How Failure and Entrepreneurial Vision Fuel Success | Part 1: Does More Failure Bring More Success?

There is a strange idea that has been floating around the world of management for the past few decades. It is this: failure is good and should be both encouraged and embraced. 

The general idea is that failure leads to learning and hence failure should be encouraged. Some who embrace failure point to the widely adopted process of software development known as Agile, which is based on the idea of a rapid cycle of iteration via trial and error or short-cycle continuous improvement. The underlying premise is to produce a positive benefit, test it with users (or consumers), gather feedback, improve, and repeat. This is sometimes misrepresented as a methodology in which failing quickly and failing often is the most appropriate way to develop successful solutions. 

As a proposition of a general principle summed up as a slogan: if you are not failing, you are not succeeding. And from this it follows that if you want to succeed more quickly, you should fail faster. This leads to the now popular notion that workers should be encouraged to strive towards failure as the quickest route to success.

Perhaps the starting point for the virtue of failure argument was a misunderstanding of this prudent observation and advice from Paul H.H. Schoemaker and Robert E. Gunther in their June 2006 HBR article “The Wisdom of Deliberate Mistakes”:

In an environment that is changing quickly, the strategic advantage shifts to those who learn fastest—and rapid learning may require deliberate mistakes…. Leaders that understand [that to be more successful in the long run, managers sometimes have to be less successful in the short run] will foster an organization culture that encourages intelligent, deliberate mistake making. As IBM’s Thomas J. Watson, Sr., noted, “If you want to succeed, double your failure rate.”

Adherents of the virtue of failure go so far as to advocate incentives and rewards as a way to encourage and celebrate failure. (See, for example, Google X Secret Labs ‘Rewards Failure’ – BBC News and The Unexpected Benefit of Celebrating Failure.) 

How strange and counter intuitive. It seems obvious that success is the best indicator of success. Couching failure as success appears to be, on the face of it, an effort in Orwellian doublethink []. War is peace, slavery is freedom, and now, failure is success.

One thing that the alleged paradox and sloganeering that “failure is success” does is raise consciousness about a very important issue pertaining to the methodology of entrepreneurial learning. 

Failure may reveal many things including: the limitations of reality (what is possible or not); specific knowledge about reality including human motives (cause and effect); or the degree of effort or resources people are willing or able to expend to successfully achieve the intended result. As such it is true that failure is guidepost in the pursuit of knowledge.

What we are talking about as failure is a failure of achievement, of attaining a result that we intended to achieve by taking action. But the assertion that failure is the equivalent or a practical measure of success is nonsense.

At best, and importantly, failure can be seen as a constraint encountered on the road to a defined goal. Our ability to advance towards the success we desire is determined by how we deal with failure, how we learn when we encounter failure, and how we persevere to overcome failure. Failure when unanticipated reveals the underlying structure of reality and it is to reality that our thoughts and actions must conform. 

The focus should be entirely on learning and succeeding in one’s tasks, not failing. I have yet to meet a hiring manager that seeks failed candidates, and employees that fail to meet the responsibilities contained in their roles rarely put that forward as an argument for promotion or highlight those failures on their resumes. There is no evidence that failure makes one smarter or enhances one’s qualifications. The best predictor of future success is past success, not past failure. 

© 2020, Barry L. Linetsky. All Rights Reserved. 

Barry Linetsky is a Partner with The Strategic Planning Group in Toronto, Canada, where he and his colleagues have been helping executives and owners define and align their business purpose with customer values since 1994. Barry is the author of the acclaimed book The Business of Walt Disney and the Nine Principles of His Success (Theme Park Press), and an Honorary Disney History Institute Historian. Barry is also a writer, photographer, researcher, analyst, and business strategy enabler. Read his blog and learn more at

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