After a brilliant hour-long session at Adobe Max in which Jessica Hische shared incredible wisdom about how subtle changes in lettering and typography can completely change the success of a logo or typeface, I waited patiently for a chance to chat with her for our pre-arranged post-talk interview. The line of fans eager to get their copy of Jessica's book In Progress signed and snap a quick selfie highlights just how successful and influential she has become during her time as a letterer, illustrator and type designer.

Jessica spent the early years of her career working for the amazing Louise Fili, and then went on to find fame for her Daily Drop Cap and Should I Work for Free personal projects. She's worked for huge clients including Wes Anderson, Tiffany & Co, American Express, Victoria's Secret, Nike and Samsung, too.

Now, she's continuing to work on big projects as well as travel to speak at creative events like Adobe Max to share her story and inspire others who are keen to follow in her footsteps. But on top of all that, Jessica has also just become a mum to a gorgeous little girl called Ramona, so before we could get started with our interview we sped downstairs to meet her husband Russ and check on the baby, who luckily was sleeping peacefully so we had the green light to get chatting.

How to embrace motherhood whilst maintaining a successful freelance career

Naturally, the first thing I wanted to find out was how on earth Jessica is handling being a mum and managing her busy career so brilliantly. It's an impressive accomplishment and utterly inspiring for women worrying about maintaining their freelance career when starting a family. Plus, Jessica has a less squishy baby in the form of her book, In Progress, to look after, so she's busy promoting that on top of working on her client projects, too. It's making me tired just thinking about it.

An example of Jessica's talent for subtle changes that make big differences to logos. Find out more about how Jessica redesigned the Mailchimp logo here.

When I asked Jessica what her advice to others about juggling motherhood and a busy, successful career, she admitted that while she thought she would find it easier than she did, she's figuring it out and loves being a mum. “The biggest perspective that I can give for it now is that I knew it would change the way I could work, but I thought that in the short term it wouldn't be as crazy as it is,” she told me.

“My studio mate Eric had a baby while we were studio mates together, and he somehow was 10 times as productive as me the entire time that we had been studio mates together, so I saw the way that he worked around family time, which was keeping incredibly strict hours, and making sure that if you're at the office, you're working. I really have been trying to do that in a major way. I don't spend time in my office screwing around. If I'm going to screw around I'm going to be out of the office hanging out with the kid.”

“But what I didn't anticipate is how different the experience is as a mother versus as a father, just because the whole breast feeding situation is another game entirely. But the thing that is really good to know about it is that it's temporary. Thankfully, since I work for myself, and I'm in charge of my own destiny, I can know that this year won't be the most productive year for me, and in terms of how much I can travel, it's had a huge impact, but it's really temporary in the grand scheme of things and it's really however long you choose to do it. I would love to breastfeed as long as possible but if it loses its importance to me because of something else, I'm not going to guilt myself over it.”

Jessica explained that she mostly worked on her book prior to the birth of her daughter in April of this year. She finished the book in November of 2014. “It was a real challenge,” she said. “The process for creating a book is a very long-term process, and I'm a sprinter not an endurance person. I found that having to turn down a lot of work while I was working on it just to make sure I had enough time.”

“Even just setting aside time was really difficult. If you've ever dealt with managing projects on your own before, one of the things you'd have found is that you can't just put stuff down and come back to it later. There was a lot of wrangling with clients so that I had the time to do it. It was definitely a super challenge in terms of time management.”

The challenge of publishing a book

Jessica was approached by Chronicle with the idea of working on a book together. They were open to Jessica's ideas about what the book should be. “Originally when they contacted me, they envisioned it as being more like a monograph, and I was really afraid to have it be anything close to that because I'm so young.”

“I know that there are people out there that would be fine putting out books of their work when they're 30 or whatever but I felt like it was too early in my career, so I wanted to make sure that whatever it was it could be something that's useful in some way or another.”

“Originally I was like, ok so people seem to geek out about my sketches, so maybe I'll show a bunch of my sketches and then finals, and let the pieces lay where they fall, but as I was writing the book I couldn't bring myself to get much deeper into the process of how it was going, so I ended up writing a 35,000-word manuscript, so it's like a proper book. It's a very different book than I had set out to make, but ultimately it's a lot better than the book I set out to make.”

