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Creative Crushin’: Jenna Rainey Is an Artist, Boss Babe, and Mama-To-Be on a Mission

Jenna Rainey Is an Artist, Boss Babe, and Mama-To-Be on a Mission

Unassuming, unequivocally talented, and hell-bent on empowering the side hustles of others, Jenna Rainey is a creative force to be reckoned with.

I first met and bonded with Rainey in 2015 when she taught her very first online class for Brit + Co (Intro to Watercolor, obvs!). We spent a day wandering around the Mission talking about our creative journeys, the power of Instagram, all the places we want to travel to, and eventually starting families. Well, three years later, and I’ve got a tot of my own and Rainey’s got one on the way! Over the last three years, Rainey has made an impressive name for herself in the watercolor world, teaching countless workshops, publishing a book, and, most recently, saying sayonara to the wedding industry and shifting her focus to teaching other creatives how to be the boss.

Just a couple weeks ago, Rainey paid us another visit and filmed her latest class, Intermediate Watercolor: Plants + Succulents.

We had a chance to catch up in person and over email and, once again, I find myself totally inspired by this whip-smart creative. Anjelika Temple here, Founding Partner and Chief Creative Officer of Brit + Co, back with another inspiring edition of Creative Crushin’!

Brit + Co: First off, for our readers who don’t know all about you from my interview with you three (yes, THREE!) years ago, give us a little bit of your backstory.

Jenna Rainey: Three years?! Wow! Well, to keep a long story short, I never knew art would be my career path. I grew up in San Clemente, CA, a little beach town in Orange County. My mom and both of my grandmothers were decent artists, but art was never something I pursued or took seriously. I went to school in Chicago to be a music therapist or do something similar in that field, and between school, working as a server at a bar, then at a financial planning office, and figuring out what I wanted to do with my life, I found a box of random art supplies that was mixed in with my stuff during my move from Chicago back to southern California. Because I hated my corporate desk job so much, I eventually opened that box of supplies and started playing around with the stuff inside, which was old brushes, some calligraphy and old acrylic paint, and eventually started posting work on my Instagram six years ago! Just after four-ish months of posting my work on the ‘gram, I started getting a steady amount of inquiries for commissions and custom stationery jobs, so I quit my day job and founded my first company, Mon Voir! It was a crazy time.

B+C: Tell me more about the turning point when you were able to turn your side hustle into your main hustle.

JR: When I quit my corporate cubicle job six years ago to start doing creative entrepreneurship full-time, I started as a pointed pen calligrapher for weddings. I didn’t paint with watercolor yet, I had never touched an Adobe program in my life, and I knew nothing about what starting a business and an agency would entail. Was I good at calligraphy at this time in my “career”? Nope. But people were hiring me, so I didn’t pay much attention to that. Every inch of me just dreaded waking up and commuting to my nine-to-five, and all I could think about was getting home and doing art things at my kitchen table. That is what fueled me to quit. By no means was I ready financially for the career move and to start a business... the first couple years were really difficult, but I’m so glad I did it!

B+C: What’s been the hardest part about working for yourself?

JR: Every small business owner/solopreneur, when they decide to go from an employee to owning their own thing, takes on a slew of job descriptions. I think this is difficult for most people, but for me, I was 23, incredibly naive, thinking that working for myself meant I could do what I wanted, when I wanted, etc., but it also meant I had to learn accounting, bookkeeping, how to be a good salesperson, marketing, and the list goes ON... and basically overnight! This has made for a lot of hustle, lots of late nights, and turning down the trips and hanging out with friends, just to stay on top of things. It has gotten easier over the years, but man, those first couple of years were a STRUGGLE!

B+C: What’s the best advice you’ve received about growing your business?

JR: Don’t fear the fire! It’s so easy to be timid as an artist, especially with all the amazing work out there on social media. I teach a lot of in-person workshops and so many people that attend are lacking confidence and are afraid to post their work, or start a business, or continue to paint, etc. because they’re afraid of the hard stuff. That hard stuff is bound to happen, but that’s what refines you and makes you BETTER! I’m so thankful for all the hiccups and mistakes that I’ve encountered in my business. They’ve made me never forget what not to do, ha!

B+C: Since you were able to take this leap and start your own thang, tell us more about how the team that makes the magic happen has evolved.

JR: When I first started it, I was just this chick and doing all the things. Packing and shipping orders, responding to upset customers, sales, etc., with the occasional (no, pretty often actually) help from family members... man, those first few years would’ve been a disaster without my parents and my husband’s help! But as of about three years ago, I was able to start hiring help. I now have a mostly remote, small but mighty team of people working for me doing everything from email upkeep, editing book manuscripts, web designer/upkeep, some video and editing work, and some social media advertising help. I still have my hand in every area of the business — it is a small business — but it is so nice having a team of people helping me! It’s freed up extra time for me to devote new projects and jobs and takes all the stuff off my plate that I hated doing!

B+C: You recently re-branded and relaunched your business as (formerly Tell us more about what inspired this shift and what you hope to achieve with your new vision.

