Cultivating your creativity
TLDR:
Creativity isn’t magic. Specific behaviours and environments can boost creativity such as pushing yourself to put more ideas into the world, working across disciplines, procrastinating to allow your mental “background processes” to run, exposing yourself to crazy ideas more often, and adding constraints which force you to think differently
Where do your most creative ideas come from? Some people swear that their dreams are the source of deep insight. Others claim that their best ideas come to them when they have a shower and let their minds wander. In fact, screenwriter and director Aaron Sorkin has taken this to the extreme by taking 6-8 showers per day when he’s experiencing writer's block and needs a reset moment. Real creativity can feel magical. That “ah-ha” moment is hard to describe or define. This appearance of magic means that there are lots of misconceptions and urban myths that circulate about creativity. Today’s post is going to instead look at the science and psychology of it - what we know about how creativity takes place and how you can change your behaviour to make you more creative.
The importance of creativity is not limited to the arts. Creativity is key to innovation and problem solving and in a world of increasing complexity, businesses need creative workers to drive progress. I’m also a strong believer in having a growth mindset, the idea that attributes like creativity are not fixed but instead fluidly change from time and effort. So if you put effort into learning how to be creative you can get better at it. But in order to do that you need to understand what creative people do, how they work and how they think. This post will outline 5 trends in the habits of creative people that we could all benefit from replicating when faced with a challenge we need to think differently about:
Quantity over quality
Cross-pollination of ideas
Procrastination can be productive
Desensitization to “crazy ideas”
Constraints push you to think differently
In all 5 of these cases, I’ve included practices that you can try out for yourself. Like any good user-facing product or service, I’ve been trying to follow my own advice and do all 5 of these things in the last few months. It’s been fascinating but it’s not always been easy! This post is intended to help you cultivate your creativity, but like growing something in your garden, getting more creative requires practice, patience, care and consistency.
Quantity over quality
One of the easiest ways to have more creative ideas is to have more ideas. You can throw the ones that don’t work in the bin and build on the gems that provide real value (see my post on when to commit, grit or quit). This works because good ideas often don’t feel like good ideas until they collide with reality. This is even more true for creative ideas than it is for tried-and-tested areas - because creativity tends to involve novelty: either in the content that’s being created, the application of an existing idea to a new domain or the novel linking of two distinct areas.
Volume also drives learning. The process of releasing something forces you to push things all the way through to execution, where the real messiness of most creativity materializes. Pushing things to execution earlier allows you to spend the remaining time doing a greater variety of work which also promotes learning and expertise.
Creative people can work so rapidly because they tend to steal more. Creativity is inherently iterative. New ideas build on other new ideas and new practices involve small adaptations to existing practices. Austin Kleon has an excellent manifesto on this which is aptly titled “Steal like an Artist”. Strategic stealing allows you to skip the work that isn’t valuable and jump to the bits that are novel. It also prevents you from staring at a blank page, which can often be the most intimidating step in the creative process. But not all theft is the same. Austin has a nice list of features of good theft below:
But even if you steal like an artist, pushing for volume normally isn't easy. Adam Grant's excellent book Originals looks at the attributes of creative individuals and he finds that they tend to be more comfortable settling on "good enough" versions of ideas before pushing them into the world. Instead of constantly refining and tweaking their work, pushing for perfection, they are more like to just hit “send”. Often the last 20% of a bit of work takes 80% of the time, so one way to push for a higher quantity is to get comfortable skipping this last 20% altogether.
Another reason that this is hard is that people worry about how others will perceive their imperfect content. But these worries can be addressed. Creation is vulnerable; it takes intellectual risk to make something new and as noted above it won’t pan out all the time. If you work in a group, creating a psychologically safe environment where people trust each other is key to enabling people to take “scary” risks (see Amy Edmondson’s excellent book The Fearless Organization). This involves building trust, by opening up to others, communicating directly and avoiding a blame culture.
Cross-pollination of ideas
But quality of ideas does still matter…
There is a school of psychology that argues that all of creativity is just the linking of two or more, separate abstract concepts together in a novel (and adaptive) way. I think this is a little narrow, but the core of the idea is true: lots of creation comes from the applications of existing good ideas in a new domain.
