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Last Minute Eurotrips, Self-Sabotage and 2-Year Olds on Planes

July 2, 2024

Have you ever dreamed of jumping on a plane and running away? 

Wanting to live the laptop lifestyle and work from anywhere but unsure how to *actually* do it without your business burning down? 

Wonder how all of those people on Instagram every European summer actually afford to do it? 

In a week, I am jumping on a very last minute plane to Eurosummer, family (including a wild 2-year old and lively 4-year old) in tow. 

This hasn’t been something I’ve had on the planning list for a long time (please listen to last weeks podcast episode where I share about losing my Mum for more context on my snap decision). 

More than anything? 

This trip is an exhale. 

This trip is therapy. 

And, this trip is a complete disconnect from reality, to reflect, honour, enjoy and heal. 

At the same time, I know there will be some wondering how I can be so lucky or privileged to make this happen. Which, of course, I am. 

But, it’s not all that. And maybe, it could be possible for you too. 

If you’ve ever dreamt of an extended trip and feel compelled or inspired to make it happen, in today’s podcast episode I am going to share how I’ve done it, what it is costing, my thoughts, fears and nerve-citement around doing it with young children and all of the nitty gritty. 

Let’s dive in. 

My Decision to Book a 2-Month Eurotrip With Four Weeks Notice

For a few years now, I’ve followed a particular account on Instagram. 

It’s a luxury hotel in Austria. 

Random, considering that I don’t really follow travel accounts at all. 

But, I remember the moment I came across it. I was scrolling, and happened across what looked to me like a huge exhale. 

It was peace, calm and tranquility all wrapped up in a hotel. 

The hotel was a wellness spa in Austria – surrounded by mountains, and a hot spring and everything I never knew I needed. 

The last few years have been a lot.

I think they have been for many of us. 

I can palpably SENSE the feeling of collective tiredness. 

For me, when COVID kicked off back in March of 2020, I had a 5-month old and a brand new group coaching program. 

I was fresh off the back of my first panic attack, struggling to juggle the competing priorities of what would very soon after become a million dollar business and a baby that truly just didn’t sleep. 

There was no “maternity leave”, that was a luxury I wasn’t able to afford. 

Time rolled on, and two years later I was pregnant with my second little one. 

Still depleted when I reflect back, and again no “maternity leave”. 

It was business, and babies and difficult responsibilities caring for my loved ones. 

The last two years came straight off the back of that, and right now?

There’s only one thing I know for sure. 

That a semi-colon right now is the ONLY right answer, business and life wise. 

Not a complete stop (I love what I do too much). 

But a pause, and a lightening. 

Cue the Instagram hotel. 

It popped up in my feed a couple of weeks ago, and intuitively I just knew. 

I need to go there, I thought. 

That place is my exhale.

The Universe Conspires to Help You

Three weeks later, I have four plane tickets, a fully booked two month itinerary and a departure date. 

Plot twist: I’m not staying at the hotel. 

But I AM going to the beautiful Dolomites where it’s located, surrounded by mountains and fresh air and everything my soul needs right now. 

My biggest learning? 

My gosh — when you REALLY want something and starting taking action, the universe conspires to help you. 

There are SO MANY REASONS why I could have told myself that this trip won’t work: 

“I have TINY CHILDREN – including a wild 2-year old who can’t sit still for two minutes let alone 14-hours on a long haul flight”. 

“It’s JUNE and I want to go to Europe on the Australian exchange rate with less than four weeks notice – it’s going to be booked out, prohibitively expensive and wildly overcrowded”. 

“You have a BUSINESS to run.. And you’ve been grieving for six weeks with barely a moment to work, now is NOT the time to go away”. 

“It’s not realistic”. 

All stories I told myself.

And yet, here I am – going anyway. 

In so many ways, the universe has conspired to help me. 

I committed to going, and through aligned action and intention so many of those beliefs have been toppled over.

Here’s how. 

“It’s Too Expensive” 

To my OWN surprise, I have managed to make this trip happen without breaking the bank.

The big thing to note here is that I didn’t know that most of the things that happened would be possible prior to making the decision to go. 

