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Beware the Dark Side of Entrepreneurship — 2 Signs That You Should No Longer Be CEO Holding on to your role as CEO might only make things worse for all involved — yourself included.

By Clate Mask Edited by Micah Zimmerman

Key Takeaways

  • If you are running yourself into the ground leading your business, everything will suffer.
  • Moving into a role better suited to your strengths is bold, selfless and admirable.

Opinions expressed by Entrepreneur contributors are their own.

Many founders eventually become the chief executive officer (CEO) of their own company, which can be a seemingly natural path to take. But for some, it's simply not the right fit. Unfortunately, this can be a hard conclusion to come to. Some founders don't see the signs until it's too late, while others miss them altogether, which can wreak havoc on a company over time.

So, how do you ensure you're not overstaying your welcome as CEO? Here are two signs it might be time to give up your tenure as CEO and apply your talents elsewhere in the business.

Related: Stepping Aside: When To Walk Away As A Leader

Your business is your identity

Founders have every right to be proud of the company they're building and for it to be a key part of who they are. But if your role as founder and CEO is your entire identity, expect trouble ahead. To start, it's unhealthy to see yourself and your work as one and the same. This can diminish your personal life outside the office and take you on an emotional rollercoaster inside it. Instead, successful CEOs must be able to emotionally detach from their businesses.

If your emotions are inextricably connected with your company, you won't be able to make the objective decisions you need to make. It's also highly likely that you'll white-knuckle your grasp on every area of the business, leaving no room for others to have a meaningful role. An emotional shift has to happen, from an all-in founder to a level-headed CEO who still cares while simultaneously knowing they are more than the business. If you can't make the shift? You shouldn't be CEO.

Related: 9 Signs It's Time for You to Step Down as a Leader

You have entered the dark side of entrepreneurship

The most successful CEOs are the ones who learn to lead from a healthy place. But the reality is that even top CEOs experience what I call the "dark side of entrepreneurship" at one time or another. When you're in the dark side, you choose unhealthy coping mechanisms to handle the stress of working on your own business beyond what your body and mind can handle.

Sometimes, this can result in unhealthy behaviors such as drinking too much or taking drugs or medication to manage your days. Other times, it can result in depression, damaged relationships, loneliness, divorce, health problems or even death.

Take an honest inventory of where you stand. Do you give everything you have at work, meaning you're depleted and emotionally numb at home? Has this reduced the health of your relationships with your spouse or children? Do you regularly turn to drugs or alcohol because it's the only way you can escape your stress or avoid feeling guilty? Is your mental health in shambles? If any of this sounds familiar, holding on to your role as CEO will only make things worse for all involved — yourself included.

If you have indeed entered the dark side of entrepreneurship and are running yourself into the ground leading your business, everything will suffer. It's not an if; it's a matter of when. To make thoughtful decisions and guide an entire organization, you must be physically, mentally and emotionally healthy.

If you're the right person to be CEO but going through a rough patch, sometimes you can stay the course. Maybe you need to work to establish healthier habits, get past mental health obstacles with a professional or hire a business coach to help in other areas. But if you're unwilling or unable to put in the work to get to a place of optimal health, it's time to step into another role.

Related: 5 Signs You Need to Step Back as Founder of Your Startup

If not CEO, then what?

Being the CEO of a company comes with a certain level of prestige, which is one reason many founders want the position. But it's also hard to give up the title when you created the company. It's your brainchild, and you're deeply invested in its success. It might feel wrong to imagine someone else steering the ship. Where would that leave you?

If this is how you feel, you're not alone. But it might be time to consider a different perspective. Being an effective CEO requires specific skills that some founders have and some do not. Don't take it personally if you fall into the latter category. Instead, consider where you can contribute the most value.

Moving into a role better suited to your strengths is bold, selfless and admirable. For some, that might mean moving into a chief operations officer (COO) role or a chief revenue officer (CRO). For others, it might look completely different. Just remember that the CEO role isn't for everyone, and that's okay.

If you put your health and the health of the business first, both of you will succeed.

Clate Mask

Entrepreneur Leadership Network® Contributor


Clate Mask is the entrepreneur’s guide and CEO and co-founder of Keap, the leader in small business automation software. He is a NY Times best-selling author and a national speaker on entrepreneurship. His passion is helping small businesses conquer the chaos and grow their business.

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