Winning in the Middle of the Pack: Realizing True Success in Business and in Life

ACKNOWLEDGMENTS

Introduction

When I got my first big promotion while working for a major Wall Street firm, one of the first things I did was ask my assistant to order me personalized sticky notes. By doing this, I could constantly reinforce a message I had come to use so often in my management career. The printed message on the sticky note read: Do The Right Thing.

By repeating those four simple yet precious words to my employees, I wanted to remind them to keep in mind what was at stake. We needed to do the right thing for the benefit of our clients' financial well-being. We needed to do the right thing to enrich the experience of our co-workers. We needed to do the right thing to manage risk and be compliant for the regulators. We needed to do the right thing for the protection of the company's reputation. I went through thousands of those sticky notes. And the message began to haunt me.

How ironic that as powerful and healthy an axiom as that was, especially in the financial services profession, when viewed from a slightly different perspective, those four words were also the source of my own greatest weakness and pain. Do The Right Thing. For whom? Not for myself, certainly. That's rarely what I did. I had been programmed – and had programmed myself – to think of the things that I should or should not do based on how they may affect others, not me. I never took the liberty to adjust my view of those four words to try and answer the question for myself.

Certainly as a business management concept and as a guideline for setting a moral compass, Do The Right Thing is pure and complete in its message. But it wasn't so clean and neat to put into practice. Do The Right Thing caused me to focus on such things as how I should manage my business in order to make the boss happy – and the bosses came and went and each had different ideas of what The Right Thing was. It caused me to focus on how I should do things to keep some of the office's million-dollar producers happy – and that invariably created a tug-of-war between doing things to benefit them and doing things to benefit the company, the client or the other employees. It caused me to do things to keep my spouse happy – which most of the time would result in me compromising the right thing for others, including waiters I felt she was rude to, friends I saw her alienating and doctors I believe she lied to in order to obtain pain pills when I had injuries.

Doing The Right Thing was causing me to focus on everybody else and their needs over my own. I was bouncing from person to person, situation to situation, reacting in order to make peace, trying to please others, or attempting to squeeze myself into the molds that my life had created. I was making decisions that inevitably trapped me in those words. This was simply not the right way to live my life – and it's not the right way to live yours.

The truth is, if we make all of our decisions based on other people's needs and desires, we can never know what we are fully capable of achieving. We may obtain all kinds of successes, but we will never find our own personal, self-fulfilling limits. By accomplishing things according to the prescriptions written by others, we are forced to live in denial about our true abilities and what we can accomplish. This causes us to strengthen our own self-developed handicaps, to find comfort in our bad habits, and ignore the effects they have on us – on our minds, our bodies, and our abilities.

Over time, this settling allows for varying forms of self-delusion, until we reach a point where we believe we are too old, too busy, too accustomed to our own ways to do anything other than what we have always done. Without even realizing what we are doing, we avoid taking actions, we accept our self-imposed limitations, and we deny ourselves the chance to see what we are truly capable of achieving.

In order to break the self-limiting cycle of Do The Right Thing (for Everyone But Myself), I had to start doing things differently. I needed to change my style of management. I needed to take control of my personal life. I needed to focus on myself for once. I needed to change my views so I could see what Doing The Right Thing for me was. There are many powerful, life-changing, and effective vehicles for personal growth, but the one I used for this transformation was endurance athletics.

Just so there's no misunderstanding, I have never won an event. I have never stood on the podium. I have never carried a trophy home. I am what is known as a middle of the pack athlete. I am the nameless, faceless, unsung guy who doesn't come in first and who doesn't come in last, but who starts and who – most of the time – finishes. But although I'm that guy, I have countless wins that are larger than any trophy or first-place medal. From that first start line in Georgia that had me inline-skating 87 miles from Athens to Atlanta; to the many hometown 5Ks, 10Ks, marathons, and ultra-marathons I've run; to the 12th Ironman triathlon I finished; to the exhilarating, mind-bending tribute race I ran for my beloved sister, I have stood on my own private podium many times. Through dozens of remarkably difficult circumstances and challenges, I have won a thousand mental and physical battles against myself and the boundaries that I had previously known. And it has been sweet.

In the beginning, however, it was just me and my self-imposed limitations. I immediately saw that if I was going to do anything meaningful in life, for me, there were going to be some huge barriers to overcome and some really big changes to make. I can be methodical about things if I have to be, but I am much more comfortable taking on more than I can chew and then figuring out how to get through it. Anything important that I have ever taken on, whether at work or in life, seemed to be slightly, and sometimes substantially, over my head. I love big challenges. Overcoming big challenges helped me counteract continually feeling like I was not achieving enough. Taking on extreme physical challenges – although a perfectly humbling undertaking – was just the right amount of big and unpredictable.

