
Are you caught in the insider trap?
Are you caught in the insider trap? Learn to identify signs of leadership stagnation and explore effective ways to reset your approach for sustained success....

by Michael Watkins, Chris Donkin Published May 2, 2025 in Brain Circuits • 3 min read
a. Join a non-profit board and become a school governor.
b. Google “productive things retirees do”, then take a nap.
c. Check my emails constantly – I’m bound to be deluged by ex-colleagues needing my help.
a. Launching a mentorship network for young professionals.
b. Finally learning a foreign language. Or maybe the ukulele. We’ll see how the week goes.
c. Training the dog to go for a walk on its own.
a. Of course. I’ve already prepared slides, a TED-style opening, and a themed playlist.
b. Maybe – if it’s somewhere with good food and no dress code.
c. Only if I can do it virtually – from my hammock, in a bikini.
a. Consulting part-time and guest lecturing.
b. Dabbling. Light dabbling. Maybe heavy dabbling in summer.
c. Mostly doomscrolling and liking cat memes.
a. I help people grow.
b. I schedule invitations to lunch with friends. And some ex-colleagues.
c. A little bit of this, a little bit of that… I’m in my “experimental” phase.
Mostly As: You’ve swapped your executive title for Chief Fulfilment Officer. Your new life will bring you excitement, joy, and a renewed sense of self.
Mostly Bs: You’ve obviously given some thought to what comes next, but retirement will be much more fulfilling if you plan how to imbue it with purpose.
Mostly Cs: You might be in for a shock – without the corporate infrastructure that previously filled your days, you are at risk of feeling adrift.
While board positions are a natural extension of executive experience, the most fulfilling post-retirement careers often transcend conventional corporate roles. Identify opportunities that align with your interests while allowing you to apply your leadership experience in new contexts.
Imparting your knowledge and experience to future leaders is particularly rewarding for retired executives. Teaching and mentoring roles often lead to unexpected personal growth as you articulate and examine your own leadership principles and experiences.
Post-retirement entrepreneurship fundamentally differs from traditional business leadership. Retired executives can pursue ventures driven primarily by purpose and passion, free from the pressures of shareholder expectations and quarterly results. These endeavors often focus on solving societal challenges, allowing you to combine your business acumen and personal values in ways not always possible in a corporate setting.
Creating a portfolio of activities that leverages your capabilities in meaningful ways will bring you fulfillment and a genuine sense of purpose in retirement.

Professor of Leadership and Organizational Change
Michael D Watkins is Professor of Leadership and Organizational Change at IMD, and author of The First 90 Days, Master Your Next Move, Predictable Surprises, and 12 other books on leadership and negotiation. His book, The Six Disciplines of Strategic Thinking, explores how executives can learn to think strategically and lead their organizations into the future. A Thinkers 50-ranked management influencer and recognized expert in his field, his work features in HBR Guides and HBR’s 10 Must Reads on leadership, teams, strategic initiatives, and new managers. Over the past 20 years, he has used his First 90 Days® methodology to help leaders make successful transitions, both in his teaching at IMD, INSEAD, and Harvard Business School, where he gained his PhD in decision sciences, as well as through his private consultancy practice Genesis Advisers. At IMD, he directs the First 90 Days open program for leaders taking on challenging new roles and co-directs the Transition to Business Leadership (TBL) executive program for future enterprise leaders, as well as the Program for Executive Development.

Chris Donkin is Managing Partner at Savannah Group. He advises clients operating at the intersection between established industrial markets and disruptive new technologies on how to identify, attract, and develop leaders with the attributes to succeed in an increasingly volatile and complex business environment.

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