Meet Crystina Castiglione of The Messy Painter!


Happy Boss Babe Wednesday! I’m so excited to introduce you to Crystina Castiglione of The Messy Painter. Crystina is a new mom to a baby boy & was born in New England. Her work is inspired by everything coastal and colorful, so it’s perfect that she grew up in Florida & lives in Sunny St. Pete, a city of endless color and ocean vibes. The Messy Painter launched in 2014 and specializes in custom watercolor designs and calligraphy for wedding stationery and events, as well as watercolor and ink textile, pattern and illustration designs, art prints. Lately she’s been hard at work on architectural commissions, like of The Stovall House, Tin City Shops, the Biltmore Hotel, & Tampa General Hospital. You’ve probably seen her work on Instagram or maybe you’ve attended one of her workshops at Whim So Doodle. She’s seemingly everywhere these days! I love that her business name is ‘The Messy Painter’. Painting is messy and so is life. Creativity isn’t a straight line and neither is success. There’s so much to learn from Crystina and her story & you’ll be totally charmed by her openness. Enjoy her words & stay boss. xx -G

Take a peek into Crystina’s daily life!

Tell us about yourself and what you do!

I am a watercolor artist, illustrator and all around creative! I am also an art educator; having spent many years in the classroom I now teach workshops at the local art supply shop Whim-So-Doodle. I've been painting, drawing, sketching, photographing and consuming as much visual material as I can my entire life. I genuinely believe that there are few things more important in life than what you can craft with your own two hands - I also find it's the best way to communicate how I view and perceive the world around me. I truly love anything that allows me to "make" - cooking, building, painting, writing - all of it. I create watercolor paintings and prints inspired by my travels, the New England coast where I grew up, the Florida coast where I've now lived a majority of my life, vintage illustration books, daily life and all things foodie. Currently I'm really into exploring architectural design elements and buildings; there is such a rich history of story telling woven into how something was built, I'm obsessed with illustrating that. I also create custom, hand painted wedding stationery and calligraphy, patterns for textiles and fabrics, and illustrations for various freelance projects. Occasionally I take on interior murals and hand lettering projects for local businesses, and I also teach watercolor workshops for adults at local businesses.


How did your business begin?

My business began 3-4 years ago when I was still teaching high school art and I found myself completely drained and exhausted from the rigorous schedule of teaching, unjust practices of public education, and the confines of the classroom. As an art teacher, I was ironically not practicing any art myself. I knew that something in my life had to change if I was ever going to be happy, and that I needed an exit strategy from that career. As a starting point, I signed up for a week long summer art institute for teachers at Ringling that I won a scholarship for in Sarasota. It was there that I met a professor who had worked for Hallmark and practiced watercolors. It was my first real lesson in watercolors and the first "ah hah" moment I had about the possibilities of what I could do with my artwork besides selling originals in a gallery setting, which had never truly appealed to me anyways. After cornering the professor of this workshop and asking him for advice on what those beginning steps are to get started, I started practicing watercolors and lettering everyday. Once I had a small body of work built up, I put together a portfolio, a website and started and artist Instagram. These things took me years to learn to curate, style and brand, (and I've still evolving on all of that!) From there, I entered a contest for the "Beall's Next Florida Artist" with 5 of my watercolor paintings and was selected as a top 5 finalist. After eating a slice of humble pie, and not winning, I was called back to do freelance work for Beall's - and thus my first official client was born, and so was The Messy Painter. It's since morphed and evolved into many other creative realms, but I've always been so grateful for those two specific opportunities for giving me the push I needed to know what direction to take with my artwork.


What’s 1 challenge you’ve faced and 1 success you’ve had since you’ve created your business?

