UBA103 - You Win or You Learn
A Philosophy for Creative Risk and Cultural Impact
This article is inspired by Leila Fataar said when I was on her podcast 'Cultural Voices' dropping soon
"You can measure performance, but you can't always measure presence."
In the creative industry, there are no failures: only outcomes. Some outcomes align with our vision, others teach us something we couldn't have learned any other way. This mindset shift from "success or failure" to "winning or learning" fundamentally changes how we approach risk, creativity, and growth.
But there's something deeper at play here. The most meaningful creative work doesn't just succeed or fail in conventional terms: it lingers. It shapes perception. It shifts culture.
The Binary Trap
Too often, we frame our projects, campaigns, and creative endeavours in binary terms. Success or failure. Hit or miss. Win or lose. But this framework is limiting and, frankly, inaccurate. It reduces the complex, nuanced world of creative work to a simple scoreboard.
When we only measure success in terms of immediate wins, we miss the deeper value that comes from experiences that don't go according to plan. We discount the insights that emerge from the messy, uncertain middle of the creative process.
Beyond Data: The Cultural Waterline
This is where the conversation becomes truly interesting. Data and information are important: we need metrics, we need accountability. But they're not the complete way to assess many of the projects we work on. The most meaningful creative work transcends the immediate project and moves into culture, creating a halo effect that ripples through brand perception and leaves a waterline mark on society for years to come.
Creative failure isn't binary: it's radiant. Some projects miss the mark but generate disproportionate curiosity or cult appeal. Others achieve what spreadsheets can't track: a halo effect that ripples out for years, subtly reshaping how a brand is perceived or how a cultural movement gains traction.
When creative work aligns with cultural energy, it doesn't just succeed on delivery, it becomes a reference point where one bold move continues to illuminate future decisions, collaborations, and consumer expectations. Think about the campaigns, installations, and experiences that people are still talking about years later. They may not have delivered the highest click-through rates or the most immediate sales, but they shifted something cultural.
This cultural impact is often invisible to traditional measurement but creates value that compounds over time. It's what makes creative leadership so different from operational leadership. You're not just managing teams and timelines: you're shepherding work with resonance potential. Data can track impact, but it can't always track meaning.
The Learning Mindset
What if, instead, we approached every project with the understanding that we will either achieve our intended outcome or gain something equally valuable: knowledge, insight, experience, or perspective that prepares us for the next challenge?
This isn't about participation trophies or feel-good platitudes. It's about recognising that in creative work, the process of attempting something ambitious often yields returns that aren't immediately visible on a profit and loss statement.
Consider the projects in your portfolio that didn't launch as planned. The campaigns that got killed. The concepts that were deemed "too risky." What did you learn from those experiences? How did they shape your approach to subsequent work? Often, these "failed" projects become the foundation for future breakthroughs.
Take Nike's Nothing Beats a Londoner (2018). It was pulled for legal reasons, yet its creative DNA influenced countless campaigns that followed: from both Nike and its competitors. Technically: a failure. Culturally: a waterline.
Sometimes winning means:
Taking a creative risk that expands your capabilities
Building stronger relationships with collaborators
Discovering a new technique or approach
Understanding your audience in a deeper way
Developing resilience and problem-solving skills
Creating work that leaves a cultural waterline
When we expand our definition of winning to include these less tangible but equally valuable outcomes, we create space for more experimental, boundary-pushing work.
The Learning Portfolio
Just as we curate portfolios of our creative work, we should curate portfolios of our learning. What insights have emerged from projects that didn't meet their original objectives? What patterns do you notice in the challenges that arise repeatedly? What skills have you developed through navigating uncertainty?
This learning portfolio becomes as valuable as your creative portfolio: a repository of wisdom that informs future decisions and builds confidence in your ability to handle whatever comes next.
Cultural Impact and Organisational Change
Organisations that embrace "you win or you learn" create cultures where people feel safe to take risks, experiment, and push boundaries. They foster environments where innovation thrives because the downside of attempting something ambitious is learning rather than punishment.
This doesn't mean lowering standards or accepting mediocrity. It means maintaining high standards whilst creating psychological safety around the exploration required to reach those standards.
More importantly, it means recognising that some projects succeed in ways that extend far beyond the initial brief. They create cultural moments, shift perceptions, and establish new conversations that continue long after the campaign ends. These cultural waterline marks become part of a brand's legacy: invisible to quarterly reports but invaluable to long-term brand equity.
Failing Better
Failure has been cleaned up. TED-ified. Made into a bullet point. But real creative failure: the kind that hurts, that goes public, that shakes your confidence, is often where your voice sharpens. It's where intuition replaces PowerPoint.
Creative leaders have a responsibility to take risks that matter: not just to the campaign, but to the culture. The goal isn't to eliminate failure: it's to extract maximum value from every experience, whether it unfolds as planned or takes you somewhere unexpected.
This means choosing creative directions that are risky, meaningful, and memorable. Not safe. Not optimised. Not A/B tested into cultural nothingness.
Moving Forward: Leave a Mark, Not Just a Metric
The next time you're evaluating a project outcome, ask yourself: What did we win? And what did we learn? Both questions are equally important, and the answers to both contribute to your growth as a creative professional.
Some projects will win in the traditional sense. Others may teach more, reveal more, and echo longer in ways that data simply cannot capture.
You win or you learn. Either way, you move forward. Either way, you leave a mark.
Written by Mark
