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Selling a Business: The Emotional Journey

Earlier this year, we launched this new section of our blog, meant to let subscribers know what businesses our network is selling and what businesses we have buyers for. It will appear here at the top of each post. If interested in buying or selling, let us know. Feel free to forward the information to anyone you think might like to see it.

LOOKING FOR: Roofing companies specializing in new (retail) residential as well as insurance work. Revenue: $5m-$50 million; EBITDA: >$1M-$10M. Location: Continental U.S. and Canada    in**@Wo**********************.com

3 June 2024: Selling a Business: The Emotional Journey

In the realm of entrepreneurship, few decisions are as emotionally charged as the choice to sell one’s business. For many founders, their venture is not just a source of income but a labor of love, a manifestation of their dreams and aspirations. Thus, when the time comes to part ways with this creation, it’s akin to bidding farewell to a dear friend or even a child. Letting go emotionally when selling a business is a profound journey, one marked by introspection, acceptance, and hopefully, eventual liberation.

At the outset, the decision to sell can evoke a myriad of emotions: uncertainty, nostalgia, anxiety, and even grief. After all, the business represents not only financial investment but countless hours of dedication, sacrifice, and hard work. It’s natural to feel a strong sense of attachment, as if parting with the business is akin to relinquishing a piece of one’s identity.

Acknowledging these emotions is the first step towards letting go. It’s essential to give oneself permission to mourn the end of this chapter, to honor the journey that brought the business to fruition. Reflecting on the milestones, the challenges overcome, and the lessons learned can provide closure and pave the way for acceptance.


Our next Thursday Special in The Brokers Roundtable℠ is scheduled for the 30th and will focus on what real estate agents don’t know about selling businesses. In the meantime, don’t miss Office Hours (“Ask Me Anything”), workshops, Live Streams, Thursday Specials and more.

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As many of you long-time readers and Members of The Brokers Roundtable know, this is exactly what happened to me back in the late 1990s. I sold a business that wasn’t for sale. I was completely unprepared for the sale itself but also – and more importantly – for the aftermath. Selling a business – one that you’ve started or grown or lived with and nurtured for years – is an emotional experience of the first ran. The seller, as well as the business, must be prepared for the dramatic shift his or her life will certainly undergo. Emotional acceptance is the ultimate hope.

Acceptance, however, does not come easily. The process of selling a business is often fraught with uncertainty and complexity, adding another layer of stress to an already emotional experience. Negotiations, due diligence, legalities – each step can feel like navigating a labyrinth of paperwork, the disclosure of competitive and confidential data, unwanted publicity and the gradual realization that you will ultimately no long be “who you are”. In the midst of this whirlwind, it’s easy to become overwhelmed and lose sight of the bigger picture.

Yet, it is precisely during this tumultuous phase that the seeds of liberation can sown. As founders navigate the intricacies of the selling process, they are forced to confront their attachment to the business head-on. They must grapple with difficult questions: What does the business mean to me? What am I willing to let go of? What am I holding onto out of fear or insecurity?

In facing these questions, founders may discover a newfound sense of clarity and purpose. They may realize that the business, while a significant part of their journey, does not define their worth or identity. They may come to understand that letting go is not a sign of failure but rather a testament to their resilience and adaptability.

Moreover, the act of selling a business can be an opportunity for personal growth and self-discovery. It forces founders to confront their fears and insecurities, to step outside their comfort zone and embrace the unknown. In doing so, they may uncover hidden strengths and talents, paving the way for new opportunities and adventures.

Of course, letting go is easier said than done. Even after the ink has dried and the business has changed hands, founders may find themselves grappling with a sense of loss or emptiness. It’s natural to feel a void where the business once stood, to yearn for the familiar rhythms and routines of running the business you’ve been identified with for many years..


Courses! Courses! Courses!

Many of you have asked if our Flagship Course, “Learn How to Value and SUCCESSFULLY Sell Businesses“, could be made available on a module-by-module basis. Instead of enrolling in the complete course, could you enroll only in the module(s) you wanted? We’re happy to report that this is now possible.

We’ve broken our Flagship into six separate modules (or module groups) to give you all the flexibility you need to learn only what you want to learn – and we’ve moved them all over to the new Brokers Academy in The Brokers Roundtable . The Flagship is still available but the modules are now available individually.

You don’t need to be a Member of The Brokers Roundtable℠ to access any of these courses but if you are, you’ll receive a 20% discount on any course you enroll in. If you’re not yet a member of The Brokers Roundtable℠, you can learn more – and get access to all the talent and resources – here. 


Yet, amidst the grief, there is also room for gratitude and celebration. Selling a business is a testament to the founder’s vision, perseverance, and tenacity. It is a testament to the countless lives touched and the impact made, however small or seemingly insignificant. By honoring the legacy of the business, founders can often find solace in knowing that their efforts were not in vain, that they have left a lasting imprint on the world.

Ultimately, letting go emotionally when selling your business is a journey of transformation. It is a journey that demands courage, vulnerability, and self-reflection. It is a journey that challenges you to confront your fears, embrace the unknown, and trust in the wisdom of letting go.

In the end, it is a journey towards liberation – liberation from attachment, from fear, from the shackles of the past. It is a journey towards freedom – freedom to explore new horizons, to pursue new passions, to redefine success on your own terms. It is a journey towards a brighter, more expansive future, where the possibilities are limited only by the bounds of your imagination.


Our course, “Learn How to Value and SUCCESSFULLY Sell Businesses, teaches you how to accurately value and successfully sell businesses.

But to reach that point, preparation for the event – an event that is inevitable – is critical.

In our business brokerage courses we underline the importance of preparing the seller, as well as the business, for the transition. We’ve posted previously on how critical seller preparation is and that training is the direct result of my own experience more than 25 years ago. As recounted in this post, the story Lorna Davidson tells of the evening of the sale of her business is both poignant and illuminating. But after reading of her reaction, you may be able to imagine the emotional impact selling a business is likely to have on its owner; even one who has tried to prepare.

The Bottom Line

As we’ve often explained, selling a business ain’t for sissies – and we’ve posted a series of discussions in the Resources area of The Brokers Roundtable describing the six general steps a seller must be prepared for when selling a business.  And though many of theses steps involve the mechanical aspects of the event – which often for a time distract the sellers from the psychological aspects – the emotional impact, if not prepared for, can be devastating.

So, if you find yourself standing at the crossroads of selling your business, remember this: letting go is not the end of the journey, but the beginning of a new chapter. Try to embrace it with an open heart, and who knows what wonders await on the other side. This will be easier if you’ve prepared; if your next stage is in view.

I’d like to hear from you. What topics would you like me to cover? How can we tailor these posts to be more useful to you and your business. Let me know in the comments box, below, or email me at jo*@Wo*******************.com.

If you have any questions or comments on this topic – or any topic related to business – I’d like to hear from you. Put them in the comments box below. Start the conversation and I’ll get back to you with answers or my own comments. If I get enough on one topic, I’ll address them in a future post or podcast.

I’ll be back with you again next Monday. In the meantime, I hope you have a safe and profitable week.


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NOTE TO READERS: Our “Searching For…” feature has been moved to our online community, The Brokers Roundtable℠. It will appear there exclusively from now on.


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The author is the founder, in 2001, of Worldwide Business Brokers and holds a certification from the International Business Brokers Association (IBBA) as a Certified Business Intermediary (CBI) of which there are fewer than 600 in the world. He can be reached at jo*@Wo*******************.com

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