Hire a photographer who has experience taking headshot and modeling photos.
Hire a makeup artist with experience in creating camera-ready makeup.
Pick your indoor and outdoor photo shoot locations (if the photographer did not already suggest them) and make sure you can utilize them on the day of your shoot for free.
Gather your five changes of clothes and try them on ahead of time to make sure they fit and look fantastic.
Gather any accessories you'll need to accentuate or complete the five outfits you chose.