Canada’s meeting place for freelance writers and creators
Established 2010
Canada’s meeting place for freelance writers and creators
Established 2010
The first time a freelancer considers teaching rarely feels official. It happens halfway through an email. Or in the middle of a conversation with a colleague. Or while explaining the same thing for the third time in a week, when it suddenly becomes clear that what feels routine to you…isn’t routine to everyone else. That moment—quiet, unceremonious, easy to dismiss—is often where teaching begins. At a recent Canadian Freelancers Guild panel on How to Teach What You Know, a group of freelancers who now teach through workshops, courses, and speaking engagements talked about how that realization showed up for them. None described a grand decision to become a “teacher.” What they described instead were patterns: repeated questions, shared struggles, and the slow recognition that their everyday freelance experience already contained lessons other people were actively looking for.
Long before most freelancers think of themselves as educators, they’re already doing the work of teaching. They explain their process to clients. They give feedback to collaborators. They mentor junior freelancers. They edit drafts, walk people through systems, and troubleshoot problems in real time. Over time, those explanations start to repeat—and repetition has a way of revealing where knowledge lives. Over years as a journalist and editor, donalee Moulton began to notice the same sticking points coming up again and again. What felt obvious to her was consistently confusing to others, and that gap—between familiarity and understanding—became instructive. Teaching doesn’t require encyclopedic knowledge. It requires noticing where people slow down, hesitate, or get stuck. If you can identify those moments, you already have the raw material for a workshop, a course, or a talk. A useful test is boredom: if you’ve explained something so many times that it feels almost automatic, there’s a good chance it’s exactly what someone else needs to learn.
Knowing something and claiming it are two different things. For many freelancers, the hesitation isn’t about content—it’s about authority. Am I experienced enough? Do I need credentials? What if someone knows more than I do? Many freelancers recognize this hesitation as a familiar version of imposter syndrome—the same voice that shows up when pitching, raising rates, or taking on more visible work. In the context of teaching, it often sounds like a question of legitimacy: Who am I to stand at the front of the room? Through his work teaching journalism in both academic and professional settings, Mark Kearney has seen that learners aren’t usually looking for perfection. They’re looking for clarity—someone who has navigated the terrain and can help them avoid common mistakes. In many cases, being only a few steps ahead is an advantage. You still remember what was confusing. You haven’t forgotten the early missteps. That proximity often makes teaching more relevant, not less. Teaching doesn’t require having the final word—it requires having a useful one.
Most freelancers don’t begin teaching with a fully formed course or a polished syllabus. They start with something much smaller: a guest lecture, a short workshop, a one-off session for a community group or conference. These early attempts are rarely elegant. They’re often overstuffed, overprepared, and underestimated in terms of effort—and that’s normal. Several panelists spoke about the early impulse to give participants everything: every resource, every lesson, every caveat, all at once. Paying attention to what people actually ask for can be clarifying. Robyn Roste, a writer and instructor, described how repeated questions helped her narrow her focus. Teaching became less about covering all possible ground and more about helping people move past specific obstacles. The first version of a workshop or course isn’t a final product. It’s a draft.
As teaching becomes more regular, different challenges emerge: time, energy, pricing, and emotional labour. One of the most common early mistakes freelancers make is over-delivering—packing too much into sessions, underpricing their work, or assuming that teaching should be driven purely by generosity. While generosity matters, sustainability matters too. Teaching is labour. It requires preparation, performance, follow-up, and revision. When those costs aren’t acknowledged, burnout isn’t far behind. Designing teaching work that can be repeated without depletion is essential. Michelle Waitzman, an editor and educator, emphasized choosing formats that fit both temperament and capacity. Some people thrive in live workshops; others prefer asynchronous courses. Some enjoy discussion-heavy sessions; others do their best thinking in structured presentations. The goal isn’t to choose the most impressive format—it’s to choose one you can realistically sustain.
Throughout the panel, one idea surfaced again and again: teaching isn’t separate from freelancing—it’s an extension of it. That means the same principles apply. Clear scope. Fair pricing. Defined boundaries. An understanding of who the work is for and what problem it solves. Teaching becomes far more manageable when it’s treated as a professional offering rather than a personal favour. This shift—from “sharing what I know” to “offering something of value”—often makes the difference between teaching that drains you and teaching that lasts. It also helps freelancers make clearer decisions about what to say yes to, and what to leave on the table.
One of the quieter insights to emerge from the conversation was how teaching changes the freelancer, not just the audience. Explaining your work forces you to articulate instincts you may have taken for granted. It sharpens your thinking. It reveals gaps in your own understanding. In many cases, it strengthens your core practice. Teaching isn’t just a way to pass knowledge on—it’s a way to look at your own work more clearly. That feedback loop—between doing, explaining, and refining—is one reason many freelancers continue teaching once they start, even when it’s challenging.
Teaching doesn’t begin with confidence. It begins with attention. Attention to what you know. Attention to what others ask. Attention to where your experience might help someone else move forward. You don’t need to wait until you feel ready. You don’t need to know everything. You don’t need to call yourself an expert if that word feels heavy. You just need to notice the moment when something you know could help someone else—and be willing to try. For freelancers curious about teaching but unsure where to start, the full CFG panel on How to Teach What You Know offers candid stories, practical perspective, and reassurance from people who didn’t set out to become teachers, but became effective ones by paying attention to what they already knew.
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