Finding Inspiration in Random Ways

Water flowing over hands

serendipity / ser-ən-ˈdi-pə-tē / noun  -  an aptitude for making desirable discoveries by accident.

Am I becoming obsolete?

I had to ask that question after gaining access to GitHub’s Copilot. You know, that AI paired programmer that “helps you write code faster and with less work.” I love it and use it constantly. But will it put me out of a job?

All I know is this: we, as humans, can think abstractly, creatively, and come up with wonderful ideas. That ability –the ability to ideate – will become increasingly important as more mundane tasks are automated away.

What can you do to improve your ideation skills? Introduce some randomness! Here are five strategies to do just that.

The Halls of Knowledge


I’ll let you in on a secret… your university library.

Yes, that “ancient” concept – a physical building stacked full of books. Now hear me out…

How often are you exposed to intriguing thoughts, ideas, and concepts? The more exposures you have the greater your chance of coming up with a novel idea.

Many new ideas also arrive at the intersection between domains. Where can you find a richly curated source of knowledge on interesting topics? Where can you find information from a wide variety of fields? At a library!

Go down to your nearest university library. Pick a topic and start browsing the stacks. Then go to another subject. Maybe move over a few aisles? The physicality of the library offers something a Google search simply can’t provide.

Random Wikipedia

Another fun idea generation hack: have a random Wikipedia article automatically pop up whenever you open your web browser. Use the random article link on the left side of the main Wikipedia page.

Ever heard of chicken glasses? Wikipedia is a great source of entertainment, randomness, and inspiration. Use it to your advantage.

The Power of Twitter


Twitter, when used properly, can help boost your idea generation rate. If you aren’t already using it, then you are doing yourself a disservice.

The key to using Twitter effectively is to ruthlessly prune who you follow. If someone is posting stupid stuff, unfollow them. You can always add them back later.

Here are some follows I can recommend:

Vicki Boykis (@vboykis), David Ha (@hardmaru), and Elvis Saravia (@omarsar0), are great if you’re in the data science and machine learning community. You might as well follow me too (@timothyvh)! (shameless plug, lol)

But remember, randomness is good in your search for inspiration. Don’t only follow people within your domain, be it data science, health care, or whatever field you’re in. Cast a wide net and follow a diverse group of people.

Venkatesh Rao (@vgr), Ben Reinhardt (@Ben_Reinhardt), and Tim Urban (@waitbutwhy) consistently expand my horizons.

David Perell (@david_perell) is also a gold-mine of insight and ideas. His thread, below, on “Lateral Thinking with Withered Technology”, is quite pertinent to this post too. Give it a read. Then start curating your Twitter experience.

Meet Me in the Hallway

The joke at Python conferences is that the “hallway track” is the place to be; that is, spending time in the hallway, talking to friends or strangers, is preferred to scheduled talks. From experience, where else will you hear a story of (il)legally winning thousands in online poker with your own AI bot? If I’m at a conference (in person), you can meet me in the hallway.

I dare you to go one step further. Attend a random conference on something you know nothing about. I did, and it led me Japan. Thanks Animethon!


John Seely Brown, former director of Xerox PARC, discusses the process of attending a random conference in the video below. As John says, “people tend to isolate themselves from the flows of new knowledge and the people creating them.” Attend that random conference and drink from a river inspiration.

Oblique Strategies


Maybe you’re working on a project and in a creative rut. Perhaps you’re dreaming of new features for your product but aren’t feeling the “inspiration”. Are you close minded? What to do?

Brian Eno and Peter Schmidt found themselves in similar situations as they worked on their artistic endeavors. Independently, they wrote down prompts to make them think differently and break down roadblocks. They combined their efforts and created a deck of cards with the prompts, calling them Oblique Strategies.

A few examples of the prompts:

  • Make a sudden, destructive unpredictable action; incorporate
  • Towards the insignificant
  • Honour thy error as a hidden intention

Oblique strategies are a form of lateral thinking. They force you to look at a problem in a nonobvious way. It is like injecting a little bit of randomness into your brain. Just enough can help you get out of that rut.

Here’s a website with the oblique strategies. Try them out!

Generating creative ideas is a skill in demand. Experiment with the five strategies I’ve outlined and use randomness to your advantage. May serendipity be your guide.