The Emotional Rollercoaster of Selling Your Business: From EBITDA to Exit

When you enter into the world of selling a business you’ll soon discover it is both exhilarating and exhausting. Exciting and rewarding, an emotional rollercoaster. From the first time you ask how long does it take to sell a business to should I sell my business? I advise my Sellers to buckle up and prepare themselves for the ride of their life.


Selling a business is often portrayed as a purely financial transaction—a strategic move to secure a substantial payout. But behind the scenes, there lies a tumultuous emotional journey that business owners embark upon when parting ways with their life’s work. The process of selling a business is not just about numbers and negotiations; it’s a rollercoaster ride of triumphs and tears that can leave even the most seasoned entrepreneurs emotionally drained. As someone who has witnessed this emotional side of selling businesses firsthand many times over, I believe it’s crucial to shed light on the deeply personal and often unspoken aspects of this process. Remember it’s about preparing the Owner and the company for sale.

For Entrepreneurs

For many entrepreneurs, their business is not just a means to make money; it’s an extension of their identity and a manifestation of their dreams. Every triumph, setback, and milestone is etched into the very fabric of their being. Every scar, bruised ego and stubbed toe is quickly pulled out of your memory for review. Even your customer base is part of the many memories. So, when the time comes to sell, it’s no wonder that a flood of conflicting emotions emerges. Excitement mingles with sadness, pride intertwines with doubt, and a sense of relief dances with a sense of loss. It’s an emotional cocktail that can leave even the most stoic business owner feeling like a ship caught in a tempest. The good new is you can retain the services of a ship’s captain and crew to help navigate the sometimes murky, rocky and wavy waters. In the form of a local Business Broker, a firm offering M&A Consulting services, business intermediary, sell side advisory or a Sale Advisor. You will definitely require help with the M&A Due Diligence Checklist. This can be very draining.


One of the most prevalent emotions experienced during the selling process is a profound sense of attachment. As an entrepreneur you’ve likely put years, if not decades, of your life into building the business. Nurturing it, watching it grow, and sacrificing your time, energy, and personal lives to see it succeed. Consequently, letting go of something that has become a part of your identity can be intensely challenging. It’s like saying goodbye to a close friend or a beloved family member. It is not easy.


In addition to attachment, entrepreneurs grapple with a host of other emotions. The fear of the unknown can loom large, as they face the uncertainty of what lies ahead. Selling a business means stepping into a new chapter of life—one that may lack the familiar routines, the sense of purpose, and the comfort of your dedicated team. The fear of losing your sense of purpose and relevance can be overwhelming.


Alongside fear, there can be a profound sense of accomplishment and pride. Selling a business is a validation of the blood, sweat, and tears poured into the venture. It’s an acknowledgment that your hard work has paid off and that you have successfully created something of value. However, this pride can also be tinged with a touch of sadness, as entrepreneurs bid farewell to the day-to-day interactions and the sense of fulfillment that came with building their business.


Moreover, selling a business can bring about a myriad of logistical and interpersonal challenges. Negotiating deals, dealing with legalities, and managing the expectations of employees and stakeholders can take a toll on one’s emotional well-being. The weight of responsibility and the pressure to make the right decisions can feel suffocating. Entrepreneurs may question their judgment, worry about the impact on their employees’ lives, and grapple with the bittersweet reality that their business will never be the same, without them.

Despite the emotional turbulence, selling a business can also be a liberating experience. It offers entrepreneurs the opportunity to redefine themselves, explore new passions, or simply take a well-deserved break. It can be a chance to regain a sense of balance in life and rediscover the simple pleasures that were overshadowed by the demands of running a business. The act of selling can be an act of self-care, a way to reclaim one’s life and prioritize personal well-being. It’s not unusual for a Seller to say they look forward to spending time with grandchildren. Perhaps to make up for time not spent with their children. I know several Sellers who cherish walking their grandchildren to school in the morning.

Coaching Advisor

Recognizing and acknowledging the emotional side of selling a business is essential for both entrepreneurs and those who support them throughout this process. From providers of coaching for business owners to family business coaching, a financial advisor business coach or a sale advisor. Entrepreneurs need a safe space to express their fears, doubts, and conflicting emotions without judgment. They need a strong support system, comprising friends, family, and trusted advisors, who can provide a listening ear, guidance, and reassurance. It’s crucial to remember that beneath the facade of strength and resilience, entrepreneurs are humans too, vulnerable to the profound emotional impact of parting ways with their creation.


Selling a business is a multifaceted journey that goes far beyond financial gains. It’s a testament to the blood, sweat, and tears invested in building something meaningful. Entrepreneurs experience a range of emotions, from attachment and fear to pride and relief. Understanding and addressing these emotions is essential for the well-being of business owners as they navigate the emotional rollercoaster of selling their life’s work.

Are you asking yourself how long does it take to sell a business? Or should I sell my business? What are the steps to selling a business and how much do I sell my business for? What is EBITDA and EBITDA margin? Do I need a business value consulting professional to calculate value of a company? If you’re looking for tips for selling a business from someone who specializes in family business coaching and consulting, you’ve come to the right blog.

As a trusted business advisor and sale advisor providing sell side advisory services I appreciate the opportunity to share my years of experience working with Owners just like you. In fact you may want to consider our online program ‘Sell Your Business 4 More.

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