There’s just something about Target.
It draws you in with its bright red bullseye and before you know it, what was supposed to be a quick in-and-out for laundry detergent is a $156.23 checkout with who-knows-what in your cart.
I’ve long been a Target stan, but it wasn’t until I became a mom that I joined a silent sisterhood of women who see it as more than a store; Target is often a refuge in those early months of motherhood when you’re cooped up with a blob of an infant and no clue how to pass the time during their wake windows. Target is climate controlled, has a Starbucks waiting for you and aisle after aisle of colorful items to catch your little one’s eye and snatch your credit card. It’s the sense of familiarity and aspiration to curate the perfect wardrobe- self care routine- or home. So, it’s fitting that a stroll through Target, something we’ve no doubt all done a time or two, is the origin story for what lead to one of the most recognizable designs on its stationery aisle within the course of just a few years.
Before she would go on to create the gorgeous watercolor designs and distinctive patterns that helped grow Simplified’s following to more than half a million between Facebook and Instagram (compared to just 315,000 or so combined in 2017, according to published reports)- and push its revenue far outside the lines of its typical planning pages, Jessa Bray was that new mom wandering through Target, in the oil boom town of West, Texas… isolated and restless.
“When I had my son, everything kind of just stopped. Everyone told me that it was going to be crazy and chaos filled, and it was in its own way, but I was so bored,” Bray said. “I remember sitting there and being like, I don't know if something's wrong with me, but I'm very unsatisfied with just being here.”
“I loved him. I loved playing with him and taking care of him, but I wanted to do something, and feel like I was contributing,” Bray said. “I'd walk in stores like Target, and Marshalls, and Hobby Lobby and look around at the things that like I really wanted to use in my home to make it feel like a home, because we were a young family and that's the dream, and we couldn't afford any of it. We were just in a part of our life where like that was impossible. So, I went home and I was like, well, I'll make it.”
Jessa was the girl with good handwriting growing up. Though she had no formal art training, she made it a point to rewrite her notes in school to be pristine, and so she found immediate connection with word art through calligraphy and lettering. What started as an effort to make their house feel like home, led to an Etsy shop and a full-fledged wholesale line, Flax and Wool Designs.
“One sale turned to fifty, fifty turned to paying bills,” Bray said. “But the dream was always Target. I wanted to see myself in Target.”
This is the part of Jessa’s story where you may think it’s actually mine. She turned to social media, honed in on her investigative reporting skills, and searched through geotagged posts at Target’s headquarters in Minneapolis until she tracked down the Senior Trend Constructor for the retail giant. And then, aiming right at the big red bullseye, she took her shot.
“I messaged her,” Bray recalled. “This is so random, but would you look over my line sheet and just tell me if I'm crazy, or if this is kind of good?”
The first major review of her designs was better than good. It landed Jessa an invite to the twin cities to teach a workshop for Target’s design team.
“I thought I died. I'm pretty sure that is when I peaked,” Bray joked. “She hooked me up with so many meetings that day. I met incredible people… they presented it that, we’re going to let you meet the people, we’ll see what happens organically ,and kind of go from there. I was so grateful, even for that.”
The trip to the mothership didn’t lead to any of her wholesale products being picked up, but there was still a lot of significant work coming Jessa’s way; including the massive ask of lettering the floor of the original Paper Goat Post location in Orlando's Ivanhoe Village, and the very public writing of the names of all 49 victims of the Pulse Nightclub shooting along the windows of The Guesthouse in Orlando, after the Bray family moved back to Central Florida.
“It was just so emotional. It was really connected to so many people that were grieving, and for the city that was grieving, and the families, it was awful,” Bray remembered. “That was such a small thing I could have done, and it kind of showed me that, lettering is just not lettering. Art is not just art. The impact that it can hold is pretty big and wide.”
By then, you could buy wallpaper designed by Jessa (in fact, you still can, here), and a signature style was being solidified. The impact of her lettering and designs started to catch the eyes of some big names, and just as she slid into the DMs of that Target bossbabe, she one day opened her own inbox to find a message from a name she recognized; the creative director at Simplified, a stationery and lifestyle brand best known for its planners that sell out within days every.single.year.
“Do you do patterns, or are you freelancing pattern-type things? I love your art,” Bray recalled. “And I kind of posed it as, why don’t I paint something, and you can tell me if you want to pay for it.”
For all you non-freelancers… that’s not typically how it works.
“This was when I had that feeling of, I don’t feel like I deserve to be in the room. Big, big, tall, imposter syndrome.”
The gorgeous watercolors with telltale florals of delicate pastels turned out to be perfect for the polished, preppy fanbase of Simplified planners. A beautiful minty blue and foiled pineapple design was selected from the freelance gig.
