The Risk of Following Caitlyn Jenner


I am 100% supportive of Caitlyn Jenner’s journey of self-actualization, as well as anyone’s effort to “follow their passion” or “trust their instincts.” However, from the moment of Caitlyn’s unveiling, I have wondered whether any of the media, drooling in anticipation of a new quote from the former Bruce Jenner, would describe the risk of widely sugar-coating and encouraging a Caitlyn-like makeover strategy.

I am not referring to gender transformation but to personal transitions of any type. When researching a piece for the Harvard Business School blog, I often conduct surveys of groups such as CEO’s, women professionals, grandmothers, and even golfers. It would be interesting to measure the percent of people who would admit to being unhappy about some important aspect of their lives: their job, wealth level, looks, spouse, children, parents, health, habits or weight.

It is likely that many, at least a sizable minority wish they could radically change something about their lives. Why don’t they? Caitlyn Jenner did it after many years of internal strife, but change is daunting and difficult to accomplish, as evidenced by the multitudes who remain unhappily mired in their job, marriage, persona, and lifestyle. Also, most people have responsibilities that they cannot avoid or are unwilling to reject.

It is too simple to say that the lack of fame, money and numerous helping hands, many of whom will get something in return, are the major deterrent to a new and better life. The truth is that most transformations require money, time, effort, emotional balance, and fortitude. I suspect that often the person seeking the transition can succeed on some of these criteria, but one or more remain elusive. For example, at one point I considered shifting my career to investment banking and had an outstanding offer on Wall Street. I turned it down because it would have been absurdly inconvenient to commute from Boston where my husband’s business was located. I had a home and a family in one place and it was not realistic to think that, with four children, I could successfully manage a two city lifestyle.

How does Caitlyn Jenner fit into the picture? Because the media has made it looks so easy: from her perfectly coiffed hair, professional applied makeup, and sculpted nails to her designer gowns, created for her 6’2”, 185 pound frame. Even though she has explained how much suffering Bruce Jenner endured, caught in a miserable life of lies and how painful the surgeries were, the press has presented this transition as seamless and somehow inevitable, a perfect story of the unhappy prince becoming the happy princess. The E! Network, on which her new reality show will air, has also embraced and showered her with a lucrative contract.

There is no doubt that Caitlyn has the money to withstand a prolonged period of unemployment, if her metamorphosis forced her to take time without a pay check, but can most people? In general, we need to support ourselves and our families, something that Caitlyn admits that she didn’t do financially or emotionally for many years in the eighties and nineties.

We are also afraid of failure, whether it’s a physical operation, a test for a certification, a career changing interview, or a move far from home. I commend Caitlyn for her perseverance and even her willingness to be the very tall woman whom everyone will notice wherever she goes. No one goes to this effort just for attention.

However, despite the joy and fulfillment that Caitlyn expresses today, the journey away from Bruce is obviously not a roadmap for everyone. The risks inherent in giving up one job, career, lifestyle, face, or body for another can be extreme. In many cases, you simply can’t go back again if the passage is not successful. We have heard that this decision took decades to make as Bruce and then Caitlyn weighed the scope, costs, and potential outcome. This diligent consideration of the gravity in embracing a new direction is an aspect to Caitlyn Jenner’s transformation requiring equal coverage to the Cinderella-portrayed results.