The One Thing that Makes the Ultra-Successful Miserable

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* To address previous reader comments, I am sure what I describe in this article can pertain to many Western countries – I am simply writing from my American perspective.

It always surprises me when I uncover an insight into my own culture. I did an undergrad in Anthropology and lived on three different continents, so when something has been in such plain sight my entire life, I wonder why no one else is writing about it.

Humans love stories. We tell them to pass on valuable cultural knowledge, to entertain, to move us emotionally, and how we tell our personal story not only can shape how others view us, but how we view ourselves.

According to renowned author Kurt Vonnegut, every great story has one simple structure: 1) Man falls in hole. 2) Man climbs out of hole.

But what if you never fell in a hole? What if you were born into a family with plenty of resources, a good upbringing, school was relatively easy for you, you studied what you wanted, you became great at it, you started a business and it made you millions? What if you got everything that was promised to finally make you really happy – you married someone great, have great kids, they’re happy and doing well in school – only to find that something inside you felt wrong, heavy, like there’s something missing?

Having worked with hundreds of successful entrepreneurs and business owners over the years, the vast majority of these clients who “have it all” suffer from the same thing: guilt.

The guilt is from not having suffered. Funny, isn’t it? Incredibly successful people who have never really suffered, end up suffering for not having suffered. It’s like a form of Surivor’s Guilt (which is now grouped with Post-Traumatic Stress Disorder or PTSD in the DSM-V) in which family, friends and colleagues seem to have this story of suffering that is either ongoing or something they overcame, and the client feels guilty for not having gone through any serious ordeals to achieve what he/she has.

Regardless of your religious affiliation or lack thereof, American culture has a deep-rooted Protestant Christian psyche. In the Bible, when Paul goes through an enormous amount of suffering and near-death experiences, God’s answer to him when he pleaded for healing the thorn in his flesh was basically “be grateful you’re alive and stop being a little bitch.” There’s a repeated association throughout with a lack of suffering being associated with being a sinner. It’s as if suffering is noble and good, and if you don’t do it, you’re just not a good person.

So here’s the message: you can’t achieve or have anything good come into your life without paying the price of suffering. When good things happen, many of us are waiting for the bad thing to happen in order to balance it out. In fact, we criticize people who have had it easy. Even many parents who are attached to their own story of suffering, who went to great lengths create a life for their children to minimize suffering, ironically end up berating their own children for “having it easy” or being “soft.”

When working with these “ultra-successful” clients (I used quotations here because most of them would not classify themselves as successful), I repeatedly find this guilt as a big driver of their lack of satisfaction. They may have carried around this extra heaviness for years thinking that’s just how it has to be.  It isn’t, and getting the right professional to help you lighten the load may be just what you need.

What’s your story of how you got to where you are today? How much of it has suffering in it? What areas came into your life easily and without suffering?

About Paul Paul Strobl, MBA, CPC


Paul Strobl is a Personal Coach for CEOs and Business Owners focused on running successful businesses in line with their personal values while nurturing personal and professional relationships. He has extensive cross-cultural experience as a location-independent entrepreneur for the past decade and has traveled, lived in or run a business in over 30 countries. Originally from Houston, Texas, he is currently traveling around the Balkans with his bilingual Argentine mutt Sheila.