How to see like a designer: The hidden power of typography and logos

Jessica Hische is a lettering artist and author who has built custom typography and logos for brands like Apple, Nike, and Penguin Books. In this episode she walks Lenny Rachitsky through how she refreshed his newsletter and podcast logo, and shares how product people can learn to read typography and logos like a designer.

01Key learnings

• Startups can launch with a quick, internally made logo, then invest in a custom refresh once the company is more stable, avoiding spending heavily on brand before a possible pivot.
• Signs it's time to upgrade a logo include a broader rollout of the brand, printing swag or hosting events, or needing assets that scale poorly.
• A custom logo or typography makes your brand harder to copy than a freely available font, which matters once success attracts imitators.
• Start a logo refresh by agreeing on the goal: a subtle fix that most people won't notice, or a bigger shift to attract a new audience while keeping core fans.
• Test logo versions in real contexts early, and check for unintended readings such as the Jeni's apostrophe that made the word look awkward.
• To learn to see like a designer, screenshot fonts that give you a feeling, group them, then notice shared traits like weight, width, spacing and edge softness.
• Designers adjust letterforms optically, so lowercase letters often look perfect only after deliberate tweaks; zooming in on a single letter in Figma reveals this.
• Choose brand assets that are easy to use so teammates with taste can apply them correctly without a huge brand book.

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.