If you’re a millennial feeling like the traditional career path has let you down, you’re not alone. I hear it every single week from people inside our community – smart, capable professionals who did everything “right” and still feel stuck. They went to uni, got the degree, landed the job, and yet they can’t get ahead financially. The house feels out of reach. The career ceiling is getting lower. And now AI is threatening to make their role redundant.
I recently sat down with one of our Digital Investors Program graduates, Steph, to have an honest conversation about what millennials should actually do about all of this. Not just the mindset stuff – we covered that in a previous chat – but the real, actionable steps to start building a business and create genuine lifestyle freedom. Steph is uniquely qualified to ask these questions because she’s literally lived the transformation. She went from being a burned-out teacher who never saw her kids to replacing her full-time income within 12 months through digital skills.
What follows is the side hustle action plan that came out of our conversation – the same framework that has helped hundreds of our students make money online, build assets, and take control of their futures. Watch our full conversation below to hear Steph’s incredible story firsthand.
Stop Researching and Start Doing — The First Real Step
One of the first questions Steph hit me with was simple but powerful: “What is the actual very first step that you should take outside of developing your mindset to make this a reality?”
It’s a great question because I see so many people get trapped in what I call the “research loop.” You feel productive because you’re consuming content, watching YouTube videos, reading articles — but you’re not actually doing anything. You’re not building. You’re not earning. You’re not learning through action.
My answer? Start small, and start with a digital-based business. Something that uses online skills. And the very first foundational skill I believe everyone should learn is — surprisingly — not AI. It’s how to build a website.
Now, I know that might sound basic, but hear me out. When you learn to build a website, you’re not just learning a technical skill. You’re developing problem-solving abilities, entrepreneurial thinking, and the resilience to push through when things break (and they will break). As Steph put it beautifully:
“The skills that I gained learning how to actually build that website were not just technical. You learn those entrepreneurial mindset strategies because you’ve got to think on your feet. You’ve got to problem solve. You’ve got to not chuck your laptop out the window and have a hissy fit that it doesn’t work.”
If you outsource everything to AI from day one, you skip that critical learning. And I can tell you from 20 years in this space — the foundational understanding of how the online world works is what gives you longevity in business.
If you’re ready to learn these digital skills through a proven, step-by-step framework with coaching support and a community behind you, I’d encourage you to check out our Digital Investors Program. It’s the same program Steph used to completely transform her life in just 12 months.
What If You’re Not Technical?
Steph asked me this directly, and I’ll give you the same answer I gave her: We live in the AI age. Get over it.
I don’t mean that dismissively. I mean it as a mentor, not your mother. You have a choice right now. You can stay working nine to five and see how that works out in ten years. Or you can commit to learning some tech skills that will serve you for the rest of your life.
I wasn’t technical when I first got online either. That’s where my motto came from — “Don’t think, just do.” I had to tell myself that every time I was nervous about hitting publish or building something new. Doing something is always better than doing nothing.
And here’s what I recently realised: the thought processes I learned building websites with WordPress 15 years ago are exactly the same thought processes needed to work with all these new AI tools. The foundations translate. That’s why I keep coming back to this — whether you like it or not, you need to learn some technical stuff. Down the track, you can outsource it or let AI handle the heavy lifting. But you’ve got to understand how it all works first.
The Earn-While-You-Learn Path: Become a Digital Advisor
So if you need to learn both business skills and technical skills, where do you start? Steph asked me exactly this, and my answer is what we call the Digital Advisor path.
I’ll be honest — it doesn’t sound particularly sexy. Everyone wants to jump straight into buying and renovating websites for big profits. But the Digital Advisor path is honestly the quickest way I’ve seen people who are completely new to business get up and running to start a profitable online side hustle.
Here’s how it works:
- Learn to build a basic website. There’s zero financial risk — it costs practically nothing and just takes some time and effort.
- Build a few websites for local businesses for free or at cost. This gets you your reps and a portfolio.
- Start charging and gradually increase your prices. A simple technique: tell people, “I’m retraining in a new skill and happy to do it at cost price at first. I’ve got three slots left.” Then each time you do another round, you bump your prices up.
- Get amongst business owners. This is the hidden gold. While you’re helping local businesses, you’re getting a front-row seat to how real businesses operate — lawyers, plumbers, tradies making serious money. You start to see opportunities everywhere.
Steph is a perfect case study for this. She knew nothing about business when she started. Within 12 months, she had earned enough to replace a full-time teacher’s income. And along the way, she learned more about running a business than four years at university ever taught her.
Think about that. It’s like an apprenticeship, except you own the business. You learn on the job, the lessons stick, and you’re getting paid while you figure it all out. Way quicker than uni, and you don’t end up with a HECS debt hanging over your head.
Dealing With Fear: What’s Scarier — Trying or Doing Nothing?
Fear came up a lot in our conversation, and I think it’s the elephant in the room for most people considering this path. Steph framed it perfectly:
“What’s scarier — trying something new and maybe failing at it, or not trying something new and being stuck in your job, or seeing your job become redundant and then having nothing else to back it up?”
