Working on your business vs in your business

As entrepreneurs, we are reminded, constantly of all the different hats we must juggle. How many times have you introduced yourself as the salesman, marketing head, R&D, product developer and Ops person of your business? Well, you’re not alone.

This is not an anomaly within the start-up industry because most businesses begin with an idea turned into a reality by a solitary founder. When the idea transforms into a company, the solitary founder turns into a team of many, and the entrepreneur has already mastered being the Jack of all trades.

But as businesses mount their growth path, this trait, previously viewed as a strength, quickly descends into a weakness. Entrepreneurs unknowingly become their best employees, begging the question, who runs the business?

According to the Pulse Survey on Business Leaders and Productivity by The Alternative Board, 84% of business owners work over 40 hours a week, and 1 in every 10 feels continuously overwhelmed by their responsibilities. Additionally, the average business owner reports getting only 1.5 hours of uninterrupted, highly productive time each day.


Michael E. Gerber, American author and entrepreneur who coined the phrase ‘work on it, not in it’ 35 years ago, said, “If your business depends on you, you don’t own a business – you have a job.”

Michael E. Gerber, American author and entrepreneur who coined the phrase ‘work on it, not in it’ 35 years ago, said, “If your business depends on you, you don’t own a business - you have a job.”

What’s the difference between working ‘in’ your business vs working ‘on’ your business?

Working in your business entails activities that do not necessarily require the founder to execute. These tasks can typically be fully delegated and do not require the founder to complete the job.

Working on your business includes activities that necessarily require the founder to be directly involved. Generally, these cannot be completely delegated or completed without the founder.

The infographic below lists out some examples:

Working in your business

Answering queries
Making payments
Sending invoices
Shooting a video
Writing a social caption
Sending out BD emails
Following up on emails
Proposal creation
Putting out fires
Logistic coordination

Working on your business

Updating business plan
Updating financial projections
Setting business goals
Upskilling
Maintaining investor relationships
Maintaining mentor relationships
Increasing efficiency in processes
Exploring new market opportunities
Identifying business collaborations
Building personal resilience

Working in your business 
Answering queries
Making payments
Sending invoices
Shooting a video
Writing a social caption
Sending out BD emails
Following up on emails
Proposal creation
Putting out fires
Logistic coordination

Working on your business
Updating business plan
Updating financial projections
Setting business goals
Upskilling
Maintaining investor relationships
Maintaining mentor relationships
Increasing efficiency in processes
Exploring new market opportunities
Identifying business collaborations
Building personal resilience

How to balance working in your business and on your business?

At the foundation of it, business coaching experts agree it’s a change in thinking and perspective. Entrepreneurs ready to fastrack their growth must orient themselves to the mindset that the business in its entirety is the product.

Many entrepreneurs view their business as a place of work where their job is to sell a product or service every single day. They get bogged down with the day-to-day, and their fingers are dipped into too many jars, which fills their time. They appear to be working very hard, and they also delude themselves into believing they’re doing their best for their business. But as Caterina Fake, co-founder of Flickr, says very aptly, “So often people are working hard at the wrong thing. Working on the right thing is probably more important than working hard.”

Entrepreneurs must remember that the business is not their life; instead, the business serves their life. 

Here are some easy habits that can help you make the switch and start working more  ‘on’ your business:

1. Audit your time:

Start by creating an inventory of what your typical work day looks like and label the activities. Ask yourself simple questions for each:

  • Did I have to do this myself?
  • Did I take longer than required to complete this task?
  • What did I miss while working on this?
  • Can I delegate/ automate/ outsource this task from now on?
  • How can I set up an efficient system to delegate/automate/outsource this? (ie. Do I need to invest in an AI automation subscription? Do I need to pass it on to a team member? Do I need to hire?)

