Working “In” vs. “On” Your Business: Finding the Right Balance

If you’re new to our weekly entrepreneur newsletter, welcome! Each week we research the issues impacting small business owners and entrepreneurs, then share insights, strategies, and expertise to help you overcome challenges and achieve your goals. Enjoy today’s edition!

In This Issue

• Defining “In” vs. “On”: What these terms really mean and why it matters.
• Ideal Time Allocation by Revenue Milestone: Insights from The Pumpkin Plan on where you should focus your efforts.
• Shifting to Big-Picture Leadership: Practical steps for delegating, automating, and systematizing.

In vs. On: What Does It Really Mean?

In the Business are day-to-day activities directly tied to operations and revenue: selling, delivering services, invoicing, troubleshooting, and managing emergencies. It’s the hustle that keeps the lights on.

On the Business are high-level, strategic tasks: planning new offerings, building systems, guiding your team, and setting the long-term vision. These activities take your company from where it is now to where you want it to be.

Most founders start by doing almost everything themselves. Over time, scaling requires shifting more energy “on” the business—leading and shaping it rather than getting buried in the details.

The Right Balance at Different Revenue Stages

According to The Pumpkin Plan, the ideal split between “in” and “on” evolves as you hit revenue milestones. Use this as a guideline to self-assess:

• Under $100K: ~80–90% In, 10–20% On
• $100K–$250K: ~75% In, 25% On
• $250K–$500K: ~60% In, 40% On
• $500K–$1M: ~50% In, 50% On
• $1M+: ~20–40% In, 60–80% On

If you’re feeling overwhelmed by daily tasks while revenue climbs, it’s time to shift more attention “on” the business.

Making the Shift: Practical Steps

1. Delegate & Empower
   • Identify non-core tasks you can hand off.
   • Train and authorize your team to make decisions—reduce emergencies landing on your desk.
2. Automate Wherever Possible
   • Use tools for billing, scheduling, email marketing, and other repetitive workflows.
   • Document each process so anyone can follow the same steps.
3. Systematize Your Offerings
   • Focus on your most profitable products/services.
   • Prune low-value offerings to simplify operations and free up your time.
4. Schedule “On” Time
   • Block weekly or monthly slots dedicated solely to strategic planning and innovation.
   • Treat these blocks as unbreakable CEO appointments.
5. Measure & Adjust
   • Track how you spend your hours.
   • If “in” tasks creep back up, revisit delegation and systemization until you find the right balance.

The Bottom Line

At every stage of growth, the balance between working “in” and “on” your business must shift. By delegating, automating, and systematizing, you free yourself to lead with vision and strategy—building a company that supports your long-term goals and gives you the freedom to enjoy both work and life.