The days of having only one headshot or studio bust portrait for your business is over. It used to be that you only had a few places to put a portrait and design space was limited.
We have the internet now.
You have a lot of available web-real estate that you need to use. There are too many content spaces to fill for one portrait to satisfy. You don't need a glamour shoot and tons of lights and craziness. You just need a few nice environmental portraits that places you within your business's context or in the communities in which you work. It's about approach-ability. More on that in part 2.
But what about people recognizing me? Won't people find it weird that I have inconsistent headshots or portraits across my social media spectrum?
No. We all use Facebook (or should be...) and we are all used to seeing profile photo updates, tagged photos, and many different portraits of people. Having multiple portraits is actually a benefit to you. As long as you stay away from offensive or polarizing imagery.
Having multiple portraits opens the door to creating more connections. People will ignore the photos or portraits that don't appeal to them and will hone in on the ones that do speak to their unique personality. So it's like having variations of your personality that are uniquely tailored to different types of people.
A good portrait shows people how you look. A great portrait speaks to people about who you are. It lets them emotionally connect with you as a real person and not just a facsimile. This is the main reason that the 'High-School-Portrait' style headshots are a waste of time. If you're broke and just need something to put up I would still suggest not using one of those for your portrait. It says "I'm just like everyone else."
You need a photographer that you are friends with and will work to create portraits that show who you are. It is no easy task but it is extremely rewarding. Wouldn't you prefer to be seen as warm, caring, professional, and fun instead just another agent with a blue backdrop.