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Jacky Sherman

Jacky Sherman

The Consultant's Consultant ...

The Art Of Bowing Out Gracefully

Jacky Sherman

CREATED BY JACKY SHERMAN

Published: 25/02/2026 @ 09:01AM

#KitchenTableConception #PubInspiration #BossFrustration #RedundancyRescue #BusinessBaby

Conceived on your kitchen table, down the pub, after a particularly frustrating meeting with your boss, or that awful moment when you were told you were being made redundant, your business became your baby ...

Bowing out gracefully, Leaves fall with the gentle breeze, Nature's final bow

Bowing out gracefully, Leaves fall with the gentle breeze, Nature's final bow

For years, you nurtured it, spent long days getting it off the ground and despite the roller coaster of highs and lows, you achieved success. Now, it's time for you to let it grow up and leave you.

Like any proud parent, as well as deciding the practicalities of how best to leave, there is also an emotional charge; a sense of loss, a change in your identity, perceived status or fear that all your work will be in vain!

The choice of subject for my blog post this week is drawn from the conversations I've had, particularly with older business people, that enough is enough; it's time to sell up, close down, move over or move on.

Now, any business advisor will tell you that the time to start thinking about your exit strategy is when you initially start up. That's how you structure the business, manage the finances (both the business's and your own), and build a knowledgeable team around you.

This all facilitates a smooth exit!

The reality is that most small business owners don't do that unless they had grand ambitions in the first place to scale up the business and make millions. Even fewer prepare themselves for the impact that emotional charge may have on them and their decision to sell up.

Now, I'm not an expert in the technicalities of buying or selling businesses, but I have worked with many individuals where these personal emotional responses caused issues with the sale and handover of the leadership of small companies.

I thought I would share a few stories with you. Except for Meeli's direct quote, to protect client anonymity, these stories are composite examples of various clients I have worked with over the years. They are intended to give you a flavour for the range of emotions that arise when people consider selling their business. They fall into four broad categories of types of sale.

  • Just shut up shop - A common scenario right now, although not many are as lucky as Andrea. She had ceased trading as a consultant after a successful career. She had followed her exit plan and had a good income from her pension. Her partner was still working from choice.She hadn't considered how much of her identity was invested in her business, and it gave her a purpose in life to be in service to others. She also felt she couldn't bother her friendship group as they were essentially still working. So, now she felt pretty lonely and at a loss on how to fill her day.

  • Straight sale and walk away - Amir - Amir owned a small business, and now aged 62, wanted to sell up to spend more time with his wife. He had a buyer, and there were no complications in the sales process. Except he found himself prevaricating. He had taken on the business when his father had died suddenly in his early 60s. He had also taken on the role of being the main support for his mother until her death a year ago.We discovered through conversation that he had actually copied his father's life plan regarding how he should live his life. But his father had never had the opportunity to retire, so Amir had no model for how to be in that role.
  • Straight sale and walk away - Margaret - Margaret ran a small boutique agency and sold it to pursue her other interests. However, she stayed in touch with her old staff as they had become friends over the years. They had not taken to the new owners. They would often tell Margaret about the latest 'scandalous' activity and how unhappy they were. As a result, Margaret was considering repurchasing the company. I have been surprised over the years by how often I've heard a similar story.
  • Stay on as an employee/advisor - A common step in selling a smallish business is for the owner to stay on in the company for a while or even take a permanent position. I've heard and witnessed many examples where this didn't work out for most of them. There are many versions of this story published on Forbes over the years, including this from Meelie Akapl: "I had feelings of betrayal. Although I knew I had decided to sell my business, I still felt somewhat stung by others taking the helm and changing things. In the back of my mind, I'd find myself wondering whom do these people think they are, anyway?"
  • Stay on as Chairman of the family business - Early in my career as a consultant, I used to buy appointments from a telemarketing firm. This meant that I would turn up to see the company with very little information. I was in one such meeting with the chairman of a small manufacturing company. He had a beautiful, imposing office with a green leather-topped desk. Everything I asked him about his company, he told me it was fine and all covered. Then I asked him why he had agreed to see me. He replied that he was bored. His son, now the CEO, was running the company. He asked if I would like to meet him, as he could probably use some help. He got up and led the way into a bustling, cramped open-plan office, where he introduced me to his son.

What conclusion can I draw from these reminiscences and stories? Firstly, I would suggest you plan your exit strategy long before you need it, especially if you're going to sell.

Set up your business to be robust in managing without you. Most importantly, though, prepare yourself emotionally for letting go, and if you're retiring, make sure you have decided what you're going to do instead.

Not just in using the extra time you are going to have, but in ways that give you fulfilment, a clear identity and friendships outside of the business.

Then you can let your baby grow up whilst you bow out gracefully.

Until next time ...


JACKY SHERMAN
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If anything I've written in this blog post resonates with you and you'd like to discover more, it may be a great idea to give me a call on 07970 638857. Let's have an initial chat over a coffee and see how I can help you.

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#KitchenTableConception #PubInspiration #BossFrustration #RedundancyRescue #BusinessBaby

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