Why would anyone cut off their foot—only to have it sewn back on again?

That’s how the last couple of months have felt as I moved my business from using contractors to having employees.

The contractor model was working. The business was successful. Nothing was “broken.” My foot was doing exactly what it was supposed to do. So why change it?

As I looked ahead to my 2026 business goals and talked with my accountant, it became clear that some of the changes I wanted to make simply didn’t fit well within a contractor structure. To grow the way I intended, I needed to evolve to having employees.

At the decision stage, I was comfortable. It was well thought out, informed, and strategic.
Decision made. Cut off the foot.

Then came the pre-op work… and that’s where reality set in.

Suddenly, I needed to:

• Engage an HR firm to create an employee handbook
• Navigate multi-state labor laws and compliance requirements
• Find a payroll company that could handle different state wage policies
• Write compliant job descriptions
• Register with federal and state labor and unemployment departments
• Decide on holidays, closures, and internal policies
• Create policies for things no one warns you about (AI usage, social media, technology, pets, children in the workspace…)
• Update business and unemployment insurance

So many moving pieces I hadn’t fully appreciated when the phrase “move contractors to employees as of January 1” was first said out loud. It sounded so simple at the time.

The real challenge wasn’t the decision—it was putting everything back together.

Sewing the foot back on.

I wanted the transition to be seamless for my contractors, now employees. I didn’t want their work interrupted. I wanted clients to experience a smooth transition they barely noticed. So the work happened quietly, behind the scenes—connecting the pieces, tightening the processes, and making careful adjustments so the business could function exactly as it had before… just under a different structure.

I’m happy to say the foot is working.

There are still a few final stitches happening, but the system is functioning—and the growth potential for Office Allies is now wide open.

If you’re considering moving from contractors to employees (or hiring your first of either) and want to talk through the realities, feel free to reach out. I’m happy to share my experience and point you toward some excellent HR and payroll professionals who helped along the way.