Afraid of Failing

WARNING: If you are looking for an easy feel good read; STOP now! This one will ask you to look your fears in the face.

“Afraid of Failing” is the #1 issue that people bring up when talking about a new entrepreneurial venture. If you are starting a new side hustle, expanding your product line or offering your knowledge base as a consultant, fear of failure is part of it. We all fear failure in different ways. For some it is debilitating and we never seem to “take action.” For others, it’s motivating and we will do anything not to let fear beat us, including taking unnecessary risks that lead to more failure and more fear. Neither extreme is healthy for you or your business.

So, what to do about it?

Define Logical Action

This is a simple exercise I practice many times a year when growing my own businesses. I separate “Fear” from “Failure” then figure out how to reduce the impact of “failure” by defining failure, logically looking at solutions and taking action against failure. Below are my fears of failure and what I do about them. You can swap out my fears and get real with your own.

Define your fear of failure

  • Fear:  “an unpleasant emotion caused by the belief that someone or something is dangerous, likely to cause pain, or a threat.”

I don’t know about you but I experience a fearful “unpleasant emotion” in business for 1 of 2 reasons:

1) Other people’s opinion of me

2) Not being able to pay the bills

So what would create opportunities for others to have a negative opinion of me or for me to run out of money? Well, failure, of course!

  • Failure: “catastrophic lack of success.”

Catastrophic is a key word in this definition. In life and entrepreneurism you have to define what a catastrophic lack of success is. Obviously not all failure is bad or even unwelcome. We all like and benefit from trial and error in some aspects of life. It helps us learn and grow. However, in some parts of life or in large doses, failure is uncomfortable or even detrimental.

Here is what I think of as failure that has catastrophic potential. What equals a lack of success for me? Similar to my fears,

1) Doing something that would negatively impact a coworker or client

2) Making a decision that would cause me to run out of money

There you have it. If I don’t hurt people and if I keep more money coming in than is going out, I can avoid failure. So how do I do that? Use logical parameters to hem failure in.

Get logical about failure:

This is easier than you may think. Simply (and I mean really keep it simple) write down what you should do to keep failure from happening. Lets look back at what equals failure for me and match up the logical parameters I have in place to keep me safe.

Relational failure:

  • Failure = Doing something that would negatively impact a coworker or client
  • Logical Parameter = Treat others as you want to be treated. If you mess up, apologize and fix it.

It’s simple and effective. When I follow the golden rule, people appreciate the care and return the favor with positive opinions about me. Sometimes this seems too simple compared to my complex fear of failing. But at the end of the day, when I do what is right, I can logically stand by what I did and focus on executing my plan rather than on my fear.

Financial failure:

  • Failure = Making a decision that would cause me to run out of money
  • Logical Parameter = 1) Keep an emergency reserve of 90 days expenses. 2) Take chances with less than 10% of net income.

These logical parameters are simple, yet rooted in real financial data.

  1. Emergency Reserve: As a consultant who takes clients through high risk business opportunities, I know my sales cycle, client pipeline, and projected cash flow. I know that I can recover just about any loss of income in less than 90 days. Therefore, keeping a 90 day emergency reserve available for my business is a logical safety net.
  2. Taking reasonable risk has become a religion for me. I LOVE taking risks. It’s in my DNA and upbringing. I rarely find a risk daunting. However, in the past I have found myself bruised and broken in the canyon of financial loss after jumping off a cliff of opportunity because I felt like I could leap across to the other side of success. I have become a student of business fitness and canyon measurement. I know how far my business can jump without missing the mark. Like any athletic endeavor, we have to push ourselves to achieve the next level of success, so I push in ways that allow me to “fail” in controlled steps that are never more costly than 10% of net income (company profit).

It is good to risk for gain. It is wise to risk with parameters.


This is where the rubber meets the road. Where the hard choices are made and the reality of your choices are realized.

My action items are practical and attainable.

  • Other’s opinion of me – To keep others feeling good about me and my businesses, I review each strategy and tactic before and after execution, looking for ways to do what’s right for others. This keeps me aware of the needs of those around me and helps me learn from any mistakes. There is no reason to make the same mistake twice.
  • Not being able to pay the bills – To make sure the lights stay on and I don’t have a stroke, I keep score and NEVER break my financial rules, because I am “too far in” or “almost there” on any opportunity. I set reasonable benchmarks where an opportunity needs to be for me to spend more money or time. If it’s not hitting the targets, I am not going to spend the time or money to keep pushing. I know that may sound like giving up, but in the world of entrepreneurship, failure is a real thing. It happens more often than success. I don’t mind failure because I can afford it if I stay logical. The minute I fall for the emotion of an opportunity is the minute before I lose more than I should. Small, measured, logical failures often lead to success. Define what small, measured and logical failures you can afford and start learning so you can succeed. Following this plan, you will eventually find the path to success and you will have resources to make the big push once you do.

Well, there you have it. My open soul befor you. My fear of failure and how I use logic to take positive and successful action.

BTW – If you work this out on one of your everyday fears, you will notice your fear beginning to diminish. It’s a cycle. Taking real, sustainable, positive action to overcome our fears often leads to less fear. Get out there and beat your fear.

Attached is a table that may explain how I follow these steps. I am also including a mind map that may help you visualize how to find your fear of failure solution.


Failure Logical Parameter


Other’s opinion of me Doing something that would negatively impact a coworker or client Do what is right for your staff and clients. If you mess up, fix it. Review each strategy and tactic before and after execution looking for ways to do what’s right for others.
Not being able to pay the bills Making a decision that would cause me to run out of money

Keep an emergency reserve of 90 days expenses.  

Take chances with less than 10% of net income.

Keep score and NEVER break your rules because you are “too far in” or “almost there.”