Boredom Generates Inspiration

Kyle T Webster, photoshop brush master and children book author talked about his love of boredom at Adobe’s 99U 2019 conference in NYC.

Some of Kyle’s biggest career achievements can be traced back to being bored. Usually bored people means non-productive people. So I was skeptical when I first heard his boredom theory, but he went on to describe three of his crowning achievements all due to boredom. 

His talked touched on a topic I’ve been thinking about for a while, but couldn’t quite put my finger on it. The best I could come up with was discontent. Kyle‘s premise is that our entire lives have been optimized and our tools have been designed to squeeze the maximum amount of productivity out of the day, or at least something that feels like productivity. 

Our news is written in bite-size chunks of 280 characters or top 10 lists that distills down entire topics and bodies of knowledge into 1,000 characters. When we have 15 seconds of downtime our phones come out and our heads go down—at stop lights, our heads our down. When waiting for our food to be delivered, our heads our down, illuminated by the glow of screens.

This isn’t necessarily bad. I love my iPhone, and I’m not giving it up anytime soon. However, Kyle is making the case for being cognizant of device use in contrast to boredom. Boredom is allowing your mind to wander. To connect dots in unusual ways. As Kyle put it, ‘Boredom is a blank canvas for the mind.’  Let the creativity bubble up through boredom.

Throughout your day, when you find yourself on your phone, either scrolling through Instagram or reading the latest news, ask yourself ‘Is this necessary?’. Sometimes the answer is no, and sometimes you might be better off putting that phone away and relish in your own boredom.

Okay, so?  

Kyle’s message resonated with me instantly. I’ve been thinking about stepping away from technology and finding an industry a bit more tangible. I’m starting to find technology tedious. Companies investing huge amounts of cash into minor things like new ways to re-share a photo of a grumpy cat, or inventing new technology with little to no impact or market, other than it’s ‘cool’. 

But what I started to realize is that I’m essentially burned out. And Kyle paints a great picture of a small way to recharge and refill your creative tank—boredom. Boredom to let my mind wonder and get excited about different and unique ideas. Boredom to let new interests and ideas percolate in my brain, spur creativity, and help me recharge.

Adobe 99U 2019 Recap

Adobe was nice enough to invite me to the 2019 Adobe 99U conference, where the theme was ‘Future is Creative’. During the two day conference, presenters did a good job of exploring creativity without being too tactical or prescriptive. I captured notes on some of the conversations that resonated with me the most.

Dr. Vivienne Ming

AI + Creativity

Dr. Ming and her incubator, Socos Lab, have been exploring how augmented intelligence influences creativity and the future of creative workers. Dr Ming has a unique, and empowering take on AI in the creative industry. Based on her work and the trends she’s seeing, she’s confident that AI will replace some jobs, but it will create many more creative jobs.

AI can turn vision into reality. But only creatives can create the vision.
— Dr. Vivienne Ming

She sees AI taking some of the tactical and execution work in the creative industry. For example, she foresees a future where one might be able to describe a scene and the computer can generate the related animation, reducing the demand for many 2D and 3D animators.

Creativity is useless unless you have the courage to do something with it.
— Dr. Vivienne Ming

The industry has some time for these Artifical Intelligene and Machine Learning engines to get to a point where they can seamlessly integrate into a creative workflow. But while that’s happening, it’s important that creatives learn business and strategy, because pushing pixels to turn strategy into reality might no longer be a designer’s competitive advantage. 

Zach Lieberman

Lyrical possibilities of code

Zach founded a school to enable students to use code as their medium for poetry and art. He shared some phenomenal work he and his students worked on, but what really stood out to me was the ‘10 Rules’ for his class. 

My big take away here is that people should always be learning—treat any environment you’re in as a classroom. Look for opportunities in which you can learn and grow, and help others do the same. 

Boredom is a blank canvas for the mind
— Kyle T. Webster

Kyle is the Photoshop brush guy. If you learned design in the 90’s and early 2000’s, then you know exactly what I’m talking about.

Kyle’s topic wasn’t about brushes, though. He focused on the dividends that boredom can pay in creativity and career growth. 

Ultimately, you have to give yourself permission to get bored. Our lives of hustling and productivity hacks ensure our minds are turned on from morning to night. We’re geared to squeeze meaning out of every moment of the day. But this means you’re always on task, and new little creative bursts of ideas aren’t finding themselves into your brain. Allowing yourself to get bored means these little bits of creativity can bubble up into your brain. Try it.


