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Jessica Crowell Astrella: The Art of Rewriting The Future

You know those people who can make anything look like a million bucks? They can write their name on a piece of paper and make you think it belongs framed over the fireplace, or displayed in a fancy art museum?

Jessica Crowell Astrella is exactly that person and then some. She’s turned her talents into a career with a combination of ambition, bravery, and an unmatched work ethic. Sleepless nights, long days, and a passion for creating - you can’t stop this illustrator, calligrapher, designer-of-all-things-beautiful.

Jessica Crowell Astrella in her creative studio workspace

Always effortlessly put together and on the move with a mission, she's got that special something that stands out...You know that saying "bet on the person not the company"? If I were a betting woman, I'd put my money on her...

Born with artistic bones, Jess grew up drawn to all things creative. When it was time to head off to college, she naturally started out as an Art Major, then panicked, ultimately graduating with a degree in Political Science. Fast-forward a few twists, turns, and corporate jobs later, she found herself seeking a more meaningful career (and life) in Austin, Texas.

creator Jessica Crowell Astrella working on design in studio

"There came a time for me when it became undeniable. I wanted to do so many things and be so many people in my twenties, but no matter where I was living or working, the creative pursuits would ooze out in weird ways. I glommed onto tasks at work like addressing our holiday party invitations by hand, or designing and implementing a chalk art wall with our values writ large. I always wanted to do those things more than everything else, and always got positive feedback from them and it just struck me eventually that this is not a drill. This life is not a dress rehearsal for another one - this is IT and if I want to feel truly fulfilled and at home in my own skin and in this world, that I needed to pursue a life of creating visual art."

I find that a lot of artistic people settle for different careers based on stability, but eventually find themselves drawn to artistic tasks or hobbies like a magnet. Business in art can be very unpredictable, but Jessica found a way to create stability within her very own companies.

While in Austin, Jess found herself crafting custom illustrations, logos, branding, and lettering for her friends and people within her network; J.RoCro Arts + Letters was born. Her calligraphy skills quickly grew with every envelope and letter, and in turn so did her business and the possibilities.

"I picked up some invitation jobs fairly quickly - mostly based on the kindness of my network of friends. I practiced calligraphy daily and got some envelope orders, so my calligraphy got better and better. Eventually I had a body of work, and a brand: J.RoCro Arts + Letters. It exists to provide original, thoughtful, relatable paper goods + illustration in the form of stationery, custom house + pet portraiture, greeting cards, and art prints.

After a few years, the wedding work and the products I was able to offer sort of grew and took on a life of their own so I decided to build a brand specifically to serve wedding and event clients. It’s a totally different workflow. That brand is Boarding School Collective and we provide bespoke paper goods and signage for weddings and events. I employ a small team of women in Austin who help me...We do everything from place cards to giant signage installations on paper, fabric, wood, mirrors, you name it."

creator Jessica Crowell Astrella working on design in studio

Jess now splits her time between the two businesses and has since made another move, but this time home for good. She and her husband Matt are in the midst of renovating a beautiful home in Portland, Oregon to find new inspiration and to establish roots. The two met while working in New York at an advertising agency in the city, and a just a taste of their new daily life sounds like a dream (and with a recent remolded – sometimes a nightmare).

My husband and I both currently work from home, which is in the final stages of an overwhelmingly involved total remodel. His company is on Central Time so he’s usually already on a call by 7 AM, so when the dog (a black lab rescue named Mozzarella) and I wake up at 7:45 AM we head to the pioneer cemetery in our neighborhood. I’ve never been much of a morning-routine person but I really treasure my quiet mornings there with her.

"By the time I get back to the house and eat something and get coffee made, it’s usually 9:30 AM and I climb up the little spiral stairway to my office studio - it’s a lofted mezzanine area over our living room and has two skylights and bright white walls; my dad and I laid the bamboo flooring ourselves. It’s the first dedicated workspace I’ve ever had. I worked out of our bedroom for 3 years in Austin! I’m so grateful for it."

From a bedroom office to a dedicated creative space, and from a corporate job to the boss lady of her own business (well – two really) Jessica Crowell Astrella is thriving. But the work didn’t do itself. A lot of thought, careful planning, and persistent pursuit brought her to this point in her life, and it’s something to be proud of.

"I feel so much more sure of my abilities and skills and also what I’m not great at. I feel like I’ve stopped phrasing my career choice as a question mark, and can share it with an exclamation point, now."

Want some advice? Here’s what she shared:

// In general, find ways to hustle and work like crazy but not burn out. Learn how to say no - if that means increasing your prices so that you can take on less work, do it!

// Build a network of like-minded women, similarly self-employed women. It’s isolating to work alone, and getting dinner with a group of people who can say, “hey! I’m dealing with that, too!” once a month is life-giving.

// Specifically in this line of work, don’t take shortcuts. One online course does not make you a calligrapher! Practice, put in the time, try a million different tools and supplies, find what works for you. Develop your own style and don’t copycat other artists - people should hire you for your own look. If they want *that* look, they should hire *that* person instead - and learn how to gently but firmly communicate that to clients.

// This is not a hobby. This is your job. Make sure you demand the respect and compensation that it entails.

// And for goodness sake, limit your time on Instagram.

[ Unless you are following her account @j_ro_cro ]

Jessica Crowell Astrella illustration lettering design floral watercolor logo

Images, illustrations & signatures provided by J.RoCro Arts + Letters and Boarding School Collective.

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