Personal Journey - From Pinstriped and Briefcased Banker to Janitor, Part I

by Jim Wellington
(Chicago)

This "shoe" photo is my logo. The size ten Ferragamo captoe shoes I wore as an investment banker on the left, still with the imprint of my toes and soles, bought for a New York conference. They were my pride and joy, but I have not worn them for many years. On the right are the boots I wear to work today. I use the logo on my emails. It represents my before and after experience. It is an experience of transformation.

Transformation can come gradually or it can come as a shock. For me, though the process took time, it began with a shock.

The man I was when the shock came no longer exists - or only in photos and in my own memories. Twelve years ago I was an extremely successful corporate executive. At the age of 46, I was a Vice President of Finance, in charge of high-end European hedge funds at an investment bank based in New York. I had a large and well-appointed office, an extraordinarily busy schedule that included traveling to international cities on a regular basis, and a clearly planed future. My income was substantial. I should add, however, that my debts were substantial as well.

That life came to a halt, an abrupt stop one morning when I returned one morning from a trip to London; I drove directly to my office and found a letter. It was from my wife. It was six pages long. She told me she was leaving - in fact, had already left and had moved in with friends in another state. We had been married for fourteen years and she had enough.

I sat stunned as I read her letter. I felt as if I had fallen on ice and come down on my head. One sentence summoned up her thoughts: "I became convinced that you cared more about your Italian shoes than about me." I cared more about two pieces of cow hide than about my own wife. I wanted to scream inside. She was gone.

That was the beginning of the change.

Was she unfair? No. She was more than fair. This had been coming for a long time. She is an extraordinary woman. She had worked at our marriage. I did not. That does not mean I refused. I simply didn't see any problems. My marriage, like my job and my Porsche and my office and my MBA, were extensions of myself. Even she was. The news hit me like a blow on the head, or rather, a series of blows. I was reeling, dizzy, breathless and utterly confused. I was not a man who was confused. I was not a man who was afraid or uncertain.

I should state here that I was not a terrible person. I did not actively hurt others. And I am not for a moment suggesting that the corporate life is a bad one; for some it is exactly the right fit. My problem was simple: I had no sense of identity apart from my image. There was no "there" there. To use T.S.Eliot's phrase, I was a hollow man.

I decided to put myself to a test. Was my wife right? The results would determine my next steps.

The following day I dressed for work as usual in a state of shock; I felt that I was in a state of suspended animation. Just as I was leaving at 6:15, I had the idea for a challenge. I would put myself to the test. You might call it a test of my narcissism or a test of my image. I called it at the time a test of courage. How much did my image really mean? What was underneath the beautiful suit and the handmade shoes and the stock portfolio?

I made a decision. I would not go into the office that day. I would go into the city, but as a different man. I would take the train, not my car. I would not go in as “James Wellington, Corporate Financier”. I would go in without anything to tell people who I was.

I purchased a pair of plastic flip-flops, a tie-died T-shirt, a vinyl ball cap and a pair of sweat pants. The total charge: $23. I then went home and proceeded to transform myself. It was much, much more difficult than I ever would have thought possible.

Please be patient with references to designer labels. For the man I used to be, they affirmed who I was and gave me, the identity that I called "myself".

First I removed my Cartier wristwatch (pricey symbol of the importance of time to an executive), cuff links and tie pin (expensive jewelry that had no practical importance), and slid my business school ring off my finger (symbol of my training and education).

Then I took my crocodile skin wallet out of my pocket, and left it, along with my driver's license, credit cards and business cards on the dresser; my identity and my money were all left behind. I took enough for train fare and a cup of coffee.

I left the Coach briefcase (symbol of business success) of my and the Wall Street Journal (symbol of business information) on the table.

Then I sat down, and after a few minutes of hesitation, untied and slid my corporate executive feet out of those Italian shoes my wife had mentioned. Yes, those Ferragamo cap toes were polished like mirrors. The soles and heels were barely broken in. The leather was the very best quality. I always made sure of that. I liked the way my suits cuffs broke over the tops of the shoes. They were intimidating and impressive. They were a vital part of my uniform and part of me.

But not that day. I put the cedar shoetrees back in them and then peeled off the pair of brand new black Brooks Brothers dress socks I had just put on.

This will sound crazy, but my heart was pounding. For a moment I stood in my bare feet, still in my perfect suit and tie, every hair in place, filled with anxiety and fear. I was dismantling my identity, piece by piece. Then I took off that beautiful pinstriped suit I had made in London, with its satin lining and its perfect fit, the silk necktie, the suspenders, the starched shirt and even my tee shirt. Then I put on that tie-dyed shirt and the sweatpants, and then, the flip-flops. My wife had been right. Those Italian shoes were not merely very important to me: they told me who I was. But I literally gritted my teeth and slid my bare feet into those cheap plastic shoes. The final touch was putting that vinyl baseball cap on top of my hundred-dollar haircut. (Is it really possible that I spent that much on a haircut? It is another lifetime)

When I left the house that morning I felt a sensation of shame. I looked around furtively to see if anyone recognized me. I did not drive my Porsche to the station. I walked the quarter mile, for the first time. It was a cool day, but drizzly and damp. I walked quickly and by the time I arrived, I had wiped slight streaks of sweat across my face, shirt and arms. This only added to my feelings of exposure. I felt vulnerable, foolish and awkward. But that was only the beginning. I boarded the train and sat with the usual commuter crowd. But I did not have my uniform, which was my identity. I did not know where to look as I took that familiar ride into the city. I looked nothing like my executive self, which was the only self that I knew. I felt adrift, empty and stripped.

In the city, I wandered through the streets and noticed the reactions. The deference and respect, at times tinged with an envy that I enjoyed, that usually greeted me had vanished. Most people simply ignored me. But when I entered stores to browse, I was asked twice to leave. The salespeople who usually treated me with respect were guarded. I had no core of self to rely on. All I had was my image, and that had been left at home. My new image, flip-flops, sweatpants, sweaty cap and a tee shirt, was not something to command respect.

When I arrived home that night I started facing the desolation that was inside me. I felt that I was entering a vacuum. I had utterly failed the test. The process that began with my wife's leaving could not be stopped; the experience of going without my image had left me shaken to the core. For several days I remained in the house, trying to absorb and understand what was happening. All my values and goals and achievements began to seem meaningless to me. I looked back on all that I had accomplished and realized that I had my image in mind at all times.

And I became aware that other people really existed for the first time. Does that sound weird? I understand your response. But until that time, other people were just actors in the play of my own life. Now I began to see others as individuals. The image had been a protection but also a barrier. I began to notice the world around me, including landscapes and the natural world. Good things were happening to me as the old self was destroyed, but at the time all I could sense was the stripping process. My life and my self were crumbling away. My ambition and my drive went with them, for a while. My corporate job suddenly seemed repulsive to me.

After six days I made a series of decisions that were played out over several weeks. I called the stunned CEO of my company and quit my job. I arranged to give the house to my wife; I did not want a painful or messy divorce. This was the one thing I could do for her. I sold off my stock and bond portfolio, providing enough for her to live on for a comfortable amount of time. I gave the rest away. I found that there are many, many charities out there that need money. This was an attempt on my part to do something with the money I had made that would actually help someone besides me!

To read PART II CLICK HERE