We’re excited to introduce you to the always interesting and insightful Jacqueline DelBrocco. We hope you’ll enjoy our conversation with Jacqueline below.
Jacqueline, appreciate you joining us today. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.
Taking risks is a huge part of being an artist. There’s a famous quote – The more you’re willing to try something that might not work, the more you’re thinking like an artist. I can’t remember who said it but whoever it was, they were dead on.
When I first started out, I jumped at almost any opportunity that came my way. My advice to young creatives is to do the same. It’s the only way to figure out what really ignites your passion and as a bonus, you gain valuable experience and knowledge along the way.
Early on in my career, I went through a period like most that was so full of unknowns. I felt lost and unsure of what move I should make next, let alone what I wanted to ultimately do with my life. I think the solution to this dilemma is to just keep moving. Keep trying. Keep DOING.
The most helpful advice I heard back then was to embrace failure, rather than fear it. As a perfectionist, I found this concept strange at first, but when you think about it, it makes sense. If you’re too afraid to fail, you’ll rarely try anything new or different from what you already know. This makes progress and growth nearly impossible. Failure is not an end, it’s just another step along the way, teaching and redirecting you a little bit closer to a more favorable outcome.
Growing up, my parents constantly encouraged me to pursue with enthusiasm whatever interested me. No matter what it is, as long as you’re always working hard at SOMETHING, you’ll make progress. And in the end, every little thing you do, every little experience, will add up and pay off somehow.
Following that advice into my early 20’s, I kept myself busy participating in public art projects, responding to calls for entry, giving artists talks to any group who would listen, conducting informational interviews with any artists or gallery owners who would talk. I showed my work in whatever group or solo shows I could get into, I entered art competitions, taught myself how to build websites, took on a number of freelance clients… I even accepted a position as the local showcase director for a national artist network headquartered in LA. (I flew out to Hollywood to train for 3 days and remember thinking to myself, “Is this totally crazy?”) I was working fulltime as a graphic designer at a corporate company back then, so taking on a second full time gig was a bit much…. But an opportunity that exciting was just too tempting to pass up! Over the next year, I directed large bi-monthly multi media showcases in Cleveland, each exhibiting 40+ local artists of all different disciplines. Through this experience, I met so many amazing, talented, individuals and felt completely immersed in the most positive, creative energy. It was incredibly inspiring to be exposed to so many different ideas, mediums, styles and people. I think this was when the first tiny seed of the live event painting concept was planted in my head.
During those earlier years of wonder and creative exploration, live painting was just one of MANY ideas I pursued. At first, it was basically an experiment, another creative idea to see how it would go. For my first official “hired” event, I had to write up a proposal and do some serious convincing just to earn the opportunity to paint a fundraising gala for FREE. Now my live paintings sell for $3,000 – $7,000 each and I’m usually booked for the year before January hits. That first event might have cost me at the time, but it was an investment. And one that paid off greatly!

Jacqueline, 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’m an artist, software designer and what people usually find most interesting, a live event/wedding painter. If you’re not familiar, the idea is that I paint your event while it’s happening. I start out with a blank canvas and as your celebration unfolds, the scene that I’m painting develops right before your eyes. It’s a wonderfully unique form of entertainment for guests as they watch the scene come to life over the course of an event and it’s been especially popular for weddings. Not only is it a unique way to wow your guests, but the end result is a completely one-of-a-kind work of art capturing the energy and memory of the couple’s big day – Something that can be cherished and passed down for generations.
Live event painting is definitely a niche market, not a lot of artists do it, and I’m really thankful to have stumbled upon this path over 10 years ago. It all started by painting my musician husband for fun while he performed. I realized how exciting it was to paint surrounded by people, rather than alone in my studio and luckily, the surrounding people enjoyed watching me too. I went on to paint a variety of charity events for local non-profits and after painting an event at the Cleveland Museum of Art, the museum recommended me to one of their brides. That ended up being my first live wedding painting and everything spiraled from there. (I still paint other types of events too, but most of the events I paint these days are weddings.)
Building this business has surely been an exciting journey and I’ve learned a lot over the years. Each new painting and event experience is another opportunity to refine my technique. My personal, unique painting style is at the foundation of what I do and I’ve always aimed to stay true to my individual instincts as an artist, in hopes that my paintings would stand out from other live painters out there.
I often mention Renoir as one of my greatest painting heroes. It’s nothing short of magic the way his paintings look so energetic and almost messy up close, but from far away, blend together into a perfectly orchestrated scene. Following in the footsteps of the Impressionist School, I love working with paint to try and achieve this same magical balance in my own artwork. It’s a way of painting that feels most natural to me and I believe it to be especially well-suited for capturing the dynamic energy of a celebration. My own personal flavor of Impressionism includes a lot of excited brushstrokes and paint splatters, particularly in the crowds. I try to paint not only what I see, but what I feel while I’m there, while I’m in it.
A lot of the other wedding painters I’ve seen online tend to lean more towards realism, and that’s totally fine. Art is subjective, that’s part of what makes it art! But for me, I prefer the messy energy, the brustrokes, the paint splatters… it communicates more emotion, more feeling. And the thing that really keeps me going is the challenge of finding that perfect balance between realistic, recognizable portraits and raw, inspiring, energy!
What’s the most rewarding aspect of being a creative in your experience?
It’s probably no surprise that I would say painting weddings is fulfilling work. Each time I deliver a finished piece, it brings me so much joy to see a couple relive the memory of their big day through what I created for them. After putting so much time, energy and heart into a creation, there’s nothing better than to see it truly appreciated.
