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Amy Osborne: ‘You are epic. Your headshot should be epic’

Amy Osborne of Ozzy Headshots is an American headshot photographer and retouching artist based in Wilmington, North Carolina. She’s an associate photographer of Peter Hurley, a creator of retouching tutorials and calls herself a proud fan of Affinity Photo.

Here she shares a glimpse into her origin story, set at the scene of a highway motorcycle crash. She touches on free-range rebel retouching, the comforts of virtual classrooms and more.

Tell us a bit about yourself and how you got to where you are today.

I made a vow once, laid out on an interstate highway—If I survive, I will help people, make the most of myself, and make the most of my life. I didn’t realise I was the vowing type, but a brush with death can arouse a sudden vast shift in perspective. For me, it felt like suddenly waking up. I could see the dream I’d been thrown from and the reality I’d landed in. The next thing I knew, I was vowing.

The scope, scale, and specifics of what happened next make for a longer story, which I’d love to share with you sometime. The short story is I devoted myself to the vow I’d sworn on my life to honour.

What lead you to focus on headshot photography in particular?

I’d always wanted a pro camera. I decided to go for it in 2017, rightly concluding it was aligned with my vow. Someone I barely knew, a virtual acquaintance, told me I would love a particular photographer. He gave me a name, Peter Hurley, which I typed into a search bar.

I was taken. He was so good! When I discovered he was actively coaching, big on self-development, and a total kick, I joined his Headshot Crew without another thought.

To be a highly skilled and well-regarded headshot photographer and retoucher—this became my goal. While I already had nearly two decades of retouching experience, I was starting from scratch in professional photography. I had earned a master’s degree in an unrelated field years earlier. Rapidly attaining proficiency in one speciality can act as a gateway. It did for me and I saw no reason why I couldn’t master other specialities. I loved my virtual classrooms, especially those at Headshot Crew, but also CreativeLive, YouTube, and elsewhere. I was learning up a storm, in my loungewear at all hours (with popcorn).

Before the year was over, I’d made good progress toward my goal. I’d earned a place for myself among Peter Hurley’s esteemed associate photographers, his one and only in North Carolina, and I’d released my first retouching tutorial, which was well-received despite being pretty primitive. I hope to continue developing my potential as a headshot photographer, retoucher, and instructor, but we never know how much time we have and that’s the point.

Who are your typical clients?

I love my clients. I’d say my typical individual client is gutsy, purpose-driven, and excited. No more waiting for someday, waiting for conditions to be perfect, waiting for permission. Usually, by the time they seek me out, they’ve seen the striking difference a thoughtful personal brand makes and they’re all in. Individual and corporate clients alike pay attention to how the pros present themselves. They get it.

What happens when you meet a new client for the first time?

My clients know from our correspondence that I’m at their service.

In the studio, I encourage my clients to kick off their shoes if the spirit moves them, unpack their things in the dressing room, and stay as long as they’d like. Unhurried service is a luxury and this is a high-end experience.

On-location corporate events can be a bit of a whirlwind, but a lot of fun. I recommend allowing at least 15 minutes per individual, even though the magic sometimes happens faster. There is less time for rapport building, coaching, and playing with different looks, but we can make every minute count.

Why do you think people get anxious about having their photo taken?

I tell my clients they’re in good hands whether they’ve got butterflies or they’re as cool as a cucumber, whether they enjoy having their picture taken or they struggle to find peace with their appearance. Many of us carry around thoughts of perceived flaws and maybe even feel uniquely flawed in some ways.

I always love to hear my clients tell me they felt at ease shortly after arriving. Others take a little longer to warm up. This is a human experience. As a photographer who also happens to be a speech-language pathologist, I come to each photoshoot with a built-in therapist. My clients know they can tell me anything. Many perceived flaws are common occurrences. Many are fixable, something we can work with, or something we can workaround.

How do you prepare for a day of shooting? Does your process differ between shooting at the studio and shooting on location?

To prepare myself, my gear, and my space for a shoot, I fall back on my tried-and-true routines. I take the best care of my most essential piece of equipment (i.e., me). Rest and recovery, nutrition and hydration, stretch and relaxation—having my own wants and needs met allows me to better meet the wants and needs of others.

Shooting on location can be a workout. I may eventually hire a strapping young character to transport my gear to and fro while I watch (with popcorn), but I still do it myself. I give myself bonus points for speed, efficiency, and grace. I like to help my clients feel at home with me, even when we’re technically in their space.

What do you feel is the most challenging and most rewarding part of a shoot?

The ultimate challenge is to attain the ultimate reward, which is a delighted client who looks radiant and feels like a star. The effect has been known to last for days and months and longer. Have you ever loved a picture of yourself? I highly recommend the feeling. You are epic. Your headshot should be epic.

“The ultimate challenge is to attain the ultimate reward, which is a delighted client who looks radiant and feels like a star.”

What photography equipment do you use?

