Go to uni, get a good job, climb the corporate ladder, buy a house, and everything will work out. That was the promise. And for an entire generation of millennials, it’s turned out to be one of the biggest lies ever told.
I’ve been buying, renovating, and selling businesses for over two decades now, and Liz and I have coached thousands of students through our eBusiness Institute programs. But recently, I sat down with one of our incredible graduates, Steph – a former high school teacher turned digital entrepreneur – and she opened my eyes to just how dramatically different the playing field is for millennials compared to what my generation experienced.
This conversation hit hard. And I think every millennial (and every burnt-out professional, regardless of age) needs to hear it. Watch the full interview below.
The Lie Millennials Were Told
Steph put it bluntly, and I have to say, she’s right:
“We were sold a bit of a lie as millennials. We were told that if you work hard in school, you get a good job or you go to uni, work for four, five years, whatever it takes, get married, climb that corporate ladder… then you’ll have enough money to buy a house and then you can have these kids and everything’s great. Go on a holiday once a year. And I am looking around and I don’t know anyone who is really living that life if they are a millennial.”
Think about that for a moment. Two parents working long hours just to pay for daycare for kids they hardly see. No holidays. No breathing room. And arguably, these are people earning well in their jobs. It’s just not translating into the kind of life previous generations were able to build.
Steph was a high school teacher – a respected, stable career. Her husband Jack is a high income earner. And yet, when we sat down and looked at the numbers during her coaching, there was simply no money left after the essentials. No room to invest, no room to get ahead, and certainly no room for the kind of financial freedom that previous generations achieved through property and steady employment.
I’ll be honest – and this is the first time I’ve really said this publicly – Liz and I have had many conversations acknowledging that in some ways, it was so much easier for us. Our friends who took the corporate route 20 or 30 years ago all bought property, and many of them are millionaires now here in Australia. For millennials, that same path is essentially closed. Borrowing over a million dollars in your early twenties to buy a house is not a wealth-building strategy anymore – it’s a massive anchor of risk.
Why Business Is the Only Real Answer for Millennials Who Want to Get Ahead
So if the old playbook doesn’t work anymore, what do you actually do? After coaching thousands of students – millennials, burnt-out corporates, parents desperate for more time with their kids – my answer is very, very clear.
You have to have your own business.
There is no way you can possibly get ahead in this day and age without getting leverage of some kind. And you simply cannot get leverage working nine to five. There aren’t enough hours in the day. Your income is capped. Your time is controlled by someone else. Your holidays are dictated by a policy document.
Now, I know that might sound confronting if you’ve spent your whole life being told that a stable job equals security. But here’s the mindset shift I need you to make: I see business being more secure in the future than a nine-to-five job, especially now with AI. Jobs are going to change dramatically. People who have their own income streams, who have built real skills and real assets, are going to be the ones who thrive.
If you’re a Type A personality – a high achiever, a hard worker, someone who’s always driven to do more – you already have every trait you need to succeed in business. Grit, determination, the ability to push through hard things – these are the exact same qualities that every successful entrepreneur has. You just need to redirect that energy away from making someone else wealthy and toward building something of your own.
This is exactly the journey that Steph went on, and it’s the same journey hundreds of our students take inside our Digital Investors Program. We teach everyday people – teachers, nurses, corporate professionals, tradies – how to start a profitable online side hustle and build digital assets that generate real income, on their own terms. If you’re ready to explore what that looks like, I’d encourage you to check it out.
The Instagram Trap: Why “Looking Successful” Keeps People Stuck
Steph raised a point in our conversation that I think is absolutely brilliant, and it’s something that holds a lot of millennials back from making the leap.
“People think that getting their $1.5 million house, you can immediately see like, ‘Oh, look at this beautiful house that I’ve got.’ But the mindset shift is – that is an anchor. That $1.5 million worth of debt… at least it looks good in your Instagram pictures.”
She’s absolutely right. A beautiful house with a crushing mortgage is not wealth – it’s a cage that photographs well. And meanwhile, building a business? It’s not glamorous. It’s not the stuff you put on Instagram. But it’s the stuff that actually sets you free.
Think about any genuinely successful person you admire. Read their biography. Watch their story. What traits do they all share? Grit. Determination. The willingness to do unglamorous work for years before anyone notices. They weren’t posting selfies in front of mansions they couldn’t afford. They were grinding, learning, building – and eventually, they had real wealth to show for it.
I say this to people all the time: embrace the hard stuff. It’s what makes you successful in life. It builds you into a better person. And it has the knock-on effect of showing your kids what real achievement looks like. Do you want your children looking up to you as someone who had the Instagram-perfect life but was secretly drowning in debt? Or do you want them to watch you build something real – something that gave your family freedom?
