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March 22, 2017

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In his notes for The Last Tycoon, F. Scott Fitzgerald wrote “there are no second acts in American lives.” Meanwhile, former baseball star, Alex Rodriguez, is working on a reality show for CNBC that may help either prove or disprove that premise.

Looking at TIGER 21 Members though, it’s clear that the notion of there being no second acts in American lives is clearly wrong. Every day, I am meeting and working with successful entrepreneurs who have chosen not to rest on their laurels but instead are already thriving in the second act of their lives ‚Äì or in some cases the third or fourth act.

Certainly, there are good reasons why second acts for successful people are considered especially challenging, but nobody at TIGER 21 ever confused challenging with impossible.

The Myth of No Second Acts

It’s easy to see why F. Scott Fitzgerald’s quote and the circumstances around it may have propagated the myth that there are no second acts in American lives. After all, The Last Tycoon was an unfinished novel, and Fitzgerald himself died in his mid-forties.

As for A-Rod, his new venture raises interesting questions about the myth of no second acts. Following his long and often controversial baseball career, A-Rod has launched a television program featuring former star athletes who have fallen on hard times financially. The premise is that A-Rod will be helping those former athletes find advice that will help get their finances back in order. Whether these riches-to-rags stories will simply serve as a reminder of the difficulty of staging a successful second act, or whether A-Rod’s venture will prove successful enough to make him a positive example of a second act, remains to be seen.

Already though, between the eras of Fitzgerald and A-Rod there have been plenty of examples of successful second acts. To name just a few:

  • Byron “Whizzer” White followed a professional football career by going into law. He went on to serve for over 30 years on the United States Supreme Court.
  • Bill Gates became one of the richest men in the world by founding Microsoft, and after stepping down from day-to-day responsibilities there he has distinguished himself by pursuing the Bill and Melinda Gates Foundation not just as means for distributing his money, but as a laboratory for experimenting with better ways that charity can change lives.
  • Richard Branson became a multi-millionaire in the 1970s by launching a successful recording label; he became a multi-billionaire subsequently by parlaying that success into a diverse group of multi-national companies.
  • And then there was that actor named Ronald Reagan….

Beyond those and many other prominent examples, TIGER 21 itself represents something of a third act. The organization was founded by Michael Sonnenfeldt after he had firmly established his entrepreneurial success in real estate and followed that as Chairman of Carmanah Technologies and pioneer investor in alternative energy technologies. Given the scope of TIGER 21 today, Michael clearly has found a third act that not only touches his own life but those of many of his peers as well.

The Challenges of the Second Act

While it may be an overstatement to say there are no second acts in American lives, following up on success certainly carries some special challenges. These include the following:

  • The ‚Äòone big idea’ can be hard to follow up. Some very successful businesses are based on an inspired innovation or unique insight that revolutionizes a market or creates a new one. It can be a lot to ask to then repeat that kind of lightning-in-a-bottle idea.
  • Not all skills are transferrable. Some people are specialists and some are generalists. Specialists might be brilliant in a given field, capable of designing and executing product innovations that drive a business to success. However, they might not be as successful in less familiar businesses. Generalists are less likely to initiate breakthrough products or services themselves, but have the type of organizational and market insight to lead diverse businesses to success. In other words, specialists may have more initial impact than generalists, but may find it harder to duplicate that success in a different pursuit.
  • Passive management is harder for some than active management. Successful entrepreneurs sometimes turn out to be poor investors. Whether it is managing people or choosing investment vehicles, some entrepreneurs are less adept at delegating responsibility than they are at steering the ship themselves.
  • Few people notice your early failures. The impression that second acts are often failures is created in part by the fact that we pay more attention to people once they succeed ‚Äì thus their subsequent ventures are subject to added scrutiny. Entrepreneurs often experience disappointment a few times before they finally succeed, but only the failures that follow success are under the microscope.

Succeeding Again

It is arguable whether second acts are harder or easier than first acts. On the one hand, breakthrough success in business or any endeavor is hard enough the first time, so repeating that success is never a given, especially if you are trying a different field. On the other hand, it doesn’t hurt to pursue a new venture with the experience, wealth, and contacts that come with having been a successful entrepreneur.

Whether it is a new field of business or a familiar one, or whether you are pursuing your second act in something outside of business altogether, one key may be to take a little time after your first act to decide what you really want your second act to be. One of the roles TIGER 21 can play as a learning community can be to help prepare you for that second act – whether it is as an active entrepreneur, passive investor, philanthropist, or otherwise. Through exchanges with fellow TIGER 21 Members, you can both get a feel for the scope of opportunities out there, and some ideas on how to succeed in those pursuits.

Members of TIGER 21 have already succeeded at least once. There is a good chance that those who choose a second act will succeed again, and with the right choices, perhaps find success even sweeter the second time around.

Barbara Goodstein SignatureBarbara GoodsteinPresident & CEO of TIGER 21