But besides the obvious, I think the most rewarding aspect of being an artist is the challenge and the thrill of it.
It’s easy to do as you’re told. To follow guidelines and step by step milestones already set in place and figured out for you. That’s the appeal of the corporate ladder I think. The reason so many people end up in the rat race. I’m not saying there’s anything WRONG with that… it works great for some people and that’s wonderful for them. But for most creative people headed down that path, there will always be a yearning for something else. Something different. Something MORE.
Don’t get me wrong, I’m not anti-office, anti-corporate world. I just say, do it YOUR way. There are tons of job opportunities for creative people out there, in corporate and non-corporate environments alike. More importantly, who says you need to be categorized by picking just one? (I truly hate being categorized.)
After several years of focusing on my paintings, directing art shows and doing freelance design work, another opportunity presented itself that really caught my attention. It was a position as a designer at a software company and I jumped at it with just as much curiosity and excitement as ever. I ended up loving it so much I’m still working at that company fulltime, going on 9 years now. While I ALSO paint weddings. For me, this is my perfect balance. It might seem crazy to some, but as creative people, why should we do things conventionally?
As a kid, if someone told me I would grow up to be a live wedding painter/software designer/artist, I would probably say “Is that even a real thing?” Well, it wasn’t back then but I can say with full confidence it is now! Our world has changed a lot, and these last couple years have been especially transformative. Everyone’s talking about hybrid work models and I say take it a step further. If a variety of work environments (home/office/on the go) might help you find balance, what about a variety of work itself? To find MY balance, I prefer to have multiple careers, multiple projects, multiple things going at all times. It might sound backwards, but this is actually how I avoid burnout.
Why put all your eggs in one basket? If you do, your work categorizes you. Instead, own who you are and really BE a creative individual. Selectively and deliberately allocate your energy towards whatever “work” (jobs, projects, creative endeavors, collaborations etc.) works for you. In my experience, this mindset allows me to do my best work, give my all, and results in the best outcome for everyone involved. One creative project usually fuels another.
The key of course is finding the work you truly enjoy so you don’t feel like your efforts are futile or that you’re always working for “someone else”. And the only way to find that work is by taking risks, experimenting, and trying as many different things as you can until you fail/redirect your way to that sweet spot.
I think the most exciting part about being an artist is that you never know what that next project will be, what new challenges you’ll have the opportunity to solve and conquer, and what new creations you’ll be able to bring into existence. It keeps the thrill in life infinite!

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
At the risk of sounding cliche post pandemic, I have to say my biggest “unlearned” lesson was finally outgrowing the whole “exhaustion as a badge of honor” mindset.
An individual’s level of exhaustion is by no means a sign of their work ethic. If anything, it’s a sign of stupidity and poor prioritization. This toxic mentality somehow became ingrained in our society and I’m glad to see people finally speaking out that it’s time for a paradigm shift. It IS possible to be incredibly hard working and also take care of yourself at the same time. In fact, if you don’t, your “hard work” will inevitably hit a wall and you’ll be forced to deal with it whether you want to or not (ironically making you LESS productive as a result).
That being said, years ago I fell into the trap of thinking that my heightened stress level and visible exhaustion were admirable side effects of my extraordinary grit. Naturally, the harder I was working the more tired I would appear, right? Wrong. Busier = More Successful? No.
I don’t mean to sound judgy. This was SUCH an easy trap to fall into…. But I’m happy to wake up and realize now that there’s a much more healthy and sustainable way to be productive and accomplish things.
I will ALWAYS love the thrill of a deadline, the challenge of biting off more than I can chew and chewing it anyways, finding that state of flow and creating/painting/working for hours on end because I don’t WANT to stop… But that’s just it. There is a HUGE difference between working in a state of flow and working in a state of stress. After working many hours in a state of flow, you’re glowing, you have MORE energy, you’re excited about what you’ve been working on! But after working in a state of stress, you’re tired, you lack energy, you’re burned out and exhausted. It’s unhealthy to broadcast the latter as if it’s something to aspire to… especially for young people. As a parent now, it’s amazing how every little thing I do is first filtered through the lens of “How is this going to affect my son? Am I being a good example for him? Am I showing him the right way to do things?” I would never want my children to spend so much time and energy on work that the result was detrimental to their health… so why would I ever see this behavior in myself as something to be proud of?? Funny how having kids can be such a reality check!
There are few things I love more than being super productive and busy working on something that excites me. I live for the thrill of dreaming up ideas and then making them happen. And the greater the challenge, the sweeter the victory. Who doesn’t love the feeling of accomplishment and achieving goals? But it needs to be done in a healthy way or it’s neither enjoyable nor sustainable. A successful creative life is a marathon, not a sprint. The longer, healthier life you live, the more you will be able to create and achieve. Take care of yourself, work smarter and more productively in a state of flow, and you’ll achieve greater results in the short term and over the long run.
Easier said than done? Fair enough… If you find that you’re feeling much more stress than flow, that’s probably a sign that it’s time to try something new. This could be a new approach to how you’re doing your current work, or by taking on a whole new project or type of work all together. When things become stagnant, you feel like a hamster on a wheel and stress takes over. If you’re not happy, then make a move, change things up, and figure out a way to be excited about your work again. It’s a challenge for sure, but I don’t think anyone chooses a creative life because they’re looking for the easy route!
Contact Info:
- Website: https://www.liveweddingpainting.com/
- Instagram: @ClevelandEventPainter
- Facebook: https://www.facebook.com/Jacqueline.DelBrocco
Image Credits
Tamara London Photography, Discovery Photo, Emily Millay Photography, Nathan Peel Photography