Start Small, Reduce the Risk: The Beauty of Digital Businesses
Now, I don’t want anyone listening to this to think I’m saying you should rush out and quit your job tomorrow. Even though that’s exactly what Steph did – she looked me in the eye and said “there’s no Plan B, burn the ships” – I actually coached her through a more measured approach first.
Here’s what I always tell people: start small.
When Steph decided to leave teaching, we reverse-engineered what she actually needed. And the reality was eye-opening. After tax, after commuting costs, after all the hidden expenses of a full-time job – the amount she actually needed to replace from her teaching income was far less daunting than it seemed.
“You sort of helped me reverse engineer what I needed to get that flexibility. You’re like, okay, well, how many clients do you need? Let’s not make a mountain out of a molehill here. You’re not earning millions of dollars in your high school teaching job. So really replacing that income isn’t something that is unachievable.”
This is why I love the online business space and digital assets. Compared to traditional bricks-and-mortar businesses – and trust me, I did it the incredibly hard way with manufacturing and wholesale import businesses for 15 years – digital businesses reduce the risk dramatically.
You don’t need to fork out six figures. You don’t need a warehouse full of stock. You don’t need employees from day one. You can start for less than $5,000 to $10,000, learn the skills, build something real, and grow from there. And with AI now making so many processes faster and more accessible, the barriers to entry have never been lower.
Think about it logically. What’s the worst-case scenario? You invest some time, some learning, and a small amount of money into building an online business. If it doesn’t work out the way you hoped in year one, you go back to your job with a whole new set of incredibly valuable digital skills that make you more employable than ever. But the upside? The upside is unlimited. That’s the difference between a job and a business – a job has a ceiling. A business doesn’t.
What a Lifestyle Freedom Business Actually Looks Like
I want to paint a picture here because I think it’s important. When we talk about building a lifestyle freedom business, we’re not talking about becoming the next tech billionaire. For most of our students, it looks much quieter – and much more powerful – than that.
For Steph, it means she drops her kids off at school and picks them up. If they want a day off, they have a day off. She works on her own terms, around her family. She will never again have to ask someone for permission to take annual leave.
“I am not going to be in a job ever again, Matt, where I have to ask someone for annual leave, and I’m allowed 20 days at best. I urge people to think outside of what we’ve been sold.”
For another of our champions, Coach Calem and his partner Jenn, it means 14 to 20 weeks of holidays per year, working while they travel, completely on their own schedule. They came from full-on corporate careers and now live a life that their former colleagues can barely comprehend.
This is what drives so many people inside our community. It’s not Ferraris. It’s not mansions. It’s being there for the Mother’s Day breakfast at school. It’s not stressing about what to do with your kids during school holidays because you make money online and you work from home. It’s the quiet, powerful freedom of controlling your own time.
The Two Camps: Which One Are You In?
Steph made an observation that I think perfectly captures where most people find themselves right now. She said millennials – and honestly, I think this applies to anyone feeling stuck – tend to fall into two camps:
Camp One: People who can see there’s got to be a better way. They value hard work. They’re willing to build something. They know the current path isn’t sustainable, and they’re ready for a mindset shift.
Camp Two: People who keep taking on more debt, keep up appearances, argue about money in their marriage, and put their family under financial strain – not because they’re lazy, but because they don’t see a way out.
If you’ve made it this far into this article, I’m confident you’re in Camp One. You know something has to change. The question isn’t whether you need to do something different – it’s what you do next.
Your First Step: Change the Mindset, Then Take Action
Here’s what I want to leave you with. If you’ve been sold that lie – that a stable job, a big mortgage, and decades of grinding will somehow lead to financial freedom – it’s time to let it go.
The first and most important step is a mindset shift. Start thinking about how a business, even a small one, can be more secure than a nine-to-five job. Start looking at the people around you who have built real freedom – not through corporate ladders, but through owning income-producing digital assets.
Then start small. You don’t have to quit your job today. You don’t have to risk everything. Build a side hustle. Learn the skills. Prove the concept to yourself. And then scale from there.
Steph did it. Calem and Jenn did it. Hundreds of our students inside the eBusiness Institute community have done it. They started exactly where you are right now – burnt out, time-poor, financially squeezed – and they built something that changed their lives.
The old playbook is broken. But the new one? It’s more accessible than ever. You just need to pick it up and start.
Stay tuned for Part Two of this discussion with Steph, where we’ll dig into the practical steps – the actual “now what?” – for building your first online business and creating the life you actually want to live.
