The Business Owner’s Dilemma: Working In vs. Working On
The Business Owner’s Dilemma: Working In vs. Working On
Running a business is a balancing act.
As a business owner, you are responsible for both keeping day-to-day operations on track and ensuring the long-term success of your company.
Many entrepreneurs get stuck in the weeds—constantly working in their business—while neglecting to spend time on their business.
This distinction between operational focus and strategic planning can mean the difference between stagnation and growth.
The challenge lies in finding the balance between these two, making sure the business is not just surviving, but thriving.
The Trap of Working In Your Business
Many entrepreneurs fall into the trap of working almost exclusively in their business.
This includes managing client projects, handling financials, answering customer inquiries, and addressing day-to-day fires.
These tasks are undoubtedly important, but they can take up so much time that there’s little room for strategic planning.
Consider Mailchimp—before it became the email marketing powerhouse we know today, its founders, Ben Chestnut and Dan Kurzius, were heavily involved in daily operations.
They wore multiple hats, managing customer service, marketing, and product development. While the business was running smoothly, they realized that their heavy focus on operations was limiting their ability to grow.
Recognizing this imbalance, they made the decision to delegate more operational tasks and spend more time on strategic planning. This shift in focus allowed them to transform Mailchimp into a leading digital marketing platform that now serves millions of users globally.
Without intentional effort to step back and work on the business, owners like Chestnut and Kurzius would have stayed stuck in the day-to-day grind.
Their story illustrates how crucial it is to make time for growth-oriented initiatives.
While operational focus is necessary, too much of it can prevent business owners from looking at the bigger picture.
So, how can leaders ensure they are dedicating time to growth?
The Importance of Working On Your Business
Working on your business means setting aside time to focus on strategic growth.
This could include expanding into new markets, optimizing internal processes, or innovating products. Without this level of focus, businesses are likely to stagnate, leaving them vulnerable to competition.
In the early 2000s, Netflix was still operating as a DVD rental service.
However, Reed Hastings, CEO of Netflix, understood that DVDs would not remain the dominant media format for long.
He and his leadership team carved out time to focus on the future of their company and recognized that streaming services represented the next frontier.
Rather than staying bogged down in the day-to-day logistics of the DVD business, they shifted focus to working on the business by developing the infrastructure and partnerships necessary for streaming.
This forward-thinking strategy allowed Netflix to grow exponentially and outpace competitors like Blockbuster.
For Netflix, this shift to working on the business allowed it to remain ahead of the curve, a lesson that resonates with businesses of all sizes. If leadership had stayed overly focused on daily operations, the streaming giant might never have emerged.
Shifting from operational tasks to strategic planning is a significant move, but it’s only one piece of the puzzle.
The real challenge is balancing both aspects—making sure your business runs smoothly today while planning for tomorrow.
Striking the Balance Between Working In and On Your Business
Achieving this balance requires intention and discipline. Business owners must be proactive in delegating, automating, and setting aside dedicated time for growth activities.
Without these steps, it’s easy to remain stuck in the daily grind, where every task feels urgent but few contribute to long-term success.
A great example of balancing these efforts can be seen in Shopify, the e-commerce platform.
CEO Tobi Lütke instituted a company-wide practice called “off the grid” days.
During these days, the leadership team and employees disconnect from the day-to-day operations and focus entirely on brainstorming, long-term planning, and innovation.
This practice ensures that while daily operations continue to be handled efficiently, the team regularly makes time to focus on strategy and innovation. It’s a method that has helped Shopify grow from a small startup to one of the world’s leading e-commerce platforms.
The lesson here is that making space for strategic thinking is critical. Without it, you risk missing opportunities for innovation and growth. Business owners who implement this balance ensure their company stays agile and competitive.
Let’s look at practical steps you can take to ensure you’re making time to grow your business.
Practical Steps to Start Working On Your Business
- Delegate and Automate: Delegation is key to freeing up time for strategic work. Look for opportunities to offload repetitive tasks to your team or automate them using technology. Zapier, a company that specializes in automation, built its entire business around helping small businesses save time by automating workflows. This kind of automation allows business owners to focus on growth instead of getting caught in operational tasks.
- Schedule Non-Negotiable Time for Strategy: Whether it’s a weekly meeting or monthly offsite, setting non-negotiable time for strategic planning is essential. Following Shopify’s model of “off the grid” days, you can ensure that no matter how busy the week gets, there’s dedicated time to focus on long-term goals.
- Regularly Review and Adjust Goals: To make sure your strategy is working, you need to regularly measure progress. HubSpot uses quarterly reviews to assess long-term goals and adjust based on performance data. This keeps the leadership team focused on forward movement, ensuring the company stays aligned with its strategic vision.
These practical steps can help business owners maintain a healthy balance between working in and on their business, allowing for growth and innovation without sacrificing daily operations.
Building a Future-Ready Business
It’s easy to get caught up in the day-to-day grind.
However, businesses that carve out time to focus on growth and strategy—like Mailchimp, Netflix, and Shopify—are the ones that thrive.
By delegating tasks, setting clear goals, and regularly dedicating time to strategic thinking, business owners can ensure they’re not only managing today but building a foundation for future success.
The key takeaway?
Balancing both sides of the business is essential, and by intentionally working on your business, you’re positioning yourself for long-term success.
This blog post is proudly brought to you by Big Pixel, a 100% U.S. based custom design and software development firm located near the city of Raleigh, NC.
