This comes down to how quickly you can transcribe at home, how well you develop your "ear," and how much time and attention you are willing and able to commit to your transcription work.  Of course, you also have to find the best-paying transcription jobs, and we help you with that.

I type 80 words per minute, and when I am doing a higher-paying rush job I can make as much as $30 an hour.  On average, I make $14 to $18 an hour.  An inexperienced or entry level transcriptionist should still be able to make $7 to $10 an hour.