A silly example of this is a game I occasionally play with my partner, when we’re bored and have run out of Success/White Lotus episodes. It’s called the “but for” game. You have to take an existing product then add “but for” followed by a category of user who would never use the existing product (it’s especially easy for software products): Uber but for Dogs, Wikipedia but for DIY advice, Couples Therapy but for Co-founders, … you get the idea (although that last one is something I think would work well). You’ll be surprised how often you come up with ideas that may sound absurd but probably have something to them. Games like this work because they feel low stakes, and you are building of tried and tested products which have already been successful for one type of user.
But games aren’t the only way you can force these abstract connections together, there are two main other practices which are important: don’t overly specialise too soon and stay curious.
David Epstein’s excellent book Range argues that, in many domains, retaining a degree of “generalism” until quite late in your career leads to better performance once you do specialise later down the line. Staying broad lets you see best practices from a wide array of different areas, which can often be applied to new contexts. It also means you’re less rigid in your thinking. For example, hyper-specialists tend to say phrases like “that’s just how we always do it” more than those that specialise later. This is not always true, but it tends to be the case in fields with lots of ambiguity and complexity. But these are exactly the kind of fields where creativity is valuable!
In organisations, cross-pollination of good ideas can also come from multidisciplinary teams and regular movement of people across different parts of the org. This tends to lead to “small worlds” networks which allows knowledge to spread much more quickly. This results in knowledge sharing, which in turn helps creative ideas have a bigger impact. It also means you have way more people working on distinct creative ideas in parallel, because you have enough information to avoid duplication and the company can more effectively avoid groupthink.
Cross pollination also comes from curiosity. Frank Keil’s book “Wonder” wonderfully examines curiosity as an active process of interrogating the world around you. This involves questioning assumptions, careful watching and listening, and “free range thinking”. Sadly, Keil also provides evidence of how most people are pushed to be less curious (especially about science) as we grow older and he argues the importance of continuously asking “how” and “why” questions to retain this curiosity.
Procrastination can be productive
This third one is weird. It turns out procrastination can really help you to be more creative. But before you drop whatever you’re working on and adopt a “university essay crisis” approach to all deadlines, I should warn you that there are good kinds of procrastination and bad kinds of procrastination. Adam Grant wrote an excellent article about this in the NYTimes which we’re going to “steal [some insights from] like an artist”.
The kind of procrastination that works best is where you do the framing work for a new task but you stop before you execute too much. You have to give you brain enough stuff to work on in the background, but leave it with enough breathing space to go in different directions.
There’s two bits of evidence which explains why procrastination helps:
First, procrastination can help your recall. In the 1930s, Psychologist Bluma Zeigarnik discovered that curiously stopping a task before finishing it leads to better recall of task-related information than if you finish the task all in one go. There’s something about incompleteness that forces you to consolidates the knowledge more over time, likely because you are accessing that information regularly until you finally complete the task.
Second, recent work by Nancy Andreasen has suggested that background processing is a creative process. When you rest and let your mind wander the areas of the brain that are active are the same areas as those used when actively focusing on creative tasks. When you leave tasks unfinished, you’re likely to engage with them in this “free association” state, which leads to more creative results.
It’s worth acknowledging that there’s a bit of a trade-off here between creativity and short term productivity. Adam Grant describes himself as a “pre-crastinator”. Someone who sets out to complete work as soon as he can to get it off his plate. This is an effective way of working for “execution-focused tasks” - i.e. when you know what needs to be done and you just have to execute. But, often the feeling of being busy is distracting you from doing the “complex, thinking tasks”. These involve ambiguity or messiness and don’t necessary benefit from rapid execution.
However, if the solution is to procrastinate these more complex tasks to allow background processes to take place, how can we achieve the first goal of producing more stuff?
If we think back to the example of artists, they typically have many projects on at the same time (this is especially true of oil painters who had to wait days for the oil to dry before working on the next layer). This allows them to procrastinate on one thing by working on other things. The result is a trade-off between creative-procrastination and productive-execution. This “work-in-progress” backlog should be familiar to many software engineers, but you have to be careful to keep a limit on the number of things that are in the “work-in-progress” in case they never get finished (a practice I’ve shamelessly stolen from Kanban best practices).
Another consideration is to have deliberate “down time”. Giving your mind time to wander can be difficult in our modern attention economy. But instead of listening to music on your commute or podcasts on your walks, try to retain some space for this active but restful background processing.