2. Prioritize and Calendarize:

Identify entrepreneurial activities that you want to do every day. Create a list and sequence them based on:

  • Must do
  • If I have time

Assign the required number of minutes or hours to these activities and place them in your daily routine. Below are some examples 

  • Chalk out a clear 1-hour ‘Zoom Out’ session every day. Take this time to look at the big picture. 
  • Pre-book on your calendar, 3 hours every month with your Mentor. 
  • Give yourself 15 mins every week to brainstorm growth-hacking ideas, no holds barred; whatever pops into your head, write it down. 
  • Mark 15 mins a day to review each of your core strategies across Product, Sales, Marketing, Operations and Growth.
  • Spend 15 mins a day reviewing one business system, allocate one business system for every day in the week and solve for inefficiencies. 
  • Spend 5 minutes at the end of every day planning your activities for the next day. 
  • Allocate a heads-down day once a month when you do not take any calls or meetings. You only look inwards at your business.

3. Get Help

As entrepreneurs, we think we should have all the answers. But that’s rarely the case, with anyone, in any scenario. When decisions, tasks, systems, and people are not going according to plan. When things take much longer than they should. When your solution-scape is failing on repeat. Catch it quickly and fail forward. Help comes in many forms: 

  • Reach out to your Mentor
  • Hire a consultant
  • Reach out to a peer
  • Read a book
  • Watch a tutorial
  • Ask an expert for a crash course

These solutions can shave months, if not years, off of a business straying from their growth track.

4. Master the art of delegation:

How often have you written away your time by stitching this narrative together?  “I can do it faster.” “I like it a certain way so it’s better I handle it.” “It takes too long to explain it to someone else.” “They’re busy; I can’t add this to their work.”

Delegating has the ability to make entrepreneurs feel guilty, while not delegating has the ability to make entrepreneurs feel hyper-useful. So it’s natural to choose the latter. This infographic outlines the rewiring required in a founder’s mind to get more comfortable with delegation.

Delegation is a tool to

  • Give yourself more time to focus on moving the business forward
  • Establish trust between employees and the founder
  • Streamline efficiency for recurring work
  • Invest in employee upskilling 
  • Identify stand-out employees who can grow with the business

Delegation does not mean

  • Getting away with not doing a task 
  • Overworking your employee
  • A longer route to getting things done
  • The founder is not passionate or knowledgeable enough

Get delegation right by introducing these practices: 

  • Practice letting go: If you’re not completely used to delegating yet, start by delegating smaller tasks or delegate smaller parts of a larger task.
  • Find your delegation match: As the leader, you must have a deep understanding  of your employee’s strengths. Delegating the right task to the right person can make all the difference between a smooth transition and one that brings you right back to not delegating.
  • Communicate clearly: Provide clear briefs, guidelines and deadlines to the team member so they can hit the ground running. 
  • Focus on outcome: Don’t get too wrapped up in training someone on how to achieve the outcome. If you trust in their abilities, leave them with clear directions on the expected outcome. 
  • Give credit where credit is due: If the job has been done well, acknowledge the team member’s input and support. This contributes to a healthy, supportive environment around delegation.

Once you’re able to find the sweet spot between working in and working on your business, you will find that apart from a healthy, productive personal work culture, you’ve also created a company culture that will follow suit. Many successful entrepreneurs have birthed their own creative ways to ensure they spend enough time on upper-level strategy and decisions.

CEO of Twitter and Square, Jack Dorsey’s system boasts of a weekly rhythm – Mondays are for management and running the company, Tuesdays for the product, Wednesdays for Marcomm, Thursdays for Developers and Partnerships, Fridays for Company culture and hiring. Saturday, he takes off and Sunday is for reflection and feedback.1 

CEO and founder of Ometria says he likes to keep usage of his time under his control. He doesn’t let calls, texts and notifications distract him. He keeps specific time aside to check his phone and responds to them only in the allocated time.2

CEO and founder of Ometria says he likes to keep usage of his time under his control. He doesn’t let calls, texts and notifications distract him. He keeps specific time aside to check his phone and responds to them only in the allocated time. Matt Deceles, a serial entrepreneur, says he delegates ‘like a boss’. He believes that when we enjoy what we do, is when we are most productive. If you’re not good at something, there might be someone else who can do it faster and better. 3

If you’re a Canadian or International entrepreneur looking for business advisory support to start, grow or buy a business in Canada. Reach out to our advisory team here. TBDC has supported over 9000 local and immigrant entrepreneurs in Canada to achieve their business goals. 

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