The Business Owner’s Dilemma: Working In vs. Working On
The Business Owner’s Dilemma: Working In vs. Working On
Running a business is a balancing act.
As a business owner, you are responsible for both keeping day-to-day operations on track and ensuring the long-term success of your company.
Many entrepreneurs get stuck in the weeds—constantly working in their business—while neglecting to spend time on their business.
This distinction between operational focus and strategic planning can mean the difference between stagnation and growth.
The challenge lies in finding the balance between these two, making sure the business is not just surviving, but thriving.
The Trap of Working In Your Business
Many entrepreneurs fall into the trap of working almost exclusively in their business.
This includes managing client projects, handling financials, answering customer inquiries, and addressing day-to-day fires.
These tasks are undoubtedly important, but they can take up so much time that there’s little room for strategic planning.
Consider Mailchimp—before it became the email marketing powerhouse we know today, its founders, Ben Chestnut and Dan Kurzius, were heavily involved in daily operations.
They wore multiple hats, managing customer service, marketing, and product development. While the business was running smoothly, they realized that their heavy focus on operations was limiting their ability to grow.
Recognizing this imbalance, they made the decision to delegate more operational tasks and spend more time on strategic planning. This shift in focus allowed them to transform Mailchimp into a leading digital marketing platform that now serves millions of users globally.
Without intentional effort to step back and work on the business, owners like Chestnut and Kurzius would have stayed stuck in the day-to-day grind.
Their story illustrates how crucial it is to make time for growth-oriented initiatives.
While operational focus is necessary, too much of it can prevent business owners from looking at the bigger picture.
So, how can leaders ensure they are dedicating time to growth?
The Importance of Working On Your Business
Working on your business means setting aside time to focus on strategic growth.
This could include expanding into new markets, optimizing internal processes, or innovating products. Without this level of focus, businesses are likely to stagnate, leaving them vulnerable to competition.
In the early 2000s, Netflix was still operating as a DVD rental service.
However, Reed Hastings, CEO of Netflix, understood that DVDs would not remain the dominant media format for long.
He and his leadership team carved out time to focus on the future of their company and recognized that streaming services represented the next frontier.
Rather than staying bogged down in the day-to-day logistics of the DVD business, they shifted focus to working on the business by developing the infrastructure and partnerships necessary for streaming.
This forward-thinking strategy allowed Netflix to grow exponentially and outpace competitors like Blockbuster.
For Netflix, this shift to working on the business allowed it to remain ahead of the curve, a lesson that resonates with businesses of all sizes. If leadership had stayed overly focused on daily operations, the streaming giant might never have emerged.
Shifting from operational tasks to strategic planning is a significant move, but it’s only one piece of the puzzle.
The real challenge is balancing both aspects—making sure your business runs smoothly today while planning for tomorrow.
Striking the Balance Between Working In and On Your Business
Achieving this balance requires intention and discipline. Business owners must be proactive in delegating, automating, and setting aside dedicated time for growth activities.
Without these steps, it’s easy to remain stuck in the daily grind, where every task feels urgent but few contribute to long-term success.
A great example of balancing these efforts can be seen in Shopify, the e-commerce platform.
CEO Tobi Lütke instituted a company-wide practice called “off the grid” days.
During these days, the leadership team and employees disconnect from the day-to-day operations and focus entirely on brainstorming, long-term planning, and innovation.
This practice ensures that while daily operations continue to be handled efficiently, the team regularly makes time to focus on strategy and innovation. It’s a method that has helped Shopify grow from a small startup to one of the world’s leading e-commerce platforms.
The lesson here is that making space for strategic thinking is critical. Without it, you risk missing opportunities for innovation and growth. Business owners who implement this balance ensure their company stays agile and competitive.
Let’s look at practical steps you can take to ensure you’re making time to grow your business.
Practical Steps to Start Working On Your Business
- Delegate and Automate: Delegation is key to freeing up time for strategic work. Look for opportunities to offload repetitive tasks to your team or automate them using technology. Zapier, a company that specializes in automation, built its entire business around helping small businesses save time by automating workflows. This kind of automation allows business owners to focus on growth instead of getting caught in operational tasks.
- Schedule Non-Negotiable Time for Strategy: Whether it’s a weekly meeting or monthly offsite, setting non-negotiable time for strategic planning is essential. Following Shopify’s model of “off the grid” days, you can ensure that no matter how busy the week gets, there’s dedicated time to focus on long-term goals.
- Regularly Review and Adjust Goals: To make sure your strategy is working, you need to regularly measure progress. HubSpot uses quarterly reviews to assess long-term goals and adjust based on performance data. This keeps the leadership team focused on forward movement, ensuring the company stays aligned with its strategic vision.
These practical steps can help business owners maintain a healthy balance between working in and on their business, allowing for growth and innovation without sacrificing daily operations.
Building a Future-Ready Business
It’s easy to get caught up in the day-to-day grind.
However, businesses that carve out time to focus on growth and strategy—like Mailchimp, Netflix, and Shopify—are the ones that thrive.
By delegating tasks, setting clear goals, and regularly dedicating time to strategic thinking, business owners can ensure they’re not only managing today but building a foundation for future success.
The key takeaway?
Balancing both sides of the business is essential, and by intentionally working on your business, you’re positioning yourself for long-term success.
This blog post is proudly brought to you by Big Pixel, a 100% U.S. based custom design and software development firm located near the city of Raleigh, NC.
Our superpower is custom software development that gets it done.
