Lettering Works

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Lettering Works Business Journal - September in Review

September’s highlights included seeing more friends than I can count, adding some exciting new retailers to my list, reading a dozen books, and launching the new branding for Doughnut Gallery.

If you’re new here, welcome to my business journal. This twenty-first edition of the monthly business journal blog post celebrates the wins and serves as a space of reflection of this business journey, which has been such an important practice for me since January 2020.

Exploring Garfield Park Conservatory

Plant Sticker Collection

Lettering Works products at O’Hare Airport (via the Field Museum gift shop)

New logo design for Doughnut Gallery

The Big Wins

  • I visited Garfield Park Conservatory and added them as a new retailer! It pays to get outside of your comfort zone and ask for what you want. My entire plant collection of stickers and Chicago pizza pin will soon be available at the GPC’s gift shop. I’ll also be adding the Military Women’s Memorial to my list of retailers in October and have a couple new Harriet Tubman designs I created for them that I’m excited to share next month.

  • My postcards and enamel pins are at O’Hare Airport! Thanks to my friend Abby for sending me a picture of her with the display at the Field Museum gift shop inside O’Hare.

  • We launched the new Doughnut Gallery branding! Joe shared that “Chelsie is an artist for artists. She was commissioned to design our brand, taking into account everything we are striving to achieve, and she delivered exactly what we were looking for. Working with her was an absolute joy. If you are a fellow artist who is looking to define or redefine your brand, I PROMISE you will be greatly rewarded.” See the full brand development and interview with Joe here.

Get on the SMAA waitlist

Make Space for Everybody T-Shirt

All smiles when I have a rosemary lavender latte from 3030

General Updates:

  • I read twelve books: The Hate U Give, Outliers, Concrete Rose, OCDaniel, Everything I Never Told You, 4 Hour Work Week, Haben, White Fragility, Sharp Objects, In Cheap We Trust, The Best of the Second City, and Thinking in Pictures.

  • I launched the second cohort of Self-Made Artist Academy. I am excited to be helping a new group of artists learn the fundamentals of business and turning their passions into more sustainable careers. I introduced a scholarship to make this program more accessible. Get on the waitlist to be notified about the next cohort.

  • I am continuing to pursue airport-specific opportunities and had my site visit/phone interview to complete my ACDBE application (which will *hopefully* certify Lettering Works as a disadvantaged small business in the airport space). I also attended my first AMAC (Airport Minority Advisory Council) “Emerging Leaders” meeting as a committee member.

  • I saw a LOT of friends! While we missed having an official Staycation Day this month, I got my fill of fun through meeting up with several friends ranging from my best friend from kindergarten to my high school yearbook co-editors to my college roommate to post-college friends from Peoria to my Chicago business besties.

  • I took a weekend trip to Peoria and got to enjoy some of my favorite Peoria things including the Riverfront Farmer’s Market, 3030’s signature rosemary lavender latte, and food from other favorite local restaurants, as well as time catching up with good friends.

  • People Love Art launched the Demand Accessible Space collection. My “Make Space for Everyone” t-shirt design is now available via People Love Art’s website. A percentage of sales will support AstroAccess’ mission to make space accessible for all.

  • I prioritized my physical and mental health. I saw a new dermatologist, rheumatologist, and therapist. Hitting my insurance deductible definitely helped motivate me to get more things checked off my health to-do list. Up next is scheduling an echocardiogram, but all appears to be healthy, according to my new specialists.

  • I worked on a handful of custom design projects including a birthday poster, logo design, custom city-specific graphics for two different places, and recreating a couple existing designs in Spanish. I also onboarded a few new projects which I’ll be working more on next month.

In October, I am most looking forward to celebrating turning 28 (stay tuned for a special birthday sale!), rolling out some new custom sticker designs for the Chicago History Museum, and continuing to pursue the opportunity to sell my souvenirs at Walgreens after a successful pitch last month.


Thank you for being here, for supporting me, and for following along with this beautiful journey entrepreneurship has taken me on.

PS - Have a project you’d like to chat about? Book your 2021 project today! Bring on all the logos, branded merchandise, and brand identity projects… let’s make some beautiful and impactful things together.