How to be More Creative: The Obli Challenge - Part 1

You can now read Part 2 of the Obli Challenge here

I’ve recently finished Messy, a book about how messiness often leads to creativity and innovation because messy people are constantly exposed to new ideas and stimuli.

Aside from giving me an excuse to leave my dishes in the sink, this theme has shown up in a lot of the books and articles I’ve read. Some authors call it the “Medici” effect, other people consider it “combinatorial creativity”, and there are plenty of resources promoting the benefits of “diversity”.

The underlying premise is that creativity and innovation often comes from unexpected places so it’s in your interest to expose yourself to as many different people, disciplines, and viewpoints as possible.

But while this idea makes sense in theory, it’s hard to put in practice. Even though I know I should be seeking out new ideas and experiences, I still find myself defaulting to my comfort zone. I read content from familiar sources, discuss worn-out topics with the same people, and go to the same froyo places.

So I decided to try and exit my bubble, if only as an experiment. I created the Obli Challenge (named for reasons that will be made clear later) in the hopes of expanding my worldviews and, ultimately, boosting my creativity.

This article will explain what I’ve learned over the past few months. Regardless of whether you take up the challenge yourself (you should), hopefully you will at least find something useful about broadening your horizons.

 

Why your horizons are narrow

Before creating the challenge, I reflected on why it’s so difficult to exit my familiarity bubble. I landed on three barriers holding me back:

 

1. It’s hard to admit that you’re in a bubble when you don’t realize you’re in a bubble.

If you’re like me, you probably have certain types of people that you talk to, content that you consume, and media sources that you follow. It’s easy to believe that what you read and care about is all there is to the world without realizing that there are other possible perspectives.

Especially with more and more services tailoring news and content based off your interests, it’s become harder than ever to realize the limitations of your viewpoints. You don’t know what you don’t know and you often don’t know a lot.

 

2. Good content and discussions are hard to find.

There is a lot of less-than-stellar content out there (aka bad). Poorly researched and poorly produced, a lot of content is simply not worth your time to consume.

The same is true for discussions. Most discussions with friends are uninspiring since you tend to share the same opinions (hence why you’re friends) and most discussions with strangers rarely move past tomorrow’s weather forecast.

As a result, seeking out quality content and worthwhile discussions requires time and energy – resources that are always in short supply.

 

3. Expanding your horizons is frankly, not that fun.

Expanding your horizons is usually not like Eat, Pray, Love. New experiences are scary, learning about things that you aren’t interested in is boring, and talking to someone you disagree with is uncomfortable.

For example, I’m not interested in sports; never have been, maybe never will be. Because of this, learning about LeBron’s impact on basketball is frustrating because I’m studying a topic I don’t really care about.

This only gets harder when trying to understand opinions contrary to your own - either through a book, article, or conversation. Things get heated, conflicts arise, and the immediate reaction by most people when a disagreement occurs is to prove their rightness, not necessarily to listen.

It’s much easier to avoid the unpleasantness and just stick to what you know.

 

The Obli Challenge

So what’s the solution? One tactic from Messy that stuck with me was the idea of “Oblique Strategies”. Developed by legendary music producers Brian Eno and Peter Schmidt, the Oblique Strategies are a deck of cards, each card offering a constraint, reminder, or thought starter. Whenever a band was in a creative rut, Brian and Peter would pull out a card and the band would react to it.

Some examples would be “Try faking it!”, “Work at a different speed.”, and “Use an old idea.”

I liked this strategy because nothing says fun like having an index card dictate your every move. The bands often complained about the process, but they would later admit that the Oblique Strategies got them to exit their comfort zone and forced them to think differently.

Given that I wanted nothing more than to learn, experience, and discuss things outside my comfort zone, I wondered if I could do something similar.

 Hence the Obli Challenge was born.

 

Part 1.

First I wanted to expand the breadth of content I consumed. My initial plan was simple, read about five new topics a week through online articles. I wanted to not only explore topics I knew nothing about (e.g. Art History), but also better understand alternative viewpoints to my existing beliefs (e.g. Would Stricter Gun Control Decrease Violence).

To do this, I used a random topic generator to generate four of my topics.

For the fifth topic, I listed out my beliefs on major issues (climate change, gun control, political issues, etc.) and searched for articles that were both for and against those beliefs.  

I’ve been following this plan for the last two months and have read more than 40 articles ranging from the history of the FIFA Scandal, to the Strawberry Festival in Plant City, Florida, to Rousseau’s theory of philosophy.

Although I’m still fine tuning the details of the challenge, here are some thoughts and tips that I’ve picked up from Part I of the Obli Challenge.

 

1. So am I now more creative? Sort of…

Honestly I don’t feel more creative. Granted, I don’t know what being creative is supposed to feel like.

