What would it take for you to walk away from an eight-year career as a lawyer — a secure, full-time permanent role — to start your own business from scratch?
That’s exactly what Lucy Wood did. And in a recent conversation I had with her on our podcast, she shared the raw, honest truth about why the traditional career path stopped delivering on its promises, how she overcame the fear and isolation of making a massive life change, and what ultimately gave her and her partner Reeve the confidence to build Swell Website Design, a lifestyle freedom business on their own terms.
Lucy’s story is one I think a lot of people — especially millennials — need to hear right now. Because whether you’re burning out in a corporate job, watching your cost of living climb while your salary barely moves, or just quietly wondering “Is this really it?” — there are real, practical alternatives available to you. And they might look very different from what you expected. Watch the full interview below to hear Lucy’s incredible story in her own words.
The Traditional Path Isn’t Delivering What It Promised
Lucy did everything “right.” She went to school, got good grades, studied law at university, landed a career, and climbed the ladder. She was the model high achiever — and she racked up roughly $60,000 in student debt doing it.
After eight years practising law, she was still essentially living week to week. The stress of working 60-plus hours and having nothing left over to invest or save for a house was chipping away at her. And when she looked at the senior partners above her — the people who supposedly “had it made” — she saw them rolling into the office on weekends and not leaving until 8 or 9 at night.
As Lucy put it:
“I remember looking at the senior partners in the firm and they weren’t going home until eight o’clock, nine o’clock at night. They were still coming in on the weekend and I just realised — there’s no end goal here. There’s no breath of a moment where you go, ‘Oh, I’ve made it and I can take my foot off the pedal now.'”
That hit home for me because I saw the same thing early in my journey. I looked at people in traditional careers — people who’d been doing it for 10 years — and they weren’t wealthy and they were trapped. I dreaded the idea of being told what to do by a boss or working set hours. And honestly, that’s what drove me into entrepreneurship.
But here’s the thing: my path was different from Lucy’s. I was always going to be an entrepreneur. I was wired that way from childhood — trading toys, reading biographies of business moguls, following Arnold Schwarzenegger’s story of building wealth from nothing. Lucy, on the other hand, came from a traditional, beautiful family where you worked hard, got a job, and that was the gold ticket. For her to walk away from that security took real guts.
The Turning Point: When Enough Is Enough
Lucy’s real shift came when she had her two boys. She was on maternity leave, approaching the standard one-year mark where you’re expected to enrol your kids in childcare and head back to work — part-time or full-time. But something had changed.
“I just remember saying to Reeve, ‘I don’t think I can do this. I don’t want to live the life that I’ve seen the seniors at my firm experience, where I have to ask permission to go pick up my children early or just sacrifice that time with them.'”
So Lucy gave up her full-time role while still on maternity leave. She and Reeve started a solar installation business — a trade business — with only one income. It was terrifying. But it was also the beginning of something completely new.
What struck me about Lucy’s honesty was her description of the isolation that comes with making a decision like that. Everyone around her — friends, colleagues, community — was on the traditional path. There was nobody to bounce the idea off, nobody who’d done it before, nobody who could say “Yeah, we did that too, and here’s how it worked out.”
And that, as Lucy and I discussed, is where community changes everything.
Why Community Is the Missing Piece for Building a Lifestyle Freedom Business
Lucy and Reeve ran their trade business for about four years on their own before they found us at the eBusiness Institute. They were learning from podcasts and books — which is fantastic and far more accessible now than it was when Liz and I started out 30 years ago — but they still felt like they had no sounding board.
When they joined our community, something shifted dramatically. As Lucy described it:
“What really skyrocketed our business wasn’t necessarily the strategies that we were putting in place, but it was the community we found. We met people that were steps ahead of us and had already achieved what we were hoping to achieve. That community — being able to chat one-on-one with someone and say, ‘What did you think about that? How did you feel when you went through that?’ — that just changed the game for us.”
It was this support and community that were the real game-changers when it came to building their award-winning digital agency in Adelaide, Swell Website Design.
I can tell you from 30 years of experience: this is not a nice-to-have. It’s essential. When Liz and I bought our first manufacturing business — which was nearly bankrupt, by the way — I joined a manufacturing networking group in Western Sydney. I got to hang out with operators who were 10 and 20 years ahead of us. They mentored me, shared what was working, and gave me the confidence to keep going when things looked bleak.
Later, Liz and I invested well over six figures into education courses and seminars. We went to property seminars, Tony Robbins events, sales conferences — you name it. And at every single one, we formed friendships with like-minded people. Some of those people are still our closest friends 20 and 30 years later. We still help each other in business to this day.
If you’re serious about making a change — about building your own lifestyle freedom business, about learning how to make money online, or about creating a profitable side hustle — I’d strongly encourage you to check out our Digital Investors Program. It’s where people like Lucy and Reeve found not just the skills they needed, but the community that made all the difference.
