Cup 6 | Jessica Hische

"I don’t believe in soul mates,"

proclaimed Jessica Hische, the highly sought-after (and happily married) letterer and illustrator, as we sit in her favorite San Francisco cafe, Ritual Coffee.


She’s wearing neon leggings covered in cat faces floating in the cosmos (it’s Pilates day and cats make it more fun) as we chat with the enthusiasm and flow of old friends. Jessica is wildly talented, personable, and fun. She’s also unapologetically herself, which is just the reason I reached out to her for coffee.  

Our conversation jumped from stories about elementary school friendships, the twists and turns of her artistic career and, of course, soul mates—a topic that offered both a glimpse into her unapologetic confidence I so admired, and a lesson in decision-making.

If you don’t recognize Jessica’s name, you’ll likely recognize her work. She chased her childhood dream to “spend all day drawing” and became an award-winning letterer and illustrator. After graduating from Tyler School of Art at Temple University, she began working as a freelance designer before landing a job with her design hero, Louise Fili. After two years of hard work, she decided to fully branch out on her own and has since gone to work with clients including Starbucks, Wes Anderson, Tiffany & Co., American Express, Target, Nike and more.

A sample of Jessica’s work. 

Her talent and infectious personality online have made her an inspiration for many young designers and an international speaker (check out this great talk on her favorite topic, procrastiworking). Wherever you find her, you’re sure to witness her quirky, unfiltered, authentic self, which is refreshing to find in a world where people often are swept up in living up to someone else’s expectations.

"You seem fearless,"

I asked her (perhaps hoping a bit of her magic will rub off on me).

"I don’t think I’m fearless, I’m just really good at looking at a situation and being honest about what my motivations are."

Jessica is confident because she understands (and trusts) her decision making process. She is intentional in her actions—what she says on Twitter, who she works with, etc—and understands why she is doing what she is doing. She seems fearless because she doesn’t stress over how people will react because she has solid reasoning to back up her actions.

At an early age Jessica developed a desire to be independent: to be able to stand up for herself and be financially independent.

"In learning to survive high school, I saw that the people that fared the best were the people that were unapologetic about what they were doing. If you were very frank about all the decisions you were making, it made it easy to navigate situations".

That decision making has long been a strength of Jessica’s:

"When I was young, I was incredibly shy, but I’ve always been very decisive. Take me shopping and I’ll get everything I need in one trip and I won’t regret a single decision. I just know what I like and what I don’t like. When I was young I may have been too shy to articulate that well but I still knew what I wanted."

Which brings us to soul mates.

Jessica’s “fearlessness” is actually a strong trust in her decision making skills. She doesn’t exert much time or anxiety agonizing over the perfect choice:

"I don’t believe in the best version of anything. I believe there are a group of things that are the best thing, or work, and you chose one and you move on. And if you don’t just make a decision and move on you’ll never do anything. You’ll end up single forever."

She was referencing marriage but the theory has broad application: from toothpaste to career choices. You look at the best set of options and then trust your gut.  

Make a decision and make it work.

That’s Jessica’s mentality. 

It was great to hear Jessica’s insights because I frequently fall victim to the opposite mentality: there is only one choice that will make you happy, the rest will leave you endlessly miserable—so don’t screw up. I know this is false thinking. I also know I’m not the only person that gets caught up in this thinking. 

Jessica was sympathetic to my plight. She called it the soul mate mindest—looking for “the one” whether that be the perfect job, apartment, mate, little black dress, etc.

“I think 90% of people are in the mentality of soul mates. It’s the fairytale mentality that we grew up with.”

But life isn’t a fairytale.

"You have to look at the options and the time that you have and make the best decision, knowing you can make a different decision later."

You can’t wait around for perfect because it doesn’t exist. And if you’re waiting (anxiously) for everything to be perfect, you’re going to miss out on a lot of great things that add up to something really special.

Perhaps it was the affects of the warm San Francisco sun on a beautiful afternoon but as we parted ways after our conversation, I felt like I’d succeeded: a bit of Jessica’s magic had rubbed of on me.

She reminded me that there is more than one route that leads to a satisfied and successful life, which means theres no point in anxiously waiting for perfect. Instead, you’ve got to jump right in and trust that whatever happens, you’re capable of making it work.

You can believe in soul mates and think you get one shot at a happy life—or, you can believe in yourself and trust you’ll make the most of whatever comes your way.

The latter appears to be working wonders for Jessica.