I currently shoot Nikon and it does the trick nicely. I’m not a photography gear nut per se, but I’m very enthusiastic about the equipment I use after a shoot because that’s when I pull shots into Affinity Photo on my iMac. That said, there are a couple of pieces of photography gear I’d like to mention. I really like the Westcott Rapid Box/Rapid Box Switch lines. And I must say I’m proud of my first speedlights, Yongnuo YN-568EX. They’re impressive little workhorses two years later. Isn’t it fun when underdog gear wins the day?

We’re delighted to hear that you use Affinity Photo for your retouching. How did you first discover the app and what impressed you about it?

Three cheers for Affinity Photo and all you clever humans behind it! Nothing less than a standing ovation is in order. I believe a friend mentioned it to me soon after its release. I still have to pinch myself from time to time. Here is a robust, intuitive, highly affordable graphics software experience that grants me superpowers to do the creative work I love without a subscription, never-ending financial burden, or sacrifice. I’m a happy customer and a big fan! Bravo and thank you, Affinity Photo!

“Here is a robust, intuitive, highly affordable graphics software experience that grants me superpowers to do the creative work I love without a subscription, never-ending financial burden, or sacrifice. ”

What are your typical post-production steps for retouching your photographs?

I like to be a rebel retoucher and a free-range retoucher, but I do tend to follow a typical process. I like to be more organised and efficient when I’m recording a retouching tutorial. For my headshot work, I like a light hand. I like subtle and clean changes.

First, I go after tiny temporary issues that I didn’t bother with in real life. The usual suspects are lint, rogue eyelashes, and flakes. Next, I get to work on other temporary issues like blemishes, congested pores, hairs we may not wish to immortalise. After cleaning up the subject to my satisfaction, I remove unwanted objects from the frame, fine-tune values and tones to my heart’s content, and crop just so.

My process and methods keep evolving. I recently dug up some favourite old shots and retouched them again from scratch. In this way, older work continues to evolve with me and stay current for me.

You’ve created a series of tutorial videos entitled ‘The Art of Headshot Retouching.’ What inspired you to create these tutorials?

Yes, it would be fun to see some of you on YouTube at Ozzy Headshots. People say funny nice things about my voice. I’m glad people respond well to it. My aim is to create better and better tutorials that help, inspire, and entertain.

I love YouTube and I love this project. At the risk of saying I love everything, I’ll add that I have a special affection for retouching.

I’d been retouching for nearly two decades before picking up a DSLR camera. Though I have no recollection of my earliest retouching effort, I’m sure I was trying to edit away cringeworthy distractions from my own face. More than just wanting, I think I was needing to see a picture of myself that I liked. There was a sense of relief when I saw myself with healthy happy skin. All these years later, I love to retouch for my clients and models and I love teaching my take on the art and science of it.

You are part of Peter Hurley’s Headshot Crew. What makes the Crew so special and what has being a part of the team brought to your photography?

Headshot Crew still has me pinching myself, too. Master Jedi Hurley, as I call him, has built this fun virtual place where artists from all over the world can gather together in classrooms, on field trips, on playgrounds, in loungewear (with some kind of buttery snack). It’s where I learned very nearly everything I know about headshot photography and other styles of portraiture. It’s been essential. I used to feel like part of the Crew, but now I feel like the Crew is part of me.

You recently moved to Wilmington, NC. What’s it like being a photographer in Wilmington?

Yes, I still wake up smiling. I’ve been here a year now. It was a lifelong dream of mine to live somewhere that felt like a beach vacation. The story of how I finally made it happen involves a 100-day self-challenge. Since then, I’ve been savouring simple pleasures and settling in. I’ve loved all my Wilmington clients and I’m looking forward to meeting many more. My headshot photography business, Ozzy Headshots, became official in this beach town. It’s an exciting time for me and my young business and I wouldn’t want this chapter of my story to be set anywhere else. I love to imagine all the possibilities. I’d especially love to see the moviemaking industry revived here.

“My headshot photography business, Ozzy Headshots, became official in this beach town. It’s an exciting time for me and my young business and I wouldn’t want this chapter of my story to be set anywhere else.”

What are your interests outside of photography? What do you like to do in your spare time?

I’ve been working toward a fun belly dance goal. My aim is to become a highly skilled and well-regarded belly dancer. I’m far from mastery, or ninja status as I call it. The gap between my current results and desired results dares me to keep going. This dancing is art and science, mind and body, and mesmerisingly beautiful. I want to outdo myself through this dance. I want to see my physical capabilities.

Lastly, what advice would you give someone just starting out in headshot photography?

I always recommend Headshot Crew for the same reason I always recommend Affinity Photo—it’s just that good and it’s not hard on the wallet. I also recommend CreativeLive. Chase Jarvis has a very cool thing going over there, too, and you can find some solid Peter Hurley courses over there. If you decide to check out the Crew, please come over and say hi to me.

Amy Osborne

To see more of Amy’s stunning photography check out her website, Instagram and YouTube, where you can watch her headshot retouching tutorials and tips—all done in Affinity Photo.