However, some articles have definitely pushed my thinking in unexpected directions. After reading an article about the history of cheese in art, I spent the next few hours looking at everyday objects and wondering if they can be used as my next muse.

I’ve also realized that resolving controversial issues is never black and white. While my beliefs on most topics haven’t changed, they have become more nuanced and I have a better understanding of why I believe what I believe.

More interestingly, I’m beginning to make connections between what I read and the projects I work on. I recently finished an article about the stories of different passengers on a long-distance-train ride. It was a fascinating piece that showed the power of good storytelling.

I was (and am) working on an article about my experience as a street vendor and realized my work would be much more powerful if it also incorporated the experiences and stories of actual street vendors as well.

So maybe I’m not consciously more creative, but what I’m learning has certainly expanded how I think.

 

2. Build up a list of content sources to find articles.

For my first two weeks, I exclusively used Google to find my articles.

It was miserable.

I clicked search result after search result hunting for quality content only to find that most articles were poorly written, short on information, and/or unreliable.

By the third week I switched tactics. I spent a few hours one day compiling a broad list of media outlets, news websites, and other content sources. Rather than immediately Googling the topics spat out by the generator, I randomly chose websites from this list and typed in my topics into each website’s built-in search function.

I then skimmed through the articles that emerged and chose certain articles to actually read.

By relying on more-established content sources rather than just Google, this process helped me quickly identify high caliber content.

Speaking of which…

 

3. Be picky about what you read.

When looking for articles to read, don’t immediately read the first article that pops up. It’s important to choose articles that actually teach you something new.

For each topic, skim through 3-5 potential articles before settling on an article that you want to actually dedicate your time to reading.  Some rules I use include:

 1. Avoid super relevant or current articles. I’ve found that they are typically very narrow in scope and mostly just provide news updates.

2. The longer the article, the better it usually is. However, be wary of articles that span multiple pages because the author may just be trying to drive eyeballs to advertisements.

3. Look for graphs and infographics. If the author has dedicated enough time to create a visual, usually the author has something worth saying.

4. If it’s a list, first read one of the items on the list. If the item is vague or unhelpful, chances are the article isn’t worth reading.

 

4. Write down at least one takeaway or question for each article.

At first I read each article passively but I would find myself dozing off or forgetting what I read. It’s hard to stay focused when you’re not inherently interested in the subject matter.

To combat this, I pushed myself to apply what I learned. For each article, I made myself come up with at least one question or takeaway that I could employ in my projects. Many times the applicability was a stretch of the imagination, but at least it helped keep me engaged.

For instance, one article was about the history of the creator of Wonder Woman. I don’t like comic books to begin with and I have even less interest in the author of a comic book.

However, I still forced myself to find useful general themes such as “What will seem outdated 50 years from now?”, “How can I empower a previously disenfranchised group of people?”, and “How do I find a 6 foot tall Amazonian woman who fights crime to go out with me?”

These questions turned a fairly unengaging topic into something that was somewhat helpful.

 

5. Focus on the goal not the process

The process doesn’t always work perfectly. Sometimes a topic is obscure and there aren’t any quality articles to read. Other times a topic will spur a random thought that you will want to explore.

I typically spend 3 minutes trying to find a worthwhile article based off a generated topic. If I don’t, I immediately move on and generate a new topic.

If a topic leads me down an unexpected path, I also follow that path.

The goal of the challenge is to broaden your horizons so don’t get bogged down following the process exactly.

 

6. Set aside dedicated time to read about major issues.

When I started out, my plan was to read five different articles on five different topics. And that plan mostly worked for the four randomly generated topics.

For major issues, however, I realized that one article was not enough.

Major issues have multiple conflicting viewpoints which is probably why there are major issues to begin with. There are very few articles that lay out all sides of an issue in an unbiased way. Most articles clearly take a side and only lay out arguments supporting their side.

For example, when I was researching the pros and cons of the legalization of marijuana, some of my articles were coming from websites called “Leafly” and the “High Times” - hardly inspiring sources for objective reporting.

I spent significant time gathering and reading articles with different viewpoints to understand all the arguments and counterarguments surrounding each issue.

Because of this, I would recommend that you set aside dedicated time on the major issue topic to do the necessary research required.

 

Introducing the Obli Newsletter

So that’s Phase I of the Obli Challenge. Once again, you should give the challenge a try. At the minimum, you’ll have conversation starters to bring to your next dinner party such as how China is trying to avoid a food crisis.

However, you might also be lazy. I understand. If that’s the case, I have solution for you – do Part 1 of the Obli challenge with me.

I’ve decided to include the topics and articles that I’m reading for the Obli Challenge in my weekly newsletter. Each newsletter will contain interesting info and tidbits designed to spark creativity and discussions with your friends (or random strangers on the internet - you do you.)