How to see like a designer: The hidden power of typography and logo design | Jessica Hische (Lettering Artist, Author)

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Jessica Hische is a lettering artist and New York Times bestselling author based in Oakland, California. She specializes in typographical work for logos, film, books, and other commercial applications. Her clients include Wes Anderson, The United States Postal Service, Target, Hallmark, and Penguin Books, and her work has been featured in design and illustration annuals both in the U.S. and internationally. She’s been named a Print Magazine New Visual Artist (20 under 30), one of Forbes 30 under 30 in Art and Design, an ADC Young Gun, a “Person to Watch” by GD USA, and an Adweek “Creative 100.” In our conversation, we discuss:

• My new logo and brand!

• Jessica’s process for refreshing my logo/brand

• Why most startups shouldn’t worry about their logo/brand

• The psychology behind different typography choices

• Balancing creativity with business needs in logo design

• Jessica’s unique approach to pricing logo work

• How AI is (and isn’t) impacting the design world

• Jessica’s other creative pursuits, including children’s books and art supply stores

Some takeaways:

1. Start with a “good enough” logo: If you’re launching a startup, don’t get too caught up in creating the perfect logo from the get-go. Focus on getting something that’s “good enough” to represent your brand. You can always refine it later as your company grows.

2. As a non-designer, you can still train your eye to recognize good design. Take time to explore fonts, logos, and branding examples. Pay attention to spacing, letter width, and the optical illusions that occur in typography. The more you analyze, the better your intuition will become.

3. A flashy brand won’t save a product that lacks substance. Focus on building something meaningful first. If your product doesn’t solve a real problem or bring value, no amount of branding will make it work. Ask yourself: What is the core value we provide?

4. Typography isn’t just about choosing a font; it’s about the feelings and associations it conjures. Experiment with different styles and weights, and analyze how they communicate your brand’s personality. Look for commonalities in fonts that evoke similar feelings, and make choices that align with your brand’s narrative.

5. When developing your logo and associated graphics, ensure all elements—typography, color, and illustrations—feel like they belong to the same family. This cohesion enhances brand recognition and creates a stronger emotional connection with your audience.

Where to find Jessica Hische:

• Threads: https://www.threads.net/@jessicahische

• Instagram: https://www.instagram.com/jessicahische

• Website: https://jessicahische.is

In this episode, we cover:

(00:00) Jessica’s background

(01:32) The logo refresh process

(09:45) When to refresh your logo

(11:45) High-level overview

(18:04) Approaching Lenny’s brand refresh

(24:25) How to see like a designer

(37:53) Lenny’s new logo: where we landed

(44:07) Brand’s role in company success

(50:04) Jessica’s flexible pricing strategies and collaborative design process

(57:14) Balancing multiple creative projects

(01:01:48) Using AI in creative work

(01:05:50) Upcoming projects and final thoughts

(01:08:24) Lightning round

Referenced:

• Jeni’s: https://jenis.com

• James Edmondson on LinkedIn: https://www.linkedin.com/in/jamestedmondson/

• Figma Config: https://config.figma.com/

• Helvetica: https://en.wikipedia.org/wiki/Helvetica

• MyFonts: https://www.myfonts.com/

• Geometric sans serif fonts: https://www.myfonts.com/pages/tags/geometric%20sans%20serif-fonts

• The Rise of Fractional Executives: https://www.reforge.com/blog/leveraging-fractional-executives

• JH&F: https://jessicahische.shop/pages/my-oakland-store

• Drawling: https://drawling.shop/

• Jessica Hische’s books on Amazon: https://www.amazon.com/stores/Jessica-Hische/author/B082XDN54V

• Dreamforce: https://www.salesforce.com/dreamforce

• Bezier handles: https://www.tella.tv/definition/bezier-handles

• My First Book of Fancy Letters: https://www.amazon.com/My-First-Book-Fancy-Letters/dp/0593385012/r

• The Creative Act: A Way of Being: https://www.amazon.com/Creative-Act-Way-Being/dp/0593652886/

• Inside Paragraphs: Typographic Fundamentals: https://www.amazon.com/Inside-Paragraphs-Fundamentals-Cyrus-Highsmith/dp/1616899417

• Just Kids: https://www.amazon.com/Just-Kids-Patti-Smith/dp/0060936223

• Robert Mapplethorpe: https://en.wikipedia.org/wiki/Robert_Mapplethorpe

• The Emperor of All Maladies: A Biography of Cancer: https://www.amazon.com/Emperor-All-Maladies-Biography-Cancer/dp/1439170916/r

• Severance on Prime Video: https://www.amazon.com/Severance-Toby-Stephens/dp/B001ARYGCU

• Penco brown bag stand: https://penco.jp/en/products/db079/

• XOXO: https://xoxofest.com/

• Mariame Kaba quotes: https://www.goodreads.com/author/quotes/8156101.Mariame_Kaba

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.