Boss Like A Lady – Women Entrepreneur Series – Molly Jacques, The Letter Whisperer

Continuing after Women’s History Month, I am creating a limited hand-lettered and illustrated series of some women making history.  These women own their own creative businesses and make them successful despite many obstacles, including their own occasional self-doubt.  I hope they inspire you to make a little history of your own!

Molly Jacques
The Letter Whisperer



Molly Jacques was one of the first modern calligraphy classes I took.  I really feel it was Molly that kind of set my work ‘free.’    I have followed her advice and worked hard on my own illustrative ‘voice’.  So it was a thrill to have her participate in this series, and an honor to draw her and letter her words!


Molly’s Bio

Born and raised in a small midwestern town, I grew up alongside parents that fully encouraged my love of art and all things creative. From a young age, my passion for drawing was easily seen pinned up throughout my bedroom and the family refrigerator door. At the age of 18, I packed up all of my belongings to go study illustration at College for Creative Studies in Detroit, Michigan. In 2010, I earned my bachelors degree of fine art with a concentration in illustration.

Soon after graduation, I started working part-time for the high end stationery company Sugar Paper. Throughout my time there, I soaked up lots of inspiration and found my true passion: calligraphy and lettering. In 2011, I took the plunge into a full time freelance career and since then, have built my business from the ground up. My work is strongly grounded in word aesthetics, ranging from lettering and calligraphy to typeface design and traditional illustration. As an independent illustrator, I’ve had the opportunity to work with a wide variety of clients like The New York Times, Nike, The Wall Street Journal, Google, Disney, Martha Stewart, and Tiffany & Co.


What do you think your greatest mistake was or is? Trying to do everything on my own. While it’s absolutely possible (we’re capable of amazing things), I’ve learned over the years that delegating certain tasks I’m not so great at is such a life saver. I started working with my art rep Joanie in 2012 and it really changed my perspective on freelance illustration. She’s helped me in ways I never would have known to help myself.

What is the worst advice you ever received?  I guess this wouldn’t be direct advice, but I feel like generally it seems like our industry promotes the idea that working all the time will make one successful. I think this is terrible advice. Working hard, diligently, and responsibly will for sure get you far but working ALL the time will just make you stressed out and possibly less productive. I try to set solid office hours and expand past those hours only when it’s necessary, like for a rush job. I try my best to use those office hours wisely and get done what needs to be done. I use my free time to refuel and simply enjoy life.

What is the best advice you ever received?  Don’t dismiss your dreams or assume you can’t do something because of money. My Dad taught me that. Obviously sometimes dreams don’t turn out as planned but they are worth pursuing even if it takes a lot of work or networking. Sometimes ideas fall flat, but it’s better to try than not at all.

What is your best source for inspiration?  My family and nature. My husband and I are into climbing and mountaineering (when we can travel outside of Michigan…). It’s been a big inspiration for me, and a great reflection of how I should approach challenging things in my life.

What do you do when you get discouraged?  Get active. Sweating things out can really help with a lot of emotional distress and aid me in seeing things more clearly.

What do you do when you doubt yourself?  Share my doubts and fears with my husband. He’s such a great companion and motivator. He doesn’t lie to me just to make me feel better but he always points out when I lie to myself.

Why LETTERS?  As I was building my senior portfolio at CCS for Illustration, I focused a lot on gig poster art. Poster art deeply embraces hand drawn text, so letters were kinda a natural transition for me. When I graduated in 2010, I was often hired to illustrate letters and things just sorta fell into place from there.

When did you know you were ‘successful?’ Ha, this is an ongoing question right? My view of success is always changing so this one is hard to answer. But, in general, I was very pleased with myself when I was able to quit my 9-5 job and work as a full time independent illustrator. At this point, I definitely was only making enough money just to scrape by but it didn’t matter – I got to practice what I loved every day.



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