Phyllis weiss haserot
Phyllis weiss haserot

President & Founder

212 593-1549


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Boomer Legacy Meet Gen X and Y Entrepreneurism

As professionals and executives become more senior, there is often a desire or expectation that they will want to devote themselves to "good works" as a legacy. Leading edge Baby Boomers, tracing back to their formative years in the 1960s, started out as a generation to be socially conscious, involved and eager to make significant contributions for a better world. As they matured and became intensely immersed in their careers, often achieving substantial recognition and financial success, some have been well on their way to fulfilling their "legacy bucket"; others have been too busy to think about it.

The philanthropic and pro bono world is watching. For example in the legal field, both the American Bar Association's Second Season of Service Initiative and some local entities such as the Association of the Bar of the City of New York have been eyeing and expecting senior lawyers nearing traditional retirement age to become a large talent pool for pro bono work. Some of these efforts may have been delayed by the effects of the great recession. Nonetheless they are as valid as ever.

But pro bono, volunteering, unpaid work is not for everyone. In our *Next Generation, Next Destination* client interviews, we have found that many Baby Boomer professionals want to continue to play in the business arena.

So I had an interesting thought. The hedge fund managers and tech entrepreneurs under age 40 have started to think about philanthropy and how to use their money to do good. But they don't want to do it in the traditional ways. They are interested in starting their own entities with a different model that combines making money with doing good things for society. Perhaps some of those seasoned Baby Boomers can link their legacy time, expertise and desire to continue to contribute with the Generation X and Y entrepreneurs for some hybrid organization that takes advantage of the best each generation has to offer.

For example, Venture for America, inspired by Teach for America, was started by Andrew Tang, former CEO of Manhattan GMAT, the test prep company. The first 50 “fellows” were placed in small businesses (under 500 employees) for a 2-year stint last year, and an expanded second round has been placed this summer – a positive sign. Tang’s goal is to help early stage businesses and start-ups take off, and he is targeting to create 100,000 jobs by 2025. At the same time, the young fellows will get the know-how and experience to start companies of their own if that’s their goal and be paid $32,000 to $38,000 a year plus health benefits. The participants receive a 5-week program at Brown University similar to training that consultants and investment bankers receive.  The companies get bright, eager young workers they can afford to hire and mentor.

I, for one, would look forward to seeing how this and other ventures can take shape. There certainly are limitless needs, causes and opportunities, particularly in health care and education to benefit a range of ages domestically and internationally, whether built on a not-for-profit or for-profit model. This certainly qualifies as the “meaningful work” Gen Yers and Boomers seek. The creative entrepreneurism model championed by the Gen Xers could bring it all together.

I'd love to hear your ideas. Please send your comments and thoughts to or share on the Cross-Generational Conversation group on LinkedIn.


© Phyllis Weiss Haserot, 2013. All rights reserved.

* The generational chronology for easy reference: Generations are defined by the similar formative influences – social, cultural, political, economic – that existed as the individuals of particular birth cohorts were growing up. Given that premise, the age breakdowns for each of the four generations currently in the workplace are approximately:

Traditionalists:                            born 1925-1942   

Baby Boomers                             born 1943-1962

Generation X                                born 1963-1978

Generation Y/Millennials            born 1979-1998  

For coaching, training and special programs on inter-generational challenges for and among 4 generations in the workplace, attracting and retaining clients and employees of different generations, and maximizing the potential of young professionals and work teams, call or email Phyllis for an exploratory talk or complimentary coaching session at 212-593-1549 or Ask about our signature program *Frontrunner 5.”

Phyllis is available to speak at your organization or at firm retreats on inter-generational relations and organizational effectiveness topics. Call or e-mail for a list of topics or to custom-tailor your own. 

Learn about our *Generational Wisdom for Mentors and Mentees* programs as well as multi-generational team facilitation. Call 212-593-1549 or e-mail