Craving Freedom? Maybe You, The Business Owner, Need a New Job Description

The Honeymoon Challenge: A Wake-Up Call

In the beginning stages of working with a client, a business owner revealed a personal challenge: She was getting married in 9 months, and her fiancé had one non-negotiable request—a month-long, work-free honeymoon. Could she do it? "I haven't taken a vacation without working in the last three years," she admitted. "I can help," I assured her. And that's how our transformative journey began.

Do you feel stuck in the business's daily operations but crave more freedom?  If you’re like most entrepreneurs, you started your business with a dream: more freedom, more profits, and the chance to do more of what you love.  You’ve poured your heart and soul into the business, taking on every challenge, task, decision, and opportunity.  While that weight grows heavy on your shoulders, a bit of you take pride in what you’ve done and are terrified of letting go.

The Trappings of Success: When Business Becomes Identity

Enter the trap of cozy familiarity.  In the early stages of your business journey, you personified the saying, “The Buck Stops Here.”  It’s been working… until now.  Maybe you’ve dipped your toe into taking things off your plate.  

Perhaps you even have a small team surrounding you, yet nothing seems to make a dent in your workload.  For instance, you might delegate tasks to your team, only to do most of them yourself, because you want to ensure they are done correctly.

You’re at the point of transformation from being the person who gets everything done to the person who ensures that everything is done.  It’s a critical point you’ll need to tackle to get your business to the next level, going from the worker to the manager. 

Transform or Get Stuck: The Entrepreneurial Value Paradox

Some business owners never make it through this transformation because being busy has become part of their identity.  

In a slightly twisted way, you’ve become addicted to the workload and the value your subconscious finds in working. It’s like an addiction to a substance. It can be challenging to break because it’s a source of pleasure, even in the face of evidence to the contrary. You need to recognize the addiction and take steps to break it to move forward.

When a business goes to the next level, who you are, your identity, and the value you bring to the business must transform.  

Depending on your addiction level to work- this transformation can be incredibly challenging, and you’ll find yourself knee-deep in an identity crisis.

Family Business and the Legacy Struggle

For freedom to be realized, your role and identity must evolve.  

This identity crisis happens early and sometimes at the exit stage.  The situation we’ve witnessed happening is the transition in a family business.  When a parent is mentally ready to pass the baton to their child, it can be hard to let go emotionally.  In part because their identity is tightly wound with being the business owner.  

This is so well known in the exit planning stage. Your advisors will work with you to define what ‘after’ the sale looks like, what the plans will be, and how you will fill your days when you realize that freedom.   

When your identity is often intertwined with your business, it can be difficult to transition into a new role or lifestyle. This is why it's essential to have a plan that considers the business owner's emotional and psychological needs and the business's needs.

The Path Forward: Emotional and Psychological Planning

What happened to our business owner who wanted to take a month off? It took us 9 months of meticulous planning to make the month-long honeymoon without working possible. In the process, we evaluated the team, ensuring the right people were in the right place.  Then, we worked individually with the team to evaluate the skills and interests for different aspects of the business.  We developed processes and tested them out.  We created cross-training plans that gave the owner the confidence that the team could handle things and excel at them.

Then, one month before the owner’s wedding, we off-loaded the tasks from the owner to the team.  During that month, the owner’s role focused more on leadership and being a sounding board to her team to troubleshoot any hiccups that might pop up.

Our owner went on her honeymoon. When she returned one month later, she sat down on Sunday night with her computer, took a deep breath, and opened her email.  Why was she so nervous?  Because she had been so used to putting out fires in the business over the last few years. She didn’t know what she would find. She had trouble trusting that all would be well.  

When she got back, I was curious and asked, “OK, what did you find when you read the emails? “ She replied, “Nothing.  Every email was about keeping me in the loop. Nothing needed my attention.”  

Fabulous - I love it when a plan comes together.  Yet our story doesn’t stop there.  The identity crisis would come a month later.  We found that the team and the tasks ran smoother without the business owner getting into the middle.  No one wanted to give back the tasks to her. That is every business owner’s dream, isn’t it?

Embrace the Crisis: Your Next Growth Opportunity

“I think I should leave the business and get a job.”  My eyes snapped up from my notes, and I solidly looked at her.  “W-h-y?”  

“Because I’m not bringing value here, no one needs me. They all have it handled.” 

She was solidly in the middle of an identity crisis. This experience is so common it just isn’t shared. Thinking about leaving the business to find a new job as the business owner isn’t a sign of weakness. It is a sign of opportunity.  As the conversation unfolded, we found that opportunity. We wrote her new job description of her elevated role in the business.  One that gave direction, protected the freedom we created and redefined the value she brought to the table. 

We see this crisis of identity as a gift.  It is like the world is telling you it’s time to shift your focus from working in your business to working on your business.  It’s an invitation to redefine your value in the business to a fulfilling and impactful identity.  Remember, you are not only building a business here. You are building a business legacy.

Your Legacy Awaits: Are You Ready?

Your truest value to the business isn’t in the tasks you perform but in the vision you set, the culture you build, and the people you inspire to follow you in your business and life. You are still the captain of your ship. Let your team handle the controls while you focus on the destination.  This isn’t about stepping back. You are stepping up.

Are you ready to move beyond crisis and unlock the next level of profits and freedom?  Dream big.  Aim high.  Let’s transform this moment into your next growth opportunity.  Remember, you are not just running a business but building a life. 

If you're at this pivotal point, our Profitable Growth Incubator or Fractional CFO Services are tailored to guide entrepreneurs like you through these exact challenges. If you want to chat about these more, find time on my schedule to meet! Let's transform your crisis into your next growth opportunity together.