“They fell in love with it,” Bray said of her first design. “It was their first watercolor design ever for the company, and they paid me for it, and we went on our way.”
But the story of Jessa Bray and Simplified was just getting started. A few months after that first freelance design, the brand posted an opening for an Art Director. Instead of a bullseye, Jessa set her sights on the pineapple, and wrote a literal love letter asking for a chance.
“I’m not one of those, but I’m going to try. What’s the harm in trying? It’s kind of my attitude about a lot of things,” Bray said. “My resume had nothing on it except my own business, and I didn’t know if I had been doing it well, you know my work because you’ve already bought it… and they hired me, and it was really crazy.”
“At the time, it absolutely was my dream job. I couldn’t think of another position I wanted more,” Bray said.
And it would be for the next five or so years. It became obvious that the diehard customers were loving her designs, a playful, imperfect addition to a very traditional southern brand; as Jessa herself described them, a perfect mix of color and class. And as about a dozen of her designs sold out, making the company a conservative guess of millions, her confidence grew and the imposter syndrome shrank.
“You just experience all those thoughts. The whole time I was putting out work, it was just kind of like, I hope this makes sense… I hope they like it. It’s like spaghetti on a wall,” Bray said. “And then probably at about year three, I started to know, oh, this is good. This one’s going to sell out. The confidence really kicked in around year three, and I can hold my own.”
“That’s when the shift started to happen,” Bray said. “I’m glad to be here, thanks for having me, but, I belong here, and this could be my room, too.”
It wasn’t her room, though. Even though her artwork was being produced and enjoyed by the masses, since it was made for someone else’s brand, Jessa doesn’t technically own it. If Simplified wanted to rework a pattern to become home décor, or a wall covering, Jessa would have little say over it. That, combined with the pressure to create more products with heavy direction, led to internal (and maybe outward) tension for the art director.
“At first, I craved it… to finally be in a company where I could have someone with experience in selling things tell me, refine this… it was very much a learning experience for me, and I’m so grateful for it because I didn’t go to school for art or design,” Bray said. “I think as I got more confident as an artist, I started to resist a little more.”
“I felt that internal strain of, this doesn’t feel like me, or this didn’t feel like how I would do it, or the best that I would have it, or the colors I wanted it in. And that’s really hard to let go of, because you put so much time into things like this, they’re like your children… it crated a very real attachment to the art,” Bray said. “That started to get really difficult.”
After heavy contemplation, conversations with her family, and prayer, Jessa resigned from Simplified in June of 2023, leaving fans and followers in shock and with many questions. For her, there were none.
“I think there's a lot of girls that think I'm crazy still for leaving. I know that I had a lot of messages, in my inbox, like, I can't believe this,” Bray said. “And I'm so grateful that people even feel that kind of connection with my work, but the feelings that I was having, were overwhelming in that it kind of wasn't even a choice. I have to go.”
“It went from not feeling like I could be in the room- to I deserved to be in the room- to I want my own room. I want to say who can come in and join me in that room,” Bray said. “I would also say that the discomfort of working on a team and working on a machine, when you’re constantly releasing things and more products are being picked up and more art is being produced, it’s very difficult to be okay with that.”
Jessa believes the feelings she experienced are why companies don’t often hire independent artists.
“I think it’s just too conflicted with who they’re created to be and to have someone else calling the shots on creativity, and that being an innate part of your being, it’s like oil and water at some point.”
The split between the brand and its art director was amicable, but Jessa admits she believes Simplified’s owner, Emily Ley, was surprised by her decision. It also came in the middle of a production cycle, with products being ordered for the next season due to lead times on customs and shipping. Jessa says steps were taken to ensure no gaps in quality or design, and her final planners will come out next season.
I’ve seen this time and time again as friends move on to new chapters in their professional careers; they take it upon themselves in the final weeks to put systems in place to protect the company or brand, even if it’s not necessarily their responsibility. To steal a line from T Swift herself, Jessa says she wanted to keep her side of the street clean upon her exit.
“We've kind of moved on, both of us,” Bray said of Ley. “And I think that it's great.”
But, now what?
“I really had only worked in this like one niche… and I know I'm good. I know that I'm good at this, but I need more I need more experience now, and more knowledge outside of just paper,” Bray explained.
What better way to learn more things than by doing… Everything. All.At.Once.
Enter Cherrywood Lane Design House, an explosion of rich color and flavor, akin to its namesake.
From the CL website, Jessa describes her specialties as graphic design, surface patterns and illustration, hand lettering and typography, branding… basically, she can take your idea and make it a brand- or take your brand and make it even better- and create an online presence that will stand out in the crowd.
