The 5 Fears That Drive Successful Entrepreneurs

“Focus” by Financial Times Photos

Whenever successful entrepreneurs are profiled, there is one term that is almost always used to describe them: driven. In fact, long before I knew what an entrepreneur was, that was as a term I often heard from the adult influencers in my life whenever I met or exceeded their expectations.

“Grant got an ‘A’ on his test. He sure is driven.”
“Grant made the team. He is driven to succeed.”
“Grant got into his college of choice. He is one driven kid.”

I heard the terms “driven” and “success” so often associated that they soon became synonymous with each other in my mind. As I have gotten older, however, and have begun trying to deconstruct the true meaning of words like “success” in my own life and the motivations that lead me to make certain decisions, I have realized that though I may make decisions that lead to successful outcomes based on an internal drive, what creates that drive is often fear. That fear is rarely identified and even less often addressed.

My current belief is that many, if not most successful entrepreneurs, and successful individuals in general, are driven by these very same fears. Our culture praises the end result without acknowledging the root cause. In order to better understand what leads a seemingly already successful person to continually seek more, while another less culturally successful person is remarkably content, I have tried to identify what drives me personally to succeed.

After studying the habits and beliefs of successful entrepreneurs, my hypothesis is that a vast majority of them are driven by the same 5 fears. Here are the 5 fears that drive me, and I believe drive most successful entrepreneurs.

Fear Of Financial Insecurity

We all want and need to make money. Bills need to be paid. Family members need to eat. We need housing, clothes, food and everything else that accompanies a suitable way of living. Beyond that, money becomes a very delicate topic of discussion. Whether you hate it, love it, or fall somewhere in between, we can all agree that money is a motivator for most people in one way or another.

A common misconception, however, is not that entrepreneurs are driven by money, but why they are driven by money. Many people assume that entrepreneurs are driven by the superficial rewards that come with financial success such as large houses, nice cars, fancy trips, etc. Those things are nice, but what people don’t realize is that often, entrepreneurial drive comes not from a need to possess nicer things, but from an innate fear of financial ruin.

There is an illusion of security that is provided by financial success. When I honestly examine why I personally want to make more money, I might conclude that I want to be able to help more people, and that is true. More money provides me with greater opportunity to help others. What is also true, however, is that one of my biggest fears in life is my family falling into financial ruin.

I have dreams where we lose our house, have all of our possessions taken away and are forced to live a hard life wondering where we will sleep and where our next meal will come from. I fear that greater than death. The chances of that fear ever coming to fruition are highly unlikely, but they drive me to succeed. Though I know internally that money only provides the illusion of true security, that fear of financial ruin is deeply ingrained in me, and therefore deeply motivating.

Fear Of Missing Out

I love experiencing new things in life. Whether it be trying a new sport, like triathlon or Crossfit, or going to a concert at an iconic venue like Red Rocks, I am never happier than when I am exploring unknown territory in my life. I would go as far as to say that I “long” for new experiences. They are my drug of choice.

Having worked in the retirement industry for over a decade now, one of the most disconcerting pieces of advice that is often given to employees is that of “put off spending money now so that you can live well in retirement.” What a travesty! You mean to tell me that I should put off doing all the things I want to do in life now, while I am healthy and have energy, in hopes that I will live long enough and be healthy enough to participate in life during retirement? No thank you.

I understand where this advice is coming from but there are too many things I want to experience now, and I’m unwilling to put them off until later. There are two things you need to be able experience life in this manner. You need time and you need money. You don’t need astronomical amounts of either, but though working a 9–5 might provide me enough money to do the things I want, I never felt it would provide me with adequate time.

I don’t want to miss out on anything in life. Whether that is a good thing or a bad thing, I don’t know. All I know is that if a Tuesday morning rolls around and my wife and I decide we want to randomly take the kids on a road trip, I don’t want that decision to be influenced by my ability to pay for the trip or my inability to take the time. My fear of missing out drives me to work very hard so that when I do want to experience life, I have the means and opportunity to do so.

