Blind Contour Bookend
Producing creative work—actually getting it out of your head and onto the page or into the world—requires you to deliberately suspend your evaluative brain at specific moments. You want to temporarily defer judgment on what might work in order to explore a new concept without prematurely dismissing it as impractical or unfeasible. To develop your creative abilities, you need to learn how to turn off your internal self-judgment so it can’t act like a censor. This doesn’t mean every idea you have is a great one, but it gives you the discipline to separate the moments you’re generating from the times you’re evaluating.
Blind contour drawing is a common practice used by artists to shortcut the distance between the eye and the hand. With practice, when the eye follows a curve, then the hand draws the same curve on the page without thinking about it. The process skips the judging brain.
This assignment adapts the practice for a different purpose: to help you locate and wrestle with your critical functions (your ability to judge and to critique). It helps you experience what it feels like to not judge your work and to let your creativity flow.
Grab a pen and paper.
Identify someone you can see from where you are sitting. You could be on a train, at a park, in a really boring meeting, or sitting across from someone else doing the same assignment.
Now, take just one to two minutes to draw this person while looking at them the entire time. Most importantly: draw the other person without looking at the paper and without lifting your pen from the paper. (If you do lift your hand, you will not be able to find your way back, and the temptation to look will be overwhelming.)
You are making a translation of what you see with your eyes into a line with your hand—without any visual feedback.
When time is up, then you can look at your drawing.
Think about what you felt as you were sketching and how you feel about your drawing now.
Reflect on the following questions:
Did you make a great drawing? (Unlikely.)
What did that feel like?
Did you laugh along the way? If so, what was that laughter about?
What did the voice in your head say?
What did it try to make you do?
What’s at the base of those feelings?
Where’s that coming from?
When is it important to judge a piece of work, and when might it be important to not judge?
This exercise helps you get into the habit of separating the process of making and creating from the process of critiquing or judging.
How to Talk to Strangers
The word stranger even implies the idea of strangeness. In everyday life you might avoid strangeness. But creative work requires you to become more open to things you find strange or unusual. Without strangeness, you are left only with sameness.
This assignment helps you confront the stranger barrier. Eventually you will find “strangeness” appealing because you know it is essential to your work.
You’re going on a series of missions that must be done outside of your home, classroom, or office.
You can do this as a solo challenge or, if you feel uncomfortable by yourself, with a partner.
Start small. Choose a path in a safe place where you will encounter other people walking. Perhaps you’re going to walk from home to the library. Now, say hello to every single person you see on the path. Do this for one minute.
How many people did you say hello to?
How did people react?
How did your behavior change from start to finish?
Your second mission is about triangulation. There’s you, a stranger, and an object that you both can see. Comment on that object in order to strike up a conversation with the stranger. You can find something to say about anything; don’t be clever, just be obvious. “Oh wow…you can get those apples from this grocery store? I didn’t know they carried them here. Are they good?”
Then converse.
When it’s over, think about the following (or discuss with your partner):
What was the object you chose?
How did the person react?
Compare this mission to the first mission.
Your third mission is harder.
Pretend you’re lost and ask a stranger for directions to a specific destination nearby.
If you get the person to give you directions, then ask them to draw you a map.
If they agree to draw you a map, then ask them for their phone number so you can call them if you need more help and get lost along the way.
If they agree to give you their phone number, then call them to see if they answer.
If they answer, thank them for their help and let them know you found your destination.
Now reflect (or discuss with your partner):
Who did you ask for directions?
How did you choose them?
How far did you get?
What was the barrier to each next step?
This mission asked you to tell a small lie. How did you feel?
Many people think no one will say yes to having an interaction with a stranger. Getting over this fear is liberating and valuable on its own. And it’s a broader reminder to challenge your own assumptions about how people behave.
A Seeing Exercise
Learning how to control your filter—so you can pay close attention to what’s right in front of you—will help you see what others miss. And the effects are powerful: the research of educators Abigail Housen and Philip Yenawine, whose work inspired this assignment, showed that this control supports the overall growth of your creative and critical thinking skills, which transfer to many areas of your life and work.
This assignment helps you slow down the connection between your eye and your brain so you can make discoveries about what you know, but don’t know you know. Lurking in this huge category of unconscious observation are thousands of opportunities for design and creative work.
Find a photograph. A documentary photograph drawn from real life is absolutely perfect. Look for a shot by a photographer interested in the everyday. Journalistic photos are sometimes too dramatic but work in a pinch. Street scenes are great; you want a lot of detail, multiple people in the frame, and some ambiguity about what’s happening. You can practice with the image on this page.
Now, ask yourself the following questions:
What’s going on in this picture?
What do you see that makes you say that?
What else do you see?
What do you see that makes you say that?
Repeat. And again. And again.
Consider keeping a journal or log and doing this exercise once a day. At the beginning, fill up a few pages per photo. Once you practice a few times, you’ll never run out of observations to record.
This assignment helps you understand how much detail is part of your daily life. Background detail is what makes the world feel vivid and real, a quality that you want to imbue all of your creative work. Noticing detail is the first step toward being able to design it into your work.
Empathy in Motion
This work calls for humility. It’s not a simple poll to see what people want, nor a patronizing exercise in superficial listening. It’s a dynamic process of connection, curiosity, and collaboration, in which you change course over and over as you encounter feedback and new perspectives.
