The first thing first: The best time to get your next headshot is after you've changed your look. This could be a hair cut or color or new glasses situation, or even something that took a little more time like weight loss. If you don't go through much physical change, then I'd recommend every 2-5 years for updating your head shot. The reason is that styles change over time just like our appearance even if we don't realize it. Don't let 15 years pass without updating your head shot! Now, the next question is often about whether or not any photo will do. The technology to take a good photos with your smart phone is here. There are hobby photographers with professional gear. The difference between using a good candid photo or a professional is the experience and understanding of what is needed in the ever changing media world. It is no longer about equipment, and more about technique and experience. I'll use myself as an example. I cut my hair short, and at a friend's party the next day, my husband captured a wonderful photo of me with a real smile. I was feeling happy and it was a fun environment for a friend's birthday party. He was using my camera, and I was so eager to share my new look that I immediately used it to update my Facebook profile, and business profiles from LinkedIn to Twitter. But, on social media, the photo wasn't as good of a fit because it has a busy background. When profile photos are 50x50 pixels in size, the key to standing out is a photo that is easy to "read" or see. That is why I updated my head shot with a simple background, and more contrasting light to show off more of my face shape which stands out on a tiny image. And, it is one reason I offer an Online Profile Portrait package - so that you have photos that stand out at various small sizes across social media platforms. My personal head shot by my husband is still wonderful and meaningful, but it is better for my About Page or personal Facebook profile than it is for my business.