The Art of Desirable Accidents: Embracing Improvisation
On The Power Of Oops
The skill to improvise is to unhesitatingly realize a desirable accident.
These moments of discovery flourish where there’s safety to experiment. Supportive making allows for creative mistaking — creating spaces where we lift each other up rather than cause tears to fall. When a community values both attempts and achievements equally, we all discover those productive accidents that lead to our most original work. In an increasingly critical world, these nurturing environments aren’t just kind — they’re the essential soil where I’ve seen true innovations take root. And blossom 🌻🌞
In the creative process, we often speak of planning, strategy, and deliberate action. But what of those unplanned moments, those spontaneous decisions that lead us to unexpected territory? These are what I’ve come to call “desirable accidents” — those unintentional discoveries that become the most meaningful breakthroughs in our creative journey.
The skill to improvise is to unhesitatingly realize a desirable accident. It captures something essential about creativity — that our greatest innovations often emerge not from rigid adherence to a plan, but from our ability to recognize and develop the unexpected when it appears before us.
Improvisation isn’t merely reacting; it’s actively engaging with the present moment with all of your creative faculties aligned. It requires presence, awareness, and a certain comfort with uncertainty that many find unsettling. Spontaneity isn’t something you can consciously strive towards as it is by definition unplanned. The paradox is evident: we cannot plan to be spontaneous, yet we can create conditions where spontaneity thrives.
Feel The Rhythm
Feeling the rhythm is more important than knowing the tune.
Think of jazz musicians, whose training doesn’t eliminate improvisation but rather prepares them to improvise more meaningfully. Feeling the rhythm is more important than knowing the tune. The rhythm provides the framework within which creative spontaneity can flourish.
This balance is delicate. People who make things tend to discount planning or strategy because:
- There’s always unpredictable events while making.
- The act of making accordingly reveals new possibilities.
Thus the act of creation itself unveils options that no amount of planning could anticipate. Each creative decision opens new doors while closing others, creating a constantly shifting landscape of possibility.
Leadership Matters
The creative leader always questions authority. Even when it is her/his own.
The most innovative minds I’ve encountered share this quality: they maintain a flexible relationship with their own plans. The creative leader always questions authority. Even when it is her/his own. The best creative thinkers remain willing to abandon their preconceptions when a better path emerges.
For those seeking to cultivate this improvisational mindset, I suggest developing what I call “supportive making” — an environment where experimentation is encouraged and failure is viewed as information rather than defeat. Supportive making allows for creative mistaking. When we remove the fear of error, we open ourselves to those productive accidents that often lead to our most original work.
This approach doesn’t mean abandoning rigor. Rather, it requires a different kind of discipline — the discipline to remain open, attentive, and responsive to what emerges in the moment. When cognitive dissonance is high, one can find and make new tunes out of the noise accumulating in one’s mind (and heart). Discomfort and contradiction often signal fertile ground for creative discovery.
Try To Remain Flexible
Programmers eliminate bugs; artists, instead, appreciate bugs. We should all be so accommodating.
The digital world has added new dimensions to this improvisational approach. Programmers eliminate bugs; artists, instead, appreciate bugs. We should all be so accommodating. Consider how unexpected outcomes might be re-contextualized not as errors but as creative opportunities.
Ultimately, embracing desirable accidents requires faith in your creative instincts. It means trusting that even when you’ve strayed from your intended path, you may have wandered into territory far more valuable than your original destination. In our increasingly structured and optimized world, this capacity for productive wandering may be more valuable than ever.
“By the time you have come to the perfect solution, the problem’s already changed.” — Jessie Shefrin
As I continue to navigate the intersections of design, technology, and art, I remain convinced that our most profound innovations will come not from perfect execution of predetermined plans, but from our ability to recognize, celebrate, and develop those unexpected moments where possibility reveals itself. The art of the desirable accident isn’t just about luck — it’s about creating the conditions where productive accidents can occur, and having the wisdom to cultivate the best ones that emerge. — JM
