When I first became self-employed, it was with a copywriting service for radio stations. I did it all myself, from the creative writing to the bookkeeping. How did that work for me, you ask? At the beginning, it was fine. I was able to get it all done. But as my ideas and my business grew, I was not able to keep up, and I lost a couple of clients because of my other clients’ deadlines. So when is it time to hire someone? Look for these two red flags: Your business isn’t growing because you spend all your time doing the production and less and less doing the marketing You can’t keep up with your work on a daily basis. Don’t worry. You can still have control of the final product; you are the boss!