Alright – so today we’ve got the honor of introducing you to Kailah Winston. We think you’ll enjoy our conversation, we’ve shared it below.
Hi Kailah , thanks for joining us today. What’s been the most meaningful project you’ve worked on?
The most meaningful project I have worked on was a mental health awareness photoshoot.
We moved from the US to the UK in 2021 and during that transition our lives were completely topsy-turvy. I was looking for groups and organizations, anything to join ahead of our arrival in the UK so that I could start making our new lives here. A lady who was already in the UK started a group and I asked to join letting it be known that I wasn’t in country yet and she welcomed me with open arms. She essentially became on of the very first people who I knew, and one of my first friends in the UK.
I knew for a while I really wanted to work with kids of all ages and I needed some subjects to shoot in order to build my portfolio. I sent her a message asking if I could borrow her son for a photoshoot. Without batting an eye she agreed and said, “of course you can and good luck with him because he doesn’t like being still for photos”. She has not only helped me but helped so so many people in the community by volunteering, being a shoulder for people, and just being a cheerleader for all of those around her.
Unfortunately, I didn’t know that she was battling depression and was on a journey of healing. She sent me a message asking to assist her in a doing a mental health photoshoot to represent her journey. For someone who has always been there and supported me, I was so honored to be asked and immediately said yes. Photography is art, and I couldn’t resist the opportunity to also use this art to help raise awareness for mental health.


Kailah , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I have always had this huge passion for photography through my whole life. From taking pictures in my mothers’ garden to images of friends at the skatepark, photography has been a constant for me. After many curve balls in life, I found myself living in the UK with two kids and wondering what I wanted for myself. After doing my daughters’ first birthday photos and a few other random things I discovered I really wanted my own photography business.
Since beginning my business in 2022 I have learned a lot and discovered that you need to stop trying to fit in a mould of what you think photography is. It’s art! It’s your art and I do my best work when I don’t feel the pressure from the industry standards. I like to think I am creative and lend myself more towards shoots that are a bit different. One of my favorite sessions was a clash of subject and surroundings. I did Pennywise and Wednesday in the bright red poppy fields of England.
The majority of my clients are returning clientelle which is the core of any successful small business but I try to go above and beyond for my people. I had a session the other night at a Cathederal and it was a family I have done a session for previously. After taking some photos, I asked them, “what didn’t you like about your photos last time?” I wanted to make sure I was giving them the best experience possible and show them their opinion and thoughts mattered to me. They expressed there was some family combinations they didn’t get last time, so we decided to prioritize those photos this time.
I am not here to just snap a few photos, throw some pretty edits on them and be done with my clients. I view myself as the crazy artsy Aunt who is always taking pictures to save their memories during that moment we are together. With as many sessions as I have done with my friend who asked me to help with her mental health session, I am sure thats how her kids see me.


Let’s talk about resilience next – do you have a story you can share with us?
Last year I did a flower mini session, my very first one in my career and I was excited but also terrified. All my slots were fully booked and the logistics of the field were all worked out. The day of the session the weather was all over the place. Due to the planning and schedule we had to move forward with the sessions and just keep fingers crossed there would be enough of a break in the weather for these clients to be taken care of. I was able to do all the sessions despite the weather being drizzly on and off. I edited all the galleries, sent them out so super excited. All done in beautiful warm tones with the flowers popping in color, and I was happy with the overall outcome.
I had one family where we had some difficulties keeping everyone together in the field and focused on the session. One of the family members had medical concerns that were not disclosed to me, and had I known ahead of time I would have been able to accommodate them better and be better prepared. But we still got some beautiful shots, their gallery is sent and I get an e-mail back saying they want a refund. I was completely devistated, my heart was in the pit of my stomach. I replied with my apologies and begged for what was wrong and what I could do to rectify this for them, with the only response being that the photoshoot wasn’t what they were expecting. I offered them more photos and a reshoot, but I was not given the chance to make it right for them.
During that time I questioned myself and what I was doing so many times. Finally, after many conversations with my significant other and myself I came to the conclusion that once in a while you have to take a loss. This was my first loss, just a few things could have made that session so much better and I took it as an experience to learn from. But it wasn’t worth stopping my passion for photography or my business I was working so hard to build. Instead I focused on continuing my education and improved my communication with my clients moving forward.


Is there a particular goal or mission driving your creative journey?
My goal driving my creative journey is to have something that is mine that I have built. My whole family is very successful and very independently driven to be accomplished. I have tried many different paths and none have worked out like I had hoped. None felt right or like something was missing to make it feel like me. After becoming a mom and having my second baby, I was becoming sad or even a bit depressed that I didn’t have a lot to show for all my years on this Earth. I wanted to make a mark, be known for something I accomplished, rather than being known for the accomplishments of those around me.
Photography is my mark, my accomplishment. I may not be an accomplished photographer to anyone but that’s OK! The point is it’s MY accomplishment and it’s for me. This is a way for me to capture the beauty in the world that surrounds us, freeze that smile in time from a loved one, and to help tell peoples’ stories through life- maybe even raising awareness about topics like mental health. Accomplishing these things makes me feel like I am doing something and I am giving something back to the world.
Contact Info:
- Website: https://www.foxtrotphotography80.pixieset.con
- Instagram: @foxtrotphotography1
- Facebook: @whatthefoxphoto



