06/09/2015 01:45 pm ET Updated Jun 09, 2016

How Caitlyn Jenner Is Helping Me Be a Better Me


When I'm not being annoyed that at 65, Caitlyn Jenner looks better than I do in a corset, I am fascinated by her courage to reinvent herself at her age and before the public eye. The more I think about Caitlyn, the more I realize I can learn from her. Even if you still refer to her as "Bruce" or if you have trouble with the whole pronoun issue, you know that the bottom line is that Caitlyn is a person. And that person made a very profound choice to undergo a radical personal reinvention in front of the whole world.

I too have gone through my own reinventions -- though thankfully, they were far less controversial and didn't require anesthesia -- but to me, they were still big changes. Fifteen years ago, I transitioned from "corporate lawyer" to "entrepreneur," and if I could have accompanied that change with a new face or new name, I would have been thrilled. It wasn't easy. And it was all up to me. And throughout the process, I had to remind myself every day who the "new me" was. And I had to convince myself (and everyone around me) that my choice was the right one.

When I see those Vanity Fair shots, I try to focus less on my questions about how hair extensions and facial feminization work and more on the very real lessons that those photos symbolize about how we can successfully reinvent ourselves.

1. A successful reinvention requires a total commitment to the new you. When we start a transition, the world around us can practically smell our uncertain footing. Everyone we encounter has a suggestion, a question, or a critique. While most are well-meaning, almost none are actually helpful. Real reinvention -- the kind that takes hold and allows us to flourish -- has a death/rebirth aspect to it that is palpable. And that is why it can be uncomfortable to look at pretty pictures of Caitlyn. We feel something like mourning for the guy on the Wheaties box. But just as there can only be Bruce or Caitlyn, there can only be one of each of us. We must throw out our old wardrobes and burn our old business cards. We must face the world as our new selves, without constantly looking back.

2. Reinvention is a solo act. Each of us in is this reinvention process alone. Family, friends, and colleagues can be supportive -- and that support is very meaningful -- but we are on our personal magazine covers alone. We must determine who we will become on our own terms. Who I will be is not something to be decided by consensus. It is my decision. It is my road to walk. And it is my responsibility to have a specific destination.

3. Reinvention is not about change; it is about authenticity. Personal reinvention is not about convincing the world that one day, we will become who we want to be. Personal reinvention is about embracing who we truly are and then being that person. That's what Caitlyn did. She didn't ask. She told us who she really is. And that is what we all must do. So when we start businesses, we must adjust our entire personas to become entrepreneurs. If we are leaving the workforce to devote ourselves to family, we must become homemakers and do it with the gusto it deserves. I've found that no one ever questions what I "am" -- but rather, only what I "want to be" or am "planning to be." Our clarity of identity determines our success.

4. Confidence is most critical when we are most vulnerable. No one reinvents themselves when life is at a high point. We start new careers when we've been unhappy in the old ones. We get divorced when marriages fail. We start businesses when we are financially strapped. Crisis is so often the catalyst for lasting change, and that is precisely why hanging on to our confidence during transitions is both difficult and critical. Unfortunately, it's hard-wired Darwinism that causes people to rally behind the strong and question the weak. Therefore, as we reinvent --as all of us do at some point-- we must do it with clarity, confidence, and resolve. No matter what path we choose, there will be opposition; to succeed, we must be expect to succeed.

Caitlyn Jenner's transformation was fascinating and inspiring to so many of us -- not only for the social change it means for our world, but also because it is rare to see any reinvention that is so total. And that rarity is what each of us must channel if we are to be successful in achieving our personal goals and becoming the people we truly are.