The Design Gym’s Highlights from the 99U Conference

The 99U conference is an event aimed at empowering the creative community. It’s not designed to teach you to “think” big; but rather to show you how to “do” big. And as with many conferences we attend, we found it to be a tremendous source of inspiration. After all, get that many creatives in a room and good things are bound to happen!

For those of you who weren’t able to make it out this year (or for those of you who were and are just curious about what we thought), we wanted to share a list of some of our personal highlights, takeaways and inspirations from this year’s 99U conference.

1. Giving Yourself Time to Enjoy Your Creative Career

Conferences like this are always a great time to lift your head above water and remember those eternal truths that we’re always quick to agree to on paper, but are fast to slip away when the days get busy. Enjoying the process and embracing our creative permissions is one of those things. As part of a growing business and small team, we feel these strains all the time, and we see them in our huge global clients as well—it affects us all.

At MoMA’s Thursday morning workshop, Creating Compelling & Memorable Physical Spaces, Ingrid Chou, Associate Creative Director at MoMA, said something that really resonated with us. In the context of planning and curating new exhibits, she explained how essential it was to afford yourself creative time and to cherish that time.

“I think the majority of you are in creative fields and if you’re not having fun then something is wrong. That little bit of energy is what we live for.” @MuseumModernArt

We also loved hearing famed graphic designer, Yuko Shimizu‘s rule for prioritizing which projects to take:

“Learn to say no. Don’t take a job if it will cost you a good night’s sleep.” @yukoart

Click to Tweet.

2. Ryan Carson’s life mapping + weekly calendar ritual

Ryan Carson, CEO & Co-Founder of Treehouse, really inspired us with the time he dedicates and the process he’s built for continual reflection and self-awareness. If you haven’t seen this video on The Atlantic about Treehouse’s 4-day work week, it’s spectacular. Ryan shared some context about how he was inspired by Wait But Why’s Life Calendar (a visual representation of the weeks in our life) to begin reprioritizing his own weekly life.

Ryan shared with us that at the beginning of every week he blocks off 20 min to go through his personal mission statement. He breaks his mission down by the roles he plays (CEO, Father, Husband, etc…) and how he would want to be described in each of those roles. If he feels he’s slacking on any of them he immediately makes sure to fill in the upcoming week with more activities suited to that role—a great way to get the week started on the right note. Each week counts!

3. Jerry Seinfeld: How to Write a Joke

Throughout the conference, 99U did a really great job of integrating humor and mixed media to keep energy high and appeal to different learning styles—something as experience designers we can totally appreciate.

A great example of that in action was when they played the New York Times video, How to Write a Joke, as explained by the hilarious Jerry Seinfeld.

4. The Sliding Scale of Giving a Fuck

Cap Watkins, VP of Design at Buzzfeed, introduced us to The Sliding Scale of Giving a Fuck—a team tool we plan to immediately start leveraging. The Sliding Scale of Giving a Fuck, essentially, is a tool that allows you to pause on a conversation or debate and quickly assess the level of importance of that given topic to each individual team member.

For example, let’s say we’re in a passionate debate on what should be our next blog post—we use The Sliding Scale of Giving a Fuck and you tell me you give 7 out of 10 fucks, while I only give 2 out of 10 fucks. It’s probably not worth the energy and tension the argument is creating—clearly, the next blog post is more important to you and I should let you roll with what you’re thinking.

It’s a pretty cool team tool when you’re getting into debate—just throw the flag and put it out there, how many fucks do you give?

5. Cap Watkins on Culture

Cap also spoke about the importance of culture and his personal deviation from the popular notion of creating “design-led” or “design-driven” organizations. In his mind, that’s no more accurate than having an ‘accounting-led’ or a ‘sales-led’ organization. Focusing on any one department to make all the decisions is too narrow, and misses the target. We agreed—Cap is thinking long term.

If you find yourself defaulting to that way of thinking, you need to work on bringing others into your process. It’s not about one team leading, it’s about having systems to solve together. This quote hit it home:

“Leadership is not a role or a title, anyone can bring that mindset. We talk a lot about building empathy with our customer but we need to start building empathy with our own organizations. That means treating our organization and cultures like real products or UX problems.” @Cap

6. SYP Cards

We’ve done a bunch of personality assessments and use them pretty actively to kick off projects, reflect on our personal growth, and check in on team dynamics. We had the chance to try out the SYPartners Superpower Cards and found them to be particularly helpful given the fun format and the quick conversations they spurred.

We immediately ordered a deck for ourselves to better understand how we can leverage our team’s super powers. Gotta love SYPartners.

7. Jason Fried, Founder & CEO of Basecamp

Jason Fried captured our hearts back in 2010 with the book ReWork—a book all about rethinking how we approach the work we do. He’s a thought leader we really respect, but also someone that inherently has customer empathy baked into how he approaches work. We were amazed with Jason’s talk and really inspired by one of his “ah ha” moments. Jason shared with the group a story about how an experience in his personal life allowed him to completely rethink the client experience.

It started with a bathroom renovation (inspiration comes from anywhere). Jason was bidding contractors, and realized he was drawn towards one in particular, even though all had been highly recommended. Upon reflection, he realized that it was a simple interaction that won him over—the contractor had taken him to the home improvement store and picked out tiles and fixtures in person. It was an expensive project, and this removed the majority of the risk and ambiguity for him.

Insert ‘ah-ha moment’ emoji here. As a small agency he had always prioritized longer, bigger projects with his clients. But in reality, his clients hated the risk and ambiguity attached with that commitment. He immediately restructured how he sold work and started doing cheap, 1-week projects in high-volume. His clients loved it, he loved it, and they saw a huge spike in revenue.

To quote Jason, when something like that happens:

“Don’t be afraid to blow it up and start over… Fall madly out of love with something you are so use to doing.” @jasonfried

Click to Tweet.


Were you at the conference this year? We’d love to hear what you thought and what were some of your highlights. Hit us up by email or tweet at us.

Andy Hagerman
[email protected]
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