How to Talk to Boomers About Retirement: A Millennial Guide

How to Talk to Boomers About RetirementIt’s time for Millennials (born 1982-2003) to have that tough talk about retirement with members of the Baby Boom generation (born 1946-1964). Unless more Boomers start stepping down soon, the path to promotions and career progress for younger generations will continue to be blocked by people who haven’t shown any inclination to leave, especially after the Great Recession devastated many Boomers’ retirement portfolios. But using logic or inter-generational appeals isn’t likely to be successful and would seem selfish or cold-hearted to most within the remarkably well-mannered Millennial generation. Instead, the talk needs to be couched in the language of Boomers and attuned to that generation’s fundamental values.

Boomers are an “Idealist generation” in the topology of archetypes first proposed by the generational theorists, William Strauss and Neil Howe. Previous American generations of this archetype, such as the Transcendental generation (born 1792-1821) and the Missionary generation (born 1860-1882) share one key characteristic with Boomers: all Idealist generations hold and are driven by strong beliefs about what is right and wrong, good and evil. This type of generation brings zeal to public life based upon its ideals, resisting compromise and determined to impose their beliefs on the rest of society, even if it means tearing down existing institutions.

By contrast, Millennials are a “civic generation” in Strauss and Howe’s categorization. Just like their predecessor—the  GI generation that came of age during the Great Depression and World War II  or the Republican generation that won the American Revolution and developed the constitutional order by which America has been governed since 1787—Millennials are “pragmatic idealists”--interested in working together to make the world better. It is this desire to find mutually agreeable solutions to problems that makes having the “talk” with their Boomer colleagues so hard for Millennials.  

But there is a way to turn the discussion into the type of “win-win” outcome that Millennials favor. The key is to appeal to the very ideals that have driven Boomers’ lives ever since they first burst upon the nation’s consciousness in the 1960’s. Since then, no matter on which side of the Cultural Revolution they may have fought, Boomers have devoted themselves to their work. They are the source of the term “workaholic” and take pride in what they accomplish at work each day. They define their very self-worth by their work, leading them to start conversations with new acquaintances by asking, “So what do you do?” To suggest to Boomers that it might be time for them to retire is almost the equivalent of asking them to die—clearly not the way to start a productive conversation. 

Instead, Millennials should begin the conversation by asking Boomers about their ideals and values. Getting them to talk about what motivated them, when they were young, to make the life choices and take the career path they have is a far better option.   Most Boomers love to talk about their youth. They think of it as the best time in their lives. Beginning this way is likely to make the opening of the “talk” both pleasant and productive.  

The next step would be to pivot from the past into the future by asking Boomers what is it that they believe they have yet to accomplish. This should be followed by a suggestion that now might be the time for the Boomer to take up the work that remains undone on their ideological bucket list before it is too late and they lose their ability to make a difference. Assure them that there are other people, maybe Generation X, if not the even younger Millennial generation, that can pick up the work in which Boomers are now engaged and see it through to completion. But, crucially, Millennials should also make it clear that no one but Boomers have the wisdom and experience, coupled with the ideals, to take on the challenges they have been too busy to tackle. At that point, moving on will become something Boomers think they should do, rather than something that is being forced upon them.  

The history of previous idealist generations underlines the importance of having these conversations sooner rather than later. Strauss and Howe, in their book Generations, capture the very different outcomes that flowed from the choices that the members of Idealist generations have made at this crucial point in their lives: “Where the angry spiritualism of Transcendental youth culminated in the apocalypse of the Civil War, the Missionaries demonstrated how a youthful generation of muckrakers, evangelicals, and bomb-throwers could mature into revered and principled elders--wise old men and women capable of leading the young through grave peril to a better world beyond." 

Suggesting that it’s time for the current  generation of Idealists, Boomers, to lead this increasingly dangerous world to a better place by putting aside their current work and taking on their last and most important challenge, is the best way for Millennials to convince Boomers it’s time to move on. It’s way past time for Millennials to do that. Don’t wait another minute to have the “talk” with a Boomer you know. 


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