It is important to understand why letting go is so hard for so many leaders. Successful enterprises tend to be built by vigorous leaders with strong opinions and forceful personalities. If you make great sacrifices, pour all of your energy and the very best years of your life into creating an enterprise or an institution, it is impossible to not be profoundly attached to your creation. The combination of a forceful opinionated personality and great love for the institution, makes it difficult to watch as a successor dismantles part of your legacy. As every disgruntled and anxious employee seeks solace and support in you, it takes a great deal of restraint to not leap back into the fray.
The second reason is that, frequently, your identity becomes intertwined with the enterprise. It is entirely natural to wonder “who am I if I am not the CEO of X?” Will people still respect me and flock to me? How do I stay relevant? After years of being in the limelight, fading away gracefully is not easy for many leaders.
-- Ravi Venkatesan
