Entrepreneurship & Family: A Balanced Path to Success

July 27, 2023

How Do Entrepreneurs Find Balance Between Career & Family?

Here's My Secret to Balance.

As visionaries and entrepreneurs, we're constantly chasing success, investing significant time and effort in growing our market and revenue. But let's not forget that life is precious and limited. While we strive for success, let's also remember the importance of improving our lives and those of our families. True triumph lies in sharing the rewards with loved ones and creating lifelong bonds with family and friends. So, let's make a proactive effort to spend quality time with them, embark on new ventures together, and create lasting memories that will stay with us forever.

The Importance of Quality Time

We visited Amelia Island in Florida for a traditional family vacation earlier this year. Even though I couldn't fully disconnect from my business, I planned to make the most of our short trip. My main focus was to ensure that my wife felt supported and encouraged to relax just as much as I did. Since I have a great team supporting my businesses, I knew I had to create a similar support system for Brittany and our daughter Evie to fully enjoy our trip. So, I arranged for a nanny at our destination and connected with the hotel concierge service to take care of Brittany and Evie's needs during our stay.

Delegation and Remote Business Management

Everything operated smoothly at my media company and roofing businesses while I was away. We have done the work to put systems, processes, and the right people in place so that I can step away without any disruption to the business. Implementing the EOS principles of vision, people, data, issues, process, and traction has been the key to keeping things on track and measurable, no matter how involved or remote I plan to be. 

Nurturing Business Relationships and Personal Bonds

This week, we've been on another trip. We decided to take a family vacation to the New Jersey coast to hang out with my good friend, Joseph Hughes, the founder of Contractor Dynamics. It was a great opportunity for Brittany, Evie, my son Sammy and me to connect with Joe's family, strengthen our business and family bonds, and enjoy quality time together. My day-to-day work with Contractor Dynamics is mostly remote, with occasional in-person conferences and workshops. The events can be pretty fast-paced, but we always make sure to gather as a team. It's so important to stay connected with Joe and his vision for the future of Contractor Dynamics.
As entrepreneurs, the strength of our relationships with our families and those we work closely with is the true measure of success. Meeting Joe's family and introducing mine was an amazing confirmation that I am working alongside an incredible person. Relationships in business are undeniably important. I feel grateful for my friendship with Joe and his family, who graciously welcomed us into their home. Seeing our families interact during this trip with Brittany by my side has been incredibly special. I can't emphasize enough how essential it is to have a supportive partner who believes in your visions and dreams.

My Journey Towards Balance

I've managed to strike a remarkable balance between my work and personal life. While I dedicated part of this trip to nurturing work relationships, I also created precious family memories. As a dad, the pure joy of organizing a day trip to show Sammy the wonders of New York City was absolutely unmatched. 
Getting to this point in my journey has taken time and purpose-driven action. Systems, people, and open lines of communication make all of it possible. My companies are in good hands, my family is my top priority, and I'm doing business with like-minded people. Finding that sweet spot called balance is the secret to making it all work.

