5 Frustrations Of An Entrepreneurial CEO

by Feb 19, 2021

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5 Frustrations of an Entrepreneurial CEO

By Marshall Krupp, Professional EOS Implementer
In collaboration with Ashley Berecz, Executive Assistant

For most business owners, setting their own schedule and making the big decisions are a dream come true.  Is that not what being an entrepreneur is all about? After all the hard work to get to the top, it should be smooth sailing, but unfortunately, being at the top comes with its own set of challenges.


Those challenges affect you, your leadership team, your other employees, and many times customers and vendors.  Denying, deferring, or avoiding these challenges only magnifies their reality.  As the business unfolds these challenges turn into real frustrations which lead to being “stuck”.  In business, we call being stuck “hitting the ceiling.  This is the place where the barriers now hold us back. The more we push, the more the barrier pushes back.  The only way to get through the barriers is to get to the “root cause” of the challenge.


As we interview entrepreneurs, business owners, and leaders of organizations, five general frustrations appear to be common.  The best way to not let these five frustrations get to you is by being aware they are common and that they will not be going away anytime soon.  They will periodically show their ugly head as the business grows. What matters is how aware you are of these frustrations and to have tools set in place, so you ultimately do not come to resent the dream that you have worked so hard to achieve. As Gino Wickman, the founder of EOS® Worldwide and the author of “Traction” and several other books states, “Problems are like mushrooms: When it’s dark and rainy, they multiply. Under bright light, they diminish.”


So, let us look at these five frustrations and gain some clarity.  With clarity, we can become more comfortable with the challenges that will lead to the solutions of the root causes.




As business owners, we need to make sure that we have the right people in the right seats on the right bus. The bus is our business.  The right seats are the positions and functions of our business. From experience, so many identify a great place to work running parallel with those they work with. So it is imperative to surround ourselves with the right people. People that we can trust and delegate to. People that we can elevate in parallel with the growth of the business.


People can single-handedly make or break our businesses. One bad seed is all we need for the rest to consider jumping ship, and we could end up losing workers that we consider irreplaceable.  Culture, morale, productivity, customer satisfaction, and ultimately, success is all driven by the right people in the right seats. When we look at our people, we may find that there are right people in the wrong seats and wrong people in the right seats.  Like a bad apple spoils the rest of the apples in the basket, the wrong people can do the same to our business organizations.


Lack of Control: 


Are we controlling our businesses, or is it controlling us? What happens in your company on a day-to-day basis? Are your meetings productive? Do your company’s values align with the values that you consider important to the company? You cannot be in 56 places at once, but if done right, you do not need to be.  Are you feeling like the train going down the track without an engineer?


What we have found is that many businesses have become successful by “accident”.  Yes, there are in many cases where the pieces of the puzzle have led to success.  However, the glue that allows that puzzle to be picked up from the table without falling apart just is not there.  In these business realities, there is no strong foundation of business control and when challenges arise, the business itself takes over control and we are simply on the ride.


This frustration of lack of control leads us to deny the reality of this situation, which ultimately comes home to roost.



Simply put, there is not enough of it. Does it seem like you are trying everything you can to make more, but the amount isn’t there? I hear the phrase, “make more work less,” weekly. It is a great idea that I know we all wish would happen, but if your profit isn’t there you may be watching your goal of working less slowly sail away.


When we ask what is the bottom line of a business, it is interesting to hear the answers: gross revenue, customer satisfaction, employee morale, productivity, etc…the list can go on and on.  The bottom line is that without profit there is no business.


Consider this, I have $1,000,000 to invest to gain a return.  I can put it into a business and generate a return (profit), or I can put it into other things that generate a return.  If I am putting it into the business and generating a return less than I would get investing it into something else, what would cause me to think that being in business is the better way of investing.  However, we made the decision to be in business.  So, at minimum, we cannot overlook the need and the desire to generate the greatest profit.


Hitting The Ceiling:


This frustration is inevitable. Businesses and people get stuck.  We know when we are stuck because we can “feel” it.  We feel it emotionally, physically, and intellectually.  Our mind tells us that we are feeling stuck.  Hitting the ceiling is not a matter of if, it is a matter of when. No matter what you do, you can’t seem to get to the next level. You’re stuck and frustrated because even if you are moving, it’s in the wrong direction. The accumulation of not having the time or resources has come to a head.


It is human nature to dismiss and deny when we get stuck.  This may be considered a failure.  So, to recognize that we are stuck, means we have to accept failure or do something about it.  The “doing something about it” may be difficult in itself.  It may be risky.  It may result in having to be held accountable or we may have to expose ourselves for who we really are…scary, huh?


However, being a deer in the headlights does not serve anything and may result in our death.  So, when we hit the ceiling and when we get stuck, we must take action and breakthrough this barrier.


Nothing Is Working:


You’re trying every single way under the sun to help make any of the above situations better, but still, nothing is working. Now, it’s 2:00 am and you’re trying to brainstorm new solutions to fix it and wondering if becoming CEO was actually what you wanted.


I’ll let you in on a little secret, being a CEO is still your dream and it always will be for most entrepreneurs. By being aware of all of the above common frustrations that we as head executives may face, we open up the door to the possibility of implementing processes that will lower your stress and frustration.


EOS® is a simple process that will teach you how to effectively handle these frustrations as they come up. As a Professional EOS® Implementer, it is my job to guide leaders and executives through the  EOS® Model and Process and help them build the pathway for success.


Whether you use the model, process, and tools of EOS® or any other system to overcome these frustrations, we need to recognize that when these frustrations manifest themselves, we have an obligation and responsibility to our leadership teams, employees, customers, and vendors to do something about it.  We cannot deny, dismiss, defer, or avoid this reality.  They will fester and ultimately explode.  There is simply too much at stake.  The choice is to live, succeed, prosper and be healthy, or simply die and let the business die with you.  It all a matter of perspective, mindset, and choice


Do you think the above frustrations are correct? Did I miss one? We are always happy to meet with anyone. So if you would like to continue this discussion further, please contact us at ashley.berecz@peerexecutiveboatds.com or go to our website www.peerexecutiveboards.com and contact us virtually. We will be happy to get back to you!



TractionPureis an affiliate of Peer Executive Boards and focused on “elevating entrepreneur businesses from complexity to simplicity” using the EOS® Model and Process.  EOS®, the Entrepreneurial Operating System® takes entrepreneur businesses on a journey of mastery of the EOS tools which enables businesses to elevate their leadership teams to make better decisions, maintain a level of accountability, and attain greater success more simplistically.  The components of EOS® are Vision, People, Data, Issues, Process, and Traction, which when used effectively attains a healthier organization with greater success.  Marshall Krupp is the founder and Principal of TractionPure2 and a recognized Professional EOS® Implementer serving clients throughout the nation.  He is also a national speaker, a past award-winning Vistage Worldwide Chair, and a past career in providing crisis management strategic service to businesses, governmental agencies, and not-for-profit organizations.


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