Why it is Hard to Leave When You Have Been in Charge

My grandfather was a multi-millionaire in the 1920s. With nothing but a third-grade education and a keen mind for coming up with new solutions to problems, he was the consummate inventor, investor, and innovator.

He also lost quite a bit, all part of the entrepreneurial journey. But he always landed on his feet, and eventually, he and my grandmother built a convalescent home empire that saw them and countless families through the Great Recession and beyond.

Years later, my father decided to take a break from his university teaching to carry the entrepreneurial legacy forward. He developed his own successful healthcare system. But a strange thing happened. My grandfather resurfaced, and seemed to appear at the most inopportune times – during meetings, negotiations, and other sensitive situations.

One day, my father had to ask him to leave the premises.

Why did it come to this?

It seemed that even though my grandfather had left his business ventures behind, he hadn’t learned how to let go.

This dynamic is more common than you may realize. Whether you are leading a family-owned business, or hold a corporate CEO position, it’s just hard to let go.

What makes it so difficult for the chief in charge who is preparing to move on?

A fly on the wall might hear this:

1. I built the baby. Who will take care of this business after I’m gone so that it continues to thrive?

I have put my blood, sweat and tears into this and it works well. It’s a matter of pride – I’m leaving a legacy, here.

2. Will the business take care of me?

Have I put the leadership and strategies in place so that the business will continue to provide me with a return? I have invested in it, and want to make sure it supports me well in my next chapter.

3. Who am I without my CEO hat?

What will I do with myself after I step away? What will the next chapter look like for me? I’m not sure who I am without this position, and I want to look ahead with excitement and anticipation to my new role, whatever that may be.

Are you in a decision-making position and thinking about releasing the reins? What holds you back?

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Patti Cotton helps executives optimize their effectiveness in leading self, others, and enterprises. Her areas of focus include confidence, leadership style, executive presence, effective communication, and masterful execution. With over 25 years of leadership experience, both stateside and abroad, Patti works with individuals, teams, and organizations across industries, providing executive coaching, leadership development, change, and conflict management. She is also a Fortune 500 speaker. For more information on how Patti Cotton can help you and your organization, click here.