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By Benny Fisher January 8, 2026
The Right Fit Leader Podcast
By Benny Fisher January 8, 2026
A few years ago, I asked Gino Wickman what he calls the work he does when he mentors and guides people. He simply said, “I’m a navigator. I help people navigate. That’s what I have fun doing now.” That answer stuck with me. I realized that I like to do the same. I didn’t set out to be a coach. What I discovered is that I’m a navigator at heart. I see the whole picture, help clear the fog, and walk with leaders through uncertainty. And while some might say I’m doing this before I should be, I believe this is worth it. I’m choosing to live as my future self now. The work I’m building revolves around three integrated pillars: the Big Fish Cares Podcast, The Pond, and Visionary Navigator Services. Together, they form an ecosystem that creates not just success in business but freedom, purpose, and authentic connection.
By Benny Fisher December 31, 2025
As this year comes to a close, I find myself filled with gratitude and perspective. Not because it was easy, but because it was intentional. This year was full in the best way. It marked growth, alignment, celebration, and a deeper sense of freedom than I have ever experienced in my life. It was not about surviving something hard. It was about stepping into something true. I want to share a bit of what this year looked like, what it clarified for me, and how I am thinking about the work ahead. A Year That Changed the Shape of My Life At the beginning of this year, we welcomed a new baby into our family. That alone has a way of resetting your priorities and sharpening what matters. Shortly after that, I sold my business . That decision was not about walking away. It was about stepping forward. It gave me space, clarity, and freedom. I was fully removed from day to day operations and able to create margin in my life that I had been building toward for a long time. We moved into a new home. A place that has quickly become a hub for family, friends, and community. We hosted three epic parties at our house. Not networking events. Real gatherings. Food, laughter, kids running around, meaningful conversations, and genuine connection. Those nights reminded me that success without shared experience is empty. I worked with incredible one on one clients and leadership teams. I got to sit with founders who were building meaningful companies and meaningful lives at the same time. And somewhere in the middle of all of that, I lost the pump. Life still happens. You adapt. You move forward. When I look back, what stands out most is not any single achievement. It is the sense that my life finally feels integrated. Business, family, faith, community, and health moving in the same direction. Freedom Has Always Been the Goal If there is one theme that has followed me my entire life, it is freedom. Not financial freedom alone. Not time freedom in a shallow sense. Real freedom. Freedom to choose how I spend my energy. Freedom to be present with my family. Freedom to work on what matters. Freedom to say no without fear. Freedom to build without being owned by what I build. For a long time, I thought freedom was something you reached after success. What I have learned is that freedom is something you choose and then build around. And once you experience it, you realize something important. The fastest way to deepen your own freedom is to help other people find theirs. That is the work I have committed myself to. Perspective Is the Lever Most Founders Miss Every founder I work with is already capable. They already take action. They already work hard. They already know how to execute. What they often lack is not discipline or ambition. It is perspective. They are inside the bottle. Too close to see the label. Carrying weight they no longer need to carry. Solving problems that are no longer theirs to solve. Chasing goals that were never truly theirs in the first place. That is where I come in. I help founders and leadership teams slow down enough to see clearly again. To reconnect with what they actually want. To align their business with the life they are trying to build. Clarity is a gift. And once it is present, momentum follows naturally. What I Actually Help With While clarity is always the starting point, the work becomes very practical once direction is established. I regularly help founders and leadership teams with: Designing and strengthening their operating system so the business runs with less friction and more ownership Sales strategy, sales training, and packaging offers that are simple, ethical, and repeatable Marketing strategy that builds trust and long term brand equity Hiring, recruiting, and interviewing so the right people end up in the right seats Building leadership teams that actually function together instead of working in silos Advising founders through private equity conversations, partnerships, and deal structure The common thread is alignment. When the vision is clear, execution becomes cleaner. Teams move faster. Decisions feel lighter. Growth becomes intentional instead of reactive. How I Work With People The most effective place to start is a full day Deep Dive session. One full day, in person. We slow everything down. We ask better questions. We surface what is real, what is assumed, and what no longer fits. Then we build an action plan rooted in clarity, not pressure. Sometimes that day is enough. Sometimes it opens the door to deeper work. Either way, people leave lighter, clearer, and more confident about what comes next. Beyond one on one and team advisory work, I also host The Pond, a private community of high integrity founders who value perspective, trust, and long term relationships. It is not about tactics. It is about being in the room with people who are building meaningful lives alongside meaningful businesses. A Few Responsible End of Year Reminders Since today is December 31 , here are a few practical considerations if they apply to you. If you are on cash basis accounting, paying legitimate expenses before year end may make sense. If appropriate, holding deposits can be a smart move. If you truly need equipment or a vehicle for next year, purchasing before year end can create meaningful tax savings. If you do not already have one, consider working with a fractional CFO in the new year. Proactive planning beats reactive tax prep. I am happy to refer people I trust. Investing in yourself through coaching, consulting, or clarity work can also be a legitimate business expense when done for the right reasons. If you do not need it, do not do it. None of this should ever be forced. If You Want to Start 2026 With Clarity If any of this resonates and you want to start the new year with me in your corner, now is a clean moment. If you want to take immediate action today, email me back. I am reserving this afternoon to talk with a few founders and we can take action today if it makes sense. If you would rather get on my calendar and talk through what 2026 could look like, we can do that too. You can start with a Deep Dive day. You can join The Pond. Or we can simply have a conversation and see if there is alignment. You do not just get my thinking. You get perspective, pattern recognition, real world experience, and someone who cares deeply about the life you are building alongside the business.  Closing Thought I have gained far more in my life than I have ever lost. Perspective. Freedom. Peace. Community. Purpose. And the work I do now is a reflection of that truth. If I can help you get clear on what you want and steer you in the right direction with precision, the results will take care of themselves. If this resonates, reach out. Today is a good day to do that. Benny
