The art of embracing chaos: understanding creativity through the ‘squiggle’
Getting started, or moving from potential to kinetic energy
Let’s start with a riddle. What’s something you can see that symbolizes the “untidy process of creativity” — as Jason Kottke called it — even if you don’t fully recognize it? I’ll give you a hint: Kottke, the O.G. blogging powerhouse behind kottke.org, put it on a t-shirt last year, selling thousands.
The answer to the riddle, the “untidy process” is visualized as a single line but not a straight line. Instead, it’s a wild, oscillating, looping scribble that twists and turns, gradually evening out its path before, more or less, straightening out.
This line is Damian Newman’s iconic ‘squiggle,’ a deceptively simple visualization of the design process that has resonated with problem-solvers across industries for nearly two decades. Here’s how Newman describes it:
The Design Squiggle is a simple illustration of the design process. The journey of researching, uncovering insights, generating creative concepts, iteration of prototypes and eventually concluding in one single designed solution. It is intended to convey the feeling of the journey. Beginning on the left with mess and uncertainty and ending on the right in a single point of focus: the design.
Kottke adds another layer to its meaning on his initial post about the t-shirt’s launch:
Although it originated in the design world, the Squiggle is handy for understanding or describing the process of many different creative endeavors. If you asked a chef, a scientist, a writer, a programmer, or an artist to describe how they got from their starting point to an end result, I think it would look a lot like the Squiggle. So what’s this shirt about? The Process of Design. The Process of Writing. Cooking. Art-making. Science. Learning a New Skill. Creativity. The Messy Process of Becoming a Better Human.
Again, here’s a breakdown of what the ‘squiggle’ might represent, according to Kottke:
- The process of design
- The process of writing
- Cooking
- Art-making
- Science
- Learning a new skill
- Creativity
- The messy process of becoming a better human
And the list could go on and on and on. Let’s dig into the ‘squiggle.’
Looking closer at the long and winding line
At first glance, the ‘squiggle’ might seem like a simple drawing, but upon a closer examination, you can see how within its tangled loops, the path grows less erratic as it gets calmer from left to right, showing how we might navigate uncertainty and work through a disorganized state to reach clarity.
Now, picture yourself at the very start of that ‘squiggle,’ all the way to the left. It could be a current situation or somewhere you’ve found yourself in the recent past. There might be a variety of factors — maybe it’s a complex problem, incomplete information, and a timeline that feels far too short. Conventional wisdom might tell you to gather more data, to wait until the path forward is clear. But in today’s fast-paced world, waiting is a luxury we often don’t have. Many times, we push forward — through the chaos, iterating, shifting, pivoting — hoping that the process and the people around us, will guide us toward clarity and, hopefully, a solution.
But even with a great team and solid processes in place, the path forward isn’t always smooth. Cue Jonathon Courtney and AJ&Smart’s notion of “collaboration chaos” or the unpredictable, messy reality of bringing multiple perspectives together. Challenges aren’t just possible; they’re inevitable. Misalignment, shifting priorities, and communication breakdowns all show up when navigating the fuzzy middle of problem-solving. Yet, it’s in this chaos that breakthroughs happen. The friction, the push-and-pull of ideas, the pivots and course corrections — these are the building blocks that lead to insight and progress. It’s not about avoiding the chaos, but embracing it as part of the process.
And then, from stage right help enters.
Strong opinions, loosely held
During my time at thoughtbot, leading the design side of the San Francisco studio, one of the most impactful things I learned was the importance of cultivating an adaptive mindset, or having strong opinions, but holding them loosely. While I’d encountered this idea before, this mindset was transformative for navigating the uncertain and often chaotic early stages of projects and processes. Whether part of a team or solo, I could commit to a direction with confidence while remaining flexible enough to adapt as new information emerged. It wasn’t just about finding a solution quickly — it was about maintaining both agility and speed throughout the process.
Whether in design, leadership, or some other role, understanding how to hold firm opinions but adjust as the landscape shifts is essential for anyone facing complex, dynamic challenges. This mindset is an integral part of navigating the ‘squiggle,’ a concept Stanford professor Paul Saffo has further developed.
