A look back at the very beginning of working for myself

Nearly five years ago this summer, I attended my university convocation.

My contract ended at a downtown theatre company and I was only just starting to dip my toes in freelancing. I tried to get a “real job”, but no one seemed the least bit interested. One of the most profound things my mother ever told me was this:

“You didn’t miss the bus, you just weren’t meant to get on that specific bus.”

I’m unsure if she meant that as a metaphor. But that has been one of the most important lessons of my successes and failures ever since. And looking back on that moment I realize that this was probably why I was hearing the word “no” so much.

I think I practised in my head every day leading up to that the question I knew everyone would ask:

“So…what’s next for you?”

By then, I was starting to have lunches with editors and write for websites. Most people I talked to saw that as an accomplishment, even if, at the time I was living off almost no money, and sleeping in my parents’ attic.

I was blogging a lot and getting opportunities to write for websites on an inconsistent basis. But I had no actual plan beyond that.