Celebrate your achievement! This might sound obvious, but it’s crucial and often overlooked. Selling a business successfully is a major accomplishment — one that only about 13% of business owners achieve. Take the time to acknowledge this milestone. Whether it’s a small personal celebration or a larger event with your team and loved ones, marking this achievement helps provide closure and sets a positive tone for your next chapter.

Selling your business is a major transaction, and a huge step in a new direction. It is easy to feel unmoored and directionless, and a significant number of entrepreneurs who sell their businesses do not have a plan for the future. What are the steps that someone should take after selling their business? As a part of this interview series, we had the pleasure to interview Jessica Fialkovich.

An expert exit strategist, small business advocate, award-winning business owner, keynote speaker, and bestselling author, Jessica Fialkovich is a recognized and respected leader in the M&A, business brokerage and franchise industries. Her company, Exit Factor, is a business consulting franchise that offers courses, programs, and services that help business owners maximize their company’s value through proven methodology. Over the last 10 years, Jessica has overseen $250+ million in transactions, worked with over 1,500 business owners, been involved with 350+ deals, and mentored her team to successfully guide more than 3,000 business owners through the buying and selling processes.

Thank you so much for doing this with us! Our readers would love to “get to know you” a bit better. Can you share the “backstory” behind what brought you to this particular career path?

Myjourney is a testament to how unexpected turns can lead to fulfilling destinations. It all began when I was 24 and launched my first business in the wine industry. While the venture was successful by most measures, it also taught me valuable lessons about the challenges of entrepreneurship, including the potential for burnout.

After three years of pouring my heart and soul into this business, I found myself at a crossroads. Despite the success, I was feeling burnt out and ready for a change. I made the decision to sell the business and return to my roots in professional services. Little did I know that this decision would be the catalyst for my current career path.

The process of selling my business was eye-opening. As I navigated the complex world of small business mergers and acquisitions, I discovered a whole new area of interest. The intricacies of valuation, negotiation, and transition fascinated me. More importantly, I recognized how challenging this process could be for business owners who, like myself, were venturing into this territory for the first time.

This experience ignited a passion in me and for the past decade, my focus has been helping business owners build sellable businesses. It’s a mission that combines my entrepreneurial experience, my knowledge of M&A, and my desire to support other business owners in achieving their goals. And while this career wasn’t something I had planned when I started my first business, it’s a perfect example of how our experiences can shape our path in unexpected ways. My journey from a young wine business owner to an M&A advisor and now the founder of Exit Factor has been driven by a desire to learn, adapt, and use my experiences to help others.

Let’s move onto the main topic of our discussion. Do you feel like you were adequately prepared for the next stage after selling your business?

To be honest, I thought I was prepared for life after selling my first business, but reality quickly proved otherwise. At the time, my focus was primarily on the exit itself — I was so eager to move on that I didn’t give enough thought to what would come next.

This experience taught me a valuable lesson. In overseeing nearly 1,300 business sales since then, I’ve realized my situation wasn’t unique. Many entrepreneurs become fixated on the exit process, neglecting to plan for the day after the sale closes.

This common oversight was a key motivator in founding Exit Factor. Our mission is to equip business owners with comprehensive exit strategies that extend beyond the sale itself. Through our franchisees and consultants, we aim to help entrepreneurs avoid the anxiety and uncertainty I faced, ensuring they’re truly prepared for their next chapter.

In retrospect, while I wasn’t adequately prepared then, that experience has shaped how I now guide others through this critical transition. It’s about creating a holistic exit strategy that aligns with your long-term personal and professional goals.

What challenges did you face in transitioning from being a business owner to exploring new opportunities?

After selling my first business, I encountered a significant challenge that many entrepreneurs face: my identity was deeply intertwined with being a business owner. This made it difficult to envision and pursue new opportunities outside of that familiar role.

The transition period was longer and more complex than I had anticipated. I spent nearly a year exploring various paths, from considering the acquisition of existing businesses to contemplating new startups. This period of searching was both challenging and enlightening, as it forced me to reassess my goals and strengths outside the context of my previous business.

Ultimately, I found my next step in franchising, a decision that has profoundly shaped my career over the past 11 years. This experience in the franchising world not only provided me with new insights and skills but also gave me the confidence and perspective to position Exit Factor as a franchise opportunity itself.

How did selling your business impact your personal identity and sense of purpose?

Selling my business had a profound impact on my personal identity and sense of purpose, revealing how deeply I had connected my sense of self with my professional role.

In the aftermath of the sale, I grappled with a significant identity crisis. I had so closely associated myself with being the owner of that specific business that I struggled to separate my core identity from what was, in reality, just one role I had played for a period of my life. This blurred line between personal identity and professional position led to a challenging time marked by intense anxiety and depression.

