The Art of Failing Forward: How to Win by Losing 90% of the Time

A recent conversation with a dynamic and successful acquaintance brought a simple yet powerful strategy to light. When asked about the key to his forward momentum, his answer was disarmingly straightforward. He simply tries a lot of things. He sees an opportunity and acts on it. He has an idea and he tests it. The whole strategy, he explained, is built on a surprising acceptance of failure.

This approach offers a profound lesson for anyone standing on the diving board of a new venture, hesitating to take the plunge.

The Principle of Volume

The core of his method wasn't a secret formula, but a law of averages. He estimated that 70 to 90 percent of his attempts result in nothing—complete dead ends. They don't work out. But the remaining 10, 20, or 30 percent? Those are the ideas that gain traction. Once he identifies something that works, he focuses his energy and pushes it forward.

This is a powerful re-framing of success. It isn't about having a perfect plan or avoiding missteps. Instead, progress is a direct result of the willingness to experiment, to accept a high rate of failure, and to recognize the small percentage of success when it appears. The entire strategy is to generate enough attempts so that the successful minority can emerge and flourish.

Decoding Resistance

It’s a common experience: an idea sparks in your mind, charged with energy and possibility. You feel a surge of motivation, a clear vision of what you want to create or accomplish. You go to sleep certain that tomorrow is the day you begin. But when morning comes, the euphoria has evaporated, replaced by a litany of excuses.

The resistance can be almost absurd. You might be on your way out the door to finally start the very project you dreamed of, and a minor inconvenience, like running a few minutes late, suddenly feels like a cosmic sign that you shouldn't proceed.

But what if this internal resistance isn't a signal to stop? What if it's the opposite? When you have an idea that generates energy, and your mind then works overtime to sublimate that energy into anything but action, you have likely found a critical point of growth. Stepping over that self-imposed barrier and doing the thing you planned is precisely what leads to development. The friction itself indicates that you are pushing against your own limitations, which is the only way to expand them.

The Inevitability of Risk

This internal battle against inaction is directly connected to our broader relationship with risk. Mark Zuckerberg once offered a compelling perspective on the subject, stating that the biggest risk in life is not taking any risks at all.

At first glance, this seems counterintuitive. We spend much of our lives trying to mitigate risk. We want a stable job, a financial cushion, and a predictable future. We try to organize everything to be prepared "just in case." In essence, we try to build a fortress against uncertainty.

The flaw in this thinking is that risk is unavoidable. The world is too dynamic and fast-moving for any fortress to be impenetrable. When you actively avoid taking calculated risks—like starting a new project, testing a business hypothesis, or introducing yourself to a new person—you don't eliminate risk; you merely forfeit control over it. Risks will happen to you. A change in the economy, a shift in your industry, an unexpected global event—these things can shatter a carefully constructed comfort zone. You find yourself in a risky situation without being prepared and without having initiated the terms of engagement.

The person who takes a calculated risk is in the driver's seat. The person who avoids all risks is a passenger. This leads to a powerful conclusion: if you don’t make a decision when one needs to be made, the decision will eventually be made for you by circumstances beyond your control. In the end, the cost of inaction often far outweighs the potential downside of a failed attempt. The attempt, even if it falls into the 90 percent of failures, provides a lesson. Inaction provides only the silent regret of a path not taken.

References

• Taleb, Nassim Nicholas. (2012). Antifragile: Things That Gain from Disorder. Random House.

  This book explores the concept of "antifragility," a quality of systems that strengthen when exposed to stressors, volatility, and risk. Taleb argues that systematically avoiding small, manageable risks makes individuals and systems fragile and vulnerable to catastrophic failure from large, unforeseen events. This directly supports the idea that not taking risks is the biggest risk, as it prevents the development of the resilience needed to survive in a volatile world.

• Pressfield, Steven. (2002). The War of Art: Break Through the Blocks and Win Your Inner Creative Battles. Black Irish Entertainment LLC.

  Pressfield identifies the internal force of self-sabotage, procrastination, and fear as "Resistance." He posits that this force is the primary obstacle between an individual and their creative or entrepreneurial goals. The book's central argument is that the mark of a professional is the commitment to show up and work despite the constant presence of Resistance. This provides a framework for understanding the psychological battle described in the article, where strong internal opposition is a sign that the work is important.

• Kahneman, Daniel. (2011). Thinking, Fast and Slow. Farrar, Straus and Giroux.

  This seminal work on behavioral economics and psychology details the cognitive biases that govern our decision-making. Specifically, the concepts of loss aversion (where the pain of losing is psychologically about twice as powerful as the pleasure of gaining) and the certainty effect explain why humans often default to inaction. We over-weigh the risks of a new venture and under-weigh the potential rewards or the hidden risks of maintaining the status quo. (See Part IV: Choices, particularly Chapters 25-28, for a discussion of how we evaluate risk and make decisions under uncertainty).