Andrew Ordway – Skipping Design School, Investing in Yourself, and Learning To Say No – Ep33

Andrew Ordway – Skipping Design School, Investing in Yourself, and Learning To Say No – Ep33

Released Wednesday, 30th July 2025
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Andrew Ordway – Skipping Design School, Investing in Yourself, and Learning To Say No – Ep33

Andrew Ordway – Skipping Design School, Investing in Yourself, and Learning To Say No – Ep33

Andrew Ordway – Skipping Design School, Investing in Yourself, and Learning To Say No – Ep33

Andrew Ordway – Skipping Design School, Investing in Yourself, and Learning To Say No – Ep33

Wednesday, 30th July 2025
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Andrew is an Independent Designer in Colorado Springs who runs a studio called Impossibly Awesome Design Co. He specializes in logo and brand identity design, packaging, and illustration. Many of you know him from attending Crop Conference, and if you've been to The Springs within the past few years and had a beer at Bristol Brewing, you probably came across his work.

I met Drew on October 15, 2022. Trust me, I found the calendar invite for our very first coffee hangout shortly after I moved to Colorado, and he's a big reason I was able to get involved in the local design community so quickly. Drew was also on my original shortlist of potential guests for this podcast, so interviewing him has been a long time coming. If you hang out with him long enough, you'll start to learn things about competitive volleyball, bourbon, the Rubik's Cube, and The War of Art by Steven Pressfield. One of the most fascinating things about Drew's creative journey is that he's completely self-taught. He didn't attend school for design, but he does hold degrees in marketing and finance. Finance? Yeah, finance.

Tune in for a talk about the pros and cons of being a self-taught graphic designer, curating his (own) design curriculum, cherry-picking the best ideas from the people he admires, and tips for getting started on a project when starting doesn't feel impossibly awesome. Follow Drew on Instagram @impossiblyawesomedesign, and check out his portfolio website: impossiblyawesome.design.

Questions for this interview.

  • Why was the Bristol Brewing project the one that helped you feel like a true professional?
  • You asked Nick Longo for help on that project. What kind of help were you looking for, and what advice did Nick give you?
  • What kind of impact has Colin Christie made on your design career?
  • What gaps or challenges have you encountered as a self-taught designer that you think could have been addressed in design school?
  • How has being self-taught helped you as a designer? In other words, what are the advantages of being self-taught?
  • Were there times when you seriously considered enrolling in a formal design program? What ultimately kept you on the self-taught track?
  • How do you like to invest in yourself, and what are some examples of things you've spent money on to help you level up?
  • Have you ever purchased a design course or a resource and felt like you didn't get your money's worth?
  • Did you do anything differently this year in preparation for the Crop Conference or during the event compared to previous years?
  • Do you remember which presentation at Crop was your favorite?
  • Do you find it challenging to stay creative and consistently generate great ideas?
  • Do you think working in-house or at an agency full-time would make it easier to stay creatively locked in, or do you think it would be even more challenging?
  • When did it finally sink in for you that you can say no to the projects you're not super excited about?
  • Do you have any tips for getting started on a project when you're feeling overwhelmed?
  • Why is The War of Art by Steven Pressfield worth reading, and how can it help us break through creative barriers?
  • Since getting married recently, is there a possibility that combining your incomes could expedite your decision to leave your day job and focus on Impossibly Awesome Design Co. full-time?

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The music you hear on the podcast is Accident by Timothy Infinite and PUSH !T by Nbhd Nick.

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