Habits For Ultra-Productivity w/ Jessica Hische

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Jessica Hische is a lettering artist, entrepreneur, designer, speaker and author who’s worked with clients like Penguin Books and Wes Anderson and recently published a book called “In Progress” which is an incredibly detailed look at her process from sketch to final deliverables – definitely a must-read for any of you lettering fanatics out there. She’s also got this amazing library of side projects like Daily Drop Cap (exactly what it sounds like), a site called Don’t Fear The Internet which teaches HTML and CSS to designers, ShouldIWorkForFree.com – a flow chart which answers that exact question – and literally 10 more. Insanely prolific.

In addition to being an incredibly talented artist Jessica is SMART, holy crap! She semi-jokingly refers to herself as putting the brain of an engineer in a creative role, but that’s really the perfect way to put it – she has a very pragmatic, analytical and no-bullshit way of looking at creativity that’s super refreshing and compelling – if you’re looking for someone to put things gently with a bunch of flowery evocative language then she’s not the one you’re looking for, but – on the other hand – if you want to hear some real talk — practical, specific advice on creating and growing a career in design or any other creative field then you’re in the right place.

Today on the podcast,

  • We get into some rarely-discussed characteristics and strengths of creatives, for example that we have an abnormally high degree of introspection baked into us because our field demands constant reflection, self-assessment and often re-invention
  • Why constraints are a creative’s best friend. You’ve heard me talk about this – while we may chafe and resist them, the truth is that constraints are an important and incredibly helpful aid to creativity
  • She talks about some of the habits that make her as ultra-productive as she is – my favorite is her concept of “admin Mondays” where she packs all that stuff into one day of the week so it never disrupts her creative work


Design isn’t just a costume that you put on a product at the end

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Some Questions I Ask:

  • Can you give us a bit of the backstory to your work and how you got here? [1:40]
  • Why do you think you shouldn’t have studied graphic design? [3:05]
  • What’s your relationship with your clients? [4:04]
  • What is something about you that if they found out they’d be surprised to hear? [11:32]
  • What was the change in your work schedule? [12:34]
  • Talk about figuring yourself out as a creative. [13:40]
  • Tell us about your personal projects. [18:48]
  • Tell me your view on going to work. [23:00]
  • Talk to me about design thinking culturally. [27:50]
  • What are some of your best habits? [34:40]
  • Do you have any routines that make you feel like a better human? [37:12]
  • Do you have a personal routine that makes you feel like a better human? [39:53]
  • Do you have any art to recommend? Something that you liked recently. [42:26]
  • What kind of advice would you give to the people following your trail? [45:05]
  • Do you have specific career advice for people who want to pursue a career like you have? [47:23]
  • What’s the biggest failure that you don’t admit to yourself regularly? [50:44]
  • What’s the biggest thing that people would be surprised to find out about you? [51:58]
  • Who do you admire? [53:19]
  • Is there a New Year’s resolution that you’ve made that you’d like to share with us? [54:38]

In This Episode, You Will Learn:

  • How Jessica took the wandering path from being a graphic designer finding her calling, being a lettering artist. [1:55]
  • Why you need to be looking for constraints. [4:10]
  • The practicality of taking your work on step by step. [6:30]
  • Why Jessica prioritizes massive impact on a small scale versus tiny impact on a large scale and how she surrounds herself with the right team to achieve that [8:50]
  • How Jessica uses easy tasks to build momentum for the bigger tasks of the day. [10:46]
  • Want to get a lot of work done? Surround yourself by people who are busting their butts. [13:00]
  • How Jessica always used the act of working to help solve or sidestep her problems. [14:40]
  • Jessica’s motherly advice about taking care of yourself to take care of other people. [15:46]
  • How prioritizing sleep was a game changer for both me and Jessica and how she uses it to extend her maximum productivity hours. [17:00]
  • How Jessica uses personal project time doing things outside her wheelhouse. [19:20]
  • How to get people to pay you to do what you want to do. [21:08]
  • The pros and cons of being a self employed artist vs climbing the corporate ladder (even in the art world). [23:30]
  • My strengths and weaknesses of being in my current role. I like getting my hands dirty as much as I like thinking big, but keep me away from the middle – I’m no manager [27:00]
  • Design is more than just putting serifs on a logo. [28:25]
  • How I learned about design thinking through a finance app pitch. [30:30]
  • Why daily use services should be vanilla. [32:00]
  • How great design is like great service at a restaurant. [32:20]
  • Why Jessica strips down and dissects problems when they happen rather than accepting them. [35:20]
  • How Jessica uses “admin Mondays” to batch her admin work and frees her mind for the rest of the week. [37:50]
  • How Jessica uses step by step guided exercise and commuting to hack her meditation practice. [40:35]
  • Jessica’s book recommendations: The Secret History and The Goldfinch by Donna Tartt and All The Light We Cannot See by Anthony Doerr. [42:35]
  • Are you consuming social media more than you’re contributing to it? Might want to flip the ratio there. [45:18]
  • Marie Forleo’s advice about comparing; create before you consume and don’t consume the compare-shlager. [46:53]
  • Why they make you take electives in college; you’ve got to try things out to figure out if you’re going to like the process of your chosen career [47:34]
  • One of the biggest positives about being a career creative is taking time to thinking about whether you’re doing things that you want to be doing [49:00]
  • Why Jessica admires how much of a great human+creative Michael Bierut is. [53:35]


This podcast is brought to you by CreativeLive. CreativeLive is the world’s largest hub for online creative education in photo/video, art/design, music/audio, craft/maker, money/life and the ability to make a living in any of those disciplines. They are high quality, highly curated classes taught by the world’s top experts — Pulitzer, Oscar, Grammy Award winners, New York Times best selling authors and the best entrepreneurs of our times.

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Post author

Dustin Gurley is an Designer, Developer, Artist, Instructor, Critical Theorist and Systems Engineer. He has an extensive background working professionally with 2D/2.5D/3D Motion Graphics, Compositing, Film, Video, Photography and client-side performance techniques as it pertains to web development. Dustin recently completed work on his Master of Fine Art degree in Motion Media Design (Motion Graphics) from the Savannah College of Art and Design. Prior to beginning his graduate work, Dustin obtained a Bachelor of Art degree in Communication Studies with a concentration in Broadcast and Emerging Media from the University of North Carolina at Wilmington. In addition to design and modeling, Dustin enjoys toying with his view camera, working with scratch film, authoring media related material and contributing to various industry conferences. When not in front of a computer, Dustin can be found with his wife, Regina Everett Gurley. The couple enjoys dividing their time between their home just outside of Raleigh, North Carolina and the beautiful North Carolina coast. Currently, Dustin serves as the Lead Instructor of Internet Technologies for Wake Technical Community College in Raleigh, North Carolina.