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By Benny Fisher January 8, 2026
The Right Fit Leader Podcast
By Benny Fisher January 8, 2026
A few years ago, I asked Gino Wickman what he calls the work he does when he mentors and guides people. He simply said, “I’m a navigator. I help people navigate. That’s what I have fun doing now.” That answer stuck with me. I realized that I like to do the same. I didn’t set out to be a coach. What I discovered is that I’m a navigator at heart. I see the whole picture, help clear the fog, and walk with leaders through uncertainty. And while some might say I’m doing this before I should be, I believe this is worth it. I’m choosing to live as my future self now. The work I’m building revolves around three integrated pillars: the Big Fish Cares Podcast, The Pond, and Visionary Navigator Services. Together, they form an ecosystem that creates not just success in business but freedom, purpose, and authentic connection.
By Benny Fisher December 31, 2025
As this year comes to a close, I find myself filled with gratitude and perspective. Not because it was easy, but because it was intentional. This year was full in the best way. It marked growth, alignment, celebration, and a deeper sense of freedom than I have ever experienced in my life. It was not about surviving something hard. It was about stepping into something true. I want to share a bit of what this year looked like, what it clarified for me, and how I am thinking about the work ahead. A Year That Changed the Shape of My Life At the beginning of this year, we welcomed a new baby into our family. That alone has a way of resetting your priorities and sharpening what matters. Shortly after that, I sold my business . That decision was not about walking away. It was about stepping forward. It gave me space, clarity, and freedom. I was fully removed from day to day operations and able to create margin in my life that I had been building toward for a long time. We moved into a new home. A place that has quickly become a hub for family, friends, and community. We hosted three epic parties at our house. Not networking events. Real gatherings. Food, laughter, kids running around, meaningful conversations, and genuine connection. Those nights reminded me that success without shared experience is empty. I worked with incredible one on one clients and leadership teams. I got to sit with founders who were building meaningful companies and meaningful lives at the same time. And somewhere in the middle of all of that, I lost the pump. Life still happens. You adapt. You move forward. When I look back, what stands out most is not any single achievement. It is the sense that my life finally feels integrated. Business, family, faith, community, and health moving in the same direction. Freedom Has Always Been the Goal If there is one theme that has followed me my entire life, it is freedom. Not financial freedom alone. Not time freedom in a shallow sense. Real freedom. Freedom to choose how I spend my energy. Freedom to be present with my family. Freedom to work on what matters. Freedom to say no without fear. Freedom to build without being owned by what I build. For a long time, I thought freedom was something you reached after success. What I have learned is that freedom is something you choose and then build around. And once you experience it, you realize something important. The fastest way to deepen your own freedom is to help other people find theirs. That is the work I have committed myself to. Perspective Is the Lever Most Founders Miss Every founder I work with is already capable. They already take action. They already work hard. They already know how to execute. What they often lack is not discipline or ambition. It is perspective. They are inside the bottle. Too close to see the label. Carrying weight they no longer need to carry. Solving problems that are no longer theirs to solve. Chasing goals that were never truly theirs in the first place. That is where I come in. I help founders and leadership teams slow down enough to see clearly again. To reconnect with what they actually want. To align their business with the life they are trying to build. Clarity is a gift. And once it is present, momentum follows naturally. What I Actually Help With While clarity is always the starting point, the work becomes very practical once direction is established. I regularly help founders and leadership teams with: Designing and strengthening their operating system so the business runs with less friction and more ownership Sales strategy, sales training, and packaging offers that are simple, ethical, and repeatable Marketing strategy that builds trust and long term brand equity Hiring, recruiting, and interviewing so the right people end up in the right seats Building leadership teams that actually function together instead of working in silos Advising founders through private equity conversations, partnerships, and deal structure The common thread is alignment. When the vision is clear, execution becomes cleaner. Teams move faster. Decisions feel lighter. Growth becomes intentional instead of reactive. How I Work With People The most effective place to start is a full day Deep Dive session. One full day, in person. We slow everything down. We ask better questions. We surface what is real, what is assumed, and what no longer fits. Then we build an action plan rooted in clarity, not pressure. Sometimes that day is enough. Sometimes it opens the door to deeper work. Either way, people leave lighter, clearer, and more confident about what comes next. Beyond one on one and team advisory work, I also host The Pond, a private community of high integrity founders who value perspective, trust, and long term relationships. It is not about tactics. It is about being in the room with people who are building meaningful lives alongside meaningful businesses. A Few Responsible End of Year Reminders Since today is December 31 , here are a few practical considerations if they apply to you. If you are on cash basis accounting, paying legitimate expenses before year end may make sense. If appropriate, holding deposits can be a smart move. If you truly need equipment or a vehicle for next year, purchasing before year end can create meaningful tax savings. If you do not already have one, consider working with a fractional CFO in the new year. Proactive planning beats reactive tax prep. I am happy to refer people I trust. Investing in yourself through coaching, consulting, or clarity work can also be a legitimate business expense when done for the right reasons. If you do not need it, do not do it. None of this should ever be forced. If You Want to Start 2026 With Clarity If any of this resonates and you want to start the new year with me in your corner, now is a clean moment. If you want to take immediate action today, email me back. I am reserving this afternoon to talk with a few founders and we can take action today if it makes sense. If you would rather get on my calendar and talk through what 2026 could look like, we can do that too. You can start with a Deep Dive day. You can join The Pond. Or we can simply have a conversation and see if there is alignment. You do not just get my thinking. You get perspective, pattern recognition, real world experience, and someone who cares deeply about the life you are building alongside the business.  Closing Thought I have gained far more in my life than I have ever lost. Perspective. Freedom. Peace. Community. Purpose. And the work I do now is a reflection of that truth. If I can help you get clear on what you want and steer you in the right direction with precision, the results will take care of themselves. If this resonates, reach out. Today is a good day to do that. Benny
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