One huge challenge I faced, especially in the beginning, was knowing when to quit my day job and focus on my business full time. I gave myself an end date of teaching of 5 years, and regardless of my savings, I went ahead and quit in May of 2017. It was really scary, but one thing I told myself was that I've always figured it out. I have never gone without anything I've needed, I've never not been able to pay my bills, and I've always had a roof over my head. I've been working since I was 16, and fully paying for myself since I was about 20, and I knew that this would be no exception. About 3 months after quitting I realized I was having trouble being home alone all day, and setting a schedule for myself. I am much better with structure and accountability from others - going from a rigid schedule like the one I had a school, to NOTHING, was too abrupt for me, and so I decided to take a part time job working for Lisa Gilmore Design as a project expeditor. This decision helped with my transition, while allowing me to focus more on my business, but still have structure to my day. Now, almost a year since that moment, I am a stay at home boss babe and boss mama - after joining LGD, I found out I was pregnant and had to AGAIN reassess and create a new plan which would allow me to work from home while caring for my baby boy. 

One success I've had since creating my business is honing and mastering my craft in a way that has made it completely unique from other artists who practice the same medium. I've worked really hard to develop a style that sets me apart, but is also recognizable. I love when people approach me and say "Oh you're The Messy Painter, I love your work, I saw it in...(insert boutique or market here" I've been able to build an amazing community of followers this way who seek out my work or give me word of mouth referrals for wedding and commission work. I've also built an incredible following of students who come again and again to my workshops, and allow me to empower them through art.


What’s the best piece of advice you’ve ever received and has it come in handy for you?

When I took that course at Ringling, I grilled that professor about how HE got started, and his best advice that I still listen to, and share to this day is "carve out 30 minutes a day, every single day no matter what and practice your craft, even if it sucks, even if you make nothing, because eventually you will make SOMETHING." Anyone can learn how to run a business, but not everyone can run a business that sells something of unique quality. It's the mastery of the skill and unique style you put on it that sets you apart. For me, that's being the best artist I can be, which is why I paint and try to learn something new to hone my craft every, single day. Also, not to fear failure or mistakes - failure is how we learn, grow and evolve, without it we would be stagnant in life. Being a "perfectionist" is overrated, unrealistic and sets us up for failure.


When are you at your happiest?

I am at my happiest when I am traveling somewhere new, and can take in my surroundings behind the lens of my camera, and then translate them into my sketchbook. While I don't practice photography as my main artistic medium, it's such an extension of me - and I love being able to gather inspiration this way. I'm also happiest when I get multiple days in a row of being able to paint for myself in my studio, late, late at night when the world is quiet with a great playlist.


What do you tell yourself when things get difficult?

One thing at a time, one day at a time. It doesn't all need to get done at once— quality work, takes measured, patient time.


What are you grateful for?

I'm grateful to have learned early in life that I need to wake up every day to a career that fills me up and makes me truly happy, rather than one for security or money. I'm also grateful for my fearlessness, there isn't too much that scares me anymore, (especially after giving birth..holy hell, I am now super woman). I believe my fearlessness allows me to speak up for myself without hesitation, take more risks and not care what others think of me or the decisions I make for myself and my business.


What’s 1 personal goal and 1 business goal you plan to accomplish this year?

Personal Goal: To set aside more "self care" time in my schedule every week and not feel guilty about it, but actually relish in it and cherish it.

Business Goal: To take all the "ideas" I so carefully wrote out in 2017 and turn them into actionable plans; my theme for 2018 is "action."


Where can you be found on a Tuesday afternoon?

Hanging with my little love bug Wylder, and painting in my studio.


Where can we find you on a Friday evening?

Making dinner with my family, or having friends over and indulging in a great glass of wine.


Where can you be found on a Sunday morning?

Taking it slow, sleeping in, making a big breakfast and reading while I snuggle with my baby boy.


Finish these sentences:

I love: inspiring others to try new things, especially creatively.

I’m always looking for: my coffee cup... I constantly forget where I put it down.

My inspiration is: things that make me feel nostalgic.

I’ll never: stop being curious about the world, there is so much I want to do, be and see!