Fear Of Going Unnoticed

Why do entrepreneurs seek out opportunities to receive press? Why do we accept nominations for awards? Why do we spend time cultivating an audience on social media? Why do we give speeches and guest lecture? Yes, taking advantage of these opportunities does allow us to accomplish two very important things.

First, it allows us to bring awareness to our company, which in turn drives profits, growth, etc. It also allows us to help educate students and aspiring entrepreneurs about what we’ve learned in our journey so far. For me, these things are very important and true motivators for what I do.

If I am really honest about it, however, another reason I relentlessly promote myself and my businesses are because I am afraid of going unnoticed. Just like the kid in middle school who punches the girl in the face because he wants her to pay attention to him, I spend a large amount of time yelling at the top of my lungs for people to look at how great I am, hoping that they will notice what I am doing and show their approval.

I do believe very strongly that having a platform allows me and other entrepreneurs to provide guidance and assistance to others who need it. When college students request meetings with me because they want advice on how to start a business, I am grateful that I have the opportunity to provide some guidance, as little as it may be. But let’s be honest. I am also glad they noticed I was even there. The fear of going unnoticed is a very powerful motivator.

Fear Of Not Mattering

What will people say about you when you die? Will there be lots of them at your funeral? Will they tell stories about you for years to come? Will your life create any lasting effect on the people you leave behind? These are the questions I ask myself all the time. I want so badly to leave a positive lasting legacy when my time on this earth is done.

I don’t necessary care if I change the course of human history or if I create a company that becomes a household name around the world. A bronze statue of my head would be pretty good looking, but I’d be ok without it. What I do want is to deeply touch as many lives as is humanly possible. I want my funeral to be full of people who profess that I had a lasting positive impact on their life, whether that means I bought them a meal when they were hungry or that I inspired them to start their very first business.

I am constantly aware of how short life on this earth is. I fear that too many people take their time for granted. Part of me wishes I were better at relaxing and not always pressing on towards what is next. The other part of me, however, is inherently attuned to the fact that our time is extremely limited, and a sense of urgency is called for if we want our time here to count for something. I am driven to succeed because success allows me to matter to more people, and I am deeply afraid of not mattering.

Fear Of Failure

I have been in sales of some sort for my entire career. Being a salesman among salesmen, we like to tell ourselves that we have tough skin and are immune to being told “no” or failing in our efforts to procure a sale. It wasn’t until I did some serious introspection that I discovered a couple of things about myself.

First, I’m not a very good salesman at all. I’m pretty good at a few other things, but not inherently talented at sales. The other thing I discovered is that I am terribly afraid of failure, and it affects me deeply when I experience it. I would love to be the guy with “thick skin” who doesn’t care how many times he fails, but it turns out that my skin is made of paper mache!

To compensate for my fear of failure, I try to create as many successes as possible. If I succeed enough, the pain of that failure diminishes inside of me. This tends to have a very positive effect on my businesses because it requires me to fully understand the things I am good at, but more importantly to admit and delegate the things I am not good at. If I try to do everything myself, there is a greater chance that I will fail. If I allow other people to do the things that I am not suited to do, our chances for success increase, as does the chance that I can avoid the stinging pain of failure. I am deeply afraid of failure and therefore look for ways to increase my chances of success.


When you get down to it, we are all the same kids we used to be in middle school, dealing with the very same insecurities we had then. The only difference now is that these insecurities and fears manifest themselves in very different ways and we are much better at disguising them. I think, however, that to truly grow as humans, which in turn allows us to grow as business owners and employees, we need to break down the walls of insecurity and work at being vulnerable and honest with our fellow man.

After all, whether it be in our personal relationships or the relationships we create in business, we are all struggling with the same issues. If our goal is to do work that truly matters and to create for ourselves and others lives that are full or experience, meaning and purpose, the quicker we are able to create that atmosphere of honesty and vulnerability, the quicker we will realize that we all have the same basic human needs. By realizing, understanding, and accepting those needs, we can then work towards helping each other live the lives we all long for.

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