Your headshot is easily one of the most hardworking pieces of your personal brand. Over the years, I’ve photographed hundreds of professionals here in my Westport studio. I’ve seen it all. The good news? Most headshot "fails" are actually really easy to avoid.

Let’s be real: most people approach a headshot session with the same level of excitement they reserve for a dental visit. There are so many myths floating around about what this experience is actually like. Most of them are just flat-out wrong… or based on outdated experiences with less than professional photographers.

A great headshot can open doors. But a less polished one can send the wrong message entirely. With the right preparation, posing, and wardrobe choices, you can walk into your headshot session feeling confident and leave with images that truly represent you at your best. Here’s a detailed checklist on what to wear, how to pose, and what to avoid - based on the same process I use every day at my Studio…

If you’ve ever felt like the camera just isn’t seeing you the way you see yourself, you are not alone. As a professional headshot photographer who is also completely un-photogenic myself (this, in fact, is why I’m behind the camera and not in front of it!), I am here to tell you that it is not you. It is almost always a combination of bad lighting, poor angles, and a lack of guidance.

This year was the third Imaging USA conference that I attended, and the second on that took place at the Gaylord Opryland Hotel in Nashville Tennessee - Jan 11–13, 2026 with over 10,000 attendees. I specifically made a point to come back to Nashville because I thought the hotel was great the first time around.. but was the second time as impressive as the first? And is Imaging USA worth the cost?

I love working with small business owners to help elevate their brand photography, and nothing makes me more excited than collaborating with a female entrepreneur from the very beginning of her venture. Mallory Blake and I have been working together since 2021 with 7 photoshoots total capturing portraits and details for her new website and social media…

As a photographer, we all spend a lot of money on gear, software, and yes even education. As someone who likes nothing more than not paying full price, I put together this list of affiliate links and referral codes you can take advantage of to get a bit of a deal on the things you’ll probably use most as part of your photography business.