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On balancing creativity and logical reasoning

First published: 21 Nov 2025 Last updated: 21 Nov 2025

I recently came across an old presentation I did for my team about finding the right balance between creativity and logical reasoning. As a fully remote team that comes together a couple of times a year, I'm reminded of this coming off the back of our recent All Company meetup in Atlanta.

I was originally inspired by this great video from John Cleese on Creativity. It was made for marketing executives, but, it has so many parallels to design or engineering at companies these days.

A lot of these ideas aren’t new (I mean the talk was done in 1991) but the shift to fully async and remote work got me thinking more deeply about it originally. I also tend to struggle with coming up with novel or truly creative ideas versus shipping the idea I know is the most technically feasible, so figuring out ways to be in a state of play or creativity is essential to me doing my best work.

I wanted to write about this today to reinforce it again for myself, but also as a way to hopefully remind you all too the importance that “play” has in being creative.

Some important factors to start...

  • Creativity is not a talent, it’s a way of operating
  • Creative people are able to enter a state of play
  • On a daily basis we typically live in a mode considered “closed”
  • You’ve got a thousand things to do and your mind is focused on being busy and somewhat anxious
  • By contrast, being “open” looks a lot nicer.
  • You’re relaxed, explorative and open to ideas (But, you probably can’t live like this forever unless you live that “van life” and are able to work on your own schedule permanently)

And some useful context on the discovery of Penicillin... Alexander Fleming, when discovering penicillin, had one empty dish of cultures amongst a series of dishes containing live cultures. If he’d been in a “closed” mode, he’d likely have thrown it away assuming it was busted. But, because he was in an “open” mode, he investigated it further and discovered penicillin as a result. Boom.

Exercising these ideas

Create an environment where you can switch between open & closed

We need to begin in an “open” mode to discover and explore ideas and get to a series of solutions. We then need to switch to a “closed” mode in order to effectively execute on the idea (convergence). We then immediately need to switch back to “open” to review these ideas and outcomes so’s not to be a “closed” Fleming in our previous example. Then back to “open” to diverge again… and so on.

Thus, aligning a lot with the way processes and tools like everyone's favourite Design Thinking or Double Diamond approaches work. The problem is, we too often get stuck in our “closed” mode when we’re in a time that actually desperately requires us to be in a state of being “open”.

Entering an open mode takes four key things

  1. Space
  2. Time
  3. Confidence
  4. Humour

Space

  • Create space for yourself away from the demands of the day. Working from home makes this complex because work and life blend so creative space can be harder to find
  • Seal yourself off. Try to block out distractions like product notifications, and all other tools. Going offline can be highly valuable here. You'll be fine, and so will your team... we make software, we don't save lives
  • Enter a true state of deep work and focus

Time

  • Set a specific period of time, and stick to it! Providing these time boxes enables your brain to switch
  • It’s easier to do trivial things that are urgent than important things that are not urgent
  • Urgency vs. Importance (see The Struggle between Urgency and Importance: Getting Your Priorities Right). Something can be Urgent & Important, Urgent & Not Important, Not Urgent & Important and Not Urgent & Not Important. Great creativity exists in the space that is Not Urgent & Important. Getting to this involves having confidence in committing to getting it done. Its easier to do little things we know we can do, versus big things we’re not sure about
  • Sometimes, the most important thing to do is sit in the space of discomfort, and continue playing instead of jumping immediately to the solution that is staring right at you. It’s about battling the anxiety that exists when you’re not confident in what you’re doing, rather than taking the idea immediately in front of you to satisfy that discomfort

Confidence

  • Fear of making a mistake is the biggest thing to impact being in a creative space
  • It’s not possible to be playful if you tell yourself that it’s possible to be “wrong” when playing/exploring
  • Its important to take risks in ideas that are silly, ridiculous or “impossible”
  • So when you get stuck, start generating random connections and allow your intuition to tell if you one of them will lead you somewhere interesting. Edward De Bono’s lateral thinking is key here.

Humour

  • Don’t be afraid to laugh at your ideas and let others do the same
  • Humour can be a great communicative device

Hopefully some of this is helpful! Rediscovering this talk I gave internally actually did inspire me to sit in that discomfort a little longer on my most recent project.

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