Business

The Challenges of Retiring from a High-Powered Job

A look at seven common pitfalls — and how to avoid them.

January 05, 2024

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  • Each year, thousands of executives retire from long and successful corporate careers. But few are prepared for the journey they are about to embark on. Based on conversations with dozens of highly respected former chief executives, the authors identified seven common mistakes, ranging from not preparing far enough in advance to thinking you can rely on your existing professional network to not realizing that behaviors that worked for you as an executive can work against you in retirement.

    It was mid-summer 2020, and Ginni Rometty, the chairman and CEO of IBM, had six months remaining on her nearly 40-year career with the company. Her longtime mentor, the revered former CEO of IBM, Lou Gerstner, had reached out to request a meeting. “He wanted to see how my retirement planning was coming along. Truth be told, I hadn’t begun to think about it. I was still running the company full time and had not been able to set aside the time,” Rometty told us.


    • Rick Smith is an executive career coach, serial entrepreneur, and co-founder of ONYX, an invitation-only community for current and former CEOs of the world’s most influential corporations. He is also the founder of World 50, the world’s leading senior executive network and learning organization, as well as G100 NGL, CNEXT, Fast Radius and Bionic. He is the Wall Street Journal best-selling author of three books on professional career management, and a main-stage TED speaker.


    • Maggie Wilderotter is a co-founder of ONYX, an invitation-only community for current and former CEOs of the world’s most influential corporations. She is also a seasoned executive who was CEO of venture startup Wink Communications for five years and CEO of Fortune 500 company Frontier Communications for 12 years. Maggie has served on 51 corporate boards in her career, and she currently sits on six corporate boards and is a senior advisor to seven companies. Maggie also owns a vineyard in California with her husband Jay.


    • Dennis Carey is vice chairman of KornFerry and co-founder of ONYX, an invitation-only community for current and former CEOs of the world’s most influential corporations. He has recruited directors and CEOs for many of the most prestigious companies in America, served on several boards, taught corporate governance at the Wharton School, and co-authored seven books on strategy, talent, and risk. He founded the CEO Academy and ThePrium, both of which are best in class forums for corporate leaders. He has held post-doctoral fellowships at Harvard and Princeton.


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