When Jessica Greenwalt was first called a tomboy, she froze. She was just a kid, catching tadpoles in a stream while at a family gathering, when her cousin said it to her. It was a completely foreign concept that playing outside could mean she was acting like a boy.

She credits her father with that — he was an electrical engineer, and as soon as she was old enough to hold a soldering iron, he was teaching her how to build little radios and messaging devices. Her options were limitless, he taught her, and she had expectations that she could do whatever she wanted in life.

“The distinction was never made for me, and I am grateful for that,” she said. “I would not be where I am now if I wasn’t raised with the sense of entitlement that a young white boy was raised with.”

Greenwalt is quick-witted, sharp, and honest. She is one of those rare people who has passions for both the arts and computer sciences, and she’s talented at both. Now the co-founder of CrowdMed, a crowdsourcing platform for medical diagnoses, she has always been a successful graphic designer.

Seattle, Washington is where Greenwalt calls home, but she went to grade school in Honolulu, Hawaii. Later, her parents ended up moving back to Washington, but when they got divorced, Greenwalt moved to San Diego with her mom. Of course, being from places other than California, she expected sunny skies, palm tree-lined streets, and surf culture. And in San Diego, that’s pretty much what she saw.

In college at California Polytechnic State University, Greenwalt took a digital media class, where she learned what graphic design was. Being an artist interested in technology, she was ecstatic — that was an art form she could actually get paid for. She called it her “career soulmate,” and decided she would pursue it.

She had started a design firm back in high school, and so she continued it in college. She made prints and logos, as well as websites using HTML Tables for neighbors, friends, and even people she found looking for help in the classified ads in newspapers. The program in college was mostly print-focused, and classes were just starting to focus on web development when she was on the way out. The majority of things Greenwalt now uses as a foundation for what she does day-to day, she learned for free online from blogs and videos.

After college, Greenwalt wanted to freelance, but her parents wanted her to get a full-time gig. So, she worked for two years at a research journal publishing company, which she wasn’t exactly passionate about. She almost left a couple of times, but the travel and pay kept increasing, so she stayed. Finally, she realized something important.

“Clearly [I was] not satisfied enough to stay intrinsically, and I could make twice as much just freelancing and work half the time. It’s what I wanted to do in the first place, have a design firm.”

Her firm, Jessica Greenwalt Design, which she had been running since 2003, grew into a bigger design firm in 2011 that she called Pixelkeet. She had the customer base from college, and relationships with designer and developers. She was in the Bay Area by then, and expanded her client base to startup founders, as well. At first, she did most of the design work herself, and then hired others and started to really run the business side of things.

That’s only the first part of her career. The second half of Greenwalt’s story is, in many ways, very different from the first, and a question she gets asked about often.

“There was a huge change in my life that did a lot to shake up things going on,” she said.

She was living in San Francisco, and was engaged to be married to a guy she knew for many years, who she had reconnected with. He worked for a startup, and around the time they started dating, he invited her to a party. Greenwalt ended up arguing about the effects of crowdsourcing with a man named Jared Heyman. He had a business card that he crowdsourced the design for, and she said it was the ugliest thing she’d ever seen. He told her maybe she could do it better, and she told him, “as a matter of fact ,I can.”

She started helping him with his web design for CrowdMed, which Heyman had started because of his sister who had been sick for three years and spent six figures trying to figure out what was wrong. He wanted to see if multiple experts could crowdsource medical diagnoses to solve cases faster, cheaper, and more accurately than specialists could.

“We started working on this thing together…working on the framework that would become CrowdMed, shortly after that party,” she said. They added Axel Setyanto, a third co-founder, and built a prototype that they tested to crowdsource wisdom to solve medical cases. Once they knew they had a product that was valuable, they flew to DC to launch it in conjunction with TEDMed. Greenwalt and her co-founders stayed up for three days coding the site and finished just in time. That trip, as stressful as it was, allowed Greenwalt to do some soul searching. The time away from wedding planning and her fiance made her think more about what she was doing in her life, and so when she returned to San Francisco, she called off her wedding and moved out.

“I don’t know that would have happened without the experiences I had [with CrowdMed],” she said. “I might just still be freelancing and living in San Francisco, and probably be married by now…I am grateful that I am where I am now, I think this feels right for me.

Earlier this year, she shifted full-time to CrowdMed and put someone else in charge at Pixelkeet named Jessica Parsons. Greenwalt is fairly certain many of her clients still don’t realize they’re talking to a new Jessica. At CrowdMed, Greenwalt is the CIO, and spends the majority of her day communicating with people on all levels about user experience and design. Her favorite parts of the day involve talking to patients and medical detectives who use the platform, to find out what they want to improve. Now, there are four people on the team, as well as a community of medical advisors and medical students that are helping promote CrowdMed on campuses and reviewing cases for the site.

“The design firm was way more relaxing, and I want to say this is intense. I definitely feel alive, there isn’t a moment where I don’t know what to do with myself,” she said. “It’s exciting, energizing, and everything is done so quickly [so there’s an] instant gratification. You see results and it’s on to the next thing. It’s satisfying in that sense.”

In her own words…

What are some of your hobbies?

“I like to host craft parties. People will come over and work on the most random things. One of my friends is a — do you know what yarn bombing is? Instead of permanent street art, it’s temporary… they’ll knit things that will cover up public property, like lamp posts, etc. So she will come out and knit her next yarn bombing project. Some people work on robots, collages, paper mache. It’s the most eclectic bunch of projects, it’s pretty cool. Since I spend so much time in front of technology, I am basically happy to do anything that doesn’t involve a machine. I do a lot of paper crafts. I like to make greeting cards. That’s incredible outlet for me.”

Looking back, what advice would you give yourself?

“I would have told myself if I could, to get advice from someone who has done this before because I kind of just did everything very experimental, just went for it. I made a lot of mistakes that took me longer to learn things than if I just asked for help initially. I would say don’t try to do everything yourself, don’t be afraid to ask for help, and people are generally willing to give advice in the Bay Area in my experience. No reason to be shy about reaching out to someone. People are ready willing and able to help here. I don’t know if it’s because of how I was raised or culture before I got out here, that made me feel like I shouldn’t be asking for things, that made it harder for me and put a greater burden on myself and made me the bottleneck for things because I had to do them all myself.”

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