Tim Brown was interviewed on stage about a number of topics on design. A few themes emerged that really stood out to me. 

Evolution Design Skill—
Tim essentially said that design is transforming as it finds it’s place in a digital world. Design craft used to focus on quality of finishing, because it had to go to print or manufacturing. But in the software world, design is never finished. Evolution and iteration of the solution based on findings or user changes is now key. Understanding this is a new skill in demand.

Make things as real as possible as soon as possible.
— Tim Brown

Design is Politics—
Another topic Tim touched on is design in organizations. More ideas fail in organizations than from market rejection. Design is politics. It’s about the relationships you form with people and organizations. 

This is key for ideas to survive a little longer, because ideas must flourish to find their real use case or purpose before they’re killed. 

Ethics in Design—
Design ethics is a growing concern in the industry. With artifical intelligence, dark UX patterns, etc., it’s no wonder. Recently there has been a call for a design Hippocratic Oath. Tim says that is the last thing we need. If designers adopted a ‘do no harm’ model, we’d never take risks or disrupt industries in desperate need of disruption. 

Designers need to be extreme learners.
— Tim Brown

Instead, Tim says we need a system or agreement to to make sure we don’t do intentional harm. This model ensures we’re incorporating humanity into design, without protecting the incumbents of bad design.

Kat Holmes

Inclusive Design


Kat has led a career focused on inclusion. One of her biggest takeaways has been that using an inclusive team leads to more inclusive solutions. It sounds obvious when said out loud, but many organizations and hiring managers haven’t caught on. A team built on exclusion won’t have the foresight to built truly inclusive solutions. So, save yourself headache and wasted iterations and start from inclusion.

Joel Beckerman

Sound First Design

Joel is a creative sound designer, leveraging his skills to build more meaningful solutions

When the sound doesn’t match the visuals, your brain believes your ears first.
— Joel Beckerman

Ears are more powerful than your eyes. I wasn’t so sure, but Joel put it into perspective. Watch a horror movie that truly scares you... now mute it and play circus or polka music on top of the video. Still scared? Probably not.

Joel says designing sound-first is actually designing human-first. Now there’s an interesting ying-and-yang pairing here between Kat and Joel’s messages. But ultimately, both advocating for an inclusive design, enabling users of all abilities and senses to experience your product.

DLW Creative Labs

How effective multidisciplinary teams are made

We used to go to work and to the factory to put bread on the table, but now we go to work for personal fulfillment, purpose, and identity development.
— Esther Perel, SXSW

Brian Quinn and Shanna Dressler of DLW Creative Labs showed dozens of reports about the future of work and the shifting of how work will be done in the digital age. All these reports say the ability to up-skill and have strong soft skills are crucial for the future. And now it’s more important than ever as more and more people go to work for a sense of identity, it’s not just a means to pay the bills.

Their research has shown top 10 human skills needed in the future workplace:

  1. An empathy mindset

  2. Team culture

  3. Good communication

  4. Accountability

  5. Strategic analysis

  6. Curiosity + instigation

  7. Collaborative problem solving

  8. Negotiation + conflict resolution

  9. Time + project management

  10. Leadership

Brian Collins

Designing Tomorrow, Better

Companies are no longer in competition with each other. They’re in competition with the future itself.
— Brian Collins

Brian set out to create a firm that did radical work at scale... and succeeded. They completely rebranded Spotify and how they engaged their customers. They built a LEED-certified gas station for BP that educated about environmental impact and conservation. 

The future is coming at us fast. So fast, it’s almost impossible to keep up. Companies are no longer trying to keep up with their competition, rather thay’re fighting the future and all the change it brings. 

Advertising is a tax on bad design.
— Brian Collins

Brian and his team have devised the ‘Knot’ that enables them to deliver radical projects with meaning. The core of this knot is the concept that future proofingis about fear, but future raisingis about hope. Future raising is about creating the maximum love for a chosen future.

He covered a lot of content, quickly. I hope there’s a book in the works.

Dr. Sahar Yousef

Science of Sustainable Peak Performace

When a phone is in the room, brain power is reduced.

Dr. Yousef shared her work and others that showed how distracting the modern workday is, and the cognitive tax we pay by multitasking. One study by the University of Texas was shocking—by placing a phone in the room with subjects, they completed cognitive tests worse. It wasn’t their phone, and it wasn’t even turned on. But just knowing it was in the room lowered cognitive abilities. 

She likened multitasking to driving a Hummer rather than a Prius. By multitasking, you’re doing the same tasks, but much less efficiently resulting with less brain power remaining.

