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The 30 Things We Learned at the 2016 99U Conference

The 30 Things We Learned at the 2016 99U Conference
Published May 9, 2016 by Matt McCue

We came. We learned. We made some sweet GIFs. The 8th annual 99U conference was another runaway success, packed with great career insights, deep dives into creative processes, and even a life-sized Operation Game Table and emoji rice krispies (Hey, we can bring the fun, too.)

Now that it’s over, we’ve rounded up the best and the brightest ideas from our speakers, which you can apply to your career today or tuck away for the next time you need a shot of creative energy. Read on for the best gems from the 2016 99U Conference.

Photo by Ryan Carson. Photo by

1. You can spend less time working, you just have to do it purposefully. Treehouse CEO Ryan Carson, keeps his workweek to a tidy 32 hours. How? By hyper-focusing. “I spend 20 minutes first thing each Monday making a list of what I want to achieve each week,” he said. “Then I take out the things that aren’t happening.” Carson’s approach allows him to devote his time to what he really needs to accomplish over the next four days. “My initial reaction was that there was too much work to do,” he said of shrinking his workweek. “But there is no rule that you have to work 40 hours a week to be successful.”

2. Deliberately break things when teaching yourself something new. “That is where the real lessons come from,” said Frere-Jones Type founder (and Alva award winner) Tobias Frere-Jones.

99U_C3-20160506-2853 Yuko Shimizu. Photo:

3. “Once you become a pro, stop getting influences from those who are in your own field,” said illustrator Yuko Shimizu. Otherwise you rip off your peers, but mainly you become a commodity. 

4. Designers should expand their digital toolkit. “We are blurring the lines between design and engineering,” said Buzzfeed VP of design Cap Watkins. “I believe designers should write code.”

5. “Leadership is not a role or title at any company,” continued Watkins. “You can be a leader anywhere in the organization.”

Effie Brown. Photo: Effie Brown. Photo:

6. Life is not fair. “I’d rather not cry about it,” said film producer Effie Brown. “I’d rather be about it.”

7. Brown on what it takes to be a strong leader: "Sometimes I've had to opt out of being nice in order to be effective."

8. Consider replacing the internship with the apprenticeship: In the creative world, we have learning (school) and doing (work) but we don’t have much for that in-between phase – the time where educated people need to learn a new skill by doing (because every job description always wants a flawless candidate.) Enter SuperFriendly founder Dan Mall who has introduced a nine-month apprenticeship at his web development agency to teach and nurture young designers. In return, Mall gains a greater sense of loyalty from the apprentice and spends less on talent. And the apprentice gets to actually walk away from the program with a new skill.

9. Social media puts an impossibly glossy shine on design, careers, and life in general. But let’s be real about that perfectly-put together construction of ourselves we’ve curated online, says New York Times graphics editor Jennifer Daniel. "Are people afraid that we can’t do it all?” she says. “Well, we can’t do it all."

10. Don’t overthink your world-changing idea. Walker & Co. CEO Tristan Walker contemplated starting a bank and fixing freight trucking in the United States – two very big, very complicated ventures he knew little about – before he created Bevel, that directly related to a familiar problem.

11. “Invite yourself to the table,” said Society of Grownups design director Kristy Tillman, whose biggest career successes have come from taking the initiative on projects she wanted to pursue, even if there wasn’t an obvious opening for her. “You get to land in a place you never would have imagined otherwise,” she said.  

12. Fried bacon, egg, and cheese breakfast sandwiches are the surest way to get people to an early morning studio session meeting on time. Thank you Shake Shack! At its studio session focusing on how to design within constraints, Shake Shack senior designer Cathie Urushibata challenged attendees to create a graphic of New York – without using right angles – and ultimately honed in on a key tenet of memorable design. “Less is more!” said Urushibata.

13. Make “creative destruction” a regular part of your routine. It sounds heavy, but it’s simply a way to look at how you’ve been producing something and find ways to make the process more efficient and effective. “The more you protect how you do things, the more rigid you become and harder it is to become creative,” says Basecamp founder Jason Fried.   