JR: Yes! So, when I started Mon Voir, I was only doing wedding work (custom invitations, calligraphy addressing, etc.), and teaching workshops. Over the years, I’ve taken on how-to watercolor books, done more teaching, and hired people under me to do all of the wedding work. Mon Voir is elegant and fits the wedding brand, but that’s not my passion anymore or what I want to continue doing. I’ve recently sold my business (Mon Voir) and taken on my actual name because my books are on shelves in stores with my name on it, I have a few licensing projects coming up soon that are going to be in bigger retailers, and I want the random customer to walk by and be able to pronounce and recognize my name (no one could pronounce Mon Voir). So, while it definitely works for the wedding industry still, it just doesn’t suit the direction I’m heading… and it’s way easier to pronounce!

B+C: Why do you think it’s important for creatives to help other creatives succeed?

JR: I’m an incredibly competitive person, always have been. I grew up playing club soccer and that competitive nature has definitely carried over into my creative professional life. While I value competition and think it definitely has its place (when it’s not at the expense of others, of course), I genuinely believe we all have a unique and valuable story to tell. When people are able to tap into that, they can be their best selves. Thankfully there are so many people in the world that I’m never worried about, past students of mine who start up companies in the same industry as me. There’s room for everyone and creativity is for everyone. I hope everyone can discover this.

B+C: How are you able to separate your personal life from your professional life? Is there even a separation there?

JR: This is definitely a tough one and something I’m still trying to get better at, but something I have pretty strict boundaries about is social media. No phones/posting before 10am or after 7pm and on days John (my husband) and I both have off. With work stuff and deadlines, I’ve gotten better at this over the years, but it still takes practice saying “no” to the good stuff in order say “yes” to the great stuff. It’s so hard, but I’ve just learned (the hard way) that I don’t do my best work when I’m overworked... it’s better for everyone if there’s some sort of balance there.

B+C: What inspires you? Why do you love to make things?

JR: I absolutely love traveling. The textures in the crumbly architecture in Europe and tile patterns in cafes, the vivid colors of fall in the PNW... it’s the most inspiring thing to me. Being able to translate what I see into a piece of art that eventually gets made into textiles or prints in people’s home is so wonderful. There’s nothing like it! Along with that, watercolor and art in general are my version of therapy. I feel completely relaxed and comfortable when I’m able to create freely.

B+C: What artists and designers do you turn to most often for inspiration?

JR: Henri Matisse and Georgia O’Keefe have been my all time biggest inspirations over the years. I’ve always been so intrigued by Matisse’s use of color and O’Keefe’s interpretation of subjects and shapes. I also like to look elsewhere for inspiration a lot, like Justina Blakeney of The Jungalow is a huge inspiration for me! Love her use of textures and colors!

B+C: I know that teaching is an important aspect of what you do, and we’re proud to include three of your classes in our roster of Brit + Co classes! What drew you to teaching and education?

JR: Teaching was something I never expected to be a part of my business. I used to teach piano lessons in high school and college, so I knew I was capable in a basic sense, but the first time I was asked to teach a calligraphy workshop, I barely knew it myself... I said yes anyway, ha! That’s just my style. But ever since that first class, I’ve absolutely fallen in love. I love problem-solving. Interpreting how different people are and how they learn gets me going! And I love seeing people come to my classes thinking they aren’t creative, and then proving them wrong!

Favorite Quote: “A candle loses nothing by lighting another candle.” - James Keller

Trivia About You: I HATE my collarbone being touched... like I can’t even have a seat belt touching it, I have to put it on my shoulder. It’s super inconvenient sometimes.

Go-to Karaoke Song: "I’ll Make Love To You" by Boyz ll Men

Favorite Art Tool: My brushes. They’re synthetic sable hair and so dang snappy.

Late Night Snack: Well, I’m currently pregnant. Typically I’m not much of snacker, but I’ve really been into pickles and mangos with cottage cheese lately.

Currently Listening To: I’ve been loving Marie Forleo’s podcast recently!

B+C: When you’re feeling creative burnout, how do you reset?

JR: Take a day completely off of my phone, nap, go outside, and go on an adventure with my husband… even if that just means going down the street to our favorite dinner spot.

B+C: What advice do you have for creatives who want to turn their passion into a business?

JR: Stay true to yourself! Your style, your aesthetic. A lot of newbies get caught up in recreating other people’s work and become stuck in a rut where they’re unable to grow and challenge themselves because of it. Oh! And get a mentor. Navigating business and all the grit it takes to grow a viable business can be isolating, lonely, and damaging if you don’t have someone helping you along with the process!

B+C: Motherhood is right around the corner for you! What are some of your hopes and dreams for your little one?

JR: I’m so excited! My biggest hope for my little is that he fully embraces who he is with every bit of confidence at every stage of life. You wanna be weird? Be weird. Want to dance? Dance! Want to cry? Cry. Oh and that he’s a nice, decent human.

Talk about mom goals. YES to being weird and being a nice, decent human! You can follow all things Rainey at @jennarainey on Instagram, and take not one but THREE of her online classes here on, including her newest one, Intermediate Watercolor: Plants + Succulents.

Time to bust out those watercolors and brush up (pun intended) on your painting skills ;)

Know of an artist or entrepreneur we should be crushing on? DM us at @BritandCo + @anjelikatemple!

Author: Anjelika Temple (Photography by Brittany Griffin and Courtesy of Jenna Rainey)

Brit + Co may at times use affiliate links to promote products sold by others, but always offers genuine editorial recommendations.