Today we’d like to introduce you to Greg Cali.
Hi Greg, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
Like many artists, my story began early. In fact, sometimes I feel like it began before I was even born—almost as if I was reincarnated into creativity. I’m sure I’m not the only artist who feels that way. As a kid, I was never discouraged from being creative. My mom always made it feel like being an artist could be an incredible career, and she never steered me in any other direction. My dad was, and still is, as supportive as a parent can be—always keeping things lighthearted and enjoyable, even during the tough moments.
I started with the classic childhood mediums: watercolors, finger paints, chalk drawings—anything I could get my hands on. Somehow, that spark never faded. Here I am, 40 years later, still using some of the same mediums and even some of the same techniques I loved as a kid. And I still enjoy them just as much.
A lifelong creative journey comes with plenty of trial and error. Over the years I explored everything: graffiti, music production, design, furniture building, painting, photography. Each chapter taught me something and shaped the artist I am today. I eventually attended California State University Long Beach, where I earned my Fine Arts degree.
In 2018, I opened TheCaliLife Gallery in Leucadia, California. Tragically, the gallery burned down in 2019 along with four other businesses. I lost a huge portion of my college portfolio and hundreds of original works—both my own and those of the artists I managed. It was devastating, but it was also a profound learning experience that still stays with me and probably always will.
After the fire, the community stepped up in an incredible way. Pandora’s Pizza invited me to run my gallery throughout their restaurant and upstairs loft. It was an amazing experience, but it came to an end when COVID hit. Closing the doors again was tough, but realistically, running a gallery during COVID would have been nearly impossible. I took it as a moment to pause, regroup, and search for a space that truly matched the spirit of TheCaliLife.
That search eventually led me to one of the most historic buildings in our city: The Guild, the old Mercantile building on Chesterfield Drive in Cardiff-by-the-Sea. This is where TheCaliLife Gallery was finally reborn. We held our grand opening in July 2025, and today our mission is to share art with the community while championing the value and impact of creative expression.
The challenges along the way have been countless—too many to list. If I wrote them all out, it would sound like a sob story. But the truth is, the wins have outweighed the losses. I’m still here, still creating, still pushing toward my goal of building a successful career as an artist locally and, hopefully, worldwide.
My mission now is bigger than myself. I want to make a comfortable living as an artist while helping create a culture where emerging artists feel confident they can build a sustainable career in the arts and where the community understands the value of supporting them.
What began as a solo journey of an artist who simply refused to quit has now become a family business that supports my wife, our two children, and a handful of pets here in my hometown of Encinitas.
The journey continues, and so does the art.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
If you’re a successful artist, I don’t believe there is ever an easy road to get there. If someone tells me their artistic path was smooth, then they’re probably one in a million.
Where do I even begin? Being an artist often feels like it’s you against the world. It feels like 99% of the people you meet look at you differently and assume you won’t be successful. Having those odds stacked against you from such a young age can really shape the way you view yourself and the world around you. I’ve tried not to let that negativity sink in, but if I said it never affected me, I’d be lying. There have been plenty of moments where I’ve questioned what I’m doing, questioned whether this path will work out, and even questioned whether it’s working out right now.
But then that relentless optimism shows up again, fueled by passion and the need to create. The journey is a series of highs and lows, constantly shifting. There are rarely long stretches of calm. The real challenge is finding a middle ground within the chaos. Learning to accept things as they come and going with the flow has become one of my super strengths. Not dwelling on setbacks and continuing to push forward is something I’ve done well. I’ve seen others give up along the way.
When you talk about a lifelong career, there’s no way to tell the story without acknowledging a long list of hard times. I remember the good moments, but the difficult ones leave a deeper mark. Losing my art gallery, losing my best friend, losing my dog, losing family members, all of it shaped me in ways I’m still processing. And in the middle of all that, my wife and I had children during COVID. Raising them while reopening an art gallery was a level of challenge that pushed me well beyond what I thought I could handle.
