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Jessica Hische (Lettering Artist, Author)20 October 2024

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

7Frameworks
15Insights

Episode overview

Lettering artist and author Jessica Hische explains how typography, spacing, weight, color, and optical corrections shape the feelings people get from logos. She walks through the refresh of Lenny Rachitsky's newsletter and podcast identity, including its goals, iterative narrowing, illustration constraints, and final return to a simple fire-and-marshmallows mark. The conversation also covers when startups should invest in branding, how to collaborate with experts, creative productivity, children's books, and Hische's selective use of generative AI for exploration and brainstorming.

Key ideas

  • People already perceive when typography feels wrong; studying and categorizing fonts can turn that intuition into design language.
  • Logo refreshes should start with broad goals—such as legibility, scalability, audience expansion, or cohesion—before addressing individual letterforms.
  • Early-stage companies often need only a workable identity; heavier brand investment makes more sense after the product and company direction stabilize.
  • Custom typography can improve distinctiveness and reduce the ease with which successful brands are copied.
  • Type designers deliberately break mathematical regularity to compensate for optical weight and make letterforms appear balanced.
  • A useful brand system provides several compatible assets while remaining simple enough for non-specialists to use correctly.
  • Creative endurance can come from switching among sufficiently different projects when attention or energy begins to fade.
  • Jessica Hische uses generative AI mainly for early iteration and brainstorming while retaining hands-on production work she finds creatively restorative.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Finance3 steps

Deferred-Buyout Creative Pricing

Keep the exploration phase cheap by billing rights separately, so a late pivot doesn't mean you already paid to own dead work.

Read →
Innovation3 steps

Optical Correction X-Ray

Blow a single letter up huge and probe its joints to see where a real type designer breaks geometry to look perfect.

Read →
Self-Mastery5 steps

Song Exploder Your Intuition

Turn a gut reaction to a design into a reusable, articulable design rule by reverse-justifying why you feel it.

Read →
Communication3 steps

The Blur Test

Take your glasses off and squint at a brand to judge its cohesion, color story, and overall feeling.

Read →
Strategy4 steps

The Goals-First Refresh Cascade

Set the scope of a rebrand by naming the goal first, then let every later round cascade from broad to narrow.

Read →
Communication3 steps

Top-Down Design Diagnosis

Before touching any detail, spend days naming the one big-picture reason a design bothers you.

Read →
Peak Performance3 steps

Variety-as-Rest Anti-Burnout

Beat burnout by switching to a different kind of work when you lose steam, instead of stopping.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 7

  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    “Today my guest is Jessica Hische.”

    ▶ Watch at ~0:30approx.
  • Jessica HischeMentionsJessica is a lettering artist specializing in typographical work for logos, film, books and other commercial applications.

    “Jessica is a lettering artist specializing in typographical work for logos, film, books and other commercial applications.”

    ▶ Watch at ~1:00approx.
  • Kristina GilbertMentionsthe founder of OneSchema

    “I'm excited to chat with Kristina Gilbert, the founder of OneSchema, one of our long-time podcast sponsors.”

    ▶ Watch at ~4:00approx.
  • James EdmondsonMentionsmentioned

    “It was drawn by a friend of mine, James Edmondson, who I love all of his stuff.”

    ▶ Watch at ~20:00approx.
  • Robert BringhurstMentionsmentioned

    “it's a really great book and incredibly accessible and not like reading like Bringhurst or something like that.”

    ▶ Watch at ~1:09:00approx.
  • Cyrus HighsmithCoinedmentioned

    “there's this book called Inside Paragraphs by Cyrus Highsmith.”

    ▶ Watch at ~1:09:00approx.
  • Robert MapplethorpeMentionsmentioned

    “trying to be an artist and make art and having that be the thing that drove everything that she and Robert Mapplethorpe did.”

    ▶ Watch at ~1:10:00approx.

Resources · 19

  • OneSchemaMentionssoftware · Christina Gilbert

    “I'm excited to chat with Kristina Gilbert, the founder of OneSchema, one of our long-time podcast sponsors.”