Holding strong opinions loosely encourages us to act or predict even when we don’t have all the information. Say you’re asked to estimate the impact of a product change or forecast the revenue potential of a new business opportunity. You might not have all the data you’d like to have, but that doesn’t mean you should wait. Instead, form a tentative hypothesis — your “strong opinion” — based on the information you have. Then, actively seek data to either support or challenge it. The key is to be willing to change your hypothesis when new information contradicts it. It’s about adapting based on what you learn, not stubbornly clinging to your original idea. In fact, the quicker you uncover contradictory information, the faster you refine your understanding and get closer to the right answer.
Saffo puts it in this way:
I have found that the fastest way to an effective forecast is often through a sequence of lousy forecasts. Instead of withholding judgment until an exhaustive search for data is complete, I will force myself to make a tentative forecast based on the information available, and then systematically tear it apart, using the insights gained to guide my search for further indicators and information. Iterate the process a few times, and it is surprising how quickly one can get to a useful forecast.
This is the core of “strong opinions, loosely held,” sometimes also called “strong opinion, weakly held.” Saffo continues:
Allow your intuition to guide you to a conclusion, no matter how imperfect — this is the ‘strong opinion’ part. Then — and this is the ‘weakly held’ part — prove yourself wrong. Engage in creative doubt. Look for information that doesn’t fit, or indicators that [point] in an entirely different direction. Eventually your intuition will kick in and a new hypothesis will emerge out of the rubble, ready to be ruthlessly torn apart once again. You will be surprised by how quickly the sequence of faulty forecasts will deliver you to a useful result.
The first step in this approach is forming a strong opinion relatively quickly. But how do you do that? You need a toolkit of problem-solving frameworks, paired with the intuition that comes from pattern recognition and experience. Tools like deductive, inductive, or abductive reasoning; developing a decision tree or issue tree; or performing root cause analysis and asking “five whys.” In a design sprint, for instance, you might craft “How Might We” statements after stakeholder or group interviews to outline key challenges and problem areas, with the group then voting on which to tackle within the workflow.
If you’re exploring unfamiliar territory, consult experts and refine your hypothesis as you gather insights. By blending structured frameworks with intuition, you can confidently form a strong opinion and iterate toward the best possible solution.
Trust the process
Navigating the ‘squiggle’ effectively requires more than just patience — it demands a mindset built on flexibility and informed decisiveness.
Newman’s ‘squiggle’ is not just a clever visual; it’s a reflection of the real, often messy process of problem-solving and creative work. From the early-stage chaos, full of loops and dead-ends, to the gradual emergence of patterns and clarity, this journey is something we all encounter in our work, regardless of our specific field.
But how do we push through that mess? How do we find clarity when the path ahead is anything but straight? This is where Saffo’s principle of “strong opinions, loosely held” becomes invaluable. By forming a confident hypothesis and actively testing it against new data, you create momentum in the face of uncertainty. And crucially, when that new information challenges your original thinking, the ability to pivot — to let go of your initial idea — becomes the real superpower. It’s not about being right from the start but iterating quickly and continuously learning along the way.
As you move from the chaotic loops to the more refined curves of the ‘squiggle,’ clarity builds gradually. Each pivot, each reframe brings you closer to understanding the problem and finding the solution. And when you finally reach that straight line — when the solution becomes clear — it’s not an end, but a signal that you’re ready for execution.
This approach applies across disciplines, whether you’re a designer refining a product, a business leader steering a team through a strategic shift/pivot, or a creative navigating the challenges of innovation. The ‘squiggle’ reminds us that chaos is not a roadblock — it’s part of the journey.
And by embracing tools like “strong opinions, loosely held,” we can turn that chaos into clarity, moving through the mess with purpose and agility.
So, the next time you find yourself at the start of a ‘squiggle,’ staring at a blank page or an unsolved problem, remember: the path forward might not be clear, but the process — however chaotic — and your instincts will guide you.
Trust it, adapt as you go, and lean into the friction. The clarity will come.
Thanks for reading. Let us know what you think, drop a comment or get in touch some other way, we’re always open to hearing others’ points-of-view — if it’s different or the same as ours.
Citations:
- https://thedesignsquiggle.com/ — Newman’s “design squiggle”
- https://www.skmurphy.com/blog/2010/08/16/paul-saffo-forecasting-is-strong-opinions-weakly-held/ — This isn’t Saffo’s original post but this blog entry outlines the main parts of his “Strong Opinions, Loosely Held” framework
- https://kottke.org/23/09/the-process-tee — Kottke’s original t-shirt announcement
- Design sprint methodology and “How Might We” statements as learned from Fjord (now Accenture Song), thoughtbot, and AJ&Smart among others
