147- Entrepreneurs can also have fear of success

Struggling Biz

In this episode of The Struggling Biz, we discuss certain themes in the area of conquering fears for entrepreneurs — not only the fear of failure (which is the biggest setback for trying to go in a new direction or taking some element of risk in your small business), but also FEAR OF SUCCESS.

This idea was promoted by Todd Henry, an author and podcaster for his show, The Accidental Creative, in an episode in late 2021, which was called “Conquering Fear.” 

In his episode, Todd talks to us about both fear and the imposter syndrome. Insofar as fear is concerned, not only does he talk about the fear of failure, but also the FEAR OF SUCCESS. And we take it one step further to relate the fear of success from the viewpoint of an entrepreneur, and not just the creative who works for an organization where he has to deliver at a moment’s notice.

For the small business owner, the fear of success can creep up when you are either at the beginning or in the midst of a project where you have over-delivered for your customer. There is great euphoric feelings at the time of this small victory, but then the client or customer may be demanding over and over again that you supersede your performance every time in the near future — and this can lead to a frustration and a fear that your success has caused, and that you may not deliver again and again the high level of performance. In many cases, you may try sand-bagging your delivery outcomes, or you may under-deliver, which can then bring negative consequences. In other cases, you may be stuck in a vicious cycle of over-delivering in which you cannot get out.


Such was one example in my own experience, where I was performing some services for someone who was a good friend of mine, and whom I did not want to disappoint. The project, however, kept changing in terms of expectations, and even though my scope of work was set firm (the way it should have been), the client (with whom I had a great personal relationship over the years) kept changing the terms, the delivery dates, and kept changing the product to be delivered due to changes in the software interface, as well as small nits that frustrated my expectations.

Now, I could NOT leave the project. I had delivered the initial project samples and proof-of-concepts, and the client continued to mount more on top for the next round. I was overwhelmed and even felt like quitting the project (although this was impossible due to the personal relationship with the client). However, I could not leave, and I was overcome by a fear of my success. Even delivering a “negative” piece of work (which I had been considering, to get out of the success category) was not in the cards, as my success rate was something to which my client had become accustomed. He could not see anything different, even though the project was costing me time, money, effort and frustration.

So I had been fearful of creating a solution and delivering it with success for the client.


Now, in the podcast episode by Todd Henry, this fear of success can be just as powerful as the fear of failure in delivering a solution for the client. But the success rate in my scenario is something that would have me under-perform and begin to have negative feelings for the project. And Todd gives other examples that he has seen where the entrepreneur is impacted.

So what can you do to avoid or face this fear of success as an entrepreneur? I strongly suggest that you consume Todd’s podcast episode from November of 2021 (as stated above) to understand the possible consequences of a great success that can turn into your own albatross.

In some cases, such as mine, you may have no other choice but to go along with the project, understanding the client and the limitations to your own creativity and delivery that have been placed upon yourself. And then you would have to plan your own exit strategy to get out of the project as soon as it is possible — both project-wise, time-wise and relationship-wise without much negative repercussions. For me, my declining health was the reason why I had to back off from this project and eventually leave it to another entrepreneur who would take up the gauntlet and deliver the final solution to the client. I would then be free from my FEAR OF SUCCESS.


We hope that this type of fear is something that you, as an entrepreneur who may be engaged in a contract for services, can recognize, plan for dealing with it and overcome it.

Your health and your business need to have your commitment to excitement and originality and creativity to attack certain projects with the euphoria of providing the solutions to your client in the area of services. We hope that you can recognize and plan for your response when overcoming the FEAR OF FAILURE, as well as the FEAR OF SUCCESS.

Thank you for your attention.

Copyright (c) 2022, Matrix Solutions Corporation and Todd Henry and michaelandmike.com . All rights reserved.