- Construction worker: Perry worked as a construction worker for several years, including at a construction company owned by his father.
- Security guard: Perry worked as a security guard at a retirement community for a brief period of time.
- Bill collector: Perry worked as a bill collector for a while, which he has described as a difficult and unpleasant job.
- Real estate agent: Perry obtained his real estate license and worked as a real estate agent for a time, but he found it challenging and not particularly lucrative.
- Playwright and stage actor: Perry began writing plays in the early 1990s, drawing on his own experiences and the people he met in his various jobs. He performed his plays in small theaters and community centers around Atlanta, gaining a local following.
- Playwright and director: As Perry's reputation as a playwright grew, he began directing his own plays, taking control of the creative process from start to finish. He self-produced and self-financed his first play, "I Know I've Been Changed," in 1992, and continued to write, direct, and produce successful plays throughout the 1990s.