Desensitization to crazy ideas
As we outlined earlier, creativity involves novelty and intellectual risk. This risk comes from the fact that creative ideas are very different to how things are done today and we all have an aversion to novel, crazy-seeming ideas. This acts as a big barrier against creativity. But, amazingly, you can train yourself to be more tolerant of creative ideas by simply exposing yourself to those ideas more often. This acts similarly to exposure therapy and over time you reset what you consider to be “too crazy”.
Innovative companies have tried to build processes around this theme. Eeke de Milliano, former Head of Product at Stripe and current Head of Product at Retool, has explained two forcing mechanisms to get teams to put crazy ideas out there. First, at the bottom of every team charter (which gets updated quarterly) there is a dedicated section for “thinking bigger” where teams are asked “if you had 20% more time, what would you do that isn’t in your plan”. Second, at both Stripe and Retool, at the start of the year the CEO sends out a blank document to everyone called “Crazy ideas”. In the words of Eeke herself, “crazy ideas are ideas that we shouldn’t obviously do, and that probably won’t work 90% of the time. However, in the 10% of times they do work, they have the potential to 10x-100x the business”. These two processes create dedicated space and time for innovative thinking to be part of everyone’s jobs not something to be done on top of other work. It also results in people seeing ideas that may seem crazy frequently enough that they start to feel less insane.
These processes work especially well because this “desensitization” process is best done collectively. Collaboration has been shown to reduce "objectiveness" (read stubbornness) relative to individual working or group working in a competitive environment. Far from talking you down from a crazy idea, a truly collaborative team works together to test robustness and remove from implementing. This once again relies on a high degree of psychological safety within your teams, and works better in multidisciplinary teams where you have diversity of experiences and ways of working.
Constraints push you to think differently
We often get told to think outside the box. However, constraints can, counterintuitively, result in more varied and creative outputs. Social media companies have known this for a while - Twitter had a tight character length limit and Tik Tok (and previously Vine) keep video lengths super short; both of these platforms benefit from talented creators making content that you can’t find anywhere else.
This can be counterintuitive. When surveyed, CEOs and leaders think that the best way of fostering innovation is by removing barriers that constrain their teams. However, these constraints can be forcing mechanisms to push people to think differently about what they are making and how they can make it.
This is especially true of ill-defined problems. Constraints can narrow the option set down enough for people to feel like they at least have an idea of where to start. But it’s a bit of a balancing act; adding too many constraints to an already well-defined problems just results in a cookie cutter approach. So adding the right level of constraints can help hit a creative goldilocks sweet spot where people can reassess their assumptions and have freedom to explore, whilst at the same time avoid decision paralysis.
One way of introducing constraints is by asking people to do less instead of doing more, a practice from Leidy Koltz’s book Subtract. This book explains that people assume solving problems comes from adding things. Without prompting or constraining behaviour, people don’t ask themselves what they can take away to make something better. This bias results in over-engineered or costly solutions to problems. To help tackle this, people build “subtraction strategies”. Rick Rubin, the legendary music producer, talks about “the ruthless edit” where he massively cuts the amount of songs he puts in an album. If they start with 25 songs and their end goal is to get to 10 songs, they start by choosing the “6 songs they can’t live without” only then do they add the 4 songs that “make it better and not worse”.
Conclusion
Being creative is not magic, it’s the result of a series of (often counterintuitive) behavours. This post has outlined 5 of the most consistent findings, but there are several other “creativity boosting” behaviours that I haven’t included:
Working in a space which has more colour and has plants in it
Working on creative tasks in the afternoon instead of mornings
One consistent pattern across many of these behaviours is retaining an openness to new experiences. Think about how you can produce more diverse outputs, value a broader set of activities which includes time for rest and avoid working in teams where everyone thinks in the same way.
If you are an individual who wants to think more creatively, or a company who wants more innovation in your teams - the practices in this post should provide a starting point for shaping the environment and behaviour to help! Many of these behaviours have helped me.
Anyway, this post is probably good enough to put into the world. I’m going to hit publish and focus on the next few posts!
Relevant reading on this topic: Originals by Adam Grant, Range by David Epstein, The Fearless Organization by Amy Edmondson and Wonder by Frank Keil
