How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life (5 page)

When I was
six years old, I got hooked on the comic strip
Peanuts.
The drawings fascinated me. They were so simple and yet so perfect in an indescribable way. As soon as I learned to read, I devoured every
Peanuts
book I could get my hands on. I declared to my parents that one day I would be a famous cartoonist like Charles Schulz. That was my goal, clear as can be. I spent countless hours with crayons, pencils, markers, and paper. I practiced and practiced. But I never became good. I wasn’t even the best artist in my class of forty kids. I didn’t give up, though.

At the age of eleven I applied to the Famous Artists School Course for Talented Young People. It was a correspondence course. This was perfect for me because I wouldn’t need to leave home, which would have been problematic. I filled out the application, drew the assignments they requested, and answered the multiple-choice questions about design. Sadly, I was rejected by the Famous Artists School for Young People because their cutoff age was twelve. I was too young. I was crushed.

My mother, in the style of the times, told me I could do anything I set my sights on. She said I could be the president, an astronaut, or the next Charles Schulz. I believed her because at that point in my life I hadn’t yet noticed the pattern of her deceptions. Her lies included Santa Claus, the Tooth Fairy, the Easter Bunny, and something about a whale eating a guy named Jonah.

In
time I started to understand something called the odds. Some things were, by their very nature, likely, and some were not. I learned by observation that people who pursued extraordinarily unlikely goals were overly optimistic at best, delusional at worst, and just plain stupid most of the time. The smart people in my little Republican-dominated town made practical plans and stuck to them. Some joined the Marines to get experience and education. Some went into the family business. Some married and became homemakers and moms. A few superstars studied hard and pursued jobs in medicine and the law. At the time, if you had asked me to name twenty different types of jobs an adult could have, I would have tapped out after fifteen. The jobs I had heard of were the ones I saw around me in my little town plus whatever I saw on television. And by television I mean the one channel we received (via rabbit ears) that had both a picture and sound.

My father worked at the local post office and painted houses at night when the weather allowed. His advice to my brother and me was to pursue a career in the postal profession. The United States Postal Service was steady work, it was mostly indoors, and it had excellent benefits. Sometimes when my mother was busy, my siblings and I would hang out at the post office with my dad. We were fascinated by the loaded handgun that was always within easy reach. Apparently the government expected its employees to resist armed robberies by reaching for their pieces and blazing away. Those were different times.

My mother decided to try her hand at selling real estate once her three kids were old enough to stay alive on their own. She became an agent and did well enough to build up some savings that would go toward our college educations. My mother told us from the time we could understand language that all three of us were college bound, like it or not. In my family, only an aunt had ever attended college. My mother decided to change that. Later, when the real-estate market got saturated with brokers and agents, she took a job for minimum wage on an assembly line, winding copper wires around speaker magnets for eight hours a day. That money too went toward our education. It wasn’t nearly enough, but it was a step in the right direction.

My mother decided that I should become a lawyer. She spent a good deal of energy convincing me that it was a good plan. The two lawyers in our town were doing well, and my grades seemed strong enough to make a legitimate run at the legal profession. I didn’t know
much about the job of lawyering, but I did like the idea of making good money and someday escaping my little town. I signed on to my mother’s plan and set my sights on a career in law. All I needed to do was figure out how to pay for college.

One day in eleventh grade health class our gym teacher/health teacher mentioned that our small school (there were about forty kids in my class) had never produced a student who earned an academic scholarship to college. He explained that one unusually tall and athletic student had managed to get a basketball scholarship before blowing out his knee in his freshman year, but no one had earned a college scholarship based on academics alone. The teacher speculated with confidence that this was about to change. He announced that one student in our grade was likely to get an academic scholarship. This news surprised me. I looked around my small classroom and couldn’t figure out whom he meant. Curiosity got the best of me and I raised my hand. “Who are you talking about?” He stared at me in a gym-coach way, either annoyed or surprised by the question. Then he answered in a confident voice, “You.”

I didn’t believe him. He was just one guy with an opinion. But my mother told me I was going to college one way or another, so I set about the task of figuring out how that happens. This was well before the days of highly involved parents. I was pretty much on my own. Our guidance counselor pointed to a wall-length shelf that was full of college pamphlets and books and gave me this valuable career guidance: Pick a few colleges that look good and fill out some applications. This was not the precise sort of career advice that one would hope for. I skimmed a few college books and felt lost. How could I possibly know the best choice for me?

Luckily, a new kid had joined my class a year earlier. New students were rare. I attended kindergarten with about thirty-five of the forty kids I graduated with, and most of those classes were in the same building. This new kid, Peter, came from some exotic city, or maybe it was a suburb, where people knew how the world worked. I followed his lead and did what he did. I decided to major in economics because Peter told me that would be a good prelaw degree. Then I followed him around in the guidance counselor’s tiny library of college information and learned that the process for applying to each college was described in those books. Eventually I picked two colleges that looked good on paper. And by that I mean the schools were located
within driving distance, they offered degrees in economics, and the photographs of their campuses were pleasing.

My first choice, Cornell, had two factors working against it. The first was a tragic men-to-women ratio that guaranteed I would graduate a virgin. The other was that I applied too late and missed its deadline. Cornell informed me that I was on its wait list. My only chance of getting into that school was if some sort of fast-moving plague killed all of the people who knew there was a deadline for applying.