Around the same time, I was also expanding a wedding and event company that I had developed over the past fifteen years. Transitioning from being the photographer to being the manager and leader of the business has been incredibly hard. I’m still figuring it out, but I’m making progress. Managing every aspect of TheCaliLife while navigating personal hardships that most people never face has been overwhelming at times. I’ve put myself in a position to eventually reap a lot of rewards, but it has come at the cost of constantly climbing out of self-doubt and many years of struggle. Even so, I remain eternally optimistic, and I feel like I’m finally starting to see life unfold in front of me.
Success as an entrepreneur, especially in the art world, depends heavily on building relationships. And as everyone knows, relationships aren’t easy to maintain. Spending years trying to build a network within your community can be exhausting. But it can also be incredibly rewarding, and in many ways, it’s the only real path to success.
Running a business, any business, is hard. Whether it’s an art gallery or a tire shop, being your own boss and holding yourself accountable is a daily challenge. Believing in yourself as a full-time creative is one of the biggest tests of all. But despite everything, the struggle has shaped me, strengthened me, and kept me moving toward the life I’ve always wanted, a life built around art.
Can you tell our readers more about what you do and what you think sets you apart from others?
For the past fifteen years, I’ve specialized in photography and videography, with a strong focus on weddings and portrait work. While many photographers choose a narrow niche, I’ve always taken the opposite approach. If something inspired me, I pursued it. That curiosity shaped my career and allowed me to explore nearly every genre of photography before naturally refining my path.
Today, TheCaliLife covers an incredibly wide range of services, including real estate photography, family portraits, headshots, product photography, weddings, and events, among many other projects that come through my door. That variety keeps my creativity alive and constantly pushes me to evolve.
Before my photography and video career took off, painting was my primary focus. I created murals and commissioned art pieces for clients throughout the community. With the reopening of my gallery, that spark has returned. I feel newly inspired to paint again and plan to dive deeper into oil paintings and, possibly, watercolors as well. It feels like reconnecting with an older version of myself while bringing fresh perspective from years behind the lens.
When it comes to my photography style, I consider it rooted in creativity, intention, and a willingness to push beyond the obvious. As a wildlife and landscape photographer, I’m drawn to the small elements in nature that most people pass by without noticing. My goal is to bring those moments to life and invite others to see the world the way I do. I pride myself on looking deeper, searching for beauty in places that are often overlooked, and choosing to see this life for its wonder rather than its darkness.
What sets me apart is my ability to blend fine art, emotional storytelling, and technical skill across multiple mediums. Whether I’m photographing a wedding, capturing a hawk in the wild, or painting on canvas, the intention is the same: to create something meaningful, something honest, and something that reminds people of the beauty that still exists in the world.
Is there any advice you’d like to share with our readers who might just be starting out?
Don’t hold back. When you’re starting out, your only job is to explore. Try every part of the craft. Photograph anything and everything. Let your curiosity lead you, and use the power of your youth to experiment without fear. Trial and error is your greatest teacher. Embrace the mistakes, the frustrations, and the failures. They are not setbacks, they are fuel. Turn every misstep into a fire so strong that you feel compelled to create something meaningful from it. That energy is priceless.
Use your younger years to be as creative as possible. Paint, think, dance, sing, wander, observe, and simply be. When you get older, life becomes a constant blend of highs and lows, and finding space for pure creativity becomes harder. When you are young, you can see the world the way you want to see it. That kind of clarity only comes once. Lean into it. Let your naivety become a superpower rather than something you eventually outgrow. It sharpens your imagination and frees you from the fears that tend to build with age.
If I could go back and tell my younger self anything, it would be this: stay curious, stay relentless, and stay in motion. Create so much that you eventually discover the work that feels like home. And once you find it, protect it with everything you have.
Pricing:
- Weddings start at $2500
- Family Session start at $395
- Real Estate Photo & Video starts at $250
- Headshots start at $100
Contact Info:
- Website: https://thecalilife.com/
- Instagram: https://www.instagram.com/thecalilife/
- Youtube: https://www.youtube.com/@GregCali-TheCaliLife
Image Credits
All photos were taken by me, Greg Cali 😉
