On Vs In Your Business: The Toxic Guru Myth

When was the last time someone asked you what business you were “on”? Never? That’s because it’s a ridiculous concept! Yet, countless business gurus insist you shouldn’t be “in” your business, but “on” it. Let’s put this toxic myth to bed.

You Must Be "In" Your Business

People don’t say they’re “on” relationships or “on” their careers. They’re in them—engaged, involved, and committed. The same applies to your business. The world’s most successful entrepreneurs—think Michael Dell, Elon Musk, or Jeff Bezos—didn’t check out of their businesses after hitting it big. They adjusted their roles but stayed deeply connected.

The idea that being “in” your business makes you less of a leader is toxic nonsense. What truly matters is how you spend your time in your business. Are you stuck changing metaphorical spark plugs, or are you strategically driving growth?

The Real Problem: Operator vs. Owner

The challenge for most small business owners isn’t being in their business; it’s being stuck in the wrong parts of it. Too many owners spend their days operating the business instead of running it. They’re overwhelmed by tasks they should delegate, unable to focus on the critical activities that build value and prepare for an eventual exit.

Here’s the truth: the leap from “Operator” to “Owner” isn’t automatic. It’s a process—a transition that demands learning, prioritizing, and often seeking outside guidance. Owners who thrive have mastered critical business skills like:

• Hiring the right people.
• Delegating effectively.
• Creating systems and processes.
• Understanding financials.
• Building a unified culture.

These skills don’t come naturally. They must be learned, often with the help of mentors or advisors.

"On" vs. "In" and the Role of Engagement

The moment you disengage entirely from your business, you’re no longer an Owner—you’re an Investor. If that’s your goal, great! But understand this: your business needs leadership, vision, and strategic oversight, even if you’re not handling day-to-day operations. It needs you in it—not as a micromanager, but as a focused leader shaping its future.

The wealthiest and most successful entrepreneurs remain engaged with their businesses, even when their roles evolve. They prioritize oversight, strategy, and culture-building—the things that add value.

Actionable Insights for Business Owners

If you feel stuck as an Operator and want to shift into the Owner role, start here:

1. Audit Your Time: Where are you spending hours on low-value tasks? Identify activities you can delegate or outsource.
2. Prioritize Critical Projects: What high-value initiatives are languishing because you’re too bogged down? Dedicate time—start with just 30 minutes a day—to chip away at these.
3. Solve Choke Points: What’s preventing you from spending more time running your business instead of working in it? Brainstorm cost-effective solutions, like hiring part-time help or leveraging technology.
4. Ask the Right Questions: Where am I confusing activity with productivity? What could I outsource to free myself up for strategic work? What can I do this week to create momentum toward a true Owner mindset?

Final Thought: Build Value, Stay Engaged

Your business doesn’t need you “on” it. It needs you in it—doing the right things. When you master the skills of prioritizing, delegating, and focusing on what matters most, you’re not just preparing your business for an eventual sale. You’re building a legacy that reflects your leadership and vision.

So, stop worrying about being “on” your business. Get busy being in it—and make every moment count.

This article is inspired by "The Road Less Stupid" by Keith J Cunningham and a recent claim by Marc Andreessen, the renowned Silicon Valley venture capitalist and co-founder of Andreessen Horowitz , that Elon Musk had managed to solve some of Tesla’s and SpaceX’s worst problems in just a single week.