous reviews. That made people comfortable to have a conversation on the side.”

These relationships also speak to a completely different kind of tenancy through these services. The Sydney housing market is not exactly known for great landlord relations when it comes to standard lease agreements. An AirBNB host, on the other hand, cares about their reviews deeply. They’re far more likely to communicate and help a guest if there’s a problem.

Within this environment, getting to know the hosts and owners can lead to friendly interactions that create the space for negotiating special deals when you’ve had positive experiences together in the past.

So was the case when the Woods had arranged an extended stay at a large Pearl Beach home. With a large garage available, it was then they decided to order a truck to bring all their possessions from storage and make some big decisions about getting rid of their belongings now they were two years deep into this new way of living.

Meeting ourselves again

You don’t have to be a hoarder to know how closely we can define ourselves through the objects we surround ourselves with. Times, places, and memories become attached to trinkets, T-shirts, and furniture, making any attempt to part with our possessions akin to deleting whole phases of our life.

When that truck arrived at that house with all those boxes, the disconnection of time spent across so many temporary homes had given the Woods a new sense of perspective on how much more simply we can define our lives and our memories.

“I used to hear about minimalists and think, oh, that’s cool. But how would you ever do that? Living out of a suitcase for over three years really helped change what I think is important,” says Gisèle .

As they opened box after box that seemed to mean so much as they were packed to leave their home in Melbourne, new eyes fell upon item after item.

“It was overwhelming to go from nothing to seeing all this stuff again,” says Trevor. “Why did I have five pairs of jeans? I even found I had 54 ties! Plus there was all this bulk house stuff. Q-tips, soap, toothpaste. We felt gluttonous having so much stuff. We felt sick.”

Of the two, Gisèle had always been more inclined toward getting rid of unnecessary things. So during the clear out process, it was Trevor who found it harder to cull ruthlessly.

“As much as the ‘we’ll need this again’ urge was replaced by a ‘why did we ever keep this?’ perspective, there were moments in my mind where I would say ‘Oh, but I remember this!’”, says Trevor. “So it was very conflicting for me.”

In the end, the process was about working out what to give away, what to sell on Facebook Marketplace, and what could be given to their kids for their apartments – and what really counted as the precious memories to keep long term. For Gisèle , the real value lay in the kinds of items that no one else would ever want. Those tangible reminders of the people we care about.

“For me, Christmas is very special,” says Gisèle . “Last year I was able to decorate our Christmas tree with all the kids’ ornaments from when they were growing up. It was the first time in years and it felt so important to do that.”

“I have cried every once in a while when I’m torn between the idea of not having the family home that everyone remembers and comes back to. What is our purpose in living this way? But the house where our kids grew up is in another country! So I know what’s important. And whether it was forced or it naturally happened, we’d be having some of these conversations anyway. But when you choose to live this way you get confronted by these thoughts every once in a while.”

The Sydney sabbatical

“The activity of figuring out where we are going to live each week and experiencing Sydney in this way together was almost like we had taken that year off to travel the world that we had talked about,” says Trevor. “We just happened to do it in Sydney. It’s just been so cool for us to experience this together.”

“It wasn’t just the places we lived. It was living in different neighbourhoods and appreciating the diversity and similarities of people. Your life is based on your routines. So living in different communities was really beneficial. And it has taken our belief that experiences are more important than stuff to a new level.”

Embracing the flexibility and freedom made possible by AirBNB – entirely within the limits of commuting range of the Sydney CBD – brought out a fresh perspective for Trevor and Gisèle . It brought them closer together. It redefined how they think about what really matters to living your everyday life. And it refocused their sense of what matters most for maintaining a sense of family unity when your family has spread its wings and moved out of home.

“I’ve become less risk averse, more easygoing,” says Trevor. “I now see that the details matter but it’s important to step back and look at the big picture, over time.”

This kind of lifestyle adventure would simply have been impossible even just a few years ago. The density of listings across AirBNB and similar services is now large enough that real options exist across most suburban regions of major cities. The ubiquity of reliable wireless broadband makes the true working lifestyle possible from almost anywhere you may roam.

“What we’ve done is amazing because it turned out to be just so doable,” says Gisèle . “I never would have thought we would have done it for over three years. There have been moments and days where you miss your rooted self, but overall it’s been such a positive experience. And AirBNB made it really quite easy to do.”

When we think of ‘digital nomads’ we often think of solo contractors working from anywhere as micro businesses, roaming the coast in their campervans or hostel hopping around Europe. Maybe we need a different name for the kind of life that Trevor and Gisèle Woods just lived for over three years in Sydney. They were a kind of digital hybrid, with the flexibility of a nomad balanced against the certainty of Trevor’s university executive role.

The couple has just made a move back to Melbourne, completing three years and five months of life in Sydney and their accidental experiment in flexible living. But while they take “a few months’ pause” on this lifestyle, they are keen to start it up again in September after they have caught their breath, observed what the new work routine will be like, and scoped out some initial possibilities in and around Melbourne.

Indeed, the Woods say they don’t think they will ever have a rented or owned home filled with their stuff again. They’re even researching a new offer from a cruise line to live on a ship for three years with a dedicated workspace that would tour the world. Follow along with their adventures and get some tips and advice on how to try simple living at their new twitter account.

Picture of Andrew Walker

Andrew Walker

CTO and Founder

The Impatient Futurist of the technology world, Andrew is on speed dial for the likes of IAG, Walmart, and NewsCorp. Andrew has built and sold businesses (making 11 people millionaires in the process), launched products, written books, and led projects for the world’s most complex organisations.

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