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Preparing Emotionally for the Closing

Seller’s remorse, much like buyer’s remorse, is a real phenomenon in the business world. It occurs when business owners, after making the decision to sell, begin to feel the weight of what this change entails. Some may even consider delaying or canceling the sale, often due to the anxiety that accompanies such a significant life transition.

After dedicating years to their businesses, many owners initially look forward to retirement with dreams of travel, spending time with family, pursuing hobbies, and all the quintessential retirement activities. In theory, this is an appealing plan—a well-deserved break after a lifetime of hard work.

However, reality often differs from the dream. Within a year of retiring, many entrepreneurs find themselves seeking new ways to occupy their time. Some even express a desire to remain involved in their former businesses. This presents an opportunity for buyers to engage with sellers, discovering which aspects of the business bring them the most fulfillment. By aligning interests and addressing emotional needs, buyers can create smoother transitions and foster cooperation from the sellers, both during and after the sale.

While we can’t provide prescriptions for anxiety, at CasinosBroker, we can offer practical, drug-free advice on navigating the anxieties that can accompany selling a business.

Find a New Passion

As we delve into the final stages of closing the sale, many of our clients pose a common question: “What’s next?” Once the sale is successfully completed, and they officially enter retirement, they embark on the exciting pursuits they’ve envisioned. However, the reality often differs from the retirement dream.

Entrepreneurs are inherently driven individuals, seeking purpose and engagement in various forms. While they may have initially thought retirement would be a time of leisure and relaxation, they quickly discover that a life of complete idleness doesn’t align with their nature. In fact, within a year or less into retirement, many clients approach us with a desire to re-engage with their former businesses.

Another challenge arises during the closing stages. Some entrepreneurs experience intense stress as they realize that, post-sale, they’ll face a void in their daily lives. This anxiety can lead to delays or even the abandonment of the sale altogether, driven by the fear of transitioning from a lifetime of work to seemingly “doing nothing.”

Fortunately, there are effective ways to ease these anxieties when selling your business. It’s crucial to recognize that planning for life after the sale is just as essential as orchestrating the sale itself. Just as you wouldn’t sell your house without a clear relocation plan, selling your business demands a well-thought-out path forward. A vague notion of retirement won’t suffice. You need to channel your energy into a new passion.

If you’re in the process of selling your business and uncertain about your next steps or contemplating retirement, I challenge you to spend time answering a vital question: “What do I want to achieve in the next 5, 10, or 15 years?”

Jotting down your short-term goals (like travel or spending time with family) and long-term aspirations (such as learning a new language or embarking on a not-for-profit endeavor) can alleviate the sense of overwhelm as the sale draws near. You can even start gathering information about the various objectives you’d like to pursue post-sale. The more detailed your post-business sale plan, the smoother your transition will be. You’ll discover that a little preparation now can save you stress and anxiety as you navigate the complex process of selling your business and stepping confidently into the next chapter of your life.

Aligning the Sellers and Buyers Interests

The seller’s interests can hold significant ongoing value for the business, spanning areas such as recruitment, sales, marketing, or the establishment of crucial alliances. These positions are often challenging to fill through regular recruitment channels. However, the previous owner might possess significant skills in one or more of these areas and could be open to working in such roles for a salary below the market rate, provided their other needs are met.

In some cases, sellers may consider commission-based arrangements if the role can be tailored to align with their preferred lifestyle. Most retirees value flexibility, and by offering this to the seller, you have the potential to create a mutually beneficial scenario. This way, you can retain valuable talent at a cost lower than the market rate, while the seller can achieve their desired lifestyle. Structuring such an agreement can also play a pivotal role in retaining key customers or employees, as key partners often find comfort in witnessing the seller’s ongoing involvement in the business.


Selling a business can be an emotional transition for many individuals. When something has been a significant part of your life for an extended period, it’s natural to feel a sense of emptiness afterward. It’s important to be prepared to address these emotions.

Entrepreneurs are known for their drive and ambition. Simply stating, “I will be retired,” isn’t enough. It’s essential to channel your energy toward a new passion or endeavor.

By taking the time for thoughtful preparation now, you can proactively manage stress and anxiety about your future as you navigate the intricate process of selling your business.

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