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Jake’s Journey: Confronting Fears and Embracing Succession Planning

Middle aged man in contemplation stance

I wonder if your story is anything like Jake's?

At 77 years old, Jake finds himself at a critical juncture. He has built a highly successful business over the decades, but now, with his health failing and the need for emergency treatment looming, he realizes that his opportunities to ensure his successors could flourish without him are dwindling.

Jake set up a board years ago, recognizing the importance of succession planning, but he filled it with people indebted to him, unlikely to challenge his decisions. The board, comprising family members, a faithful employee, and his banker, is merely ornamental, never truly functioning in matters of accountability or helping Jake with direction and planning for the business.

As Jake approaches his eighties, the pressure to act weighs heavily on him, but fear and uncertainty keep him paralyzed. He knows he has to do something, but the task seems insurmountable.


This is a common scenario among leaders who fail to seriously begin the succession planning process in their fifties. As they near the end of their journey, the emotional and psychological barriers to letting go become increasingly formidable.

I meet so many leaders in their last few years paralyzed by fear. I am dreaming of better things for you.

For decades, Jake has found himself at this crossroads of succession, but instead of seizing the opportunity to lead his successors through the process, he has succumbed to what Ken DeWitt calls “Fear Junction.”


At Fear Junction, leaders face the challenges of business, but instead of stepping forward into maturity and emotional growth, they shrink back into fear. It becomes a vicious cycle, with leaders repeatedly making the wrong choices, and lacking the courage to blaze a new trail.

One of the most significant fears that senior leaders face when confronting succession planning is the fear of losing their identity.

For years, they have been the decision-makers, the catalysts driving their businesses forward. Their role becomes intertwined with their sense of self, and the prospect of relinquishing that position can feel like a threat to their very being. Jake and many others, never fully grasp the temporariness of their role until it is nearly too late.


The statistics are sobering: 70% of businesses fail to make it to their second generation of leadership.

Jake’s lack of proactive succession planning has left his life’s work vulnerable, poised to become another casualty of poor planning. The fear of losing influence, status, and relevance within the organization and industry can be paralyzing, especially for those who have been the face and driving force behind the business for so long.

But there is hope.

By confronting these fears head-on and embracing the succession planning process, leaders like you and Jake can ensure that your legacy endures. The 7-step process outlined by Cultivating Impact provides a roadmap for navigating this emotional journey:

  • Step 1 - Confront Your Fears About Succession Planning

  • Step 2 - Establish Your Succession Planning Team

  • Step 3 - Define Your Impact

  • Step 4 - Define Your Niche

  • Step 5 - Develop Leaders in Your Team

  • Step 6 - Pass the Baton to Your Successor

  • Step 7 - Finish Well


With the guidance of a trusted coach, you can reframe succession planning as an opportunity for growth, a chance to take on new challenges and ensure that your life’s work continues to make a difference long after you’ve stepped back from the helm.

By dedicating time and energy to these critical conversations, even when it feels uncomfortable, you can create something truly remarkable – a legacy business that thrives for generations to come.

Harry T. Jones

P.S. Break the vicious cycle of fear and wrong choices by joining a Cultivating Impact Mastermind group. Get a peer advisory group that will give you the courage to blaze a new trail in building your legacy. Email me,, and put “Mastermind” in the reply to join the waiting list.

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