Article 
Self-Assessment 
Video 
August 29, 2019
Bring on Failure: Our Expert Interview With Bill Wooditch
Rachel Salaman
Share this post:
"If you want to be successful, you need to fail more!" This bold statement is the opening line of Bill Wooditch’s new book, "Fail More." In it, Wooditch aims to put meat on the bones of the old adage that we should learn from our mistakes.
According to Wooditch, a successful entrepreneur, the ability to turn disaster into triumph relies on "continual improvement through intentional practice, the willingness to embrace the process, and the ability to learn from the result."
That might sound like a lot of hard work, but it’s better than letting your failures put you off, he insists.
"Failure and success are two sides of the same coin to me," Wooditch says. You can’t have one without the other, and the sooner we embrace that, the happier and more successful we will be.
For Wooditch, fear of failure is the main obstacle to this transformation. In his book, fear of failure emerges as a sinister shape-shifting villain, lurking just around the corner of every potential achievement.
It is "the ultimate dream killer," he warns. Watch out when it urges you to "play it safe," or hijacks your thoughts in the form of procrastination or distraction.
You can neutralize this threat by recognizing fear for what it is, locating it, and then finding a way "to move forward in spite of it," Wooditch says. This will clear the way to success.
The trouble is, sometimes fear is justified. It stops us from jumping off cliffs, running in front of trains, and betting our entire life’s savings on a risky investment.
So, heeding fear can deliver two extreme and opposing results: it can save us from ruin, but it can also prevent us from truly living. How can we decide whether to take a risk, or not?
Wooditch says we need to distinguish between rational and irrational fear. The first is "an early warning system that alerts you to danger." The second may feel very similar, but it’s just a product of your imagination.
"It’s critical to recognize the type of fear that is holding you back," Wooditch elaborates. "Is it a physical threat to your body? Or is it a blow to your self-esteem, confidence and ego?" Learning the difference is crucial.
Wooditch recommends a simple tool to help see clearly in situations where fear of failure looms large: Ben Franklin's famous Pros and Cons table.
Draw a line down a piece of paper. On one side write "worst-case" and on the other write "best-case." In the worst-case column, answer questions like: what happens if your worst-case scenario becomes reality? What are the financial and reputational costs? Is this risk worth taking?
And in the best-case column, ask yourself: what’s the upside to taking this risk? What are the financial rewards? What is your strategy for achieving the goal?
This simple table will help you to see if your fears are legitimate. It will also force you to discover and confront what frightens you. As Woodwitch explains, this can be invaluable. "We need to lean into those things, because, when we do, our fear attenuates by exposure – it becomes less."
"Failure taught me that I better well know my worst-case before I even start to think about my best-case," Wooditch explains, adding that we should enlist the help of others when using this tool. At work, ask your team to help fill in the table. At home, ask friends or family.
The importance of such allies runs throughout his book. They’re essential when you’re fighting fear of failure, Wooditch believes. As well as offering a fresh perspective, they can provide vital feedback and point out your blind spots. Cultivate and cherish them, he says, and it will help you to fail more.
Discover fascinating insights from some of the world’s leading business figures with our monthly Expert Interviews, available in text or as 30-minute audio downloads.
Mind Tools Premium Club members and corporate users can listen to the full 30-minute interview with Bill Wooditch.
If you're not a Mind Tools Premium Club member, you can join the Mind Tools Club and gain access to our 2,400+ resources, including 200+ Expert Interviews. For corporate membership, book a demo with one of our team.
Is embracing failure the key to success? Do you have any positive experiences of failure? Join the discussion below!
Creating work environments that support varying needs and preferences will make neurodivergent employees – and all of us – more comfortable and productive.
“Centennial” organizations deliver benefits for communities and society as a whole, as well as for themselves.
For a long-lasting, fulfilling experience at work, it pays to think carefully before applying for a job.
