Fail Fast, Succeed Faster

Retrospective: Why Design Year Failed and a Plan for Success

Adrian Cunanan
Published in
3 min readJul 1, 2017

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Note: We’ve moved… DesignYear has pivoted to be Optimal Designer (optimaldesigner.com), please update your feeds & links!

  1. What went well?

- Strong idea to help people to “Learn Design” without going to an expensive design school.
- “The Curriculum” still gets moderate traffic as a good template for a plan to “Learn Design”.
- Deciding to publish on Medium allowed the site to have a clean design and an instant distribution network.
- Production value of Design Assets from Logo to Video Intros and Time Lapses were at an optimal level of quality considering my skillset.
- Weekly Notes were a great way to share the accomplishments and progress over the program.

2. What didn’t go as well as expected?
- Sustainability was a huge issue. 1 hour per day seemed do-able but then became a challenge within 14 days.I created one goal of documenting 1 hour of daily practice and that goal was too much.
- Daily Content creation and distribution become a time hog that would extend well beyond the 1 hour per day. It took a long time to create the videos and then publish them with schedule social media posts.
- The content became monotonous because I only did “Drawing 101”. Time lapse videos were being produced and I was running out of Beatles covers to play in the background.
- Ultimately, there was not enough preparation to make for a successful product. Plus, no viable plan or options for monetization.

3. What would I do differently if I could have a “do-over”?
- Create a plan for attack by using a “Design Thinking” approach to create a product/service offering.
- Set clear minimum and maximum goals (“Living within floors and ceilings”) to make improve likelihood of success.
- Take notes and document in the moment then aggregate and edit for weekly updates.
- Dedicate a day per Design Category or even per phase of “Design Thinking” process.
- 2 week Sprint Scheduling with Setup and Retrospective sessions.

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