From Freelance to Full-Time, Once More

One of the funniest—and lowkey annoying—things about my work life is that I seem to write more when I’m freelancing. But the minute I go full-time, my writing dries up.

Fast forward to 2025. I’m now at David Mascott Country School as the IT & Marketing Manager. Even though I’d worked with them as a contractor before, going full-time wasn’t exactly on my 2025 list. I was supposed to start in January, but we bumped it to February.

Since stepping in, it’s been full throttle. I’ve basically had to build two departments from scratch—IT and Marketing. Before this, Marketing was a shared task among managers. They’d ping me (or another contractor), get a few flyers made, post them on Facebook, and call it a day. IT was folded into the Finance Director’s job… a man with solid managerial experience but not much time for troubleshooting, sourcing tech, or running digital infrastructure.

Just like at Baker Tilly, I didn’t get much of an induction. Day one was: “Here’s the mess, fix it and send reports! 😂” So, I hit the ground running. First step? A full stock take of anything remotely IT-related: staff laptops, network devices, phones, TVs—you name it.

A. Getting Budget Buy-In

I needed money for repairs—but there was no IT budget, since the department technically didn’t exist yet. So I dusted off my old freelance sales skills and pitched the case. It worked, 90% of the time. Slowly, I began setting up a mini repair center in my office to handle maintenance in-house.

B. Building an ERP from Scratch

I was building an entire ERP system—solo. Occasionally I’d get help from some software engineer friends, but for the most part, it was just me, stitching together a system from scratch. The Accounting department was expecting it to be up on my first day of work! 😂

C. Managing Marketing in Peak Season

Oh, and no pressure, but I was also managing marketing during enrollment season. We’d just launched a secondary school and needed students fast. So weekly I was dabbling in SEO work, weekly newsletters to parents, attending school trips for pictures, social media research and other means to increase brand visibility.

A “slow” day would have me at my desk by 7:30am and heading home at 9pm. On the intense days? I’d be in by 6am and out around midnight or 1am. Wild times… but weirdly, kind of fun.

Where This Is Going

Each day feels like a mini case study in expectation management, tech leadership, and big-picture thinking. Unlike previous jobs where I was just following instructions, I now find myself in the driver’s seat—making long-term decisions, not just executing them.

Some personal milestones for this role:

• Make David Mascott an ICT hub in the province — a place other schools look to for inspiration
• Get the ERP system fully adopted across accounting, HR, student management, and enrollments
• Level up the school’s digital culture and internal comms
• Market the school so well that parents are lining up to enroll their kids two years in advance

We’re already starting to see that kind of interest, with parents asking about Form 1 spots for 2026. The momentum is building… but there’s still work to do. And I’m excited. I really believe we can do it.

Want to work with someone who can build systems and solve problems at scale? Let’s connect and bring your school or business vision to life.