The Design Business Show 211: Making Mistakes on Purpose with Laurie Rosenwald

Director : Melissa Burkheimer | January 23, 2023
Check out episode 211 of The Design Business Show with Laurie Rosenwald to learn about creating chaos and personality in a perfect digital world.

  an author, designer, painter, and educator whose impressive body of work encapsulates her vivacious, outspoken, and colorful personality. Her most recent book, How to Make Mistakes on Purpose, which was the subject of her TEDx Talk and is accompanied by a touring workshop of the same name, gives readers and audiences insight into the beautiful world of creating through intentional acts of randomness – a way of working that helps individuals get unstuck and discover new skill sets. The workshop has been conducted for major businesses and brands like Google, Starbucks, Scholastic, Buzzfeed, and Johnson & Johnson, to name a few. 

Check out a few of Laurie’s design projects below:

Here’s what we covered on the episode:

How Laurie Got Her Creative Start

  • Laurie describes her childhood and shares that she has been drawing since 3 years old and has never stopped  
  • The mindset Laurie has always had of what mattered was art and creativity – she has never focused on business or making money which has allowed her to be freer than others
  • The first paid project Laurie had was an illustration for a small editorial in the back of the New York Times
  • Most people choose to do one thing and stick with it, but Laurie shares that she’s always done graphic design, illustration, painting, and writing because she gets bored easily when she sticks to just one thing   
  • Laurie always did freelance illustration but also worked with many different magazines and newspapers doing layout design, graphic design, and editorial design
  • The story of how Laurie got the job at the New York Times Magazine by lying about her skills, but because they liked her, they taught her how to do her job
  • After working for the New York Times Magazine, Laurie worked for Condé Nast, where she worked on the first issues of Self Magazine and Vanity Fair Magazine, plus so many other projects
  • One of Laurie’s favorite projects was working on a Bloomingdale’s shopping bag in 1981, which they, unfortunately took her name off of because she wasn’t famous
  • Laurie has lived off and on in Sweden for many years and shares that she worked on products for the Swedish post office
  • In the late 80s, Laurie worked on an album cover for Joe Jackson
  • More recently, the most exciting things for Laurie to do are her own books because she gets to express herself and have the freedom to do whatever she wants
  • The story of how Laurie created her own typeface called, Loupot, which is based on a logo she has always loved 
  • Laurie started dabbling in animation while working with Nickelodeon and ended up doing an animated app with David Sedaris called David’s Diary
  • When it comes to awards, Laurie believes they don’t really matter because there are so many awards, and no one ever asks to see them – she believes it shouldn’t be what you focus on

Making Mistakes on Purpose

  • How, in the digital world, we’ve lost a bit of personalization, which Laurie believes is super important
  • Laurie explains that her workshop, How to Make Mistakes on Purpose, is more about helping people do things they normally wouldn’t and discover new things by sabotage because if you do the same thing over and over again because you’ve mastered a skill, you never discover anything new
  • The point of Laurie’s workshop is also to take the focus off doing one good thing and instead focus on creating as much as possible
  • Laurie wants to combine what digital programs are good at and what human beings are good at and combine them
  • Laurie shares a personal story about her life and how looking back, sometimes you think things are mistakes, but they aren’t
  • Because Laurie has done so many different things, her clients and projects are very diverse
  • The most important thing to Laurie is to keep creating, and if people find her, that’s great, but she’s not making it a priority for her work to be known
  • All of Laurie’s books are a combination of humor and design because she wants to entertain people
  • How Laurie feels that her books, How to Make Mistakes on Purpose and All the Wrong People Have Self-esteem are misunderstood as self-help books
  • Laurie is excited about a memoir she’s working on called, Memwah and is currently looking for the right agent, editor, and publisher and explains why she doesn’t want to self-publish
  • One thing Laurie wants to continue to do is bigger and better workshops – she shares that she’s done them for brands like Google and Starbucks
  • A goal of Laurie’s is to find great companies and venues to experience How to Make Mistakes on Purpose
  • The more digital the world gets, the more perfect the world gets, but Laurie says there’s a problem with that, and we need to bring back the random and chaos to get somewhere new
  • Reach out and connect with Laurie on Instagram, Twitter and check out her website to learn more about her


Links mentioned:

How to Make Mistakes on Purpose Book

How to Make Mistakes on Purpose Workshop

Laurie’s 2019 Invisible Talk: How to Make Mistakes on Purpose

Connect with Laurie on Instagram 

Connect with Laurie on Twitter 

Visit Laurie’s Website


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