Jessica told me that she's totally open to working on another book, because she's incredibly proud of In Progress, and rightly so. “When I got it physically I was like wow, this actually looks great. It's been a while since I had that much control over the full production of a project, because usually when I'm creating assets for stuff, even if it does end up getting printed beautifully, I'm not the person who made those calls,” she explained.

“I don't think I'll make another book of my work for some time, but I do a lot of writing on my website with advice for designers, and I would love to be able to do that in a book form.”

Working with Louise Fili

Jessica's career was propelled forwards when she found herself working with Louise Fili at her design studio in New York after graduating. She worked with Louise for two years before going it alone, but Louise wrote the forward for Jessica's book so I was curious to find out what their relationship is like now.

“We're definitely close,” Jessica told me. “I feel like, I've always been a person that really likes working under a mentor, and feels very close to the people that are willing to put the time in to help me. I feel like my relationship with Louise was always different from how some people might think of their relationship with an employer. It was always more to me than just employer and employee.”

“I feel like because I have been really respectful of the work that I did with her and was never trying to step on her toes or work for her clients, we've been able to make sure that our relationship stays really strong, because I think that's the thing that any employer ever really thinks about when someone moves on is will this person then become my competition or will we be able to be in the same space with each other. So because my relationship with her was so important I always made sure that whatever was going on wasn't going to make Louise angry with me.”

Love Stories illustration for The New York Times Book Review.

It was clear by Jessica's smile and her passion while talking about Louise that she treasures her time working with her, so I asked her to share a story about Louise.

“Louise wrote the preface for my book, and I was completely honoured that she would consider doing it, so when it came to putting photos of her in the book I wanted to show the fun that we had when I was at the office. Louise is just an incredibly professional and amazing business woman, but she's also lovely and a human being, and during my time there one Halloween I dressed up as a high school portrait. I made this costume that had a laser background and I wore these dorky glasses, and I wore it to the office . I got Louise to put on the costume and I took her picture, and I thought for sure that I'd never be able to show these pictures to the world, and when I put together the book I said can I please, please put this picture of you on the about Louise page. She agreed to it as long as it wasn't enormous on the page. It was such a fun time in my life to work there and to feel like I was growing and that I had this really supportive person making sure that was possible. It was a fun time, not just all work and no play.”

I wondered whether Jessica would ever consider taking someone under there wing in a similar way to the way Louise did with her, because it's clear that she's great at sharing her knowledge through her talks and also her blog, where she often shares advice for designers. She explained that she absolutely wants to have employees at some point in the future, but right now she's focusing on travelling and public speaking. “I feel like while I can affect as many people as I can I should. Because that's not going to be a thing that I can do forever in my life. I really see all of these public speaking occasions as a way for me to teach and encourage people to do what they want to do. I don't have the same one-on-one closeness that you would with an employee or an intern, I am able to do the same things just not as intimately.”

Does everyone need a mentor?

When I asked Jessica whether she thinks it's a good idea for all young designers, artists, illustrators or really anyone looking to embark on any career path to find a mentor, she said: “I think everybody's really different. We all need teachers for sure, but whether or not you need really intense direct mentorship is up to you personally. Some people are really great at being self starters and figuring out the world on their own because that's how they've had to do it their whole lives, but I am just not that person and I really feel like I benefit the most if I have tons of parenty figures around making me feel like I'm doing it right.”

Jessica's Daily Drop Cap project, which went on to star in a new stationery collection for Moo.

Finally, before letting Jessica head off to be with her family who were sitting patiently beside us, I asked Jessica what's she's up to now and what's next. She hinted that, she's working on a project that is “kind of a big deal but I'm not allowed to say it out loud,” so we look forward to hearing more about that in the near future.

You can find out more about Jessica and her work on her website, and her book (which is an absolutely stunning and impressively meaty full-colour hardback), is available to buy on Amazon now. You can also read our interview with Jessica from 2011 here.