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.

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.

Scaling Through Quality

In my professional life, I’m always finding myself needing to do more. Needing to scale. I’m sure everyone runs into this eventually. As you get better at your craft, develop a reputation, amass more clients, etc., your time becomes more and more limited.

A lot of people approach this by working faster, pumping out more and more work, all while quality is slowly slipping away. This is the danger zone. A slippery slope.

Don’t do this.

Instead, work slow. Be methodical in your craft. Focus on the process. Enjoy the work. Produce the highest quality work your craft demands.

Now, when it’s time to scale, look back to your past work and use that as a lever, a pattern of good work, that can inform and speed your task at hand.

This is why design patterns are all the rage—they work.

Have an Opinion

Seth Godin says one of the greatest things you can do is run a blog because it forces you to have an opinon. Time and time again I see confirmation that having an opinion leads to better career opportunities.

You become the expert on a topic. Or the critic who can always find the fetal flaw in the plan, and having your blessing is the first step towards success. Or people want you at their conference or event to hear your opinions. You get the point...

Of course, having an opinion doesn’t mean you’re always right. People often ask ‘but what if I’m wrong?’. Well, then you’re wrong. Life goes on. Even better, someone who lays out the research and facts to why they’re changing their opinion is fantastic. It helps others to learn with you. It shows maturity, growth, and mindfulness.

Anyway you slice it, having an opinion is a good thing.

Point of view is worth 80 IQ points –Alan Kay

Sometimes it's hard to have an opinion. Opinions come from experience. From seeing successes and failures. From watching things fall apart from the inside. You wouldn't expect someone to have an opinion about a book they've never read, right? It's hard to form opinions without experiencing.

It means creating things, and more importantly, sharing them with the world. It means talking with other and deciding if you agree. It means trying new things. It means getting out of your comfort zone. It means learning how other fields can impact and influence your field. Forming opinions means having experiences.

Back to Seth’s advice; it’s no use in having opinions if you’re not sharing them. Whether it’s in meetings, on your blog, in conferences, or when mentoring. How will you learn if you don’t share and get feedback? Worse, how will others learn if you don’t share?

You’re already an expert in something. And you know a great deal about other things. Give back to the world and share your thoughts. We’re waiting.

Student Portfolio Review

I get asked to review a lot of student or recent graduate portfolios, and I see a lot more come through our online career board. Many people, regardless of experience, often overlook some of the basics every portfolio should have.

Think about a portfolio—what is it’s purpose? It’s not a time capsule or a year book, merely capturing how you spent your time. It’s purpose it to show me the type of work you love doing, and the type of work you want to keep doing.

Tell me about the process

In almost every job interview, the interviewer will say ‘Now, let’s take a look at your portfolio...’. Your portfolio should tell a story. It can be how you’ve matured as a designer. Or how multi-faceted you are. Or how your unique process or point of view separates you from the rest. Whatever that story is, know it. When building your portfolio, plan the narrative of how you will walk people through it.

I want to know how you did all this great work, and that you can do it again for my team. So tell me. Tell me how you came to the refined problem, and how you came to the final solution.

Notice I say how you came to the solution, rather than what the solution is. In most cases, I don’t care about the final product concept. And as you get further in your career, non disclosure agreements might prevent you from telling me what the solution is. Rather, I want to know how you got there. What was the process? What methods did you use? What challenges did you have to overcome? What did you learn from a process and self-improvement perspective?

As you explain your process, I can get a clear glimpse of how you’d contribute on my team.

Tell me what you did

College is full of group projects—they’re invaluable at teaching you real-world lessons, both about your topic of study and people. When showing work in your portfolio, tell me what role you played in each part. Sometimes you’re responsible for the big, sexy showpiece. Other times you’re more of a supporting actor, running the project management side of things, or digitizing copious amounts notes. That translates to the real world—we need team players that can do both, and strive to fill gaps and make the team better. This shows flexibility and teamwork. This is important.

Tell me why I need you

This one can be a little bit tricky. I don’t want you to sell me on you—that’s part of the interview. But I want to see how you would be able to fit on my team. What gap are you filling? How will you contribute?

I often tell younger designers and recent grads to think about implementation. Often times you’re designing work for a fictional company or nonprofit, which means the design work never go beyond the design. But tell me about what implementation would look like.

What documentation would you provide for the engineering team—these could be specs, red-lines, link to documentation, etc. How would it scale? How will other designers build on your work? Abstract-out the design language into a system. Show best practices on how to use existing design elements, and the rules for which to extend the design language. This will help mature your design work itself, and shows you’re able to fit in a larger design pipeline.

Tell me about you

Now that we got the hard part out of the way, tell me about you. I don’t mean tell me about your favorite vacation spot, or favorite band. But rather, what part of the design process is your favorite? What type of problems do you like to solve? What type of teams do you like working on? What role in the team do you thrive in?

Colleges focus on giving you a lot of different skills and experiences in hope one or two really click. Tell me what clicked for you, and what you want to continue doing.


Lastly, relax. A portfolio isn’t a legal document. It doesn’t have to be stuffy or dry. Let some of your personality seep through the words to give me an idea of who you are. Remember you audience, however; I wouldn’t go overboard. But it’s okay to have a little fun show through. That’s why we want to hire you, anyway.