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Life & Work with Neil Sy of Chicago

Today we’d like to introduce you to Neil Sy.

Hi Neil, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
I inherited my first (Canon) film camera when I was 8 years old. This is when it all started for me.

My journey with photography has really been a story of curiosity, connection, and learning to see things differently. I didn’t start out with a perfectly mapped-out career path — photography began as something that pulled me in naturally. I was fascinated by the ability to freeze a moment in time and create an image that could make someone feel something.

I started taking/making images of People, Family, and Friends, now I specialize in Real Estate, Landscapes, Drone and Lifestyle Photography. They say that “necessity is the mother of all inventions” so I took that to heart. I owe alot to Regina (my RE companies admin) for my Real Estate Photography career. I wasn’t happy with the images that the Real Estate Photography companies were sending for my listings so Regina said, “if you can take your own pictures then take your own Damn pictures” and that was it. I started photographing my own listings and word got around and what was once my “milk-money” became my full time career.

Over time, that curiosity turned into a passion, and that passion became a career. I spent years refining my craft, learning not only the technical side of photography but also the importance of storytelling, patience, and truly connecting with the people and places in front of my camera.

Over the years, I’ve developed my craft across several areas of photography, including real estate, landscapes, aerial drone photography, portraiture, and lifestyle photography. Each one has taught me a different way of seeing — whether it’s highlighting the architecture and personality of a home, capturing the scale and beauty of a landscape, or creating a portrait that reflects someone’s story.

Aerial photography especially opened up a new perspective for me. Being able to showcase a property, a location, or a moment from above creates a completely different emotional connection and allows people to experience a place in a way they may never have seen before.

What I love most about photography is that every subject has a story. A home is more than walls and rooms — it’s where life happens. A landscape is more than a view — it’s a feeling. A portrait is more than an image — it’s a glimpse into someone’s personality.

Today, I’m grateful to have built a career doing what I love. Photography has given me the opportunity to meet incredible people, experience meaningful moments, and tell stories through images. I’m still inspired by the same thing that drew me in at the beginning — creating photographs that make people stop, feel something, and remember a moment.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
I would say overall, it has been a smoother road than many people might expect, and I think a big reason for that is because I never approached photography with the mindset that I had to be the “best” or compete with everyone else. I never started photography with the pressure of trying to prove something — I simply loved creating beautiful and meaningful images.

Photography was always about the experience for me: finding unique perspectives, capturing moments, and creating something that made people feel something. That mindset allowed me to enjoy the process and continue growing without losing the passion that brought me to photography in the first place.

Another thing that shaped my journey was that photography wasn’t my only career path. For many years, I was working at the Chicago Board Options Exchange while also being a full-time Realtor in Chicago. Those experiences actually helped me develop skills that became incredibly valuable in photography — understanding people, paying attention to details, working under pressure, and recognizing what makes a property or a person stand out.

Of course, there were challenges along the way. Balancing multiple careers, constantly improving my craft, learning new technology, and adapting to a changing industry all required dedication. Photography is a field where you never stop learning, and I think that’s part of what keeps it exciting.

Looking back, I think not putting too much pressure on myself allowed me to stay creative and authentic. I focused on creating images I was proud of, connecting with people, and continuing to grow — and that approach has carried me to where I am today.

Thanks – so what else should our readers know about your work and what you’re currently focused on?
My Real Estate back ground is a Huge Differentiator. Many photographers can take a pretty picture of a home; someone who has actually been a Realtor understands how buyers emotionally connect with a property. We (Photographers) have our own “Style” of photography and anyone that see’s one of my images will automatically know that I photographed it. That’s what I’m most proud of.

Do you have any memories from childhood that you can share with us?
I’m a product of the 70’s and 80’s, born in 1969. Growing up before smartphones, social media, and digital everything — when memories were made through experiences, not captured constantly.

My favorite childhood memories come from growing up in the 1970s and 1980s, a time when life felt a little simpler and a lot more adventurous. I was born in 1969, so I grew up in a generation where we spent more time outside, explored our neighborhoods, and created our own entertainment.

Some of my favorite memories are the simple ones — being outside with friends, riding bikes, playing until the streetlights came on and off ;), family gatherings, and those everyday moments that didn’t seem special at the time but became the memories I appreciate most today.

Looking back, I think that era helped shape the way I see the world. We weren’t constantly documenting everything with a phone or a camera, so moments felt more present and meaningful. You learned to appreciate the details and remember how things felt.

I think that may be part of the reason photography has always resonated with me. At its core, photography is about preserving those moments — capturing a feeling, a place, or a memory so it can be experienced again years later.

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Nighttime city skyline with illuminated buildings and a central street leading to a tall skyscraper with a purple-lit spire.

Young woman with long blonde hair wearing a black and yellow sports jacket, standing outdoors on a field.

Man with dark curly hair and beard smiling, wearing a gray blazer and light blue shirt, against a dark background.

Two people wearing hats and blue jackets working on a log structure outdoors, with trees in the background.

Train on tracks with city skyline in the background, clear sky, and urban landscape.

Aerial view of a baseball stadium with green field and seating areas, surrounded by city buildings.

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