This experience forced me to confront some hard truths about how I defined myself. It was a difficult journey, but ultimately a transformative one. I came to realize that my identity — even my professional identity — isn’t confined to any single role I occupy at a given time, which has not only helped me personally but has also informed how I advise other entrepreneurs. I emphasize the importance of cultivating a sense of identity and purpose that extends beyond business ownership, which can make transitions like selling a business less disorienting and more empowering.

How have you navigated the financial aspects of life post-sale, and what strategies have you implemented for long-term wealth management?

As an entrepreneur at heart, my primary instinct post-sale was to reinvest in another business venture. This approach aligns with my passion and expertise. However, I’ve been fortunate to work with an excellent wealth management team that has broadened my perspective on financial strategies.

One of the key lessons I’ve learned is the critical importance of diversification beyond business investments. While my entrepreneurial spirit drives me to seek new business opportunities, I’ve come to appreciate the value of a balanced investment portfolio that includes a mix of assets outside of direct business ownership.

This journey has also ignited a passion in me for helping other business owners create and manage wealth effectively. Through my experiences, I’ve observed a common misconception that all business owners are wealthy, when many entrepreneurs actually find themselves in what I call “entrepreneurial poverty” — sacrificing personal financial stability for the sake of growing their business. They often pour everything into their companies, maintain minimal savings, and draw minimal salaries and benefits.

This is why, at Exit Factor, we aim to educate and empower business owners to build sustainable wealth over time. We want to help our franchisees and their clients avoid the pitfalls of entrepreneurial poverty and instead create real, lasting value in their companies. Our approach focuses on strategies that allow business owners to grow their enterprises while simultaneously building personal wealth. This includes emphasizing the importance of paying oneself a fair market salary, setting up retirement accounts, and creating systems that allow the business to operate without constant owner involvement — all of which contribute to both the business’s value and the owner’s financial security.

What has been the most surprising aspect of life after selling your business, and how have you adapted to it?

The most surprising aspect of life after selling my business has been the profound shift in my perspective on business ownership and management. This change has been both unexpected and transformative.

When I owned my first business, it felt like an extension of myself — my “baby,” if you will. I was deeply emotionally invested in every aspect of its operation and growth. While this passion drove my success, it also meant that business decisions were often clouded by personal attachment.

Post-sale, I’ve developed a more objective view of business ownership. Each subsequent venture I’ve been involved with, I’ve approached as what it truly is — a financial asset. This emotional detachment, surprising as it may seem, has been incredibly liberating and beneficial. It’s allowed me to make clearer, more strategic business decisions. I’m able to assess opportunities, challenges, and potential exits with a level head, free from the intense emotional ties that characterized my earlier entrepreneurial experiences. As a result, I’ve found that I can generate better outcomes, not just for the businesses I’m involved with, but also for myself and my family.

Adapting to this new mindset required a conscious effort to separate my sense of self-worth and identity from the businesses I was involved in. In doing so, the benefits have been significant. I’ve become more adept at recognizing when it’s time to pivot, scale, or exit a business venture, decisions that can be agonizing when you’re emotionally entangled with your company.

This shift has also influenced how I advise other entrepreneurs through Exit Factor. I emphasize the importance of building a business that can thrive independently of its owner — a key factor in creating value and facilitating a successful exit.

How do you stay motivated and engaged in new ventures or personal interests after the sale?

From my experience, the key to staying motivated and engaged after selling a business lies in proactive planning. It’s crucial to start focusing on what’s next well before the sale is finalized. Waiting until after the sale to figure out your next steps can lead to a sense of aimlessness or loss of purpose. This forward-looking approach gives you something tangible to work towards and look forward to.

For some entrepreneurs, the next step might be launching into a new business venture. For others, it could be dedicating time to charitable causes they’re passionate about. Some might choose to focus on personal growth through travel or education. And for many, it could simply mean planning for more quality time with family and loved ones.

The important thing is that these plans are personal and meaningful to you. They should excite you and give you a sense of purpose beyond your current business. This excitement can be a powerful motivator during the sale process and can help ease the transition once the sale is complete.

Having a clear direction for your post-sale life can also help you make better decisions during the sale process itself. It allows you to approach the sale with a clearer mind, focusing on maximizing value without the fear of an uncertain future.

Remember, the goal isn’t just to successfully sell your business, but to transition into a fulfilling next phase of your life. By planning ahead, you set yourself up for continued motivation, engagement, and success in whatever path you choose to pursue.

How did you prepare mentally and emotionally for life after selling your business, and what advice would you give to others?

