Inspired by Bill Watterson, this article is about creativity and tactics to lead a creative life.

Bill Watterson on Creative Work

My current inquiry revolves around how I invest my time and the value I create. Over this week, I have been reflecting on essential questions about my work and business.

Bill Watterson’s insight – the Calvin and Hobbes creator – during his commencement address for Kenyon College has been ringing in my ears. I revisited his speech this week. Let me share a few select lines about creative work with you, coupled with my thoughts.

It’s surprising how hard we’ll work when the work is done just for ourselves.

This line cuts to the centre of current thinking. How much agency, choice, and control do I have over my time and creativity? I am filtering opportunities more strictly and carving out the space for work that I instigate.

If I’ve learned one thing from being a cartoonist, it’s how important playing is to creativity and happiness […] I’ve found that the only way I can keep writing every day, year after year, is to let my mind wander into new territories. To do that, I’ve had to cultivate a kind of mental playfulness.

When I reflect on my week, or even as I plan, how much time is discrete and restricted or open and playful? Where do you cultivate your mental playfulness?

it’s worth recognizing that there is no such thing as an overnight success. You will do well to cultivate the resources in yourself that bring you happiness outside of success or failure. The truth is, most of us discover where we are headed when we arrive.

That is a great challenge: “cultivate the resources in yourself that bring you happiness”. I am encouraged and provoked to think about how this looks outside the simple dichotomy of success/failure.

Please look at this summary of his speech from Brain Pickings, Advice on Life and Creative Integrity from Calvin and Hobbes Creator Bill Watterson.

“The truth is, most of us discover where we are headed when we arrive.”

Bill Watterson

Mental Decluttering

Conversations this week with leaders had a throughline about time and the hectic pace of school operations. I recalled a memorable phrase Bill Watterson used in a Calvin and Hobbes strip.

There’s never enough time to do all the nothing you want.

Perhaps this is the space for mental playfulness.

I explored some past writing, where I studied the change of pace, the impact of slowing down and how reflection needs quality time.

Freedom to wander


I feel a mental decluttering as soon as I am a few days into the break, and it allows me the freedom to peruse some connections or projects I have had to ignore.

Recently I went for a walk with my son*. I love to stroll along at his pace. It’s great. There is no hurry. He came across a tree and wandered around it several times. Exploring the possibilities, it held – feeding his curiosity. He stopped and continued to walk – but then he went back to the solitary trunk and went round again. Time was no issue.

There it was, precisely what I enjoy about the holidays during the year, no time constraint – freedom to wander off but then return to a thought if you want to. That is what I want from a teaching job – built-in reflective time to explore ideas. Not as a bolt-on or rooted in the time away from school, but intrinsically part of your working routine. A routine that understands and values how vital that time is.

*My son was about two years old when I wrote this. It is incredible how quickly these habits change as they journey through school.

The pace of life and the structures of time define us.

Lose Yourself In Your Work

Let’s round out this issue with Bill Watterson’s suggestions for a creative life/process:

  1. You Have To Lose Yourself In Your Work
    “My comic strip was the way that I explored the world and my own perceptions and thoughts. So to switch off the job, I would have had to switch off my head. So, yes, the work was insanely intense, but that was the whole point of doing it.”
  2. Create For Yourself
    “Quite honestly, I tried to forget that there was an audience. I wanted to keep the strip feeling small and intimate as I did it, so my goal was to make my wife laugh. After that, I’d put it out, and the public can take it or leave it.”
  3. Make It Beautiful
    “My advice has always been to draw cartoons for the love of it, and concentrate on the quality and be true to yourself. Also, try to remember that people have better things to do than read your work. So for heaven’s sake, try to entice them with some beauty and fun.”
  4. Every Medium Has Power
    “A comic strip takes just a few seconds to read, but over the years, it creates a surprisingly deep connection with readers. I think that incremental aspect, that unpretentious daily aspect, is a source of power.”