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Work ON Instead of IN Your Business

I’m guessing you’ve heard the phrase, “Working ON your business instead of IN your business.” It’s not always clear what this phrase means. If you know what it means, you may have difficulty understand the benefit of working ON instead of IN your business. And, if you understand the benefit of working ON instead of IN your business, you may have difficulty accomplishing this feat. In this post, I want to answer all three questions.

What is Working On instead of In Your Business?

I want you to imagine a pump that's operating in a pond. The pump creates a beautiful water fountain by drawing water from the pond and pumping it into the fountain mechanism spraying water into the air. This process is repeated perpetually.... until the pump breaks. You then repair the pump and turn the switch on, and the operation continues as it had before. In simple terms, you are working ON the pump.

Now, let’s imagine another machine. This is a money-making machine. The inputs to this machine are: 1) your money; and 2) your time. There are two outputs: 1) profitably cashflow; and 2) beneficial products and services to your customers. When most business owners first start out, they have little money and a lot of time. Therefore, they tend to be the primary worker in their business. This is working IN your business.

Once your business gains momentum with a steady flow of customers, you hire other workers and manage those workers. You are still working in your business, but others are doing most of the direct work on behalf of your business.

At some point, you hire managers and become the CEO who is creating the vision of your company, watching various characteristics of how your company is operating; and then tweaking things as you go. You may care about customer satisfaction, overall profitability, employee satisfaction, and product quality. At this point, you are officially working ON your business.

Why is Working ON Your Business Instead of IN Your Business a Benefit?

Let’s go back to our fountain pump illustration. Let’s say that you happen to be one of the water molecules running around the fountain loop. You run through the pump, then to the fountain, then get sprayed into the air, and then flow back through the pond to the pump. Now, the pump breaks. Who will fix the pump?

In the small business reality, you'll try to do both; working in your business and fix your business when it breaks. This dual role works if you have few customers. As soon as you grow, it’s important to hire others to do the work. If you don’t, you'll forever be working IN your business.

There are several benefits of working ON instead of IN your business:

  1. Your perspective will be of your entire business machine instead of one aspect of your business at a time.

  2. You will own and run a business instead of a working in a job.

  3. Your business can grow because you’re not the bottleneck.

  4. Your employees will get a leader rather than an over-paid co-worker.

  5. Your personal income will be substantially higher.

The greatest benefit is that you'll be in CONTROL. Can you imagine the water molecule trying to troubleshoot and fix the pump? Of course not. If you want to control your business, you must be outside of the workings of your business.

Why is Working ON Your Business Instead of IN Your Business so Hard?

As luck would have it, most good entrepreneurs are good workers.

As I’ve coached business owners they go through four stages from working IN to working ON their business.

Sole Worker

The first stage is the worker... out of necessity. With little money to hire someone and you must do the work to earn money to hire someone else.

Even when money is available, you're tempted to remain a worker. Why? Because you're used to it. When you hire someone else, you micro-manage that individual to get them to do things exactly as you would've done them as the worker.


The second stage is to allow new employees to do a specific role in the company while you fill a role that you feel you're best at performing. For instance, the new worker may directly serve the customer, while the owner will sell and market for the company.

The owner stays in this role often believing and new employee cannot fill that specific key role in the company.


The third stage is to manage employees within the company. You are hiring and doing performance reviews for staff. When trying to transition out of this role, it's difficult to find a replacement. You want someone who understands the entire business, doesn’t cost a fortune, and is preferably an employee who already works for you.


At this final level, the business owner is finally the Chief Executive Officer or CEO. They are responsible for management, large financial decisions, investment opportunities and being the entrepreneur, they had always hoped to be.

Business owners have resistance at each one of these transition points. Even when they transition, they try to transition back. The quicker a business owner can transition successfully through each growth point, the sooner they will experience the benefits of working ON their business instead of IN their business.

How Do You Work ON Instead of IN Your Business?

We’ve discussed the advantages of working ON instead of IN your business. I want to now share some tricks to making these transitions.

Financial Plan

Each time I take on a new business owner client we construct a 10-year financial plan. This plan shows growth of the company from a financial perspective. My client sees that cash is present to hire new employees and step into a new role themselves as the company grows. This planning and expectation allow the business owner to have an automatic trigger that helps them prepare for each transition point.

For instance, if there will be five employees at $500,000 of revenue, they must transition to manager at that revenue point, or their company will fail to reach the next revenue objective.

Leadership Training

If you’ve never managed people, the first time can be challenging. Without formal training, you will resist becoming a good leader which will prevent you from achieving the proper growth of your business. When you understand how to lead people in a responsible way, you'll be much more likely to embrace leadership responsibility required to transition through each growth point.

Hire a Business Coach

A coach sees your business in an objective way. You see your business from the inside. Before you are able to work ON your business, a business coach will give you an objective view of how and when to transition to grow your business.

There you have it…. I hope you now understand the WHAT, WHY, and HOW to transition from working IN your business to working ON your business. I have developed proven methods to help my clients move through these transition points quickly. If you’d like to learn more about my business coaching practice, please visit my website at:



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