The Failure Trophy: What Event Marketing Taught Me About Real Leadership

Forced to abandon our successful in-person Creative Jam playbook overnight, our team stood at the edge of pandemic uncertainty—until my mentor’s counterintuitive advice to “fail spectacularly” unlocked a journey of experimentation that would transform our events in ways we never imagined possible.

When the pandemic forced our Creative Jam events team to go entirely virtual, we found ourselves in completely uncharted territory. Our in-person playbook? Useless. Our event pipeline? Irrelevant. Our confidence? Let's just say it took a serious hit.

Enter my mentor, Ben, who somehow managed to be the calmest person in our digital war room.

He said that this was the perfect opportunity to fail spectacularly. I thought he was joking. He wasn’t.

But I knew what he meant. He had already tasked me to scale the program by transforming in-person Adobe Creative Jam events into virtual ones.

For over half a decade, Adobe’s Creative Jam program had been running with great success and brand recognition. These in-person design competition events were held all around the nation, stopping at different cities and companies to gather teams of designers to use Adobe software and develop an app prototype to solve a challenge in just 3 hours.

Before the pandemic, I experimented with webinar formats and hired teammates to support them while the rest of the Jam team toured the country with successful in-person competitive events at universities and commercial headquarters.

The virtual Jam program, which I lovingly named Creative Jam LIVE, drew up to 450 live attendees but averaged ~200 per event. Not bad, but not great.

When the pandemic hit, all of a sudden everyone was on my team. With in-person events no longer possible, our entire operation needed to pivot to virtual—and fast. This sudden shift created the perfect testing ground for Ben’s philosophy about embracing failure.

The Permission to Fail

In an industry obsessed with celebrating attendance numbers and engagement scores, Ben's approach felt radical. While other leaders were demanding guaranteed wins during uncertain times, he was actively encouraging us to experiment—even when those experiments might flop.

“It’s okay if we don't hit our registration goal,” he’d say, “as long as we learn something valuable that shapes our next attempt.”

This wasn't just empty talk. When our first two-day Jams underperformed despite weeks of preparation, Ben didn't ask who was responsible. Instead, he asked, “What did we learn that we couldn’t have discovered any other way?”

That simple reframing changed everything.

The Creative Jam Laboratory

With the pressure to appear perfect removed, our little virtual Jam team transformed into something closer to scientists than event planners. We started treating each event as an experiment with a hypothesis to test:

• Would bringing on judges from well-known and ‘cool’ companies impact registration numbers? (Spoiler: dramatically, but not always in ways we predicted)

• Does breaking a day-long virtual event into multiple days increase or decrease overall engagement? (The answer was complicated and customer-dependent)

• How would changing the incentive structure increase challenge submissions? (This one, we played with the most)

Some experiments worked beautifully. Others failed spectacularly—like when our Jam winners weren’t responding to texts and couldn’t call them to the stage to accept their grand prize (and that’s when we realized we needed a line producer). But each attempt, successful or not, gave us data we couldn’t have obtained any other way.

The Counterintuitive Math of Innovation

What I’ve come to understand is that innovation follows a counterintuitive formula:

Success isn't about minimizing failures. It’s about maximizing learning opportunities.

When our team stopped trying to maintain a perfect batting average and started swinging for the fences, our approach to virtual events evolved faster than other teams. While they carefully rolled out minor tweaks to avoid any possible failure, we were rapidly iterating through ideas—some brilliant, some disastrous, all informative.

The most valuable insights often came from our least successful attempts:

• Without a prepared script, our chat moderator struggled to respond quickly to conversation shifts during the networking segment.

• Reviewing scripts and cue sheets as a team before rehearsals strengthened our remote production process, mirroring our in-studio standards.

• Technical failure during our first multi-university Jam led to creating backup plans that later rescued several events.

Our experimental approach paid off. For example, before the pandemic, the Disney Creative Jam LIVE event had 750 registrants, with 290 showing up and attending live.

With Ben’s encouragement to embrace learning through experience, combined with pandemic pressures, we were pushed to innovate more aggressively to improve and exceed targets.

By April, our attendance surged dramatically. The Airbnb Jam attracted over 3,000 registrants with 1,766 attending live, while the Netflix Jam drew nearly 7,500 registrants with 2,864 students participating in the live event.

Leading Through Uncertainty

Ben’s approach to leadership wasn’t just about embracing failure—it was about redefining what success means in uncertain environments.

Traditional management often treats failure as evidence that something is wrong with the system or the people within it. Ben understood that in rapidly changing circumstances, failure is evidence that you’re pushing boundaries and adapting.

His perspective came down to a simple question: "Would you rather have a team that never fails and makes incremental progress or a team that fails productively and makes exponential progress?"

Put that way, the choice seems obvious. Yet most organizational cultures still punish failure so severely that people become risk-averse by necessity.

The Practical Magic of Failure

This isn’t just philosophical—it’s intensely practical. When I started leading my own team, I tried to bring this failure-positive approach with me, and the results speak for themselves:

• Team members bring problems to light earlier when they know failure isn’t career death

• Innovation happens faster when people aren’t paralyzed by the fear of making mistakes

• Resilience becomes a core competency rather than an occasional necessity

• The overall quality of successes improves because they’re built on lessons from previous failures

I still remember one team member who reported that students were not able to see Creative Jam brief PDFs while on their mobile phones. Instead of disappointment, I felt excitement. “Perfect,” I said. “Now we know exactly what doesn’t work, and we can build something better.” (Easy fix: we moved Jam briefs to HTML pages, and our student participants were ecstatic.)

The look of relief on her face was priceless—and the improved Jam brief she developed afterward became one of our most successful templates and was faster to create.

The Leadership Challenge

The challenge for leaders isn’t just giving lip service to the idea that failure is acceptable. It’s creating an environment where productive failure is genuinely valued—where people don’t just hear “it's okay to fail” but believe it because they see it in action.

This doesn’t mean celebrating all failures equally. There’s a world of difference between careless mistakes and ambitious attempts that don’t quite work out. The former should be minimized; the latter should be examined for their learning potential.

Ben taught me to ask better questions about failure:

• What specifically didn’t work as expected?

• What assumptions did we make that proved incorrect?

• What would we do differently knowing what we know now?

• How can we apply this learning immediately?

These questions transform failures from embarrassments into assets.

Key Takeaways

In a business landscape that often feels allergic to anything less than perfection, creating space for productive failure might be the most important advantage you can give your team.

The pandemic brought us a fluid and fully remote production system and the experimental mindset that turned virtual necessity into opportunity—and the knowledge that our biggest failures often laid the groundwork for our biggest innovations.

Scott Belsky, our former Chief Strategy Officer and EVP of Design & Emerging Products at Adobe, recently posted this on LinkedIn:

I fully endorse this approach. Taking bigger risks and embracing quick failures allow us to learn faster and achieve success sooner.

So here’s to the leaders brave enough to encourage smart risks. To the teams willing to learn through trial and error. And to redefine success not as the absence of failure, but as the presence of growth.

What’s the best thing a failure has taught you lately?

This article is dedicated to mentors like Ben, who know that showing people how to fail productively is one of the greatest gifts a leader can give.