When I left my full-time media job in November and went freelance, I was excited about the possibilities of writing what I wanted, when I wanted, for who I wanted. After all, I watched so many people go through media layoffs only to secure dream gigs and book proposals shortly after. And while it could seem risky to leave a comfortable staff position, many of the writers I knew who did it ended up getting more ambitious projects and higher salaries in the long run.
At the same time, I was worried about the usual hurdles: Would I make enough money, and could I pay rent if I didn’t? What if no one took my pitches and I couldn’t figure out why? Would I be able to keep track of all my ideas, deadlines, and invoices — or would I eventually fall apart just trying to stay afloat?
I only thought of these questions (and felt well-prepped for self-employment) because of the advice of other writers. Without even realizing it, I had internalized Tweets of freelancing tips for a long time, so much so that when I reached out to my first few editors, I didn’t waste hours crafting the perfect message