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From Pinstriped and Italian Shoed Banker to Janitor, Part III: Why Did You Do It?

by Jim Wellington
(Chicago)

These Before and After Photos Suggest the Transformation I Experienced As I Moved From Corporate Executive to Blue Collar Worker

These Before and After Photos Suggest the Transformation I Experienced As I Moved From Corporate Executive to Blue Collar Worker


Why did you do it? You had the world in the palm of your hand! You were the most high-powered corporate executive I have ever known! Now look at you! cried the exasperated young man, looking at me in utter bewilderment.

Those were the words of a former colleague of mine in the corporate world a man who had heard about my story through others and who had not seen me since the day I walked away from my mahogany desk and my carpeted office and the world of mergers and acquisitions and into the world of blue-collar labor and pick up trucks.

He had seen the story I posted about the dramatic transformation of my life, and decided to find me a few weeks ago. He did indeed find me, working my night shift at a corporate office building. He is a successful and still rising executive; I am a menial worker. The irony is: I trained him in his first job, when I was an investment banker and he was a trainee.

Now he stood there as impeccably dressed and well-groomed as I used to be, and he found me wearing a very greasy sweat shirt over an even greasier janitor's uniform. I haul trash as part of my job as a janitor, and was throwing heavy plastic bags into a dumpster when he found me. His hair was as neatly cut as mine had always been. I wore an old cap and a few day's growth of beard.

I was genuinely happy to see him. I remembered him as a hard-working, honest and good-natured worker, and I could see that he had not changed. But I had, and he was so stunned that he poured out his frustration and confusion while I listened as patiently as I could.

I reached out my very dirty, calloused hand in its very dirty polyester sleeve, and he reached out his manicured hand in its pristine starched white French cuff, cuff link, watch and the sleeve of his pinstriped suit. It was as if I were shaking hands with my younger self. But he did not see any resemblance. To him, my decision to leave the world of success and white collar affluence was beyond comprehension.

How to explain that though I had been very successful, I had not been happy or content? I tried. I talked about my wife and her disappointment with me, and the pain I had caused her. I talked about the emptiness I had known, and the peace I now had. I told him about the new relationship I had with a woman I had met on this job, and how I now paid more attention to her than I ever had to my wife.

His response was "You are dating a woman you met on this job? What does she do?"

I told him she was a clerk at a convenience store. He said nothing.

There was a gulf between us. I did not blame him how could I? If I were in his position, I would also have been stunned. He remembered me as a hard-charging, ambitious hotshot executive who was obsessed with making money and equally obsessed with looking perfect. In my days as an executive I had a Porsche and a fortune in stocks and bonds, a beautiful home and corporate accounts everywhere.

He reminded me that I used to have my shoes polished at my desk while making deals. I burst into laughter. Yes it was true. Now here I was preparing salvage for a reclamation yard, wearing rigger boots! I told him I had not worn corporate leather business shoes since I left my old life, and that I had given away all but one of the many pairs of shoes I used to own.

He was silent again and then said something that struck me as true: He said "You must have had some regrets! Something must have been hard for you! You make it sound too easy!"

And he was right. But I had teachers along the way.

Part IV CLICK HERE

You may enjoy reading the entire series of articles by Jim Wellington where he shares his journey to finding his authentic self.

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From Pinstriped and Italian Shoed Banker to Janitor, Part III: Why Did You Do It?

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Jun 07, 2008
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Fascinating
by: John G

Interesting and challenging story. I thought about it a lot. Thanks

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