Is it Time You Gave Up? A Leadership Coaching Case

The owner of a big printing shop had been preparing to sell his company for months. When he came close to the date to put out the offer, he kept coming up with dramas at work he needed to fix. He asked to reschedule our coaching session. I asked for five minutes of his time.

First, I reflected to him what I saw happening in the past month, that little problems where escalating into disasters and he was uncovering issues that were never bothersome before. He asked me if I thought he was making up stories.

“No.” I said, “but I do think you are going out of your way to find difficulties that need your attention.” I let my words sink in before I said, “You don’t have to sell your business if you don’t want to. If this morning, you had signed the papers to sell today, how would you feel now? If you instead tore up the papers, how would you feel? Which action made you feel the worst?”

He said the thought of selling made him feel sad.

I asked, “What’s the loss?”

He said his colleagues were like family and he didn’t like the idea of leaving them behind.

“Are you willing to live with the loss to meet the goal you set for yourself when you sell the business?”

After a long pause he said he didn’t want the loss. He didn’t want to sell. He also didn’t want to look stupid. He felt telling people he wasn’t going to sell after all would be embarrassing.

“Which is worse, having people think you can’t make up your mind or not seeing your work family every day?”

“But what will people say if I stay?”

“Are you worried about their judgment or how you will explain yourself?”

“I don’t know what to say.”

“You just gave me a brilliant reason for staying – you like the people you work with.”

He decided to end his search for a buyer.

Some goals are good to hold onto no matter what. Some seem to be good when you create them but then don’t inspire you later on. Sometimes other circumstances arise that make your goals less meaningful. Blindly marching forward with your goals could leave you with more regrets than joys.

Whether you are making career goals, business decisions, or life choices, the moment you make the decision you should create criteria to evaluate if you should stay on the path or not in the future. Once on the path, your emotions can get in the way, keeping you from changing your mind when your procrastination is signaling it is time to reassess your goal. A good checklist will keep you from mistaking your desires from your fears.

When you make a decision, write down:

  1. Why did you make the decision?
  2. What outcome do you expect? Why is this important to you?
  3. What are you leaving behind? How will you replace the loss or what is more important to you now?
  4. What will you gain by sticking to your plan?
  5. What might you regret by sticking to your plan?

Keep the questions close and set an appointment with yourself to review them monthly for long term plans and weekly for more short-term goals. Or you can work through the questions with your leadership coach. Answer the questions honestly. Is it more important to save face or to be happy? Living with people’s negative judgments of you is generally short lived, especially if you are clear why you have changed course. Living with regret lasts forever.


  1. As a financial and retirement planner, this story was very poignant to me. I help people with the “numbers” part of decisions like retirement or selling a business but what is often even harder for them is the emotional piece. These questions you pose will help me help my clients with these types of decisions – thank you!

    • Marcia Reynolds says:

      Glad to help Melissa. Emotions always impact logic. You have to clear the way first before the “pros and cons” conversation makes sense.
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