A leading career coach finds her livelihood on the line when her rival dares her to use the career-launching skills she brags about to transform a mysterious homeless man.

If all is at risk is her livelihood the stakes don’t seam high enough – she can always get a job waiting tables…
What if she was called out by her rival in public on stage in front of the largest audience she has ever taught whilst being broadcast live to the nation on TV. This way her reputation and legacy are at risk which I find more interesting than her livelihood.

Also the homeless man being mysterious doesn’t add to his character and therefor sounds strange as a description of the homeless man. If the description was that he is a drunk, an illiterate or mentally unstable then her challenge is even greater and as such the description of the homeless man contributes to the concept. Otherwise if you are trying to setup a plot twist where by the homeless man is a plant by the rival then it is not coming across and in any case it would be better to leave such twists for the synopsis so no need for the description to be mentioned in the logline.

Secondly best to describe the inciting incident as a significant event that forces the MC into action as appose to a state of being the MC “finds her self in”. Then make the goal a derivative of the inciting incident. Best to define her goal in specific terms what exactly does transform the homeless man mean? He must be working a full time job in 30 days? A part time job? He must be working as senior management in a company in 30 days?

My try:
After being challenged on live TV by her rival a leading career coach must protect her reputation and legacy by transforming a homeless man into a gainfully employed business person with in 30 days.

Hope this helps.