One of the first executives I coached was a golden boy — let’s call him Christopher. In his early thirties, he was bright, handsome, and well-spoken. He had a beautiful wife and three lovely young children. He had been promoted four times in the past twenty months. From others’ perspective, Christopher was leading a charmed life. He had it all. 

So why was he coming to see a psychologist? Underneath his polished exterior, Christopher was paralyzed and overwhelmed. When we finished our first meeting, I offered to see him again in a week. He paused and replied, “If it’s ok with you, I’d like to come back sooner than that.” So I scheduled a meeting for us in four days.

Christopher and I finished our work together about nine months later. He had put a lot of effort into his coaching, getting to the roots of what was undermining his confidence and enthusiasm at work and rebuilding his energy and sense of purpose. In our final meeting, I asked him if there was a particular moment in our work together which was especially impactful for him. Without hesitation, he responded, “It was when I asked you for an earlier session and you gave it to me.”

That was a powerful lesson for me. To be honest, I had imagined it might have been some especially intelligent thing I said in our conversations that accelerated his progress. But no. I had given him an earlier session when he asked for it. Of course I had given him an earlier session — I always try to respond to my clients’ scheduling requests. So what was the big deal?

By responding matter-of-factly to Christopher’s request for help, I had sent him a powerful message. I had recognized his vulnerability and quietly responded to it. My answer made him feel safe and heard, and it gave him hope that together we would be able to relieve his distress.

Over the years since then, I have coached many “Christophers” — highly successful people who look as if their lives are easy and perfect. I know that under that surface they are often just as insecure and over-stressed as the rest of us. Don’t get me wrong. I’m not pretending that everyone has to cope with equal challenges in their lives. Some of us start out with huge advantages: good health, loving families, economic security, clever brains. Others have to claw their way up against massive odds.

I recently read an article by Tavi Gevinson, founder of Rookie magazine, on why she was closing the publication. In it, she makes a sort of professional bogeyman out of “Bryce,” her name for young dudes who rule the world. Others sometimes use “Chad” or “Trixie” to describe these highly successful people who seem to have it made. 

Given my experience coaching this “type,” let me ask: How about if we don’t make them into caricatures? How about if we stop assuming that we know what it’s like to be in another person’s skin?

It’s true that those of us who got a head start don’t always acknowledge our good fortune. The old adage that “some people are born on third base and think they hit a triple” acknowledges that. But even if you were born on third base – even if your name could be Bryce or Trixie – that doesn’t mean your life is always easy or pain-free.

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