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Home Leadership

You Don’t Have To Beat the Odds — Just Play Them: Why Experimentation Drives Success

Winning ideas come from volume, not luck. Learn how leaders can turn unlikely bets into breakthroughs that shape products, science, and art.

Kyle Austin YoungbyKyle Austin Young
November 6, 2025
in Leadership
Reading Time: 3 mins read
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You Don’t Have To Beat the Odds — Just Play Them Why Experimentation Drives Success

Smart teams win by flooding the idea pool, using AI to push boundaries, and testing bold bets early.

Top-tier workplaces often boast a cafe, a fitness center, and nap pods. Ben & Jerry’s offers something much more unique—a cemetery. The Flavor Graveyard honors the legacies of ice creams that are “dearly depinted.” But the headstones are more silly than somber, featuring funny epitaphs for flavors such as “Holy Cannoli,” “Purple Passion Fruit,” and “Rainforest Crunch.”

Why does Ben & Jerry’s work so hard to celebrate these flops? Because failure is an important part of their business model. 

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When the company began operations in 1978, it entered a space with several established competitors. To carve out market share, leadership decided to invent exotic new flavors exclusive to the brand.

The result, in part, is over 300 discontinued ice creams. But over time, the strategy paid off, and the upstart organization produced several breakthrough ideas on the road to becoming the top selling ice cream brand in the United States.

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It’s a story all of us could learn from. We’re taught to prioritize high probability opportunities and pursue quality over quantity. In many contexts, this is wise advice, but every organization will face dilemmas where none of the paths forward offer a high chance of success. 

There simply isn’t a way to predict the popularity of an ice cream flavor with a whiteboard and an erasable marker.

In these moments, leaders have two options:

Pick one unlikely idea and try to “beat the odds.”

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Experiment with a long list of ideas, creating numerous opportunities for success.

Four Proven Strategies to Turn Experimentation Into Success

The appeal of option two is apparent at face value, and new research has uncovered strategies to help us exercise this often overlooked opportunity more effectively.

Incorporate artificial intelligence into your brainstorming. 

While new research has uncovered notable limitations in AI’s decision-making ability, recent studies also show that AI can serve as a valuable brainstorming tool. 

Its automated nature offers something similar to persistence in human ideation. Its ability to suppress “unrelated categories of knowledge” mimics focus. 

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Finally, AI’s lack of a personal agenda represents a quality similar to flexibility. While it’s still important for human leaders to take responsibility for outcomes, adding a persistent, focused, flexible thinker to the team is rarely a bad idea.

Evaluate your ideas against a clear definition of success. 

We’re often warned that too many options will overwhelm our thinking. History doesn’t fully support that claim. 

The quest to invent a practical incandescent lamp centered around one key issue: finding a filament that could get hot enough to glow for long periods of time without catching fire or burning out. 

Thomas Edison outcompeted his peers in pursuit of valuable patents by experimenting with 6,000 different plant materials. Through this inglorious process, he discovered an unlikely winner—carbonized bamboo. 

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Standards are an antidote to decision paralysis. Define success, and ideas worth pursuing will be more likely to reveal themselves.

Don’t settle for ideas that come easily. 

We often assume that once we’ve run out of easy ideas, there must be no good options left. This leads many people to undervalue ideas that don’t come easily — or to stop brainstorming altogether. 

Researchers out of Northwestern have dubbed this the “creative-cliff illusion.” As brainstorming drags on, it’s true that the frequency of ideas will usually decline. It’s also true that you might begin to feel tired and frustrated with the process. But studies show that, despite how you feel in the moment, the quality of your thinking will usually improve after the pace of new ideas slows down.

Pursue low probability steps early in your experimental process. 

Production thinking emphasizes the longest pole in the tent. Probabilistic thinking emphasizes the steps with the longest odds. When testing ideas, reordering projects to frontload unlikely prerequisites to success is a straightforward way to fail fast — and uncover opportunities with high potential ROI.

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Whereas people who get lucky are the winners of societal odds, people who try repeatedly act like their own miniature society, experiencing both the predicted failures and the predicted successes in a given set of circumstances.

Mozart composed over 600 pieces of music. Beethoven wrote over 700. Van Gogh painted and sketched so prolifically, he averaged roughly one new work of art every 36 hours for 10 years. 

Add these case studies to the stories of Ben & Jerry’s and Thomas Edison, and we find that — across disciplines — quality often lives on the other side of quantity. 

Whether you’re trying to launch a successful product, reach an important scientific discovery, or create enduring works of art, playing the odds can make unlikely successes closer to inevitable.

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Kyle Austin Young

Kyle Austin Young

Kyle Austin Young is the author of SUCCESS IS A NUMBERS GAME: Achieve Bigger Goals by Changing the Odds (Hay House Business, November 11, 2025). He is an award-winning strategy consultant for high achievers, entrepreneurs, and leaders in a wide range of fields. This work has given him the opportunity to develop and refine a powerful system for accomplishing big, meaningful goals that focuses on understanding and changing your odds of success. Kyle is a popular writer for Harvard Business Review, Fast Company, The Boston Globe, CNBC, Psychology Today, Forbes, and Business Insider.

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