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Retirement Reimagined

Regardless of the length of the runway, retirement shouldn’t be an event but a process, ideally one of self-discovery, fulfillment, and expansion.
Reuben Cohen, Managing Director, North America International Center for Executive Options (ICEO)

There was a time when the word “retirement” conjured up images of gold watches, golf clubs, gardening, and grandchildren. From the perspective of businesses, it was a defined event, often occurring when employees hit a certain age. For individuals, it was a rite of passage, generally signaling the culmination of one’s career. Embarking upon a life of leisure was the well-earned reward for decades of service.

Not anymore.

Today, more often than not, “retirement” implies approaching and/or arriving at a key inflection point in one’s life/career – not an end point. Some approach this inflection point with considerably more line of sight than others – perhaps as much as three to five years. In other cases, people see this coming much more quickly than they might have anticipated, sometimes with as little as a few months’ visibility.

Regardless of the length of the runway, retirement shouldn’t be an event but a process, ideally one of self-discovery, fulfillment, and expansion. 
Some paths could be financially rewarding: taking one’s skills in new directions such as full-time roles in private equity or startups, paid board or advisory work, or branching out to adjacent industries or sectors. Other opportunities, while they might generate income, are really about non-financial rewards – like mentoring, nonprofit board service, writing, teaching, or going back to school. In many cases, it involves a mix: professional plus non-professional endeavors, allowing more time for hobbies, family, travel, service, and philanthropic activities.

In my 20-plus years helping corporations and executives rethink, reimagine, and redefine retirement, I’ve observed the following:


  • For many leaders, “planning for retirement” means only addressing the financial implications, with little thought given to the important aspects of what happens next.
  • The greatest obstacles to embracing the retirement journey are most often related to mindset.
  • Not everyone’s retirement will look the same because the experience is deeply personal. Supporting executives begins with understanding their individual needs, meeting them where they are, and opening their eyes to the range of possibilities that lie before them.
  • Creating a partnership between the company and the executive in navigating this transition benefits the organization as much as it benefits the individual.


Successful executives have been deeply engaged in their careers for decades. Their motivation goes far beyond money; they derive enormous satisfaction and fulfillment working at a certain level and pace, and this strongly factors into how they self-identify. Such individuals generally don’t just flip a switch on retirement day. All that has made them successful over all these years still resides within them. Some people want to tap into these success traits going forward; others want to tap into more latent traits that their professional lives have precluded them from fully leveraging.

Yet it can be disconcerting – and maybe even a little frightening – to face the unknowns associated with one of life’s biggest pivots. An irony is that the more successful people have been, the more reassurance they may need that there is something else out there for them. We help shine a light for people on what that future path can look like. More often than not, these executives are surprised – pleasantly so – when we help them open the aperture to the opportunities available for them to explore. 

People often don’t plan for the “what’s next” aspect of retirement, either because they are busy pursuing their careers and advancing their company’s business imperatives or simply because doing so may introduce more ambiguity into their lives than they have an appetite for. That’s precisely why it’s important for companies to consider offering support. 

While it might at first seem counterintuitive, giving executives the freedom to think about what’s next – before they must confront it head-on – allows them to maximize their contributions while supporting the succession-management priorities of transitioning one generation of leaders to the next. An executive who’s distracted and anxious about retirement won’t be as engaged in their role as they otherwise could be. 

It’s worth noting that people often have and exert a great deal of agency when it comes to deciding it’s time for a change. This may come as an epiphany or a gradual realization, but either way, they are finding themselves needing to move in a new direction.

Numerous things can open a line of sight into this inflection point we call retirement. Whether it’s the company or the individual that sets the timing – and whether it is age-related or not – this represents an opportunity, for the executive, the company and its next generation of leaders.

If you are beginning to think about what retirement might look like for you, or if you are a corporate leader charged with considering how to manage retirement and succession issues for your executives, here are a few important questions to ask:


  • How open are you to exploring your possibilities for what’s next? 
  • How well do you understand your range of options? 
  • How prepared are you navigating uncertainty as you explore those options?
  • How important is making an impact and what does that look like going forward?
  • How much can you learn from others who shaped a meaningful path?


Retirement is an opportunity to be intentional about what comes next. To lean into an open mindset, explore possibilities, and engage existing networks while building new ones. The rewards can be much greater than you imagine.