14. For max efficiency, work in weekly cycles, said Fried, who added that most work – even big projects – should be able to be done in six weeks.

15. Multi-tasking can seriously strain your creative muscles. "We don't have enough creativity because we don't focus on one thing at a time," said The Confidence Game author Maria Konnikova.

16. Reach for a great outcome of a project, but judge it based on your effort (and not solely on client feedback.) "You can control the effort you put in and what you create, but [you] cannot control the reaction to that work,” said Ryan Holiday, author of The Obstacle is the Way.

William William Deresiewicz. Photo:

17. We’re entering a new age of creativity where we have more chances to get attention, but also less money flowing into the arts. “The arts that are in the best position to avoid disruption are those that enhance the experience or environment,” said Excellent Sheep author William Deresiewicz. 

18. Start each day by asking yourself how much risk you want to take, said Michael Bungay Stanier, author of Do More Great Work. Let your answer guide your workday.

19. "Your employees want more feedback…but not more performance reviews,” said Know Your Company CEO Claire Lew.

Photo: Ayse Birsel. Photo:

20. “What’s nice about the design process is that it’s pen and paper. If you wake up tomorrow and don’t like what you did, draw something else,” said Ayse Birsel, co-founder Birsel + Seck LLC. And the same way you design, well, anything you can also design your career and life.

21. “The best consultants get paid up front in advance,” said Double Your Freelancing founder Brennan Dunn. “They don’t invoice on 30-day net terms.”

22. Sometimes we can’t see our most obvious strengths and weaknesses. Suss them out by practicing “active listening,” said Chris Guillebeau, author of Born for This. To do this, interview your colleagues about yourself. “The more you listen to their answers,” said Guillebeau, “the more you will find out about yourself.”

23. Doing “the boring stuff is what weeds out the wantrepreneurs,” said Jeff Sheldon, founder and designer of Ugmonk.

Bob MANKOFF Bob Mankoff. Photo:

24. There is a strong correlation between creativity in humor and creativity in other fields. “Humor is a distortion of our reality in some way,” said The New Yorker’s cartoon editor Bob Mankoff. “Take something normal and turn it on its head."

25. Don’t look to the trends for inspiration: “Sometimes it’s better to look at what is out there and go the opposite way,” says Shinola design director Richard Lambertson.

26. Words matter. Even in the world of design where images tell the story, it’s critical to be able to clearly describe your ideas. "The more specific you can be with your idea's character, the more unique it will be," said Verdes partner Greg Matson, whose company created a new kind of dictionary for creative minds, Brownie’s Guide to Expertly Defined Ideas.

27. User research can be done on a limited budget because it doesn’t require an army of product testers. "You'll uncover 85 percent of common usability issues with five people,” said Spotify user researcher George Murphy.  

28. Daily to-do lists are a waste of time. Because eight unstructured hours give you too much time to, well, waste time. Instead, take an idea from our friends at SYPartners: Set time limits for finishing your work in smaller increments, like 30 and 60 minute intervals. Then write down what you actually attempted and accomplished, during those intervals, so that at the end of the day you have hard data to hold you accountable with your productivity.     

29. View failure as an important part of guiding where you should be investing your time, energy, and money. As Fred Seibert, the founder of Frederator Networks, put it, "We're in the business of failure. We have to look at a bunch of things, produce them, and see what succeeds." One you spot and discard the failures, you can allocate your resources towards the winners.

Photo: DJ Windows 98. Photo:

30. DJ Windows 98 aka Arcade Fire’s Win Butler + the Museum of Modern Art space after hours = an amazing closing night party.

See you again in 2017. To get a heads up the moment tickets go on sale, sign up for our email newsletter.

More about Matt McCue

Matt McCue is the former editor of 99U. He lives in New York City, but he is willing to travel long distances for a good meal. Find him on Twitter at @mattmccuewriter.

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