When I sold my first business, I found myself unprepared for the emotional and mental challenges that followed. The truth is, at that time, there weren’t adequate support networks or advisors focusing on the psychological aspects of this significant life transition. My experience was more challenging than it needed to be, and that realization became a driving force behind the creation of Exit Factor.

Preparing for life after selling your business is a long process — it can often take multiple years. It’s also an emotionally taxing journey. Throughout the sale process, advisors and potential buyers scrutinize every aspect of your business, deals can fall apart unexpectedly, and the uncertainty can be overwhelming. You need both support and mental toughness to navigate this successfully.

My advice to others facing this transition would be:

• Start early: Begin thinking about and planning for your post-sale life well before you’re ready to sell. This gives you time to adjust to the idea and explore new possibilities.
• Build a support network: Surround yourself with people who understand what you’re going through. This could include mentors, other entrepreneurs who’ve sold businesses, or professional advisors who specialize in business transitions.
• Work on your identity outside of the business: Start cultivating interests and relationships that aren’t tied to your role as a business owner. This helps ease the transition when you’re no longer in that role.
• Prepare for emotional ups and downs: Understand that it’s normal to feel a range of emotions, from excitement to fear to sadness. Acknowledging these feelings is an important part of the process.

What are some common misconceptions/assumptions about your options/next steps after a business sale?

One of the biggest misconceptions about life after selling a business is the assumption that owners immediately step into a blissful, carefree existence. This idealized view of post-sale life is not only inaccurate but can also be harmful, as it leaves many unprepared for the reality they face.

In my experience, the much more common scenario is quite different. Many owners, even those who have achieved highly successful exits, often go through an intense period of depression or emotional turmoil after the sale.

This might seem counterintuitive at first. After all, isn’t the goal to work hard, build a successful business, and then enjoy the fruits of your labor? While that’s part of the picture, it overlooks a crucial aspect of an entrepreneur’s life and personality.

For most business owners, particularly high achievers, their business isn’t just a job — it’s a central part of their identity, daily routine, and sense of purpose. They’re accustomed to operating at full throttle, often working 60+ hours a week, constantly solving problems, and driving growth. The abrupt shift from this high-intensity lifestyle to one with seemingly no responsibilities can be profoundly disorienting.

What sounds like a dream scenario — no more stress, no more long hours, complete freedom — can actually become a source of anxiety and discomfort. Many owners find themselves struggling with loss of identity, lack of purpose, boredom and restlessness, and decision paralysis.

It’s crucial to understand that these feelings are normal and don’t negate the success of the sale. However, being aware of and prepared for these potential challenges can make a significant difference in navigating the post-sale period.

What role has your network played in helping you find new opportunities or passions post-sale?

My network has played a crucial role in my journey post-sale, both in terms of finding new opportunities and in shaping my current business and passion project, Exit Factor.

I’m fortunate that almost my entire business and personal network consists of fellow entrepreneurs. This network became an invaluable resource when I was navigating the post-sale landscape and searching for new opportunities. The shared experiences, insights, and understanding within this community of business owners provided not just practical advice, but also emotional support during a time of significant transition.

When I began conceptualizing Exit Factor in 2018, I leaned even more heavily into this network. I engaged in numerous one-on-one conversations and group discussions with fellow business owners, all of which were very eye-opening. They revealed common threads of worry, uncertainty, and a lack of comprehensive support for business owners contemplating or approaching an exit. It became clear that many of my peers were grappling with the same issues I had faced — not just the technical aspects of selling a business, but also the emotional and personal implications of such a significant life change.

They also helped me identify the gaps in existing support systems for exiting business owners and informed the holistic approach we now take at Exit factor — addressing both the practical and emotional aspects of business transitions.

How do you define success now, and how has that definition evolved since selling your business?

My definition of success has undergone a significant evolution since I sold my first business, reflecting my growth as an entrepreneur and as an individual.

When I first started in business, like many entrepreneurs, my concept of success was heavily tied to personal recognition and achievement. I was laser-focused on metrics like revenue growth, market share, and industry accolades. These tangible markers of progress were how I measured my worth and the worth of my business.

However, as I’ve matured in my entrepreneurial journey, my perspective has shifted dramatically. I’ve come to view my businesses through a different lens — as financial assets rather than extensions of my personal identity. This shift has profoundly impacted how I define and measure success.

Now, I approach my business ventures much like I would evaluate a stock investment and focus primarily on two factors: the value of the business and return on investment. This more objective, finance-driven approach doesn’t mean I’ve lost my passion for entrepreneurship. Rather, it allows me to make clearer, more strategic decisions that benefit both the business and my personal goals.

I also place a higher value on work-life balance and personal fulfillment. Success isn’t just about the numbers on a balance sheet, but also about the quality of life my business endeavors allow me to lead.