Chapter One

It’s Supposed to be Hard

“Why does it have to be so hard?”

I had asked myself that question over and over and over throughout my life, a hundred thousand times. I asked it while I was sitting on the curb crying, trying to decide whether to run 49 miles through what I thought would be a certain hell in 100-degree weather in the mountains on no training, or to crawl one mile back past the start line, get into my car, and drive home to hide beneath my covers. I asked that question when dealing with nasty politics at work: Just doing the work was hard enough. Why did it have to be that much harder and that much more stressful because of politics? I had asked that question when going through relationship woes, and while sitting in the waiting room of a hospital while my daughter went into emergency surgery, and when remembering the difficulties of having parents who were 38 years apart in age and unequipped to be good role models for me. I had asked that question while seeing my kids grow up too fast, and missing my girlfriend when she took an entirely-too-long trip, and when I finally decided to quit smoking. I had asked it when faced with reprimanding good employees gone bad, and when another corporate restructuring left me out in the cold, forcing me to rebuild my career under yet another upper management regime. I pondered that question when managing the office through the shocking suicide of a popular co-worker, and when I faced the reality of needing to find the courage to divorce what I felt was a too volatile, too mean, over-drinking spouse.

I had asked that question to death. So much of what seemed like it should be easier in life wasn’t anything but too hard. I quietly carried the burden of that frustrating thought. Think about all the times that you may have asked yourself that very question. It is an all-too-common and comfortable place to go to in the face of difficulty, adversity, or even simple inconvenience – and spending energy wrestling such a rhetorical perplexity wasn’t getting me any farther in business or in life. Something had to change so I could use that energy in a less wasteful way.

In late March 2000, I broke down and asked someone who I trusted could provide a real answer to the question, “Why does it have to be so hard?” I’ve never really had a mentor in life. I have learned a lot from a great many people, but, a mentor? No. I haven’t been that fortunate. Maybe it’s been my stubbornness or my independence. Maybe it’s been circumstance and fortune (or misfortune) that has prevented it. Maybe it’s simply been bad timing. But my boss at that time was a major influence on all facets of my life, though I doubt she ever knew it. It was partly because of who she was – one of the most powerful female executives at a major Wall Street firm – partly because she came along in my life when I had the greatest amount of turmoil, and partly because of where I was in my business life when I worked for her. Whatever the combination, her experience and perspective was the perfect backdrop to help form, shape, and reinforce many things inside of me.

I trusted that this person would hear me and offer her wisdom and insight and sympathy. We were managing a large number of very large producers inside the largest retail brokerage office for the largest Wall Street firm at the time. In the town of monster egos, Beverly Hills, we were managing on this huge scale during the last part of the late 1990s’ bull market, through the subsequent crash known as the “Tech Wreck” in the spring of 2000, and through the horrible events of 9/11. I’m not sure a day went by in those couple of years that we weren’t dealing with really big stuff.

So, in March 2000, the stock market was going completely crazy. Gains and losses – especially in technology stocks – were insane, changing daily and sometimes hourly. It was the last, few, desperate breaths of air in the balloon, and the balloon was about to burst. It was as though the cap had been taken off a fire hydrant and I stood in front of the flood while the day screamed, “Open wide!”

A particularly important client, the co-founder of an early-generation Internet search provider, had a large, eight-figure account with us. A much smaller client of the same broker (who happened to have the same account number as the very large client, save for two transposed numbers) was spooked by the market’s feverish rise and called to put in a “sell-all” order. The order was placed, but the person in operations mixed up those very two numbers and erroneously sold out the eight-figure client’s account instead of the small client’s. The next day, the market started three record days of gains. The mail took three days to deliver to the eight-figure client the confirmation that he had been mistakenly sold out prior to those gains. That was not good. A frantic call from client to broker led to a heated argument between broker and operations. A desperate and quick investigation revealed that the eight-figure client was entitled to a reinstatement of his long positions and the branch was left to absorb a nearly $900,000 error.

This was an easy equation in a Wall Street firm: A very large client needs to be made whole to the tune of nearly a million dollars of the firm’s money, so somebody is going to get fired. It was not going to be the broker. It was not going to be the manager. Someone had to be terminated to save those two hides and show that “action” was taken. It didn’t matter that the computer systems didn’t have the correct checks in place. It didn’t matter that the broker didn’t review his trade blotter so he could point out the error immediately. It didn’t matter that there was not a simultaneous electronic confirmation system in place. It also didn’t matter that the operations clerk was an exemplary employee and a single mother of two who had simply made a keypunch error. Someone had to be fired. If the market had moved the other way, of course, the client probably would not have said anything to the broker about being accidentally sold out, and he would not have fought with operations, who would not have needed to recover a million dollars of money the client wasn’t entitled to, and that clerk would have gone on being a valued employee and providing for her family. But that’s not what happened.

Although I was very accustomed to handling difficulty, managing though very intense situations, relying on myself to carry huge burdens in order to solve problems and improve situations around me, it still got to me at times. I fired that poor operations clerk, and sat there handing her tissues. Later, I opened up to my boss, who had by example and in specific instances taught me about people, power, class, strategy, confidence, general principles, relationships, and so much more. “Why does it have to be so hard?” I asked.

“It’s supposed to be hard, dear,” she said, starting off in her soft British accent, a slight, wry smile of experience wrapping the words perfectly, and the charming sparkle brought on by power and pleasure in her eye, as she settled into her role as preceptor to her most attentive student.

“If you want a friend, get a fucking dog. We do hard work here.” Her crass finish, void of any compassion, left no room for misinterpretation. In very short order, she basically prevented me from letting my guard down around her in the future, and though I kept my own level of sympathy and compassion, it was a great lesson to learn.

When I think of the times I’ve heard her saying those words inside my head, as if to try and answer the question in my mind, it’s usually been a result of something that happened that was out of my control. There have also been many times in work, in life, and in endurance sports when the words rang particularly true, and when they finally settled into the right part of my psyche and helped me out. They gave me a new point from which to focus my burdened mind and heart.

Now, when things get really hard, and especially when the circumstances are self-created, I hear myself repeat the words, It’s supposed to be hard…. I have learned that most things worth having or worthy of our gratitude are probably things that aren’t going to come easily.

The Longest Run

At no time did I hear those words – It’s supposed to be hard… – louder than in the latter stages of the longest run I’ve ever done. It was a 104-mile epic run I did in honor of my sister in 2012.

No matter how many tough 50-mile runs, 24-hour “Relay For Life” cancer-awareness events, Ironman triathlons, or other events I finished, the desire to run 100 miles was very strong in me. It was like a nagging little itch that I couldn’t quite reach deep enough to scratch. No matter how much I pushed myself doing other events, running 100 miles seemed to be a really hard thing that I needed to do. Since I didn’t even come close on my first attempt at that distance, I was all the more curious to see if I had it in me to run that far. As a middle-of-the-packer, I could never really be “prepared” to run 100 miles. I could only be prepared to try and run 100 miles. And in the summer of 2012, I was finally, properly prepared to try.

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