    ▶ Watch at ~4:00approx.
  • Jeni's Splendid Ice CreamsMentionscompany

    “when I did a refresh for Jeni's Ice Cream, which is a really like amazing ice cream brand based out of Columbus, Ohio.”

    ▶ Watch at ~16:30approx.
  • San FranciscoMentionsplace

    “When I first moved to San Francisco, I moved to San Francisco from New York.”

    ▶ Watch at ~23:30approx.
  • New York CityMentionsplace

    “When I first moved to San Francisco, I moved to San Francisco from New York.”

    ▶ Watch at ~23:30approx.
  • ConfigMentionsevent · Figma

    “I talked about this a bit at Config.”

    ▶ Watch at ~25:30approx.
  • HelveticaMentionsproduct

    “So, you can take like a typeface like Helvetica, right? Like just the one everybody knows, right?”

    ▶ Watch at ~28:30approx.
  • Song ExploderMentionspodcast · Hrishikesh Hirway

    “a really fun exercise to do is like to sort of Song Exploder your intuition, you know?”

    ▶ Watch at ~30:00approx.
  • MyFontsRecommendswebsite

    “or go to MyFonts or like a place where there's like a ton of fonts, and like just search for something.”

    ▶ Watch at ~31:00approx.
  • MergeMentionscompany · Merge

    “This episode is brought to you by Merge.”

    ▶ Watch at ~43:00approx.
  • PlaidMentionscompany · Zach Perret and William Hockey

    “Think of Merge like Plaid, but for everything B2B SaaS.”

    ▶ Watch at ~43:00approx.
  • FacebookMentionscompany · Meta

    “the reason why we're in the Bay is because he got hired by Facebook back in 2011.”

    ▶ Watch at ~47:30approx.
  • MetaMentionscompany

    “my partner works at Meta on GenAI stuff.”

    ▶ Watch at ~1:02:00approx.
  • Stable DiffusionUsessoftware · Stability AI

    “trying to run it through Stable Diffusion to get Stable Diffusion to generate instances of my lettering in different styles.”

    ▶ Watch at ~1:03:00approx.
  • ClaudeUsessoftware · Anthropic

    “I have found that sort of like Claude and and Chat GPT are very good for things like that.”

    ▶ Watch at ~1:05:00approx.
  • ChatGPTUsessoftware · OpenAI

    “I have found that sort of like Claude and and Chat GPT are very good for things like that.”

    ▶ Watch at ~1:05:00approx.
  • Inside Paragraphs: Typographic FundamentalsRecommendsbook · Cyrus Highsmith

    “there's this book called Inside Paragraphs by Cyrus Highsmith. It's very small and very digestible.”

    ▶ Watch at ~1:09:00approx.
  • SeveranceRecommendstv show · Dan Erickson

    “Severance was like my favorite TV show I think I've ever watched.”

    ▶ Watch at ~1:12:30approx.
  • PencoRecommendscompany

    “there's a Japanese brand Penco and they make a lot of wonderful stuff. I carry a lot of their stuff in my store.”

    ▶ Watch at ~1:12:30approx.
  • Lenny's PodcastCoinedpodcast · Lenny Rachitsky

    “You can find all past episodes or learn more about the show at lennyspodcast.com.”

    ▶ Watch at ~1:21:30approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 4

Hot Take06:30

A Logo Won't Drive Your Company's Culture

Jessica pushes back on founders who believe the logo will set the company's culture. The product, team, and people drive things forward. Brand assets do real work, though: they generate internal and external excitement and tell people what to expect, much like a book cover should signal what's inside.

  • The product, team, and people you assemble are what drive a company forward, not the logo.
  • Brand assets generate both internal and external excitement.
  • A logo tells people what to expect from the thing they're about to engage with.
  • A book cover should give incredible insight into the interior and set the tone, not hide it.