I was chatting with one of our clients recently — a young engineer in his early twenties earning a six-figure income. He was worried about quitting his job. I asked him, “Mate, how secure is your actual job?” He burst out laughing and said, “Yeah, it’s actually not.” Engineers are increasingly being replaced by AI. There’s no room for upward movement.
So I asked him: What’s the worst-case scenario of quitting your job for 12 months and having a proper crack at this? You can always go back to engineering — to a job that may not have any security anyway.
My gut response to anyone feeling fear about the future is this: you have to retrain in digital and AI skills. You literally have to find another way. It’s coming whether you like it or not. If you can’t beat the robots, join them.
Practical Advice If You’ve Got a Mortgage and Kids
Now, I want to be real here because Steph pulled me up on something important. A lot of the business advice out there comes from people without dependents, without mortgages, without the reality of being up at night with children. As Steph said:
“So much of the advice out there — being blunt — comes from men who do not have children, who have all of the time in the world. There is a unique set of challenges, particularly for mothers.”
She’s right. And if you’re in that position — a parent with a mortgage who can’t just quit tomorrow — here’s what I recommend:
- Get a part-time job if you need financial security while you retrain.
- Use your evenings and weekends to learn digital skills. Think of it like doing an MBA — a couple of hours a week of focused study adds up fast.
- Talk to your partner. Get them on board. Ask them to support you by helping create the space you need. Steph’s husband Jack gave her a 12-month runway, and that partnership was critical to her success.
- Surround yourself with a positive community. The journey isn’t always easy, and having people who’ve been on the same path — coaches who’ve quit corporate, other mums who’ve made the transition — makes an enormous difference.
The worst-case scenario of taking a year to have a crack at your own business? It’s like taking a gap year. If it doesn’t work out, you go back to what you were doing. What have you lost? Twelve months. But if it does work out — and I’ve seen it work out hundreds of times — everything changes.
The Common Pitfalls That Trip People Up
After coaching thousands of students, I see the same mistakes come up again and again. If you’re about to start your journey to make money online, watch out for these:
- Going too big, too fast. I see people hear our success stories and rush out wanting to buy a six-figure online business straight away. That’s dangerous if you don’t have a business background. Start small. Buy a small website. Build a few sites for local businesses. Get your reps in first.
- Underestimating the learning curve. Studies show that when you’re learning a significant new task, it takes you seven times as long as it will once you’re proficient. I know I should probably be out there saying “do our course and get rich quick” — but it doesn’t work like that. Respect the learning process.
- Poor time management. This is especially critical for time-pressured parents. You need a clear vision, a strategy you’re working on every single week, and realistic goals based on the time you actually have available.
- Not understanding business financials. If you’ve only ever earned a PAYG salary, you probably don’t understand how business finances work — and that’s a pitfall in itself. When you earn a dollar in a business, you can compound it far easier than earning a dollar working for someone else.
Your Business Is an Asset — This Is How the Rich Actually Get Rich
I want to finish with what I think is the most important concept for any millennial to understand. It’s something that completely opened Steph’s eyes when we first discussed it, and I watch it transform people’s thinking every single time.
Rich people own assets that they control. And typically, those assets are businesses.
When Steph quit teaching after years of service, do you know what she got? A pen. Literally, a pen. Years of her life traded for time, and she walked away with nothing to show for it.
But now, just over a year into building her own digital business, she has an asset she could sell. Something worth real money. That’s more than a pen. That’s a fundamentally different financial trajectory.
Look at another couple in our community — Derek and Courtney. Within just two years, they’re earning upwards of $50,000 per month. That means their business asset is worth over a million dollars. They couldn’t have saved even the deposit for a million-dollar house in that timeframe. Yet here they are, sitting on the equivalent of a million-dollar property with no loan attached.
This is why I keep saying: start thinking about your online business as an asset — every bit as valuable as physical real estate. Within a year or two of building a lifestyle freedom business, you could be sitting on something worth the equivalent of a property, with no mortgage, no bank breathing down your neck, and complete control over your financial future.
That’s the real opportunity for millennials right now. Not another degree. Not climbing someone else’s corporate ladder. Building a lifestyle freedom business that pays you while you own it, grows in value over time, and gives you something real to show for your effort.
Your Next Step
If this resonates with you — if you’re tired of the pen at the end of the road and ready to build something that actually matters — then I’d encourage you to stop researching and start doing. Learn the foundational digital skills. Build your first website. Get amongst business owners. And surround yourself with a community that will support you through the tough bits.
Our Digital Investors Program is designed to take you through this exact journey — from complete beginner to confident digital business owner — with coaching, community, and a proven roadmap. It’s the same program that helped Steph replace her teaching income in 12 months, and it could do the same for you.
What’s the worst that can happen? You take a year, have a crack, and learn skills that will serve you for the rest of your life. And the best that can happen? Everything changes.
