What happens when an ultra-high achiever decides to start an online business while managing an environmental consultancy, raising a neurodiverse child as a single mum, and shutting down a failed startup? For Hillary Chapman, it meant creating a six-figure digital agency that perfectly marries her corporate expertise with newfound digital skills.
Hillary’s journey from corporate environmental consultant to award-winning digital agency owner isn’t your typical success story. Living just six kilometres from Melbourne’s CBD, she juggles major infrastructure projects, single motherhood, and building websites for corporate clients—all while maintaining the kind of work-life balance that seemed impossible in her previous corporate role. Her transformation story offers hope and practical insights for anyone looking to escape the corporate rat race. Watch her full interview to understand exactly how she made this remarkable transition work.
The Ultimate Multi-Tasker’s Starting Point
When Hillary first joined the Digital Investors program in 2022, her plate was already overflowing. She was running her own environmental consultancy since 2005, working on major infrastructure projects across Victoria. But the real challenge wasn’t just professional—her daughter was struggling with daily school attendance as a neurodiverse child, creating constant uncertainty in Hillary’s schedule.
“We always used to joke that if it was big, new, different and never been done before then it had my name on it,” Hillary explains about her environmental work. This appetite for complex challenges would prove both a blessing and a learning curve in her digital journey.
Adding to the complexity, Hillary was simultaneously trying to launch a Software as a Service (SaaS) startup from her kitchen bench. The venture ultimately failed, but the experience taught her valuable lessons about focus and realistic goal-setting that would prove crucial for her digital agency success.
The Accidental Agency That Changed Everything
Hillary’s original plan was to build a portfolio of her own websites, but her mentors suggested starting with local client work. Following the program’s recommendation to join BNI (Business Network International), she discovered a chapter just 700 metres from her house that met at a time she could actually attend—and they needed a web developer.
“I have an accidental agency really. I never really planned it,” she admits. “But I went, well how often is that going to happen that something’s actually easy that I could actually do?”
This serendipitous beginning led to something unexpected—Hillary discovered she genuinely enjoyed the sales process. “I discovered actually that the sales part I really enjoy because I just talk to people. I act like I’m interested and I am interested,” she explains. Her natural curiosity about different types of projects, honed through years of environmental consulting, translated perfectly to learning about various businesses and their digital needs.
Leveraging Environmental Expertise in the Digital Space
What sets Hillary’s agency apart is how she’s strategically leveraged her environmental background. Rather than starting from scratch in unfamiliar industries, she’s attracting clients from sectors she already understands intimately. Her current client roster includes offshore wind consultants, geotechnical engineering firms, and major infrastructure contractors.
“They were just so relieved to have somebody who actually understood what they were talking about,” she says about her engineering clients. “You just understand what an o-co is and you know all this kind of jargon that other web developers wouldn’t know.”
This expertise allows Hillary to charge premium rates—$3,000 and up for websites—because she can have meaningful conversations with technical clients and truly understand their customer avatars. She’s even built a directory site for all offshore wind projects in Australia, combining her industry knowledge with digital skills in a way that creates significant value.
Learning to Focus and Say No
One of Hillary’s biggest lessons has been learning restraint. As someone accustomed to tackling complex, never-been-done-before projects in her environmental work, she initially approached digital marketing the same way.
“Initially it was like a kid in a candy store. ‘That’s a great strategy, that’s a great strategy, that’s a great strategy’ and then I’d try and have a go at all of them and I’m like I’m not getting anywhere,” she reflects.
The turning point came when she committed to the basics: “One of the things I really had to learn with Digital Investors is to just stick with the basics and do the vanilla and do it over and over again.” This shift from complexity to consistency became her secret weapon, earning her the program’s Award for Excellence for simply doing “reps, reps, reps.”
Hillary also learned to strategically turn down work that didn’t fit her niche. “I realise that it just takes some of those things that are tricky—with my environmental consultancy, if it’s tricky, it’s got my name on it. But with websites if it’s tricky and difficult, I’m handing that off to somebody else.”
Managing Time as a Single Parent Entrepreneur
The logistics of running two businesses while single parenting required creative solutions. Hillary’s strategy involves time blocking her days around school hours, though she admits “it doesn’t work perfectly.”
“I’ve kind of separated my day into blocks and then I try and get organised at the beginning of the week of what I’m doing on what day,” she explains. The key has been outsourcing where possible—graphic design is handled externally, and her Philippines-based assistant Addie (retained from the failed startup) has become “phenomenal” at building websites.
Hillary’s environmental consulting background in project management has been crucial: “I was already pretty good at project management and it’s something that’s been extra challenging trying to manage two businesses at the same time, but we just focus on what do we need to do to progress.”
From Startup Failure to Six-Figure Success
The contrast between Hillary’s failed SaaS startup and her successful agency highlights why the digital agency model works so well for time-constrained parents. The startup required constant hustle and external marketing—difficult when you’re “basically stuck at home having a neurodiverse child where you have to be at home a lot.”
The agency model, by contrast, allows Hillary to work from home, serve local clients through networking, and leverage existing expertise. Within two years, she’s built a six-figure business that complements rather than competes with her existing consultancy.
“It’s taken about two years to get into the flow,” she notes, emphasising that the keyword research that once took “days and days” now happens much faster through practice and experience.
Key Success Strategies for Aspiring Digital Entrepreneurs
Follow the Program: Hillary’s success came from doing exactly what her mentors recommended, even when it wasn’t her original plan. “If I’m going to get success I should follow the program and do what I’m told,” a principle that has also guided other families in building their own digital agencies.
Leverage Existing Expertise: Rather than starting in completely unfamiliar territory, Hillary found ways to apply her environmental knowledge to digital services, creating unique value propositions.
Master the Basics: Focus on consistent execution of fundamental strategies rather than chasing every new opportunity or technique.
Build Your Support Network: Hillary emphasises how crucial the Digital Investors community has been during challenging times, providing both practical help and emotional support.
Know When to Say No: Learning to refer difficult or time-consuming projects to others has allowed Hillary to maintain focus and manage her limited time effectively.
The Road Ahead
Hillary’s story demonstrates that it’s possible to start an online business even under the most challenging circumstances. Her journey from overwhelmed corporate consultant to award-winning digital agency owner offers hope to anyone feeling stuck, mirroring the success of other professionals who walked away from lucrative corporate careers for more freedom.
Now that she’s established her agency foundations, Hillary is expanding into portfolio websites that complement her existing work—including a business networking directory that leverages her BNI connections. She’s found ways to make her various business interests work together rather than compete for her limited time.
“There is light at the tunnel,” as her mentor Matt Raad noted, and Hillary’s transformation proves that with the right strategy, support, and commitment to consistency over complexity, even the busiest professionals can build successful digital businesses alongside their existing commitments.
For anyone considering a similar journey, Hillary’s story shows it’s not about having unlimited time or resources—it’s about making strategic choices, following proven systems, and staying committed to the fundamentals that create real results.