“Some people start a company and think the logo is going to drive the culture of the company, which I don't think that that is…”

Jessica Hische · 06:30
#branding#startups#logos
Hot Take07:30

Don't Blow Venture Money on Brand Before You've Pivoted

As a self-described contrarian in the brand world, Jessica warns founders against a massive brand exploration too early. Companies often pivot when a competitor ships first or the technology stalls, so a heavy up-front brand investment becomes wasted money. Internal teams can handle the scrappy early work, and she comes in later to smooth it out.

  • Brand people say brand is everything and needs a significant early investment; Jessica disagrees for early-stage tech.
  • Companies frequently pivot because a competitor ships the same thing or the underlying tech gets postponed.
  • Investing heavily in a full brand vision from the jump is throwing away money if you have to pivot.
  • Internal teams are capable of the early holding-page and deck work; a pro can refine it once there's traction.

“if you invest super heavily on like the whole brand vision from the jump, sometimes it's like throwing away money if you have to pivot.”

Jessica Hische · 08:30
#branding#startups#budgeting#contrarian
Hot Take44:30

When Brand Should Be Invisible

Jessica distinguishes two kinds of companies. For some, brand is everything, they repackage non-innovative information so a broad audience can access it, like popular-science authors digesting medical papers. But for many, the brand should be somewhat invisible so the product itself becomes the star, where the delight is that nothing gets in your way. The right role for brand depends on the company's ethos.

  • Some companies are pure brand: they repackage existing information so a broad audience can access it.
  • Popular-science authors are the model, digesting complex data into something normal people can read.
  • For many products, delight comes from nothing getting in your way, so brand should recede.
  • Figure out your company's ethos to decide brand's place in the equation.

“But for a lot of people, the brand should be somewhat invisible so that the thing itself becomes the star.”

Jessica Hische · 45:30
#branding#product#philosophy#contrarian
Hot Take1:18:00

There Are 10 Good Answers to Every Question

Jessica credits her effectiveness to being incredibly decisive: she believes there are roughly 10 good answers to any question, so she can look at 10 gray sofas, spot two or three categories, and pick quickly rather than agonizing. She extends this to a freeing philosophy, that nothing is ever 100% perfect, and chasing the last 0.2% can eat your whole life when you could move on.

  • Being decisive comes from believing there are ~10 good answers to every one question.
  • Maximalists need to see every option before choosing; she sorts into two or three categories and picks fast.
  • Typography could go 50 million directions; the value is someone naming the valid paths.
  • Nothing is ever 100% perfect; the last 0.2% can consume your whole life, so move on at 'nearly perfect.'

“there's 10 good answers to every one question.”

Jessica Hische · 1:18:00

“that last like 0.2% you could spend your whole life trying to do that or you could move on and do other things and understand…”

Jessica Hische · 1:19:00
#decision-making#creativity#philosophy#productivity

Explainer· 5

Explainer09:30

The Sign It's Time to Upgrade Your Logo

Jessica explains the practical trigger for a logo refresh: the moment you're about to physically invest in your brand at scale, like printing swag for new hires or hosting a conference. She also argues that a custom logo or typography protects you from copycats, since anything built on a popular or free font is trivially easy for competitors to imitate.

  • A good time to refresh is when you're about to roll the brand out more broadly (new site, expanded app).
  • Physically investing money in branded stuff (swag, a conference) is a natural refresh trigger.
  • Many companies start with a logo built on a popular, widely available, or free font.
  • If your success is easily copyable, competitors will repeat your branding to trick your customers; custom type is a defense.

“but with success comes people climbing up behind you trying to copy your success.”

Jessica Hische · 11:00
#branding#logos#typography#startups
Explainer25:00

How to See Like a Designer: Trust the Feeling

Jessica argues non-designers are better at reading typography than they think, because humans are endless absorbers of patterns. Spotting something that's 'a little bit off' is a safety instinct, the same way you sense a plate of food looks wrong before your brain names it. The exercise: look at fonts and simply write down what feeling each one gives you, without overanalyzing.

  • People constantly absorb visual patterns even when they don't consciously digest them.
  • Noticing something is 'off' is a safety mechanism; your body knows before your brain does.
  • You don't need typography vocabulary to sense whether a logo feels right.
  • The exercise: look at fonts and note the first feeling each gives you, without overanalyzing.