“Not boring, very full of personality, and just kind of reflecting all of the work that they've already put in,” Bray said. “Those are the people that I'm working with to build brands with and brand identities with, and that has been super incredible and very rewarding.”
She’s now building out full websites for clients in addition to lettering and logo work, and potentially most exciting, licensing, through the help of her new agent, who brings her ideas that she can latch onto or throw back.
“I feel like I’m in a movie. It is incredible. It is the coolest thing to be on this side of creative work and having this range of trends to create for and manufacturers to create for, and stores. It really has been the coolest experience and I’m super grateful,” Bray said. “Just being able to say, no, I'm not going to do that, something's more important and I can choose that. That kind of freedom is everything.”
But the newfound freedom comes as her most famous work to date continues to live on under someone else’s brand. On the Cherrywood Lane website, much of her portfolio of pattern work links back to Simplified or one of its retailers. She knows that, at any time, those could pop up in new products and continue to make someone else money into perpetuity.
“I think I'd be lying if I said that wasn't hard. I think anybody in my position would be lying if they said it wasn't hard,” Bray said. “Once that feeling got too overwhelming is really when I started to know, okay, if this isn't sitting right, you have a choice. You can stay here and if you're uncomfortable that's not going to be fair to you, and it's not going to be fair to them because there's no way to put your best work out experiencing feelings like that, I'm convinced.”
Much like the TV news business, Jessa described noncompete clauses may keep new designs from entering certain spaces for awhile. But that doesn’t mean she’s not producing, and though she can’t yet reveal all the details, as we say in news, here’s a little tease: what’s coming is BIG.
“That’s something I struggled with when leaving, too, was that the last time I see my stuff in a big store? The answer is no,” Bray said. “And more stores than I’ve ever been in. It’s very cool, and very surreal. Still very much a pinch-me-moment of, oh good, it worked. The jumping worked.”
That leap of faith was, indeed, faith-based. I can’t write about Jessa without writing about her faith. In fact, back in those West, Texas Target aisles, inspired by home décor she couldn’t afford, the first designs she made for her own home and wholesale line were scripture-based, using the repetition in a way she can describe far better than I ever could:
“When I started lettering, I started lettering scriptures that gave me peace and hope and comfort. And I didn’t believe them,” Bray recalled, noting it was a tough time for her marriage and as new parents. “I had a really hard time believing the words in the Bible to be true, and the words that I had been raised on my whole life. To be in that place and feeling the way that I felt and dealing with what we were dealing with, I decided, if my heart's not ready, I'll just memorize it.”
“There's this verse in the Bible that says, ‘Lord, I believe, help my unbelief,’ and I remember feeling that exactly,” Bray said. “I know somehow this is probably true, but I don't feel it right now. I'm not experiencing it. So, I would letter the verses over and over until I believed them.”
Her trajectory is now beyond belief. Not only can she buy her designs in her favorite store, but more are coming, and a Cherrywood Lane Home line for Target doesn’t seem too far-fetched (it’s not in the works just yet- at least that I can confirm- but we’ve all seen the power of manifestation during this blog post alone!)—but navigating your own business requires some serious self-reflection, especially for a creative mind like Jessa’s.
“You have to know your limits; you’ve got to know how to manage your time. I think that the biggest mistakes that I made in entrepreneurship early on and the biggest mistakes that I made at Simplified early on were writing off some toxic traits of mine like procrastination and just assuming that I'll be able to do it without writing it down in a list like a normal human,” Bray joked. “Those things add up, and if you cannot balance your time, if you cannot know your capacity and your boundaries, you will overcommit every time. You will under-deliver, most times.”
But perhaps more importantly than knowing your limits, Jessa has a piece of advice as bold as any of her patterns- Know Your Worth.
“Know what you're worth. Know that there is a transition that happens from being grateful to be in the room, to you deserve to be in the room. Know how to identify that transition because it's an important one,” Bray said. “Don’t be a crappy human. Treat people the way you want to be treated. And if you are given the chance to take a chance, just do it. Because the worst that could happen is they say no. And that is like so elementary, but like, why not?”
From Beyond The A-Block: I feel incredibly lucky to call Jessa a friend, and to have an original design in my home. In 2021, when we were both pregnant and she was in the throes of work for Simplified, Jessa was an integral part of our story by taking her talents to our nursery, giving us a surprise mural which we used as a gender reveal. We both had baby boys toward the end of the year and I am dreading the day that my guy wants to paint his room something new, but with Jessa just a call or text away, I have no doubt she will be able to execute whatever his mind dreams up.
And if you made it this far... Jessa may kill me, but you have to see this video she left us while she was doing the work in our home! I laugh every time. Love you, JB!