But, I did set an intention. 

Some way, some how, I want to bankroll this trip in a way that it doesn’t completely break the bank. 

Here’s a few ways that this ended up happening:

  1. Flights on Points

    For the past few years, all of my expenses have been run through a credit card that I pay off each month. Over time, I have accumulated significant points.

    Here’s the link to the card I use (I get points if you use my code, my travel fund thanks you).

    Note that you should absolutely do your own due diligence when choosing a credit card. It won’t be right for everyone.

    For one, it costs $1750 a year just to hold, so you need to be confident your spend and the benefits will outweigh that cost.

    For me, they do.

    There are really savvy ways you can use and optimise your point spend for business class flights. I did this last year with the help of the fabulous @thepointscoach.

    This time around, I have four people to fly to and from Europe, and so business class – even with points hacks – wasn’t possible with the late notice.

    However, I have completely covered the cost of our economy flights with my points bank, so we are essentially flying to and from Europe for the cost of the fees, which is about $1500.

    It saved me around $15,000 straight off the bat.
  2. Reduced Cost Accommodation

    When I first started researching accommodation for this trip, I was disillusioned to say the least.

    95% of places were completely booked solid, and the places that were available were only available at sky high prices.

    Add to that requiring spaces that would fit 4 people – and each additional person after two people costing a significant amount more on top of the base room rate – and it felt prohibitive and impossible.

    Buuuut, of course, I love a challenge.

    Here’s how I have offset accommodation costs.

    a) Booking direct

    Often, I found that going through the booking sites was more expensive, especially with additional people.

    So, I would search the booking sites for accommodation, and then Google the places I wanted to stay and contact them directly.

    For the most part, they were more affordable and  they didn’t charge for additional persons when I specifically asked.

    b) Strategic accommodation

    We are slow travelling through Europe, with a week in most places so that the kiddies have time to calibrate.

    Often, Airbnbs and apartments have reduced weekly rates, and we will also be able to cook some meals at the accommodation.
  3. Home swaps

    I signed up for a home swap company, and have secured a couple of home swaps which has made accommodation free.
  4. An unexpected tax refund

    One of the side-effects of changing my business model over the past twelve months is that – for the very first time in my seven years of running a business – my business revenue didn’t grow.

    In fact, it reduced by about a third.

    Last weeks (and two weeks AFTER having already committed to the trip), I had my annual tax planning meeting with my accountant.

    “Your business revenue is down a little” – he said.

    I nodded (it wasn’t new news).

    “AAAAND”, he continued, “that means you have been overpaying on tax over this year”.

    “You’ll be receiving a refund”.

    I blinked.

    If that isn’t the universe conspiring to help, I really don’t know what is. 

“I have TINY CHILDREN – including a wild 2-year old who can’t sit still for two minutes let alone 14-hours on a long haul flight”. 

This is true.. And I’m scared.

I’m very realistic.

This is going to be a trip with challenges, likely tantrums and tears too.

But also, it will be magic.

One of the only gifts that come from losing someone you love as much as life itself is that life is such a fleeting gift. 

Nothing is guaranteed, and right now is really all we have.

In many ways for me, right now is the ONLY perfect time to take this trip. 

Next year, my little boy starts prep. He’s already starting to grow into a boy, and not the squishy little man I have had for the past four years.

Over the past few months, my caregiving responsibilities have been such that my time with that has been limited. I grieve that, and I can see how much they need their mum.

Whether I jump on a plane or not, I know for a fact that this season requires me to give more of my time and attention to them.

They need it.

I want it.

And I will never get this time with my littles again.

Sunny might not remember it, but Jimmy will – and we will.

The memories we will make over the upcoming eight weeks, I have no doubt, are the most valuable investment I could make right now.

And, for more on my thinking on this, I highly recommended reading these two books:

Die with Zero by Bill Perkins, and Four Thousand Weeks by Oliver Burkman. 

My heart bursts at the thought of it.

And yes, there will be hard times – I will document them on Insta, if you want to come and follow along (@steviedillon_)

But as my (very crass and “keep it real”) friend reminded me –

“Take the trip! You have to wipe mouths and butts anyways, you might as well do it in Italy”.

