Being Your Own Boss vs. Being Your Own Worst Enemy: Navigating Impostor Syndrome, Procrastination, and Distractions

June 11, 2026 11:30

"Are you working hard, or hardly working?" As a freelancer, the answer is often both - and neither feels quite right.

Burnout, mental health struggles, and balancing varying workloads seem to be recurring topics among freelancers.

Almost everyone seems to deal with these challenges and while it is comforting to know that we are not alone in this, what are we doing to improve things?

This session looks at three common hurdles - impostor syndrome, procrastination, and distractions - through the lens of freelancing, where there's no boss to validate your work, no teammates to keep you accountable, and no structure to keep you focused.

No productivity hacks or step-by-step guides. Just an honest conversation about what it's really like and why these struggles are so common when you're your own boss.

If you've ever felt alone in these struggles, this session is a reminder: you're not. We're all in the same boat, trying to figure out how to be kinder to ourselves.