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Building a Bucketlist Business

April 2, 2024

In 2007, I spent six weeks in a hostel in the middle of Guatemala just “because”.

My brother, our friend Trav and I spent the last three months backpacking through Mexico and Central America, and I still had three MORE months before my one-way ticket to London departed from Rio.

Truly, I’d never felt so free.

The two years prior had been spent working like a donkey, with good people but in a field I hated.

The endgame? Admission to the Supreme Course of Queensland as a lawyer.

It was an accolade I spent 7 years working towards..

Only to quit, 6-weeks to the day later.

Trapped and scared of ending up a 67-year old partner in a top-tier law firm wondering what on earth had happened to my life, I had ended five years of uni and two years of Articles by handing in my resignation and jumping on a plane.  

And so, there I found myself in a computer shop in Puerto Escondido, Mexico, on a steaming April afternoon checking my emails when my brothers friend messaged us on Facebook.

“Wanna come visit?” – he wrote, “I’m just down the road in Guatemala!”

(Side note – that was my first EVER Facebook message, and little did I know that 16 years later it would have spent the better part of a decade ruling our lives).

We looked at each other.

Of course we would. It wasn’t even a QUESTION.

We were free. The world was our oyster. And we could do anything, be anyone, go anywhere!

And so it came to be that I ended up spending the best, most carefree, most FUN 6-weeks of my life living out of a backpack in a dingy hostel dorm room in Antigua.

Acutely aware that I had opted out of life for a little minute, and feeling grateful as heck for it.

Five years later, I started my online business chasing that kind of freedom again.

And on the surface, the promise of it all felt..  intoxicating.

Time freedom – to work when I wanted!

Location freedom – to go back to Central America, or London, or ANYWHERE BUT HERE!

Financial freedom – to make more than a doctors wages working on the goddamn INTERNET!

I wanted it.

The sense of adventure.

The possibility.

The wonder that came from not knowing what would come next.

The Tuesday afternoons spent outside (and not in an air-conditioned cubicle)


And so, like so many of us to, I dove HEAD FIRST into the heady world of INTERNET BUSINESS.

The problem?

That with a complete lack of guardrails to keep me in check..

An unfettered ability to DO MORE and MAKE MORE and ACHIEVE MORE..

And way more people yelling mini-orders at me than the one piddly boss I  left my corporate job for (Slack dings! DMs! Comments! Answer me!), the reality didn’t quite match the label on the box.

“With an online business, you can be FREE!” – they cry!

Except, that you aren’t really.

Not when you’re tied up in knots working 14-hour days to and “maximising your productivity” to earn the six and seven figures held up as hallmarks of success.

“With an online business, you can swap the 9-5 and do something DIFFERENT” – they cry!

Except that you’re not THAT different when you’re the 6,000th person recycling a trending Instagram audio reels to share your “thought leadership”.

“With an online business, anything is possible!” – they cry!


It all reminds me of the tale of the fisherman and the businessman.

Getting allllll caught up in the relentless pursuit of more, but ultimately – what for?

Here’s the tale, if you haven’t heard it:

Here’s what I realised in the process:

That I was really, really proud of what I’d achieved in the 7 years prior since I’d started my business.

.. Even though I was a late bloomer.

… Even though  I’d spent FAR TOO MUCH of my life *ahem my twenties into my early thirties* waiting for the weekend and losing myself in happy hour.

.. And even though I’d veered a little off course in building the wrong model for me.

With every misstep, I’d had the tenacity, courage and clarity to course correct and keep chasing after my dreams.


I realised that I was in NO WAY DONE YET.

That in many ways, I was just getting started.

In 1990, I was a gawky 8-year old printing hundreds of copies of her own “Especially For Kids” newspaper and handing it out to every student in my Grade 3 classroom.

And, ever since then, I’ve known one thing for sure:

“A successful businessman on vacation was at the pier of a small coastal village when a small boat with just one fisherman docked. Inside the small boat were several large yellowfin tuna. The businessman complimented the fisherman on the quality of his fish and asked how long it took to catch them.

The fisherman proudly replied, “Every morning, I go out in my boat for 30 minutes to fish. I’m the best fisherman in the village”.

The businessman, perplexed, then asks the fisherman “If you’re the best, why don’t you stay out longer and catch more fish? What do you do the rest of the day?”

The fisherman replied “I sleep late, fish a little, play with my children, spend quality time with my wife, and every evening we stroll into the village to drink wine and play guitar with our friends. I have a full and happy life.”

The businessman scoffed, “I am successful CEO and have a talent for spotting business opportunities. I can help you be more successful. You should spend more time fishing and with the proceeds, buy a bigger boat. With the proceeds from the bigger boat, you could buy several boats, eventually you would have a fleet of fishing boats with many fishermen. Instead of selling your catch to just your friends, you can scale to sell fish to thousands. You could leave this small coastal fishing village and move to the big city, where you can oversee your growing empire.”

The fisherman asked, “But, how long will this all take?”

To which the businessman replied, “15 – 20 years.”

“But what then?” Asked the fisherman.

The businessman laughed and said, “That’s the best part.  When the time is right you would announce an IPO and sell your company stock to the public and become very rich, you would make millions!”

“Millions – then what?”

The businessman said, “Then you would retire.  Move to a small coastal fishing village where you would sleep late, fish a little, play with your kids, spend time with your wife, stroll to the village in the evenings where you could sip wine and play your guitar with your friends.

I love it.

It sums it all up for me.

And gives me a sense of slap-in-the-face perspective when I start getting all caught up in that Internet silliness again.

Because so often, in the pursuit of “more and better”, we can forgot why we set that goal in the first place.

I’m seven years into business now.

A little older.

A little wiser.

