Pitching and the Art of the Follow-Up

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.

A proper desk space is not a prison, but somewhere you can escape from when you need to. Rest is just as important as productivity, so make sure to factor in that as well when you’re making your space your own.

If it feels like social media advice ages faster than almost anything else in freelancing, that’s because it does. Platforms change. Algorithms shift. Features appear, disappear, and reappear under new names. And yet, freelancers are still told—often urgently—that this is the year they really need to get social media right.

In a recent Canadian Freelancers Guild workshop on Pitching and the Art of the Follow-Up, freelance writer, editor, and instructor Robyn Roste walked participants through that exact moment—not as a tactical dilemma, but as a professional one. The central idea running through the session was simple but reframing: pitching isn’t a transaction. It’s the beginning of a relationship. And follow-up, done well, is part of that relationship—not a breach of it.

Many full-time freelancers wake up one day a few years in and realize that this way of working has become a way of life. Less of a stopgap between jobs and more of a satisfying business that you could see yourself continuing to do—forever? 

In an era where online visibility can make or break a freelance career, two marketing experts reveal the strategies that actually work—and bust the myths that waste your time and money.

In February, I spent a day at the Valuing Human Creativity in the Age of AI conference in Ottawa—an event that brought together artists, writers, technologists, and policymakers to wrestle with a question that feels increasingly urgent: What happens to human creativity in an era when machines can produce words, images, music, and video in seconds? And what does it all mean to freelancers?

Fifteen years ago, Story Board launched with a simple but ambitious intention: to give Canadian freelancers a place to learn, connect, and advocate for a better, more sustainable creative career.