6 Of The Biggest Challenges For CEOs—And How To Embrace Them

I always knew I wanted to start my own business. With so many entrepreneurs in my family, I’ve always seen up close how rewarding (and challenging) it can be to build a business. Regardless, the idea of building something from scratch and running my own show always appealed to me. I knew it wouldn’t be an easy road, but I had a support system and role models that made me believe it was possible, regardless of the challenges CEOs face.

“Someday” came when my job as the chief marketing officer of Martha Stewart Living Omnimedia was unexpectedly eliminated. At first, I felt vulnerable and uncertain. But those feelings quickly dissipated, replaced by a liberating realization that there was no better time than now to begin my entrepreneurial journey.

Thirteen years of incredible work (and countless challenges) alongside my team at Stanton & Company later, I’m glad that I stepped into that journey. Every single day, faced with new, unexpected ups and downs, I’m choosing to stay on this path.

6 of the biggest challenges for CEOs

I remember the first few weeks of running my own business like it was yesterday. When you sign the LLC documents and are suddenly all in, there’s no turning back. And that thought eventually spurs another one—a big one: the realization that when challenges arise, the responsibility to address and handle them falls on the CEO. And you alone.

CEO challenges

Photo source: For CEOs, It’s Still About Developing Leaders: Strategy Is Nothing Without Effective Leaders to Execute (DDI)

These are six of the biggest challenges I’ve faced as a CEO, along with tools for managing those challenges.

1. It may take you some time to make money. Any money.

I’m not talking about just a few months, either. It can take years of pouring your heart and soul (and a lot of cash) into a business before you see any profit.

I was fortunate—my savings and a little loan from my grandfather was enough to get things started. My business partner and I were frugal, limiting overhead costs and waiting until we were established to begin hiring. Nonetheless, it was quite stressful to go from having a consistent income to none. And especially tough not knowing when the money would start rolling in.

If you’re thinking of starting a business, do a worst-case scenario forecast to see how long you might be waiting before you take your first paycheck. Better to have a sense of this ahead of time so you can plan accordingly.

2. Be ready to accept full responsibility for anything and everything that goes wrong.

When you screw up, when your employee makes a mistake, or when a client is upset—even when your office is burglarized (true story). As the founder, every issue is your responsibility. You can’t point fingers, because even someone else’s mistake is ultimately your fault as the person who hired them. This is especially tough for people coming from corporate environments, where blame is often shared throughout a team or deflected toward someone else.

If you’re not the kind of person who can look in the mirror and say, “Damn. I really screwed that up,” then my honest advice is this: Don’t start a business. Founders need to be comfortable with owning everything about their businesses. The good, the bad, the ugly—it’s all on you.

3. When a problem arises, you’re the problem-solver.

Holding yourself fully accountable for problems is the first step—actually solving them is the real challenge.

And constantly resolving issues requires an incredible amount of mental resilience. It’s exhausting to finally straighten out a client issue only to be interrupted by another halfway through a deep breath.

My advice to founders on this subject is personal, not practical (because you know how to handle your business if you’ve started your own): Don’t be too hard on yourself when you become overwhelmed by work. Unwind. Find time to decompress and, if you have someone to vent to, vent. It really, truly helps—especially knowing that you need to be ready for tomorrow, another day full of new and unexpected challenges as CEO.

4. Are you comfortable asking for help?

Not everybody is.

Founders who are too proud to ask for help or advice (and there are many—it comes with the territory) need to understand how important it is to be vulnerable and willing to ask for help when you need it. There are lots of smart people out there who are happy to share their insight. You just have to ask.

So, founders: Appreciate the value of those around you—employees, mentors, fellow founders, etc. There’s a strong link between successful businesses and founders who are humble enough to turn to their peers for help when they need it.  

5. People think running your own business will grant you freedom—but the opposite is true.

In the grand scheme of things, you will not gain freedom when you start a business. Once you do it, it’s with you 24/7—your daily life consists of constant monitoring, overseeing, worrying and sometimes obsessing.

It’s important for founders to know what they’re getting into. And that means understanding that there will be times when you feel overwhelmed or even trapped. It’s possible you’ll never take a vacation where you can completely leave work behind again. But for me, that’s OK. It’s worth it. Make sure it works for you, too.

6. You have to take a total leap of faith. There are no guarantees.

I’ve saved the most important point for last.

Even if you have the best idea in the world and a foolproof business plan, failure is still a possibility. And that’s a very scary, uncomfortable reality to come to terms with—especially for people who know nothing but success. And that discomfort is perpetual, not just at the beginning of starting your business.

There’s no way to eliminate this fear as an entrepreneur. And there’s nothing I can say that will make you feel better about it … and that’s OK. Because the best way to handle fear is to allow it to fuel you.

Ultimately, these (and other) challenges will arise in some shape or form for every CEO. And coming to terms with their inevitable arrival before they’re staring you in the face is imperative. Because being mentally prepared for founder life may make a difference. At least you know what you’re getting yourself into. And good luck! 

Amy Stanton is the founder and CEO of Stanton & Company, a full-service marketing and PR agency, and the co-author of “The Feminine Revolution.”

  • Originally published April 9, 2019, updated June 26, 2024