“This doesn't smell right to me and your body knows it before your brain knows it.”

Jessica Hische · 26:00
#design#typography#perception#exercise
Explainer28:00

Why Slightly Rounded Helvetica Feels 'Printed'

Jessica breaks down the specific levers that change how type makes you feel: width, weight, spacing, and how hard or soft the treatment is. Her example: take Helvetica and round the edges ever so slightly and it suddenly feels vintage and soft, because our bodies read that softness as ink bleeding into paper rather than a hard geometric piece of technology.

  • The main levers are width, weight, spacing, and the softness or hardness of detail.
  • A tiny bit of edge-softness makes type feel 'printed.'
  • Slightly rounded Helvetica reads as more vintage or soft.
  • The softness cue works because printed ink bleeds into paper, and our bodies remember that.

“we're perceiving it like we would perceive it if it were printed on paper versus perceiving it as this like hard geometric piece of technology…”

Jessica Hische · 29:00
#typography#design#perception
Explainer33:30

The Hidden Optical Tricks That Separate Pros From Beginners

Jessica reveals how expert type designers break the rules to correct for optical illusions. Even 'perfectly geometric' sans serifs aren't mathematically perfect; designers thin strokes where they join, and narrow the tops of letters like R, to remove ink that would otherwise look too heavy. Engineers new to type make everything mathematically regular, which is her tell that someone is a fresh hobbyist.

  • Geometric sans serifs look perfectly geometric but aren't mathematically perfect.
  • Where strokes join (bowls, shoulders of N and R), designers subtract weight so the joint doesn't read as a dark mark.
  • The effect is stronger in heavier weights where 'inky moments' pile up.
  • Engineers new to type make everything mathematically regular, which reveals they're fresh at it.

“So, it's weird because you end up like creating something that's perfect and then have to make it not perfect in order to make it…”

Jessica Hische · 35:30
#typography#type-design#craft
Explainer50:00

Why She Prices Brand Work Like Lettering (and Charges Less)

Jessica explains her atypical pricing. Branding agencies bake full buyout rights into every round, so each round gets more expensive because you own everything as you go. She instead treats it like a commercial lettering project: keep the creative process lighter and cheaper, and you only pay to own the final chosen asset, not every discarded exploration. Her projects typically run $25k-$35k, less as a consultant.

  • Agencies bake buyout rights into every round, so each round costs more as you own all the work.
  • Jessica bills the exploration lightly and only charges the buyout on the final chosen asset.
  • This keeps the creative process flexible, so a last-minute stakeholder blow-up doesn't waste money already paid.
  • Most of her projects land between $25,000 and $35,000; branding peers say she should charge $60k-$70k minimum.

“I feel like the majority of the projects that I do end up being between like 25 and 35, but you know, depending”

Jessica Hische · 53:00
#pricing#branding#freelance#business

Story· 2

Story16:30

The Logo That Accidentally Said 'Penis'

Jessica recounts a refresh for Jeni's Ice Cream, based in Columbus, Ohio. The brand had put the apostrophe over the 'i' as a design flourish, but combined with a looped J it made the word read as 'penis.' It became the single most specific fix of her career, and a lesson in how logos can create misreads that insiders are too close to notice.

  • Jeni's had a long J that created an awkward pocket of white space to design around.
  • Placing the apostrophe over the 'i' plus a looped J made the logo read as 'penis.'
  • The most specific fix she's ever done was making a logo stop saying penis.
  • Logos need to be readable at a super fast glance; misreads are a common hidden problem.

“that was like the most specific fix that I've ever had to do is like make the logo not say penis anymore.”

Jessica Hische · 17:00
#logos#typography#legibility#story
Story23:30

Turning 'Hot Ham Water' Into Soup

Jessica uses a cooking analogy from her early days learning to cook in San Francisco. A beginner throws ingredients in a pot and none of them work together, producing 'hot ham water.' With experience the elements blend into a cohesive dish. Most clients arrive with hot-ham-water brands, and her job is turning that into something that feels real and unified.

