Tell me about yourself. What is your chosen area of freelance? 

I am a freelance artist and designer. I specialize in watercolor painting, illustration and calligraphy and use these skills for bespoke wedding stationery, textile and pattern design and most recently for an illustrated children's book I am putting together!

What made you take the leap from regular employment to working for yourself? 

What DIDN'T make me want to quit my job and work for myself is really the question. I was a high school visual arts teacher for 4 years, and an elementary art teacher for 1 - that last one really did me in. I went into teaching partially because I was terrified to try and make it as an artist right out of college, and partially because teaching came really naturally to me and I enjoyed it when I had students who actually gave a little bit of a shit, (which were few and far between). The reality of teaching - that everyone knows because teachers have been fighting this battle for decades - is that we were overworked (think 60+ hours a week on and off campus, plus expectations to sponsor or coach activities, show up to all kinds of meetings, professional development and mandatory "training" during any and all hours of the week and weekend), and grossly underpaid. Even with a masters degree, sponsoring two after school clubs and coaching, I barely made $42,000 before taxes..BEFORE taxes!! That's insane. So apart from feeling trapped in my classroom, hating that I never slept, never had time for a personal life, and was completely burnt out, I wasn't even making any art as an art teacher. It got to the point that I was calling in sick just to avoid going in, and because I was so incredibly drained mentally and physically, (and y'all..I've been pregnant, this was worse exhaustion wise). You know it's bad when you can't even drag yourself out of bed in the morning, so I knew I needed an exit strategy. I was tired of being micro managed by administrators and county members who were out of touch with the classroom, I was tired of battling with parents over why their children did indeed need to show up to my class to receive credit for it, and why art was IMPORTANT for all of them. I was tired of feeling burnt out and I knew I could do better, and that I had more to offer the world.

What tools do you find indispensable to complete your daily tasks?

Good old fashioned to-do lists and a pencil. My MacBook and of course my watercolor paints and brushes!

How do you structure your days?

I am a stay at home mom as well as a business owner and artist, my fiancé is also an entrepreneur. It was important for both of us that we have as much meaningful time with our son as possible without resorting to daycare, so we split the day up into two 7 hour increments. I wake up with the baby and am with him until 1, and then I typically work from 1-7, take a break for dinner and bedtime, and then resume working from 7-11. I try to break my tasks up over the course of the week so I'm never working on one project for large chunks of time - that makes me go cross eyed and a little crazy.

What’s your best advice for handling criticism?

Take criticism with a grain of salt, but be open to hearing well articulated suggestions or advice from people you respect. There are A LOT of opinions and "experts" these days on every topic imaginable. It's important to stay true to who you are and to go with your gut. If you keep hearing the same thing over and over though, that's a red flag that you may need to tune in a little harder and figure out why this issue keeps coming up.

How many years have you been in business?

5 years as a side hustle, 1 as a full time business.

Do you have any lofty goals for 2019? What are they?

SO MANY. I'm that kid who wanted to be 25 different things when they grew up...still am. I'm in the process of illustrating a children's book inspired by my son taking a trip to the art museum and putting that into a proposal to pitch to a handful of publishers. I'm also working on an online watercolor class that I currently only teach in person, but am hoping to widen my net. And finally, I am creating semi-custom stationery and an entire line of stationery products featuring my custom, hand painted designs and patterns.

Do you have routines that you follow to keep your mental health in check?

In the past I used to work myself into a panic-mode meltdown and freak out on everyone around me. As I've gotten older (and hopefully wiser!), I've learned to recognize the signs of a burnout coming and I let myself rest completely. Even if it means rearranging deadlines, or having to email clients to let them know their deadline is being pushed - I recognize that I can't be helpful to anyone if I am not 100%. I take my mental health and SLEEP very seriously, especially with a baby to take care of. I think protecting your sleep and and taking major breaks from social media/technology are the best things you can do for your mental health these days.

Do you work and travel? Where have you been while freelancing?

I travel for creative conferences or to gain inspiration, but not for the work itself. Technically I can work from anywhere, which is one of the perks of being an entrepreneur. I may have to bring work with me when I travel, but it's nice to have a change of scenery and typically lends itself to new design ideas.

What are the hardest parts of freelancing?

Freelancing in general is a scary thing. The pay can be inconsistent and not every project always pans out the way you want it to. You eat what you kill, so everything falls on you if something isn't getting done. It can be a lot of pressure and sometimes that pressure is overwhelming to the point of not being able to move at all. But if you love it enough, you'll make it work, if not, you'll keep doing the same thing over and over again.

What are your most favorite things about freelance work?

Having control over what I do next, being able to eat lunch when I want to (seriously! I used to have shove lunch down my throat in under 20 minutes when I was a classroom teacher), being able to structure my day or week the way that I want to, and being able to build in daily creativity rituals and habits that will continue to evolve my skills as an artist.

Anything else you have to say?! Do it!

I think there is still a big misconception that because freelancers don't work a traditional 9-5, and may not have an office or a staff, they somehow aren't working as hard or don't have the same commitments as someone else. If anything, we have more because (see above), we eat what we kill. If we aren't turning all of the wheels, and wearing all of the hats, then we aren't ultimately growing our business or making any money. It takes a lot of hard work, grit, determination, focus and clarity to make it work. This is not for the faint of heart or easily discouraged. When it's not working, you have to keep pushing and keep trying things.

 The Messy Painter is based out of Saint Petersburg, Florida and specializes in custom wedding stationery & calligraphy, freelance watercolor painting & illustration, and textile & pattern design. Crystina’s designs and artwork are inspired most by architecture, folk art, children’s books, nature and travel.

You can find Crystina online at and on IG @themessypainter