And these days, with two young babies that grow bigger every single day RIGHT BEFORE MY EYES, here’s one thing that I know to be true:

In five years.. And especially in ten.. I would give a LOT of money to back here.

At this age.

With these kids.

Enjoying these silly, fun little times.

And so, when I burnt down my unsustainable online business in 2023 and built it all from scratch, I was determined that my mentorship would help other people learn from MY mistakes and build it sustainably too.

That’s what I do in Lifestyle Business School.

It’s not about helping you do more, and work harder, and hustle it out.

And it’s not about maximising your productivity.

It’s about asking yourself this question:

What does success mean to me?

And then to build a leveraged lifestyle business that delivers you the answer.

Listen On: Apple Podcasts | Spotify

The Bucketlist Business

I asked myself *exactly* this question before remodelling my own business to help me build to my Lifestyle Business Sweet Spot – a simple, high profit margin business working 5-hour days with a tiny team.

And, so I thought it might be interesting for me to share what I am optimising for in pursuit of that goal.

My business bucket list, if you will.

Business Bucketlist Goal #1: The Three-Month Staycation

I want to spend three months in a different country, at least once a year.

Swapping house, swapping lives.

Getting a taste of what it feels like to drink wine from holes-in-the-wall in Florence 🍷

Or to do Sunday roast at a pub built in 1852 in Ireland 🍀

Or to take weekly Spanish classes in Mendoza ❄️

Or to do daily yoga classes overlooking a rice field in Bali 🌾

I’m optimising for a business that allows me to jump on a plane and do that, little family in tow.

And not to work 13-hour days while I’m there, but instead to work delicious half-days on projects I enjoy and then to shut my laptop and go exploring with my family.

Business Bucketlist Goal #2: Financial Freedom

They say that true financial freedom is the ability to stop working tomorrow, and KNOW that it wouldn’t affect your quality of life for the rest of your life.

I didn’t know that, for far too long.

These days, I do – and I optimise for it at all costs.

Growing my net worth feels urgent, and important.

I know it is THE thing that will allow me to sleep at night safe in the knowledge that if everything fell apart tomorrow, everything will still be okay.

I’m getting there.

Bit by bit, my business is allowing me to breathe, and sleep so very well at night.

That has only happened by intentionally optimising for a lifestyle business that is able to deliver cashflow – and the insight to know what to do with it.

The key? Not spending every cent on keeping up with the digital Joneses.

Building a high profit margin business, dropping as much of that income to the bottom line as possible and then using it to invest in assets that will one day make work optional.

Last month, I opened my investment accounts and I realised that had made more from those than from the work I had done inside of the business.

And let me tell you – that day hits different.

Passive income in a BUSINESS doesn’t exist.

But you CAN build a business that deeply fulfills you – and then use the money it generates to invest in assets that ARE truly passive.

It’s the ability to make work optional that I care about (and the fact that I love it so much that I probably wont ever even want to).

Business Bucketlist Goal #3: A Body of Work I’m Proud Of

In a world where everyone is creating 6-second reels and jostling for quick attention, here I am sitting here writing a blog that when all is said and done will likely take me three or four hours.

It’s not quick, and it’s not easy.

But here’s why  producing this type of work is so important to ME.

Here’s something I think about often:

I also know the percentage of people that come to the sales page that buy.

In three years? Nobody will remember that Reel or that caption or the stories you posted. They won’t remember your quick, 2-second comment reply, or the email you banged out at 4.50pm promoting your latest thing.

But they WILL remember this, if you take the time, and effort, to do it:

Your unique perspective.

The way you changed how they thought about EVERYTHING.

The care and attention you put into your weekly long-form content, each piece compounding to create a body of work that becomes your legacy.

I don’t want quick, fast attention..

I want to build a body of work, over time, that I can one day look back on with pride.

When I sit and reflect on what success means to me, these are the things I think about.

There’s more, of course.

So much more.

The little things, as well as the big things.

A business that affords me the time freedom, the flexibility and the financial resources, to:

  • Get my little girl out of her cot at 1pm after nap time, all blurry-eyed and babbling; 
  • Help my mama move her couch; 
  • Catch the ferry to Tipplers at 1pm on Friday afternoon, and show my kids the dolphins swimming alongside the boat; 
  • Book a last-minute trip to New York, just because; 
  • Invite an old friend on a weekend staycation to Byron, and sip wine in the sun; 
  • Breathe; 
  • Create good work I’m proud of; 
  • Google stuff for fun, and not for business;
  • Read Briannia Wiest in a single sitting and double highlight every page; 
  • Meet a friend for coffee in Burleigh without side-eyeing the time on my iPhone; 
  • Walk through the headland EVERY day, and not sit down at my laptop til 10; 
  • Go to bed at 7 and read; 
  • Travel, always and forever..

It’s not interesting or impactful for me to build a business that doesn’t give me those things.

To get to the end of my year this year and realise that in the end, I traded one “9-5” corporate hamster wheel for another.

To have all of the money in the bank, and not a spare second to show for it.

That’s not success for me, because it doesn’t give more more of what I want.

Lifestyle Business School designed for those who share my business-building ethos.

Who know that worthy things don’t come without any work at all, but equally?

Who want to spend their time working hard on something leveraged that eventually – with the benefit of time, and compounding, and your Intellectual Property doing the heavy lifting for you – gives your time back.

That’s what I help you build  in Lifestyle Business School.

The truth is that it isn’t building an online business that sets you free.

It’s knowing what you want, and building an online business intentionally designed to give you more of that.

Money, yes – but NOT at the long-term sacrifice of the time, freedom and happiness you started it all for in the first place.

Keep Listening!

Listen On: Apple Podcasts | Spotify

Design a Simple Lifestyle Business With High Profits, Working 5-Hour Days & a Tiny Team 

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