In order to make significant progress toward your personal successes, you need to begin from a place of humility – facing the reality of the harm you might have done yourself – to engage in a battle against what you know and who you thought you were, and decide that you want to be more than what you have ever been. That is the ultimate transformation point. Once honestly and truly humbled, enlightened as to who you are, and then engaged and committed and driven to accomplish and overcome great challenges (no matter how you define that for yourself), you actually learn that you can be more than what you thought you could, and more than what others said you should or could be. You can accomplish great physical, intellectual, and mental feats, no matter how they might be measured by anybody else, and learn through these personal accomplishments how to apply what you discover to all aspects of your life. If your desire to do so is stronger than the self-imposed forces that prevented you from breaking free of yourself, then you can start creating a new, wonderful reality.

The Athens to Atlanta race I mentioned marked a specific point on the timeline of my evolution. On that day – a day I stumbled into mostly by accident – I began to consciously attack the barriers that I encountered, and from then on my reality changed. Using endurance sports as my guide, I navigated the private and unknown space between the past me and the present me and came out fully immersed in a new life, living a new lifestyle, accomplishing things for myself that I had never even dreamed of doing. I became so much more in tune with what the world had to offer and what I wanted to get out of life. I began to walk my own path toward success and personal accomplishment. As a result, I became a better leader at work. I became a better father. I took charge of my personal life. I became more comfortable with who I was. I became more confident, more focused, more at peace.

Why endurance sports? As a vehicle for growth, it was my way to take a chance and begin to finally Do The Right Thing for myself. Endurance sports forced me to take a real, honest assessment of who I had become – and mostly who I hadn't become. Endurance sports allowed me to discover the wonderful challenges and hardships and victories found in the middle of the pack. The previously unknown, wonderful, middle of the pack. That's the place where nobody else is watching, the place where the opportunity for meaningful, profound growth is found. In endurance sports, the middle of the pack gives you the opportunity to find out who you can really become in life, for yourself, and is, therefore, both the most beautiful and most painful place.

You see, there is no gratification for the successful completion of most of life's struggles, because they don't often present us with a finish line. But a 5K, a marathon, an Ironman triathlon, a 24-hour run – they do have finish lines. You can measure your struggle from beginning to end. And because middle-of-the-packers are not elite athletes, winning is taken out of the equation. Unlike the athletes at the front of the race, middle-of-the-packers lack the need to battle other people for prizes or livelihood. The result is more of a pure and lonely self-reliance. There is no glory at the end of a race. No crowd cheering your name. No headlines the next day. No legacy to build. There is only a finish line and the desire to find it. The middle-of-the-packer has only himself to overcome.

The nameless and countless majority doing endurance events aren't trying to take away each other's paychecks or sponsorships or age-group trophies. The middle-of-the-packer is only trying to overcome their own personal obstacles and the cut-off time so their finish can be official. Nobody else will care what happens. Nobody else will impose their thoughts on what you should or shouldn't have done. Nobody but you will have a say in things. That's where the beauty resides. You get the opportunity to beat the person inside who is always trying to tell you to quit – and in most endurance events, you will want to quit a thousand times over.

We quietly tell ourselves to give up by not striving to become more in life than we have the ability to become. We say this for years and years until we become resigned to who we are. But from the middle of the pack, we can reverse this trend by not quitting until we cross the finish line. Once we go through extreme struggle – self-imposed struggle – and overcome it, we can carry that concept over to life and business. Along the way, we also learn so much about ourselves and about what we can accomplish. It's absolutely exhilarating.

So beauty, yes – and true, pure, life-changing beauty. But pain? Chasing pain in the middle of the pack is at once one of the greatest and most difficult things about doing long-distance events. You face constant lessons about what to do better to limit the damage, the incessant suffering, and the sheer agony that you encounter. Attempting to master the physiological demands of endurance athletics is a humbling and inspiring undertaking. It was a perfect source to provide the framework for my most powerful growth because I got to determine how much I could handle, how far I could take things, and how much I could accomplish – according solely to me.

There's no question that we cannot master life. We can't master endurance sports, either. No matter how many events I do, how many variables I take into consideration, or how much experience I get, mastery is ultimately elusive. But by pushing myself, I can attempt to become the best I can be. By pushing myself as far past the breaking point as possible, I increasingly learn how to better control my environment, understand my limits, observe the world around me, adapt to the circumstances that present themselves, and use my imagination to overcome obstacles. Those things are possible; mastery is not. Change in ourselves and in the world around us is too constant and too unpredictable for mastery. But by constantly growing and becoming more than you thought you could be, and by figuring things out for yourself in the middle of the pack, you will, at long last, truly be doing the right thing.

My hope is that by reading about the lessons I learned along my journey in the middle of the pack in endurance athletics, you will be encouraged to get out there and break down a few of your own physical and mental barriers. My hope is that you will find a path toward growth and change where you can test yourself, increase your perspective, and live a fuller, more successful life as a result. Perhaps it won't be by running four consecutive marathons along the California coast. But somewhere out there is your own middle of the pack. Go out there and find it.

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