As a Strategic Advisor, I've had the privilege of working alongside business owners who shoulder immense responsibilities — wearing multiple hats while navigating the demands of strategy and execution. One of the recurring challenges they face is determining when to work on their business and when to immerse themselves in it.

This is more than a theoretical concept; it's a pivotal question that can profoundly influence a business's trajectory. For leaders, striking this balance requires strategic clarity, self-awareness, and adaptability.

The Difference Between Working On and In Your Business

Michael E. Gerber, in The E-Myth Revisited, explains how many business owners unintentionally stunt their growth by focusing solely on technical tasks. This is working in the business—managing daily operations, solving immediate problems, and ensuring everything runs smoothly. While essential, this approach keeps you in the weeds.

Working on the business, on the other hand, is about stepping back to shape its future: refining strategy, driving growth, and building systems that allow the company to thrive independently of your constant involvement.

When to Stay In the Business

In the formative stages, working in the business is natural and often necessary. These are the moments when every sale, every customer interaction, and every process you define matters. But even as the business matures, there are times when leaders must dive back into the trenches:

• During crises or significant operational shifts.

• When introducing a critical system or onboarding a new team.

• To stay connected to customer feedback and market realities.

Being hands-on during these times grounds you. Experts like Jim Collins emphasize that staying engaged in the core operations ensures alignment between your vision and execution.

When to Work On the Business

As your business scales, your role as a leader must evolve. Research from Harvard Business Review shows that businesses often plateau because leaders need help transitioning from tactical doers to strategic leaders. Working on the business becomes imperative when:

• Growth stagnates, and a fresh strategic vision is required.

• You become the bottleneck for critical decisions.

• The business can only scale if processes rely heavily on you.

This transition demands trust—trust in your systems, trust in your team, and trust in your ability to step back and lead. It also requires a mindset shift: from working harder to leading smarter.

Avoiding Common Missteps

Staying "In" Too Long

Leaders overly entrenched in operations risk missing growth opportunities. Studies from McKinsey highlight that such over-involvement leads to burnout and stifles innovation and scalability.

Shifting "On" Too Early

On the flip side, stepping away prematurely can create a dangerous disconnect between strategy and execution. Your business needs a solid operational foundation before scaling.

Your Role Evolves as the Business Evolves

The decision to work on or in your business is not static; it evolves alongside your company's growth. Sometimes, you may need to return to operations to stabilize the foundation. At others, your focus must shift to the bigger picture.

Ultimately, the goal is to build a thriving business with or without your constant presence. This doesn't mean you're absent—it means you're present where your contributions bring the most value.

Reflection: Are You Spending Time in the Right Places?

Mastering the balance between working on your business and working in it demands self-awareness, trust, and adaptability. While it's not an easy equilibrium, finding it enables your business to grow and deliver the freedom, fulfillment, and impact you originally envisioned.

The key lies in knowing when to step back and strategize and when to dive in and connect with the day-to-day realities. Striking this balance empowers you to lead, build sustainable systems, and create lasting value.

Are you investing your time where it truly matters most?