Selling a Business a Choice that May Be Regretted for 20 Years or More

Every day we are faced with choices that will affect us over the long term. Selling our business is a crucial choice, it will impact the rest of our life as well as the future  wealth of our families. When we look back 10 years from now will it be with pride and happiness— or regret?

Some facts:

  • 45% Owners would sell their business tomorrow for the right money.
  • In any12 month period only 20% of businesses on the market actually sell
  • Businesses that go straight to market sell for only 70-80% of the original asking price.
  • 75% of former business owners regretted selling their business because they did not plan adequately for what to do next.

What are the main regrets expressed by former owners?

  • Their company was undervalued by the buyer
  • They have been unable to control the exit
  • They paid too much in taxes
  • They failed to achieve the owner’s personal goals

Here are some of the behaviours business owners may regret deeply in 20 years’ time:


Pretending to be something they are not.

A lot of business owners pretend that they are too busy to plan their exit. The truth is that they use “Being busy” as an excuse for procrastination.  I’m too busy to go to the gym, I’m too busy to take a day off. We lie to ourselves to feel better when we do not want to do something.

If we really believe something is important we find the time to do it. Making sure our family and ourselves will be able to live comfortably after the sale of the business, that our business will survive our departure, when time comes are important issues to consider way before exiting the business. Exiting our business is inevitable it is just a question of time, it will happen, whether we want it or not, we all are mortal!

Making decisions based only on money.

Making decisions solely based on money is almost never a good idea. Here are some of the many questions we should ask ourselves before exiting:

  • Do I want an on-going management involvement in the business? If yes: how long should I stay? Would I work full time?
  • Do I want to retain a financial stake in the business?
  • Have I determined what is really important to me? For example, do I wish to maximise the value I receive for my business, or are other issues as important? May be even more important?
  • To whom do I want to sell/transfer the business—to family members, financial investors, employees or competitors?  Do I really care?
  • Do I want to keep the business in the family? Is anybody in the family able to take over? If not can I train them?
  • Are there employees or others whom I want to protect or reward? Would I sell to my employees?
  • Are there other motivating factors for me? Do I want the business to retain its name and identity following my exit? Is it important that my business retain its independence?
  • What are my financial needs?
  • Does my business have all the necessary managerial expertise required to be successful in the future?
  • Does the business have an appropriate capital structure and access to further funding to enable it to take advantage of the future opportunities? 

Accepting to sell under pressure.

We should avoid rushing into selling a business, even if we are under pressure from a potential buyer or other external factors like illness or divorce. If we succumb to  pressure we are at risk to undersell our business. Working with experienced advisors to have a business continuity plan in place will ensure a smooth transition out of the business no matter if it is due to a sudden death or as planned, it will be for the benefit of the business, its clients, the owner’s family and the owner. James Joyce says: “I am tomorrow, or some future day, what I establish today. I am today what I established yesterday or some previous day.”

Business continuity is not episodic. It should be treated as a continuous practice whereby the owner and the team are prepared for transitions at any time, and at multiple levels. This should include ownership, management positions and other critical positions. A good business continuity plan should address the owner’s death, disability or retirement of the business, as well as the sale of the owner’s interests. Further, a great plan will ensure that all objectives are accomplished — that the most effective business transfer is realised, and that funds will be available to provide the owner and his/her family with the maximum financial flexibility.


We should believe in ourselves enough to go after what we deserve, whether it’s a life in the sun in Florida, an opportunity to start a new business or another exciting project. We should not satisfy ourselves with an OK business, with an OK life, we should go after what we really want … We are not doing ourselves any favours settling for something that is just OK 

Working 50 or more hour weeks until death.

We might think we have to work that much — because it’s expected, because we need the money, because we want to look good to ourselves — but when we are on our  deathbed will we  say, “I wish I’d spent more time working” or “I wish I spent more time with those I love”. Our friends and family are those people that have been supportive and made us successful. Should our business success matters more than ruining those relationships?

Micromanaging everything.

This applies not only to our business life, but also to life in general. If we micromanage everything instead of sometimes just letting go, we’ll find ourselves constantly under stress and battling anxiety rather than enjoying life.

Avoiding making mistakes.

If we are actively avoiding making mistakes in our life, then we are not taking risks. Selling a business is risky but avoiding to accept that we will have to exit the business one way or another is even riskier. We may keep up the “status quo” but we won’t be properly rewarded for a long life of efforts. After careful planning we should have the courage to put the business on the market, make mistakes, own them, learn from them and continue so the reward will come.

Thinking only of ourselves.

We have to decide with our partner what we will do after exiting our business. A lot of business owners retire and then realise that, playing golf every day can be boring, being with our partner all day can be difficult, as both of us have lived an independent life so far, traveling is costly… we should  decide if we still want to keep an occupation or discover a new hobby. When the decision is made and we agreed the way forward with our partner we have to make sure that we can afford our dream life.  We should not wait until it is too late to find realistic and adequate responses to these challenges

Not valuing our new identity.

We need to prepare ourselves, mentally, for a new social status. Our personal identity is narrowly intertwined with our business identity. We need to determine how to extract ourselves from the business and what our new image will be.  Being a business owner is who we are and who we have been for years. It is reassuring, it gives us pride and a feeling of self-worth.

Losing this social status is extremely painful and it will take us a long time to find a new identity. Separating ourselves from the business is a process ensuring that we are mentally and emotionally ready to leave our company. It will help us find other activities or interests where our talents can be valued by others to regain pride and self-worth. If we do not do it we are at risk to see our intellect declining rapidly and our joie de vivre disappearing as we will be soon forgotten by those in the active world.

The most successful succession plans are initiated years in advance. When Exit Planning is left too late, the failure to plan ahead can lead to disaster. This takes time but is worth the effort.

Are you curious about how sellable your company is and what you would need to tweak to sell it when you’re ready? Then it’s time to get your Sellability Score via the questionnaire on our website. It takes about thirteen minutes and your responses are kept confidential. Complete the The sellability Score Test Now!

If you would want to know more on how to transition out of your business and would want to explore what you should do please do not hesitate to call Jean-Bertrand de Lartigue on +44 1656 766 363 or e- mail him at

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