The only other college I applied to was Hartwick College in Oneonta, New York. Hartwick had several things going for it. It was a one-hour drive from home, so travel would be affordable. It had a well-respected nursing major, so there were more women than men. And it accepted me. It was my only option. This is when I learned that one should not seek life-altering advice from a kid named Peter whose primary credentials were that he once lived in a suburb or maybe a city. Either way, it was a bad idea to apply to only two colleges and a worse idea to choose those two colleges based on the quality of the photographs in the brochures. (Full disclosure: Attending a college with a favorable male-female ratio turned out to be genius.)

My next problem was that my parents couldn’t afford to send me to Hartwick, which is a pricey private college. So I applied for an academic scholarship. To my surprise, but not the surprise of my gym teacher/health teacher, Hartwick granted me a partial academic scholarship. I also received some small scholarships from the state of New York. With my parents’ savings, plus my own savings from mowing lawns and shoveling snow for years, I had almost enough. I figured I could work a few jobs at school and close the gap. And so my college career began. I would study economics and aim for law school later. I escaped from Windham, New York, but just barely. Things would not get easier.

A short time into my first semester at Hartwick, I discovered several interesting pastimes that might fit under the heading of adult fun. The drinking age was eighteen in those days, and I was fresh off the leash. Soon, thanks to many delightful distractions, my grades dipped below the level that Hartwick expected from an academic scholarship recipient. The dean sent a letter putting me on notice. The scholarship would be rescinded unless I got my grades up. At about that same time, I came down with a world-class case of mononucleosis. The college nurses were impressed; they had never seen a case so severe. My
glands were so swollen that my throat almost closed entirely. I couldn’t even swallow. The college physician advised me that I would be too drained and sleepy to study, and my best bet was to pack up my stuff and drop out. He suggested that maybe I could come back to college someday and start over. It was my choice, he explained, but his medical advice was to regroup, recover at home, and try college another time. I had been in college for only one semester and I was on the verge of complete failure.

This was one of those times when the difference between wishing and deciding mattered. I didn’t
wish
to stay in school; I
decided.
For the next two weeks I stayed in a bed in the college infirmary, struggling to stay awake long enough to read my textbooks and keep up to where I assumed the class would be. Upon release, I discovered I was actually a month ahead in some of my classes. My grades climbed back where they needed to be and I marched on.

I had ignored my father’s advice to work for the Postal Service. That turned out to be a good idea. I got into college without much help from my guidance counselor, and I stayed in school against my doctor’s advice. This was about the time that my opinion of experts, and authority figures in general, began a steady descent that continues to this day.

As I learned more about the legal profession, I realized it wasn’t a good fit for my personality. I’m not the sort of person who feels comfortable winning when it means the other side loses something of equal or greater value. I’d feel even worse if I were to win a victory for my client that was ill deserved and accomplished only through my weasel-tastic skills. I had been raised to decline offers of candy from family friends under the theory that I had done nothing to deserve it. I was the kind of person who needed a job that made other people happy, ideally with a side benefit of making me rich and famous too. And for that I needed a system.

I decided that my talents would be best suited for creating and running some sort of company. To acquire the necessary skills I would complete my economics degree and get an entry-level job at a big bank. I would take as many company-paid training classes as I could and learn all there was to know about business from a banking perspective. I also hoped to complete my MBA at night on the company’s dime. I was agnostic about what specific sort of business I would someday run. All I knew for sure is that I needed to be ready when the time was right.

This
brings me to my system. I still have the diary I wrote when I graduated from Hartwick, in which I outlined my entrepreneurial plan. The idea was to create something that had value and—this next part is the key—I wanted the product to be something that was
easy to reproduce in unlimited quantities.
I didn’t want to sell my time, at least not directly, because that model has an upward limit. And I didn’t want to build my own automobile factory, for example, because cars are not easy to reproduce. I didn’t want to do any sort of custom work, such as building homes, because each one requires the same amount of work. I wanted to create, invent, write, or otherwise concoct something widely desired that would be easy to reproduce.

My plan wasn’t the one and only practical path to success. Another perfectly good plan might involve becoming a salesperson who works on commission in an industry that handles extraordinarily expensive items such as rare art, airplanes, or office buildings. It might take years to get into one of those positions, but no one said success would be fast or easy. I don’t have the salesperson gene, so selling expensive items wasn’t a good plan for me. I figured my competitive edge was creativity. I would try one thing after another until something creative struck a chord with the public. Then I would reproduce it like crazy. In the near term it would mean one failure after another. In the long term I was creating a situation that would allow luck to find me.

It helps a great deal to have at least a general strategy and some degree of focus. The world offers so many alternatives that you need a quick filter to eliminate some options and pay attention to others. Whatever your plan, focus is always important.

My system of creating something the public wants and reproducing it in large quantities nearly guaranteed a string of failures. By design, all of my efforts were long shots. Had I been goal oriented instead of system oriented, I imagine I would have given up after the first several failures. It would have felt like banging my head against a brick wall. But being systems oriented, I felt myself growing more capable every day, no matter the fate of the project I happened to be working on. And every day during those years I woke up with the same thought, literally, as I rubbed the sleep from my eyes and slapped the alarm clock off.

Today’s the day.