In many situations, designers have more power than those who will wind up using or living with the results of the design work. You’ve likely experienced this when the education level, affluence, health, or social capital you have or represent is greater than that of the community in which you are working. Without consciousness of these dynamics, you can miss the mark in understanding the community’s needs. The community may then feel it’s being misrepresented or exploited, or you may implement solutions that harm rather than help.
This assignment offers one way to start actively shaping the bigger picture of the relationship between you and the ultimate
Plan to spend time together with the people you are creating with and for in advance of the “work” phase of your relationship. Specifically, arrange to travel together to the location where you and a community stakeholder will be working together on a project.
Where feasible, choose public transportation. This assignment is most useful when there is a power differential between the two people, and in this case, it should be set up so that the person with the lesser structural power knows the path to the bus or train. This helps balance the power. It creates an opportunity for empathy in motion.
Situating this assignment during transit is deliberate: you’re often side by side, instead of face to face across a table or other barrier. Instead of the heightened dynamic of one person staring, listening intently, and recording the other’s words, this arrangement is unscripted. Just like talking to kids while driving in the car, it can be a disarming moment. It is about both getting to know the other person and starting to build the relationship while taking the power dynamic into consideration.
Even if you are not working on a formal project, you can use this approach to build a deeper, more two-way relationship with someone. Travel to a PTA meeting together with another parent from a different part of town. Plan to carpool to a weekend religious service. Your goal is to experience side-by-side travel in a way that highlights the contextual intelligence of the person who might be seen as less “expert” in your pairing by conventional standards. Be very sensitive to how you ask this person to join you, and get clear on your motives—to spend some time together and build a more equitable relationship—before you suggest it.
The Solution Already Exists
The world just loves to tease us with contradictions.
Don’t shy away from building on others’ ideas when it comes to your own work. When you try to come up with new concepts in isolation, you’re unaware of what’s already out there and your ideas are less likely to be new. Rid yourself of the myth that creative genius is a solo act of conjuring original thought from thin air. It really doesn’t work that way.
A stream of ideas is all around you, if you know how to look. This assignment helps you seek relevant inspiration when faced with a creative challenge and encourages you to steal the ideas of others in just the right way.
Use this exercise when you already have a pretty clear idea of the problem or opportunity you’re trying to address and are starting to think about solutions. Just keep in mind that the solution (or some piece of it) already exists.
To start, come up with an analogue for the problem you’re trying to solve. In this case an analogue is an example of how someone else has solved a problem similar to yours but in a different context. It gives you a point of comparison. With a decent analogue, you get to borrow from something familiar to help you envision the new and unknown.
To find an analogue, think about your challenge and its core attributes. For example, imagine you’re trying to design a new way for kids to keep at it while studying. What kind of challenges come up? Dealing with repetition, boredom, and distraction? Great. What other activities have similar facets? Unless you’re a passionate ultrarunner, one that immediately comes to mind is exercise.
Luckily for you, there’s a huge industry that specializes in finding creative solutions to get people exercising (and to pay a lot of money while doing it). An interesting analogue might be the rise of aerobics in the 1980s or the more recent popularity of SoulCycle or hot yoga. Choose something obvious: you’re looking for examples where someone else has solved a similar problem in an effective way and where the hallmarks of the solution are pronounced or even exaggerated. This makes for great learning.
Armed with your analogue, conduct some research. Read articles, interview existing customers, or call up a few companies. Find enough information to take a crack at the following questions:
Why did the analogous solution work?
For whom?
How do you know it worked?
How did it transform people’s feelings?
What are people able to do now that they couldn’t do before?
Now apply some of those learnings to your problem. What jumps out of your research as the most interesting? Use your insights as the starting point to explore new ways to tackle your problem and come up with approaches that fit your context.
Looking into similar problems that have been faced and creatively conquered brings in a rich set of potential material. Sadly, it is an underused approach. It is the most effective way
to get new designers to come up with sophisticated, surprisingly novel outcomes in their initial stab at developing a new concept.
Used to Think…& Now I Think
Taking a few minutes to observe and document changes in your own thinking over time helps you make sense of what you’re learning and how you’re growing.
This assignment was inspired by a book of the same name in which experts on education reform described how their minds had changed toward the topic (or occasionally, how their convictions deepened) through their long experience in the field.
First, do any other assignment in this book.
Then take a piece of paper and divide it into two columns.
At the top of one column, write “I Used to Think…” and on the other “And Now I Think…”
On the “Used to…” side, list your previous ideas or preconceptions about the assignment activity or topic, and on the “And Now I…” side write your thoughts on the same subject after completing it.
Although every assignment in this book is designed for a specific purpose, there’s no guarantee that what you take away is what was intended. You may have multiple interpretations based on your own life and prior experiences. One goal of this assignment is to free you from my assumptions about the value of any particular learning experience and to prompt you to articulate the impact in your own words.
You can also adapt this framework to any other learning experience, on your own or with a group. Use it with colleagues after you’ve all attended a conference together or completed a team retreat. Use it with friends or family to process a political shift or an emotional event. Ultimately, you may find this phrase creeping into your everyday vocabulary as a shorthand to describe how you are developing and changing as a person and as a creative thinker and doer.