Essential Business-Building Skills: #1 Learn to Fail Wisely


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If you’ve taken the plunge to get a new company started, growing that business is bound to be frightening. That’s because building an enterprise requires you to take risks and trust your decisions without the benefit of hindsight. And while no one likes the idea, you need to learn to fail.

As an entrepreneur and a small business owner, it’s completely understandable that you fear failure. 

Yet, failure is a process and a key component in our ability to learn. In fact, failure is a critical element to building a sustainable business. It is also the sign of a great beginning every time it happens.

So, learning to fail is an essential business-building skill that protects us from the dangers of being overconfident. 

“Success is a lousy teacher. It seduces smart people into thinking they can’t lose.”

― Bill Gates, co-founder of Microsoft

How to Learn to Fail without Fear

To build Viral Solutions into a successful full-service agency, we’ve learned not to fear our failures. Instead, we’ve learned to build from them. This is one of those life lessons that come from experience, not from college.

As you seek to grow your business and yourself as an entrepreneur, you may ask: 

Fortunately, by changing your approach and beliefs about failure, you can take the opportunity to learn instead of letting your mistakes defeat you. 

1) Relax—Failures Are Rarely Catastrophic

If you want to learn to fail without fear, it’s important to recognize that failures seldom lead to catastrophe—unless you miss the opportunity by not taking appropriate action! 

Keep in mind that failure doesn’t necessarily mean your entire business will go under or that failures are a bad thing. Instead, it’s a way to find the best road to success.

2) Accept That You Are Going to Fail 

Just as in the stages of loss, the first step is acceptance. That means accepting that failures occur and that they happen in all shapes and sizes. 

You probably fear the uncertainty of not knowing what’s going to happen with your business. But you’ll be far less inhibited if you accept right off the bat that you are going to fail (at least to an extent). 

“Failure must be viewed not as a problematic aberration that should never occur, but rather as an inevitable aspect of operating in a complex and changing world.”

― Mark D. Cannon and Amy C. Edmondson, authors of “Failing to Learn and Learning to Fail (Intelligently): How Great Organizations Put Failure to Work to Innovate and Improve”

3) Understand the Fear of Success

Just as there is fear of failure, there is also a fear of success. And it can also lead to decision-making paralysis.

Many of us do not feel worthy of success, so subconsciously we self-sabotage our accomplishments. As unlikely as this may sound, it’s real, and you need to be mindful of this human trait.

Like learning to fail, the first step is to recognize and accept it. You need to understand how it’s holding you back and make a conscious effort to be aware of your strengths.

4) Grasp Self-Awareness 

As Dr. Wayne Dyer tells us, to overcome these conflicting fears, you need to understand your emotions, attitudes, and beliefs toward yourself, others, and life. In practice, achieving self-awareness by sitting, reflecting, and accepting your position is a sobering experience. 

The road to self-awareness can bring many emotions to the surface—positive and negative about our perspectives toward ourselves and others. How one feels on the inside matters. 

Self-awareness is the journey to understanding those feelings and learning to fail.

How to Build Success from Failure

As you begin to accept that you will fail at some point without suffering a catastrophe, you will feel the freedom to make the decisions you need to put your enterprise back on track. 

Here’s what to do…

1) Maintain Consistent Goals but Adjust Your Strategy and Tactics

Even when you do fail, it’s essential to continue to shoot for the same goal and do everything with this in mind. This consistency will be of comfort to you as you enter into the unknown.

Understanding what prevented you from reaching your goal is critical to getting back on the right path. With this information, you can make the necessary changes to improve your chances of success. 

“Early success is a terrible teacher. You’re essentially being rewarded for a lack of preparation, so when you find yourself in a situation where you must prepare, you can’t do it. You don’t know how.”

— Chris Hadfield, retired astronaut with the Canadian Space Agency (CSA) 

2) Take the High Road

There will come a time in your young start-up that temptation will raise its ugly head. You will have a decision to make that will either benefit you financially or move you closer to business failure. 

The latter is the right move with your new customer. Accept this failure, and it will earn you the trust of many.

3) Don’t Hide Your Failures

When the complaints become public, don’t be tempted to remove negative comments made in reviews and forums. We all make mistakes. The key to expanding trust is dealing with problems in the open and treating the situation with fairness. 

Consumers want to see that you recognize and own your mistakes. Most importantly, they want to know that you are willing to resolve any problem they believe you have created for them. Both denial and silence are terrible strategies.

4) Be an Inspiring Leader and Admit to Your Mistakes

Taking responsibility for your mistakes is not an easy task! Let’s face it: You’re going to mess up at some point. It might be something small or something large. But mistakes occur. When they do, tell your employees that you’ve made an error. 

Some might say that this is showing weakness. It is recognizing weakness, but only normal, human weakness! And it builds trust.

“I think self-deprecation is a mark of high intelligence and cunning. It shows you can understand your flaws and, at the same time, deflect some of the high expectations away from yourself. That leader is a genius who gives all the credit to the staff and team members. That’s a guy I would be inspired to work for.”

― Ted Thompson, former general manager of the Green Bay Packers 

5) Identify Failure, Analyze It, and Experiment

A line of crumpled paper balls with a perfect origami crane at the end showing how to learn to fail.

In their paper written for Harvard Business School (quoted above), Mark D. Cannon and Amy C. Edmondson wrote that successful companies see failure as a learning opportunity that is key to innovation.

As mentioned earlier, it’s generally not failure itself that causes catastrophes. Instead, it’s not recognizing or learning from minor mistakes that lead to bigger problems. Therefore, it’s important to understand organizational and social obstacles that prevent professionals from learning from their mistakes. 

Cannon and Edmondson introduced three steps to overcome these roadblocks: identifying failures, analyzing them, and encouraging experimentation.

  1. Identify failures. 

You need to develop systems to gather and analyze data to identify failures and why they happen. To help the process:

  1. Analyze and discuss failure openly.

You now need to analyze and discuss what caused the failure honestly. Again, employees must feel safe to talk about these problems openly. Also, consider the following:

  1. Encourage creativity and experimentation. 

The brainstorming process is an amazing thing. We sit down and spend time racking our brains to come up with a unique and exciting idea. But when we finally find it…we get afraid. 

Surely, you’ve had this experience before—you come across an idea so bold and creative that the prospect of it actually coming to fruition frightens you. 

Yet trial and error lead to innovation and the development of new products and services. So, as you build your team, make sure you allow for free-flowing ideas


Sometimes, it takes doing the very thing we fear to conquer that fear. Once you learn to fail and survive, you’ll find that it’s no longer so scary.

There’s a lot you can do to prepare for failure before it happens, and it starts with accepting that failure is inevitable but is rarely catastrophic—unless you let it be. 

Once you face and embrace failure, maintain your goals. Use it as an opportunity to learn where things went wrong and take the necessary action to get back on track. 

To do that, you’ll need to create a culture where people can own up to their mistakes without fear of judgment. 

Remember, honesty in leadership inspires confidence, and learning to fail through trial-and-error leads to innovation and success. These are two critical prerequisites to putting yourself back on the right path to success.

“Achievement seems to be connected with action. Successful men and women keep moving. They make mistakes, but they don’t quit.” 

— Conrad Hilton, founder of Hilton Hotels



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Filed Under: Business Tips