I am here for all of it.

“You have a BUSINESS to run.. And you’ve been grieving for six weeks with barely a moment to work, now is NOT the time to go away”. 


Actually? It’s the perfect time.

It’s not an and/or.

With a simple mindset shift, I have realised that I can very much have BOTH – business and the trip, without one needing to be at the sacrifice of the other. 

Here’s a revealing truth about me that I have recently discovered: 

I have a tendency when going through personal turmoil to tear my business down to align with how I am personally feeling.

It’s something a business friend of mine first made me aware of as a pattern she witnessed in me.

Once I saw it? 

I couldn’t UNSEE it. 

It was true!

I have often in the past taken the concept of a “personal brand business” to the next level.

Meaning that: The growth or dips in my business were often caused by whatever whim or personal circumstances I was navigating. 

It’s something that almost happened without my consciously realising in season right now, as I navigate very significant grief.

Now, I don’t think that scaling your business up or down intentionally to align with your personal circumstances is always a bad thing. 

The ability to enter growth or maintenance periods and to intentionally align the seasons of your business with the seasons of your life is a gift.

However, ALWAYS tearing down the growth or income of the business because I am personally feeling a certain way can sometimes be taking things a step too far.

A couple of weeks ago, I realised that my pattern was starting to play out.

I was feeling sad, and so I was intentionally trying to tear my business down to size.

Here’s what I ultimately realised, though:

My business – especially in its current iteration, something that I have really spent the last year making sure I was in complete alignment with – is a source of joy for me.

Tearing it down was actually just a form of self-sabotage, plain and simple.

I had nothing to gain from it. 

Instead, not only was it entirely POSSIBLE for me to run my business and to take this beautiful trip at the same time – but actually, it could be the thing that made it possible.

When I realised that, I took fast action.

For the past couple of months, it hasn’t been possible to join Lifestyle Business School because I had waitlisted it whilst I changed the model slightly (for more on my decision there, check out this two part series – part one, and part two). 

When I was in my lack and self-sabotage mentality, I had figured that I would simply keep it that way.

But instead, I updated the sale page in less than a day and set it live. 

Immediately, I made two sales.

It was validation – I can have both: 

The thriving business, and the trip.

And so, my intention for the upcoming eight weeks is to work with a sense of slow productivity whilst away.

(For more on what I mean, I recommend reading Cal Newports “Slow Productivity”).

Of course, that is only possible because I understand funnels and evergreen sales systems, and have shown up and built trust and content over a long period.
That isn’t “luck”.

It’s work, and having continually invested in myself and my business to make my dreams a reality. 

I’m grateful that this leveraged model allows me to work and travel and to genuinely enjoy both at once. 

Of course, it won’t be “full throttle” whilst away.

But it doesn’t have to be, and having my business support me in this season is a gift.

The Itinerary

And so, it’s just a few days until we jet off. 

The kids have their backpacks stuffed full of toys.

I’ve purchased travel prams, and packing cubes and am ready armed with imaginary stories of plane police to try and keep them in check on long haul flights (thanks Zoe Foster-Blake for that hot tip). 

I’m ready, and excited.. And grateful that this trip is able to give me some temporary solace (and admittedly, distraction) from the very intense grief that I am carrying.

Of course, it won’t disappear whilst I’m away. 

As much as I would very much love to simply “run away” from it, I know that my feelings will come with me and that the waves of grief will likely still crash over me at the most inopportune of time.

But also, this is good for my soul. 

When I hit the alps, and that beautiful mountain, I will exhale. 

And for all of that, I am grateful (thank you, Universe). 

The itinerary, for anyone curious?

We’re kicking off in Greece (Athens and Naxos) before an extended trip of Italy (Puglia, Tuscany, the Dolomites and Sicily) and a final stop off in my true city love, London.

Want to follow along on my travels? 

I’ll update my stories with the good, the better and the really bad (cue plane tantrum at 20,000 feet in the air).

Perhaps it might be evidence that it could be possible for you – now, or in the future. 

Ciao for now! 🇮🇹

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