Why Online Businesses Are the Opportunity of a Lifetime for Millennials
Here’s something I’m genuinely passionate about: online businesses are the ultimate vehicle for making money out of thin air.
That might sound dramatic, but hear me out. When Liz and I started, everything was bricks and mortar. Massive startup costs. Physical stock. Factories. Exports. Now? You can start an online business with virtually no capital. You’re connected 24/7, worldwide. You grab your phone and you’re instantly connected to customers, clients, and opportunities around the globe.
For millennials in particular, this changes the game entirely. Yes, the old path to wealth — buy real estate, sit on it for 30 years — is largely closed off. Anyone who bought property 30 years ago in Australia is probably a millionaire by now. But trying to replicate that today, even with two full-time incomes? It’s brutally hard.
So what’s the alternative? Get into your own business. And the internet makes that easier than ever. With AI, with the tools available now, with the ability to learn online from anywhere — the barriers that held Liz and me back simply don’t exist anymore.
I’ve said it on many podcasts and I genuinely believe it: in this day and age, it’s actually more secure to have your own business than to have a nine-to-five job. Especially with what AI is doing to industries like law, finance, and countless other traditional careers.
Start With Micro Courses and a Profitable Online Side Hustle
One of the most practical takeaways from my conversation with Lucy was her advice on how to start when you’re not sure which direction to go. And it’s something Liz and I are telling our own kids right now.
Lucy said something brilliant:
“Stop thinking about careers and career paths. Instead, just enrol in a course. Learn something new and see where it takes you. It’s almost like recognising that your asset isn’t in your career, but in your skill set.”
I couldn’t agree more. Our own son went to uni for a year doing business marketing and decided it was — well, let’s just say it wasn’t giving him the practical knowledge to actually make money. So we got him doing what I call micro courses — little courses on Instagram marketing, selling on Facebook, things that are typically $100 to $500 and give you immediately applicable skills.
Here’s my recommendation if you’re in a similar position: go with intention. Don’t just pick a random hobby course (although that’s fine to get the ball rolling). Choose something that points you toward financial independence or helps you start a profitable online side hustle. That’s the direction the world is heading, and the sooner you start building those skills, the further ahead you’ll be.
As Warren Buffett says, investing in yourself and your knowledge is the best return on investment you can get. Liz and I have lived that principle for three decades, and it has paid dividends beyond belief.
Surround Yourself With the Right People
If there’s one overarching theme from Lucy’s journey — and from my own — it’s this: who you surround yourself with determines the trajectory of your life.
When Lucy was a lawyer, everyone around her was on the corporate track. That made it incredibly difficult to even contemplate leaving. When Liz and I were starting out, our families weren’t entrepreneurs. Our old friends were chasing traditional careers. We had to deliberately seek out people who thought differently.
And here’s the key insight: once you’re around entrepreneurs and business owners — people who’ve quit the rat race or never entered it in the first place — it starts to feel normal. You realise there’s another way to live. You realise that working nine to five isn’t the only option, and that financial freedom is genuinely achievable.
Lucy made this shift when she and Reeve joined our eBusiness Institute community. She went from feeling isolated and unsure to being surrounded by people who were doing exactly what she wanted to do — many of them already steps ahead. That’s when their business truly took off.
As Lucy said:
“You can do it all online. For us, we started off where we found that community online. We still built a fantastic foundation from that. So it’s available now.”
The Bottom Line: Your Career Won’t Save You — But Your Skills Will
Lucy Wood’s story isn’t just inspiring — it’s a practical roadmap for anyone who’s feeling stuck, burnt out, or quietly terrified that the traditional career path isn’t going to deliver the life they want.
Here’s what I’d encourage you to take away from this:
1. Recognise the reality. The traditional career ladder has a ceiling — often lower than you think. Even senior partners and executives are working extreme hours without the financial freedom to show for it.
2. Start building skills, not just a career. Your greatest asset isn’t your job title or your salary. It’s your ability to create value — and that’s something you can develop through courses, communities, and practical experience.
3. Find your community. The isolation of going against the grain is real. Deliberately surround yourself with people who are building businesses, investing in digital assets, and pursuing financial independence.
4. Take one small step. You don’t need to quit your job tomorrow. Start with a micro course. Learn how to make money online. Build a side hustle. Test the waters.
5. Think online first. Digital businesses work 24/7, have minimal startup costs, and offer unlimited upside. For millennials especially, this is where the opportunity is.
If Lucy can walk away from an eight-year law career, start a business from scratch, and ultimately build a lifestyle freedom business through the skills and community she found at the eBusiness Institute — you can absolutely do the same. Lucy isn’t the only one either of course, Steph Sewell, another millennial looking to escape the corporate grind shared her story with us here.
The question isn’t whether the opportunities are there. They are. The question is whether you’re willing to take that first step.
If you’re ready, come and join us inside the Digital Investors Program and start building the skills, knowledge, and community you need to create real financial freedom online.
