New Year Reflections on CEO End-State and the Path Forward

Over the past few months, I’ve had the privilege of interviewing some incredible founding CEOs who’ve transitioned out of their roles and moved on to new opportunities. These conversations have been both eye-opening and deeply reflective, helping me uncover key themes and lessons about what I call “CEO end-states.”

A consistent thread has emerged across these stories: most CEO end-states occur when there’s a misalignment of expectations.

The Role of Misaligned Expectations

Misaligned expectations can arise in many ways—between a CEO and their co-founders, or between a CEO and their investors. Reflecting on my own experience, I vividly recall the moment my lead investor and I realized that the total addressable market for our business wasn’t large enough to justify the scale we’d hoped to achieve.

When a company raises significant capital, the expectation is clear: that business must grow into a much larger market. As long as those growth expectations are met, everyone remains aligned. But when the business starts to falter, when the growth projections aren’t met, that’s often the moment it makes sense for the CEO to step aside.

This underscores an important point: setting clear expectations early in the process is critical. These discussions should be explicit, especially after raising substantial capital. A shared understanding of what success looks like—and what failure might mean—can prevent a lot of pain down the road.

The Unpreparedness of Founding CEOs

Another key insight I’ve gained is how unprepared many founding CEOs are for the possibility of stepping aside. In most cases, it comes as a surprise, and there’s often no clear plan or system for transitioning the leadership role.

I’ve often shared my own experience—how, the moment I raised significant capital, I felt like I lost control of my business. Suddenly, my role wasn’t guaranteed, and the board had the power to replace me at any time. That shift in dynamic should be the starting point for honest conversations between the board and the CEO about:

1. What it will take for the CEO to step aside.

2. What a smooth transition process would look like.

In most cases, a CEO has years to get the growth trajectory right. But if it becomes clear that the business isn’t meeting its potential, it’s often in the company’s best interest for the CEO to step aside and give someone else a shot. Proactive planning and open communication can remove much of the awkwardness and emotional strain from these transitions.

The Aftermath of Stepping Aside

The period after leaving the CEO role is perhaps even more challenging than the transition itself. It can feel confusing, cold, and lonely. Many former CEOs find themselves in a prolonged state of limbo, trying to rediscover the magic they once had.

I liken it to the music industry: some artists produce a legendary record—or even two—but then struggle to find their voice again. Years later, some manage to experience a career rebirth, but that period in between can be incredibly difficult.

For founding CEOs, this after-transition phase should be a recognized and supported part of the journey. There should be structures in place to help founders navigate not just the act of stepping aside but the months (or even years) that follow.

The Power of Storytelling

One surprising takeaway from these conversations is how few people are willing to share their stories. Those who do, however, often find the experience cathartic. I’ve personally benefited from hearing their stories, as they’ve helped me process my own experiences.

This is why I’m so passionate about building a community where these stories can be told. By sharing openly, we can reduce the stigma around CEO transitions and better prepare founders for what comes next.

Looking Ahead

I’m not entirely sure where this effort will lead—and I use the word “business” very loosely here. But I’m excited about the potential impact of supporting CEOs through their transitions and helping them figure out what’s next.

My hope is that we can create a future where CEO transitions are less painful, more intentional, and supported every step of the way.

Thank you for reading, and Happy New Year. Here’s to growth, reflection, and new opportunities in the months ahead.

Ben Carcio - Founder CEO End State