Creativity is a particularly interesting skill to me. This is because I was into lateral thinking puzzles when I was younger. I really believe that creativity, as a skill, is under-rated and under-utilized. People (mostly employers) say they want creative people, but they do not reward you for being creative. What does ‘being rewarded’ mean? It means encouraging and fostering an environment where people can be creative, suggest crazy ideas, get the support to implement those ideas, and then if those ideas fail, still be praised for being courageous and bold. The following books are the ones that have most influenced my thinking on creativity:

Thinkertoys by Michael Michalko

I am a big fan of books that provide the tactics needed to implement the ‘theory’ covered in the book. Michael does exactly this, providing the exact activities, structures and frameworks to generate ideas. There are a ton in his book, but the two that I like:

  • Reverse assumptions technique
    • Take a problem and list out all the assumptions that you have made. For example, imagine that you are opening a new type of restaurant and want ideas on how you can make it different. One assumption you might make is that a restaurant is a place to sit-down for a meal. Reverse that assumption. A restaurant is NOT a place to sit-down for a meal. This could possibly mean: no tables and standing room only restaurant, take out food or delivery only, there is no physical location and the chef comes to your house to prepare the meal.
  • Define the challenge technique
    • Otherwise known as the five-why’s technique, this is about asking why so that you can get different perspectives on the problem. If for example, you are a salesman at a company and wanted to increase the sales, you could define the five why’s as:
    • I want to increase the sales of a product at my company.
      • Why? To increase the revenues of the company
      • Why? To make the sales quota
      • Why? To earn a commission and make a bigger year-end bonus
      • Why? To get more money to buy a yacht
      • Why? To be able to sail the open seas
    • That gives you five different avenues to explore to achieve your goals. If you want to increase the revenue of your company, you can do that by bundling products together or adding products that you can sell. If you want more money to buy a yacht, you can look at side hustles or loans. If you want to be able to sail, you can see if you can borrow a boat or find creative ways to lease a yacht.


Look ma, life’s easy by Ernie Zelinski

Ernie Zelinski is the best selling author of The Joy of Not Working (also highly recommended), and he writes a parable on how to make life easy. I love that the book is set in Vancouver (my home town) and while some of the situations are contrived, I learned a few things that are interesting to me:

  • If you do the easy and the comfortable, life is difficult and uncomfortable; if you do the difficult and uncomfortable, life will be easy and comfortable. A great way to sum up the whole book and a philosophy for success in this world. It can also help guide some of the decisions you make in your life because often times, the difficult and uncomfortable are the exact things that we need to do.
  • Two rules of happiness
    1. Be happy with who you are, where you are, with what you have
    2. When you find yourself unhappy with what life brings your way, go back to Rule #1

Essentially, you are in control of the life you want to lead. If you want to be happy, easy and comfortable, you can make your life that way.


A kick in the seat of the pants by Roger von Oech

Roger von Oech is the best selling author of A whack on the side of the head, but I chose this book because it provided me with a framework for understanding the different roles of creativity, and the tools that I can use in each of the roles.

  • The four roles that are part of the creative process are:
    • Explorer
      • The Explorer is all about finding new information.
      • One tool to use to find new information is to use obstacles to break yourself out of ruts or routines. For example, think about your commute to work. One day, you find that one of the major roads that you take is blocked by traffic or construction so you decide to take another route. That other route may actually be faster, more scenic, or even safer, but you would not have found it unless you were forced to. In a similar manner, you can introduce constraints (such as budget limitations, time, people) to develop out of the box ideas
    • Artist
      • The Artist is about creating new ideas.
      • One way to create new ideas is the idea of reversal. For example, suppose you work for your city and you have been tasked with finding a way to get rid of the pigeon as a pest. One way to frame the problem would be how to keep the pigeons away from buildings or certain rooftops. If you reverse the problem, your problem becomes, how can we attract pigeons to certain places where it is safe for the pigeons to be.
    • Judge
      • The Judge decides whether ideas are worth implementing.
      • Become a fool: Our policy is no alcohol at work. Fool: Of course we should have drinking at work. It’s an incentive to show up. Not only that, it would reduce stress and would lead to more honest communications. Our fellow employees would look better. There’d be fewer complaints about low pay. It would cut down on absenteeism – you could come to work hung over. It would improve communications; you’d tell your manager exactly what you thought. It would save on heating costs in the winter and would encourage car pooling. It would decrease job dissatisfaction; if you had a bad job, you wouldn’t know it. Finally, it would eliminate vacation: people would rather go to work. 
    • Warrior
      • The Warrior executes the ideas.
      • A great way to push past resistance and to really sell your idea so that it can be implemented, is to figure out what you are really selling. For example, an anecdote from the book: a manufacturer introduced a new line of drills into the marketplace. These were great drills, but they did not sell. The company did some market research and found that people did not want drills, they wanted holes (i.e., the product of the product). They re-positioned their ads to emphasize their drill’s “hole-drilling” power. In fact, you can take it even farther (as per one of Seth Godin’s Akimbo podcast episodes). People don’t want holes, they want to fill those holes with nails. In fact, they don’t want nails either, they want shelves. And in fact, they don’t want shelves, they want a place to put their books. And in fact, they don’t want books, they want a place to show off their knowledge to their friends. 


Expect the unexpected by Roger von Oech

  • “That which opposes produces a benefit.” Have you ever worked on two problems? One where you have unlimited resources, and another where you have limited resources? You may have found that you are more creative and imaginative when working on the problem where you have limited resources. In the same manner, if you have a problem where you are unable to generate creative insights or breakthroughs, introduce a constraint or a restriction and see where that takes you.
    • An example of this is to think of as many uses as you can for a brick. Take 90 seconds to do so now. For your next exercise, think of as many uses as you can for a brick, except this time, think only about how it can be used in a kitchen. Take 90 seconds to do that now. Did you find that restricting yourself to only thinking about the kitchen produced more ideas?
  • “Things love to conceal their true nature.” We are taught in school and perhaps at work that when you are given a problem, there is one answer that we are looking for. Except how many times have we found that the answer, the best answer, is not the first or second or even the fifth answer that we come up with? The next time that you are trying to find an answer to a problem, ask “what are the right answers?” with emphasis on the fact that there may be many right answers. This will let you and your team to get through the one answer mentality. 
    • Think about match stick problems. I link to a site where there is a match stick problem with three answers. Except there are more than three! Can you find additional answers that would work?