What role should you play to maximize the value of your business?
Change can be hard—especially when it involves evolving your role inside your own company. The tasks you handle when launching a business are drastically different from those required when the business scales.
Still, many entrepreneurs struggle with these entrepreneurial transitions, often because they haven’t taken time to consider how they must adapt alongside their growing business.
The good news? You don’t need to resist change. Instead, you can follow a clear, natural pathway that supports your company’s growth—and your fulfillment.
The Evolving Nature of Entrepreneurial Transitions
In the early days of your business, you wear every hat. You are the contributor, the problem-solver, and the person who tackles everything from sales to finance to product development. It’s intense—but it works when the team is small.
Eventually, as your company grows, your first significant entrepreneurial transition arrives: you become a manager. At this stage, you’ve hired employees, and now your role includes delegating, coaching, and guiding others. You’re still pitching in, but your focus begins to shift.
Later, you enter the next phase—becoming a leader or CEO. Now, functional leaders manage different parts of the business. Your responsibility is to manage the managers, develop vision, and steer strategy. At The CEO Project, we often find this transition—from doer to leader—one of the most difficult for entrepreneurs. It requires letting go of tasks you enjoy and trusting others with decisions.
Many people assume the journey ends at CEO. From there, it’s time to sell and move on, right? Sometimes, yes. But many entrepreneurs agonize over the idea of selling. It’s a deeply personal and financial decision. Selling means trading a living, evolving asset for static ones like cash, stocks, or real estate.
Others want to remain involved in some way—even if they step away from daily operations. Fortunately, entrepreneurial transitions don’t stop at CEO.
From CEO to Board: A Strategic Transition
As businesses mature, their needs often outpace the founder’s experience. Maybe the company becomes too large, or the market shifts. Recognizing that the company has outgrown your operational leadership is a humbling realization. But it’s also a pivotal moment of growth.
If you have the emotional intelligence to accept this, you can step into the next phase: acting as a board member or even Chairman of the Board. This role keeps you close to the business, but removes you from day-to-day operations.
This entrepreneurial transition follows the “nose in, hands out” philosophy—stay informed, but don’t interfere. You receive regular updates and profit distributions, freeing up time for other pursuits—family, travel, or even new ventures.
Still, even this transition can be challenging. One founder confided that he still had ideas to share—but his CEO wasn’t receptive. Despite holding the Chairman role and majority stake, he didn’t want to force his views. Doing so could demoralize the leadership team and undermine the business’s culture.
That’s the paradox of leadership maturity: knowing when your influence might cause more harm than good.
Becoming an Owner: The Final Entrepreneurial Transition
If you’re not ready to sell but truly want to exit the business, consider the final role: Owner.
In this phase, you exit both operations and the board. You retain ownership—but little or no interaction with the business. This entrepreneurial transition is often ideal for serial founders. It allows you to extract value from one business while freeing your time and energy to start another.
Ownership delivers financial returns and legacy without operational demands. It’s the ultimate step in a progression that began with you doing everything—and ends with you doing nothing operationally, while still reaping the rewards.
Embracing Entrepreneurial Transitions for Long-Term Value
As you reflect on your role in your business, today and into the future, ask yourself: What level of involvement will bring the most happiness and fulfillment?
Each entrepreneurial transition—from contributor, to manager, to CEO, to board member, and finally to owner—represents not just a shift in title, but a shift in mindset and lifestyle.
And remember: you don’t have to keep running your business forever. But if you want to, you can always own it.
