A good headshot is extremely important to your small business: it says a lot about the entrepreneur(s) behind the brand, is often the first chance the media you're pitching will have a change to see what you look like (often when they're deciding to use you as an expert) and it's also the first chance potential customers will get to see who you are.
Though everyone, whether they run a product or service based business, should have an updated headshot available to them at all times, a current headshot is especially important to service-preneurs and experts who are hoping to land on-air press opportunities. A television producer will directly ask you for a headshot and you must be able to deliver a professional looking image that reflects how you look today, not five years ago.
Just as you wouldn't use a sloppy looking image on a family holiday card or as your image on an online dating site, don't use one for your headshot either. In the same vein, you wouldn't use a photo from three years ago in a family holiday card or post a photo from years ago on a dating site, so don't do it for your professional work headshot. Not only is it dishonest but it won't do your press relationships any favors either.
Speaking of the press and potential customers, remember who this photo is for....Sure it's representing your brand and you, but what is the entire goal here? If you want a personal glamour shot session you want to hang in your home or over your mantle that's artistic and satisfies secret dreams of being in a major fashion spread or something similar, perhaps save that for a different photo session. You are using these shots to sell your business and expertise to potential customers and the press who will potentially be introducing you to their viewers or readers. Anything that doesn't make you look approachable, something that's a little too artistic, funky or confusing will not be doing you any good in this situation.
If you've read this far and are beginning to think, "it's time I plan a headshot session", be sure you jot down a few more notes to ensure the session is worth your time and money!