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Meet Crystina, artist, mom gives the BEST advice.

Creatives are my favorite. And my favorite thing about this creative is that she's SUPER clear on not only the realities of modern parenting but can just as easily dole out advice on how to build a digital brand. Crystina is an artist whose gorgeous paintings and illustrations make for beautiful invitations and prints, but her design work also makes it to @MomsGivingGrace, the perfect account for moms who get it. That's you, so go follow!


Name: Crystina Castiglione

IG handle: @themessypainter



First, what are the identities you lead with: Artist, Designer, Entrepreneur, Mama (or Toddler Chaser), Educator, Wine Enthusiast, Travel Junkie, Almost Wife.


How did you get here? What’s your backstory? I graduated with my degree in Art Education in 2011 and right out of the gate, I started teaching high school art. My first year was…let’s just say I learned A LOT. But mostly I learned that I did not want to keep waking up everyday, (especially not at 4:30 in the morning), to a job I didn’t love; I had over 40 kids a class, who ate me alive most days, and I was spending 65+ hours a week in a windowless classroom. I was teaching art - but I wasn’t making any and I was so burnt out I could barely pull myself out of bed each day. I slowly started taking on commissions, or projects for friends weddings - anything that would teach me something new. But the real turning point was when I became a top 5 finalist for an artist competition I had entered on a whim for Beall’s Florida Department Store. We were invited to present to their board of directors, president and design team which I was wildly unprepared to do because I had no idea what I was doing. I was in a room with 4 other artists who had long been making a career of their work - at this point I didn’t even know how to make prints of my work. I unsurprisingly, didn’t win, but I did catch the president's attention who ended up bringing me back on and hiring me to do some freelance work. This was the official start of The Messy Painter, and when I realized I could make a business of this. I took on every job I could get after this, furiously teaching myself the ins and outs of Adobe, social media, marketing - all the hats, while still teaching full time as a teacher. This time allowed me to really experiment and get extremely good at what I was doing because I wasn’t relying on it for income yet. I worked nights, weekends, in between classes - anytime I could. I had also started teaching watercolor workshops at local museums, partnering with local venues on wedding stationery, and selling my art prints at markets every weekend. Eventually I had saved up enough and gained enough client traction during year 5 of teaching that I was able to fully support myself (mind you, JUST the basics, I had to really budget to do this, but it’s been worth it!) and leave the classroom. And then, just as I started to think, “you’re doin it Crystina, you’re out on your own”…I found out I was pregnant. Pregnancy is really what propelled The Messy Painter into being the creative beauty it has grown into today. It forced me to make it a “real thing” and not just a side hustle. Since that moment, I put all of my effort into also learning how to be a great business owner and leader, and not just an artist. I am now at a huge turning point in my business and I’m finally expanding my team to be able to grow in ways I never imagined.


How did you develop your aesthetic? There’s such a huge appetite for original beautiful social-friendly art these days. Do you have a preferred medium? My aesthetic is something that evolves a litle bit more each year as I continue to hone my artistic skills - it’s definitely driven first and foremost to a commitment to practice. While I’ve always been creatively inclined naturally, I was, never naturally good at drawing or painting, I had to work really hard at it, and that took rigorous practice for years. Even now, I am learning something new almost every, single day. The foundation of my work will always be that it is hand drawn; I think it’s a feeling and style that will never be able to be replicated by a computer. I am deeply inspired by folk artists from around the world, children’s books, old encyclopedias with vintage diagrams laid out in perfect detail, interior design and architecture. I prefer watercolor and gouache, but I also do a lot of pencil, ink and digital illustrations. I typically scan these into Photoshop and then digitize the artwork from there so that I can manipulate it onto various textiles, products, etc.


Working with a lot of brides I’m sure has its ups and downs. How do you deal / help them deal? What like it’s hard? Haha no, it DEFINITELY has it’s ups and downs - you’re handling one of the most delicate parts of a bride or groom's wedding planning process and emotions are usually running really high; I’m sure we can all relate to that one family member who just has one too many unsolicited options and makes us lose our shit. I treat my brides like a I would a friend - and many of them have become friends after working together! I give them my best advice, suggestions and recommendations; I guide them through challenges by being sensitive towards their feelings and helping them arrive at the best solution possible. I like to give them pep talks and get them super hyped for their designs, which gets them excited for their wedding. Everyone thinks it’s the dress that makes it feel real, but I think it’s the invitations because now they’ve officially invited people to take part in this incredibly meaningful life event.


What’s been the most rewarding / challenging project to work on? Probably my most recent project, Moms Giving Grace, which is a collaboration between myself and 3 of my best friends. It’s the first time where I have complete creative control in a collaborative project, but I’m not solely in charge which allows me to really focus only on the design rather than wearing all the hats like I do with TMP. It’s also the first time that I’ve been able to express the side of myself that is inspired by motherhood. The challenging part of this is that we all live in different cities and we are all working moms - but as our business name suggests, we just give each other plenty of grace when things feel too overwhelming.


