From Taskmaster to Visionary: How to Stop Working In the Business and Start Leading It

Take It Easy Group: From Taskmaster to Visionary: How to Stop Working In the Business and Start Leading It

Let’s be honest: every founder starts out wearing all the hats.  You’re the marketer, the customer service rep, the product lead, and sometimes even the janitor.  But there comes a point when continuing to operate this way becomes a bottleneck, not a badge of honor.  

The phrase “work on the business, not in the business” is thrown around constantly, but most leaders aren’t taught how to make that shift.  

What It Really Means to Work On vs In the Business 

Let’s define it clearly: 

• Working in the business: 

  • Completing daily tasks 

  • Solving immediate problems

  • Handling operations

  • Managing client issues 

  • Staying reactive 

  
  

• Working on the business: 

  • Setting long-term vision

  • Building scalable systems

  • Hiring the right people and letting go of control 

  • Designing strategy 

  • Driving growth and innovation 

Here’s the kicker: working in the business often feels more productive.  You’re checking boxes, getting dopamine hits from small wins, and staying “busy.”  But busyness isn’t effectiveness, and it definitely isn’t leadership.  

Why Leaders Stay Stuck in the Task Mindset

Most founders don’t wake up saying, “I want to be bogged down with admin today.”  So why does it happen?  

• Fear of letting go: 

It feels risky to delegate what you’ve always done yourself. 

• Confusing control with security: 

“If I don’t do it, it won’t get done right” is a common belief - one that keeps you small. 

• Lack of clarity on what strategic work even is: 

Many leaders aren’t taught how to think strategically, so they stay in the comfort zone of tasks. 

• No one to elevate with you:

When your team is task-based, you get pulled back into task mode. 

What Strategic Thinking Actually Looks Like

This isn’t about locking yourself in a room to write a mission statement.  Strategic thinking is practical, and it’s daily. 

Task Mindset	Strategic Mindset
Answering every client email yourself	Building a support process with clear SOPs
Jumping in to fix a broken system	Empowering your team to own solutions
Launching things reactively	Planning campaigns based on data and trends
Hiring to fill urgent needs	Designing an org chart for the next 12 months
Doing	Designing and delegating

How to Shift from Task to Strategy - A Practical Framework 

Here’s a four-step process to help you make the shift: 

Step 1: Audit Your Time 

Spend one week tracking your time in 15-minute increments.  Label each block 

• Task = $10/hour work 

• Manager = $100/hour work 

• Strategy = $1,000/hour work 

You’ll probably find 80% of your time is on $10 work.  That’s your first red flag.  

Step 2: Identify What Only You Can Do

Write a list of everything you currently do.  Now highlight the things that only you can or should be doing as a founder or leader.  This becomes your “zone of genius” list. 

Step 3: Build the Bridge - Systems and People

Ask: 

• “What tasks can be delegated with proper SOPs or automation?” 

• “What roles do I need to hire for in the next 3-6 months?” 

• “Who on my team can be coached to think more strategically?” 

Step 4: Protect Your Strategic Time Ruthlessly 

• Block 3-5 hours per week to work on the business (non-negotiable) 

• Use that time to map goals, review metrics, brainstorm future moves, and align with your leadership team 

• Don’t check Slack.  Don’t check email.  Think deeply. 

Step 5: Mindset Shifts That Reinforce Strategic Leadership

• You are no longer the doer.  You are the builder. 

• Done your way is not always the best way. 

• Slowing down to think is a business accelerator, not a liability. 

• Every hour spent on systems gives you back 10 in the future. 

What Happens When You Make the Shift

When you truly start leading strategically, you’ll notice: 

• Your team becomes more autonomous

• You have more space to think and breathe 

• Growth becomes more sustainable 

• You stop feeling like everything will fall apart without you 

You begin to build a business that can scale, with or without you. 

Conclusion:

If you are stuck in the daily whirlwind, know this: it’s not your fault, but it is your responsibility to break free. 

Start small.  Pick one task this week to delegate.  Block one hour for deep strategic thinking.  Track your time and ask yourself honestly: Am I leading, or am I just doing? 

There’s a visionary inside you.  But first, you’ve got to put the task list down and pick your head up.  

If you are ready to escape the task trap and want a partner to help you operationalize your vision, our team of fractional Chiefs of Staff and Executive Assistants can help.  Contact us today to learn how our team can help you make it happen - one step at a time.  hello@takeiteasygroup.com or Book your free strategy call here.