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Selling a Business: The Emotional Impact

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13 May 2024: Selling a Business – The Emotional Impact

The decision to sell a business can trigger a whirlwind of emotions, ranging from excitement and relief to sadness and anxiety.

Selling a business is often the most significant financial event in the owner’s life and it generally carries both personal and professional implications. Dealing with these emotions requires a delicate balance of introspection, practicality, and support – and a solid, practical plan.

The most important part of the process of selling a business is planning – and doing so well in advance so that the owner and others that will be impacted by the sale, can come to grips with what is, inarguably, inevitable if the business doesn’t fail first.

Proper planning will go a long way toward making the transition not only successful but also but less distressing emotionally for all involved.


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Some of you know my story.

In the late ’90s, I sold a business that wasn’t for sale. Buyers, in the form of a group of investors, showed up and said they wanted to buy. Over a period of several weeks we went back and forth during which time my response was always, “It’s not for sale”; until, of course, it was. Because I was totally unprepared to sell, I was totally unprepared for the emotional roller coaster that followed.

The event triggered unexpected emotions – some quite difficult to deal with. What I learned during that period informs much of how we deal with business owners who call us when they begin to think about selling and how our courses are, to a greater or lesser extent, created to keep the emotional aspect of selling a business in mind.


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.

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Some level of emotional impact is present in nearly every change of business ownership. From the corner bakery to the $15 million health care provider, size does not diminish the impact of the inevitable – walking away from what often seems to the owner to be their “baby” – an admittedly inanimate object often endowed by the founder/owner with something akin to the humanity of an additional child.

So, while the range of emotions that attend the sale of a business is wider than what we can cover in a single blog post, let’s delve into some of the more likely ones associated with selling a business and explore strategies for navigating them.

  • Anticipation: As you prepare to sell your business, you may feel a sense of anticipation about what the future holds. This anticipation can be tinged with both optimism and apprehension. Whether you plan to cultivate a handsome vegetable garden or learn how to fly, do you know what you’ll do in the aftermath of the sale? It’s hard to understate the importance of knowing what’s next.
  • Attachment: It’s natural to feel deeply attached to something you’ve poured your time, energy, and passion into building. Recognize that letting go of your business can stir up feelings of loss and nostalgia. For the business owner, this often correlates with losing their “baby” and sometimes renders the owner unable, at the last minute, to pull the trigger an occasion that will be attended by any number of legal and financial consequences.
  • Uncertainty: Selling a business often means stepping into the unknown. The seller may grapple with uncertainty about their financial future, career direction, and personal identity outside of the business world. An owner should have the right counsel and friends outside the business with whom non-business discussions have been the rule for many years.


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

  • Relief: If the decision to sell was driven by challenges or burnout, you may experience a profound sense of relief upon finalizing the sale. We get contacted too often by owners who have just grabbed the proverbial “last straw”. They’ve found themselves ensnared in some obscure government regulation that will cost them a bundle or 20% of the employees didn’t show up for work. And burn out – 12-15 hour days, always on call to employees or clients, dealing with arcane employment rules, etc. – is a real thing. It can, after enough time, drive a business owner to say “enough Embrace this relief as a signal that you’re entering a new and possibly more enjoyable phase of life.
  • Guilt: Selling a business can trigger feelings of guilt, especially if you have employees or partners who will be affected by the transition. Part of the planning process involves preparing not only yourself but the others that will be impacted. This includes the seller’s immediate family. Our tagline – “Every Business That Doesn’t Fail Will Be Sold – EVERY ONE!” – should be gradually introduced to family and staff with plenty of time for everyone to be inoculated to the shock of what is an inevitable event.
  • Identity Shift: This is a big one – the one that most impacted me. For many business owners, their business is not just a source of income but also a core part of their identity. Selling the business can lead to a profound identity shift, requiring the seller to redefine who they are outside of their professional life. Ya gotta have plan for what’s next. Otherwise, you’ll be in the emotional wilderness in the aftermath. Learn how to sail; take up a charitable organization that has some personal meaning to you; write that book you’ve been talking about. Now that you’re now longer the owner of ABC Logistics, Inc. or ExWhyZee Widgits, you’ve got to do something to develop a new sense of who you are.
  • Financial Concerns: Even if the sale of your business yields a lucrative return, you may still experience financial concerns about managing your newfound wealth. Make sure your team is fully built out and includes a financial advisor and tax attorney to create a strategic plan for preserving and growing your assets over the long term.

The Bottom Line

In the immediate aftermath of selling a business, the seller may grapple with feelings of emptiness or aimlessness – even grieving the loss of something that was so personal. Without the daily demands of running the business, he or she may struggle to find purpose and structure in their life.

This and the identity issue were what impacted me the most and were the most difficult to overcome. But remember, my business wasn’t for sale. And while that’s no excuse for not planning, it is a partial explanation for the emotional impact. Granted, I suddenly had some deep pockets but, after many years of routinely getting to the office at 7.30, no longer did I have a specific reason to get up in the morning.

For owners who know that they’re approaching the time when a sale becomes likely, it’s extremely important to include a clear vision of life after the deal is done.

Navigating the emotional roller coaster of selling a business requires self-awareness, resilience, and support from loved ones. But most of all, it requires a plan – and not one you scratch out on the kitchen table on a Saturday evening and put the business on the market first thing Monday morning.

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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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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