What was the inspiration behind Moms Giving Grace? The biggest inspiration behind MGG is the idea that as moms, we hold ourselves to often times impossible standards driven by the pressure we feel all around us , and that we need to learn to give ourselves grace. Grace in whatever way we can, in whatever form we can, and we need to give it to other moms too. We wanted to create a community where supporting one another unconditionally, not passing judgement and finding humor in the ridiculousness that can be motherhood is the standard. We’re all just trying to do our best, and it’s a lot easier when you have a group of people that hold you up, support you, and let you talk through your plans to murder your husband but ultimately know you love them and probably won’t go through with it. When I first had my son Wylder, I started going on mom dates which were both terrible and hilarious, but I ended up finally finding my people in Jess (CFO) + Tara (CEO) . Later we added our fourth member, Erica, one of my long time best friends who fit into this little pack of slightly off kilter mama’s who was also in the same stage of motherhood as us. Not only did these ladies never judge me, they joined me in sharing all the moments I thought I’d been failing at in motherhood. Eventually we started joking that anytime someone said “ohhh, just give yourself grace,” they must mean give yourself wine and this whole parody of giving yourself grace as a mother started to unfold. There always seems to be this idea of “the mom who can do it all,” that women are trying to aspire to be and we want to be the moms who are ok if we don’t do it all because that’s not real life. We believe in extending grace to yourself when you feel like you’re not doing enough.


What’s the biggest misconception people have about building up your digital business / presence? I think in general people completely over think the social media game. I don’t think all the strategy in the world can replace you being yourself and showing what’s going on behind the scenes. People want connection, they want to relate, they want to see themselves in you. I do my best to really show it how it is - the good, the bad, the messy, the weird, the gross. I think it’s important to keep your content + ideas original, and I think it’s important to connect with your audience by just talking to them like you would a friend or a client. It’s like building any other relationship - it takes time, effort, consistency and trust.


When working with an artist, what should people keep in mind? When working with an artist on any project - keep in mind that you are hiring them for their style, and their expertise in a given area. It’s important that you aren’t seeking them out to copy another artists work or style, but are seeking them out because you value their skill or talent and you want to invest in it. Every artist has a focus or a specialization and it’s important to do your research on them before reaching out just like you would any other business or service. All of my clients come to me because they love my aesthetic and style, they trust my expertise and they value art + design.


What’s your method for balancing work and motherhood? ….And everything else that goes with it. Oh boy - balance, is there such a thing? I don’t know, but I do know that every day looks really different for me and it’s more about staying very flexible and adaptable to ever changing situations and deadlines, and *trying* not to get bent out of

shape when things go haywire. I have learned to be ok with not getting every thing done every day. Motherhood taught me the value of slowing down and resting when I need it; I no longer ignore the signs of burn out approaching, and if that means I have to take the day off in the middle of a crazy season of deadlines - that’s what I do, because ultimately my brain and body will thank me for it and I’ll be more productive following a really good day of rest. I’m also fortunate to have an incredible partner who makes a great team with me and who is (mostly) on board with my crazy schemes for organization in our week - he likes to call me the “house manager”. We check in with each other regularly and we are always asking each other how we can help the other. Little things like using a family calendar and a meal planning chart have been game changers for us. Anything I can do to take out the guesswork for my week, or simplify everyday, tedious household tasks, is my goal - this enables me to have more energy for my family and business each day. Even with all of the organization and planning in the world though - shit happens. Literally and figuratively, especially with a child. When all else fails, and I’ve stepped in human poop on my kitchen floor because poty training is the worst, or I’ve had printers spewing ink at me, or Ive spilt water all over a painting - I take it as a sign from the universe to slow back down again, and I pour a great big glass of wine.


What / who is influencing you the most these days? Oh gosh, so many WOMEN. Brit Morin, Anna Rifle Bond, Glennon Doyle, Michelle Obama (have you HEARD her podcast, it spoke SO powerfully to me as a working mother).…ok you might be noticing a trend. I am influenced by bad ass women who are also mothers. And who have proven, against incredible odds that they can build something from the ground up while being an amazing mother. I’m inspired by women who don’t sacrifice their dreams just because society tells us that mothers should be home with their children. It feels good to see that archetype changing finally.


What advice do you have for someone who’s trying to get their creative business off the ground?

1. DIVE IN - if you keep waiting to be “good” at something, you’ll always be waiting. You only get better by making mistakes and learning from them - sometimes they will be expensive mistakes (I’ve made many!), and sometimes they will be happy accidents, but they are ALL needed to propel you forward.


2. Don’t ever work for free!! You can’t build a business if you aren’t making money; don’t ever feel bad for charging what you are worth; if someone tries to cheapen your services by asking you for a lower price, they don’t value you or your work.


3. Be original - If you are always copying what other people are always doing, you will never get ahead or build something that will stand apart. Don’t worry about what other people or doing, just do what YOU want to do.


What’s the best advice you’ve ever been given? That moms are allowed to chase their dreams too. No one ever asks a Dad if it will be hard for them to go back to work after a baby, or how they will manage raising kids while being a father. Anytime I feel that pang of mom guilt for dropping my son off at daycare, especially when I haven’t had a very productive day, I remember this. Moms are allowed to chase dreams too and we don’t have to feel guilty about it

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