Dr. Yousef works with clients to improve their cognitive abilities and reduce their off-task distractions. One of her key techniques is the focus sprint, which is essentially working on a defined task in a defined block of time in an area that promotes your productivity. 

Michael Ventura


Michael talked about the work he and his company have done with various companies and governments, scaling empathy throughout teams to make them better at their job. He even wrote a book about scaling empathy and how it helps.

It’s going to slow things down before it speeds things up.
— Michael Ventura

I love this quote. It’s true about empathy, but also design thinking, and even design in general. Things will slow down as teams learn how to use new methods, or incorporate new teams and ways of thinking. But once the initial pain is over, the gains resulting in a more holistic and thoughtful process will pay dividends over time in the form of less rework, more sales, and happier customers.

Links for Week 17, 2019

How a world-class design agency organizes files
Alex shares their striaght-forward process to ensure everyone stays aligned. The Incoming and Outgoing folders are a great idea.

Implementing user insights: how to get started in a single morning
Lauren Pope breaks down a fast-tracked approach to integrating user centric thinking into any design process.

Highlighting stakeholder and leadership misalignment
Maxim (@round) shared one of his go-to stakeholder interview quesitons. I always ask for measure of success, but never thought about asking about their leadership's measure.

Workshop exercise: How would you make your company obsolte
Richard Banfield (@RMBanfield) shared a novel workshop exercise to get leadership thinking about growth:

Schedule Time to Focus

I have a fairly busy job as a director at a Fortune 10 company. I have a 12 person team, 9 major projects, three massive initiates for the year, and teams in three states and two countries. It got to be where my job was managing me. Here’s a look at a typical day:

6:00 am – Wake up, shower, feed the dog.
6:45 am – Leave to catch the train
7:15 am – Board train. Quick planning call with my team or sort email
8:15 am – Arrive at the office. Make coffee and get settled.
8:30 am – Process email
9:00 am – Meeting
9:30 am – Process email. Team is arriving, so I’m starting to field questions here and there
10:30 am – Meeting
11:00 am – Impromptu feedback with some of the team
11:30 am – Brief firefighting call with someone on my team
12:00 pm – Lunch
12:45 pm – Email meeting minutes and do a few other small tasks I signed up for from past meetings
1:00 pm – No meeting, awesome. Now… what should I do….
1:15 pm – Quick status chat with someone on the team
1:50 pm – Right, back to email
2:00 pm – One-on-one with someone on the team
2:30 pm – Meeting
3:30 pm – Catch up on email, and answer a few questions and provide a bit of feedback
4:00 pm – Meeting
5:00 pm – Catch the train home, wrapping up email or small tasks

Looking at that schedule, you’d think email is a primary initiative, right? Of course it’s not.

With such a fragmented day, I had no time to focus. The only thing I could complete in the short 15 minutes of free time was one or two emails.

My productivity went down, night-time working went up, and overall job satisfaction went down. Time to inflict some changes

Make Time for Work

First change I made was blocking out time in the morning and evening to do actual work. For this, that means creating repeating ‘Work’ blocks on my calendar. One wonderful-yet-terrible feature of Outlook is that it allows people to see your calendar is free so they can schedule a meeting. Similar to Parkinson's Law where work expands to fill the time available, the number of meetings will expand to fill your day if you allow it.

High Priority Work First

Now that I had dedicated time to work, I made sure to working on the highest-priority tasks first when I’m fresh and thinking clearest. I’ll fit the low-priority tasks in the small windows of time between meetings or in my evening work block. I use Things to constantly track tasks that need doing.

Plan the Day

The last thing I do (normally on the train) is review my schedule and to-do list for the next day. I choose the high-priority items and assign time-slots in my morning work-blocks for the next day. Now I relax for the night, knowing what tomorrow holds.

First thing I do when I start my workday is block my calendar for the day. I don’t accept any day-of meetings, unless it’s with my team or mission critical. This keeps me proactive throughout the day and keeps my plan mostly on track.

New Schedule

6:00 am – Wake up, shower, dog, train, etc.
8:00 am – Work!
11:00 am – Meetings, ad-hoc team feedback, etc.
2:00 pm – Every day I have a 1 hour one-on-one with someone on my team. Everyone rotates on a two-week cycle.
2:30 pm – Meetings, ad-hoc team feedback, etc.
4:00 pm – Work!
5:00 pm – Catch the train home and plan tomorrow’s work

Ahhhh, that’s better, right? Well, so far so good. I’ve only been doing this a month or two, but it’s already feeling better.