  • A beginner cook makes a pot of ingredients that don't work together; brands often look the same.
  • Cohesion comes from understanding how elements are meant to blend, like ingredients cooking at different temperatures.
  • Many clients arrive with disparate, un-unified brand elements.
  • The goal of a refresh is making everything feel like it came from the same universe, created by the same hand.

“I feel like a lot of clients come to me and they have hot ham water when it comes to their brand. And it's just…”

Jessica Hische · 24:00
#branding#design#cohesion#story

Q&A· 1

Q&A1:02:00

How a Lettering Artist Actually Uses AI

Asked how she uses AI, Jessica is candid about being wary of its near-term impact on illustration, but sees it as a useful tool. She experimented running her custom lettering through Stable Diffusion for a Salesforce Dreamforce project (ultimately unused). Where she finds real value is early brainstorming, like asking Claude to 'list 50 emotions' for a kids book and cherry-picking the ones that feel right. She refuses to outsource the slow, therapeutic production work she loves.

  • She's wary of AI's short-term impact on illustration but expects it to settle into a useful tool.
  • She tried Stable Diffusion to restyle her custom lettering for Salesforce's Dreamforce, but didn't ship it.
  • The slow 'sloggy' production work (moving bezier handles) is therapeutic Zen she won't hand to AI.
  • AI shines for early brainstorming, e.g. asking Claude to list 50 emotions and cherry-picking.

“I can just ask Claude like list 50 emotions and then I can cherry-pick the ones that come up that feel right.”

Jessica Hische · 1:05:00
#ai#creative-process#tools#workflow

Tool· 2

Tool30:30

The Screenshot-and-Categorize Font Exercise

A concrete exercise for training a designer's eye: go to your font folder or a site like MyFonts, search a broad category (serif, sans serif, script), page through, and screenshot the ones you like. Then categorize the screenshots by feeling (feminine, aggressive, calm) and interrogate why, e.g. a script feels 'wedding-y' so you avoid it for a cutting-edge food brand.

  • Search a top-level category (serif, sans serif, script) and page through many options.
  • Screenshot the ones you like and build a folder, then categorize by feeling.
  • Ask why each feels a certain way (a script feels feminine because it reminds you of wedding invitations).
  • Stereotypes and trends are real; an industry can usurp a whole style, so aligning to it signals that industry.

“Screenshot stuff that you like, and make a folder full of screenshots, and then you can kind of take those screenshots and start categorizing them.”

Jessica Hische · 31:00
#typography#exercise#tool#design
Tool56:00

Blur Your Eyes to Judge a Brand

Jessica's trick for evaluating a logo or brand: take your glasses off (or blur your eyes) so you can't see the detail and just read the overall feeling and cohesiveness. Bad vision, she jokes, is an asset here. She contrasts thinking 'big picture' before minutia, because people often throw detail nitpicks at her before they've identified the overall thing bothering them.

  • Blur your eyes or take off your glasses to see a brand's overall look without detail distraction.
  • Terrible vision can be your best asset for judging logos and brands.
  • Always start super top-level and ask broad questions about why something isn't working.
  • People jump to minutia (the R, the C) before naming the big-picture problem, and never get there.

“I always uh tell people that like having terrible vision can be like your your best asset when it comes to like logo and brand”

Jessica Hische · 56:00
#design#exercise#critique#tool

Takeaway· 1

Takeaway1:13:30

'Hope Is a Discipline'

Jessica shares a quote by Mariame Kaba that resonated enough to consider tattooing: 'hope is a discipline.' The idea is that positivity is a choice you build structure and practice around, not something that just arrives. She connects it to her sense of agency, that you can choose how to frame things, and that recognizing you have that power is important.

  • The quote 'hope is a discipline' is by Mariame Kaba.
  • Positivity is a choice you build structure and discipline around, not something inherent.
  • You have power in how you frame things, one way or another.
  • Feeling agency over your outlook is what keeps you from feeling like a victim.

“in order to dream of these things, like you can actually create structure and discipline around it and that it's not just something that is…”

Jessica Hische · 1:14:30
#mindset#creativity#life-advice