At some point, your business might grow enough that you need help — someone to answer emails, manage social media, handle overflow bookings. And the moment you bring someone on, you’ll run into a question that has real consequences if you get it wrong: are they an employee or a contractor? This isn’t a preference question. The IRS and the Department of Labor have actual criteria for this, and misclassifying someone can mean back taxes, penalties, and a much worse conversation