When I was ten years old, I had a dream of retiring in my thirties. I was going to buy a winter house in the mountains and a summer house on the beach. I was going to have a hot wife, a butler, and an army of kids to mow the lawn, trim the bushes and shovel the driveway. I would spend my days sitting on the balcony in slippers, smoking a pipe, and admiring all that was mine.

Unfortunately, as the dawn of my thirties approached, it was apparent that my dream was in reality, a fantasy. Clearly, I had chosen the wrong profession. But in my defense, it wasn't really my fault. It was my high school basketball coach's fault. I was going to be a professional basketball player, but the coach wouldn't allow me to pursue my career on his team. He gave me some speech about coordination and jumping ability, and then suggested I join the swim team. I ended up enjoying swimming and had a pretty good career, but guys who wear Speedos don't make enough money to retire in their thirties. There are guys who are retired that wear Speedos, but they shouldn't, not at the beach anyway. I don't care how much money they have. But I digress.

Was I a complete idiot? I had just quit my job, given up my apartment, and decided to bike across the country. I didn't have a house in the mountains, a butler, or a hot wife. I hadn't made millions, I didn't have a shoe contract, and I wasn't ridiculously famous. Ten year-old Dave would be very disappointed with twenty nine year-old Dave. I slumped deeper in the couch.

There was a time not long ago however, when I thought I'd be able to retire in my thirties. There was a time when a lot of people thought they'd be able to retire in their thirties. If you were a part of the Internet world, anything was possible. It only required timing and luck. If you were lucky, you'd get a job at a start-up early in its life cycle, accept large amounts of stock options instead of a salary, work every waking hour for four years, watch the company go public, and then sit back and count your money. It seemed everyone in San Francisco was doing it. I did it and I got lucky.

And then the stock market crashed and the Internet boom became the Internet bust overnight. All of a sudden, what used to be wasn't anymore. The new rules became the old rules and the storybook reality of the dot-coms became a thing of the past.

About a year and a half after the crash, after all the fun and excitement of working ridiculously long hours had been sucked out of my being, I found myself sitting at my desk one day, watching all that was going on around me. I had a nervous anticipation as I watched the "dot-com death march" begin. It started at precisely 10:15 and was well choreographed, well rehearsed and well executed. It should have been, it was also well practiced.

When the "march" would begin, a flock of managers would descend upon the masses, find their designated employee, tap them on the shoulder, and then escort them to a pre-determined conference room. Once in the conference room, the manager would give the employee a speech about how this was a business decision and not a personal one, and then slide a white envelope across the table. The envelope contained a final pay check, a severance check, information about insurance benefits, and a piece of paper that contained the phone number for the California unemployment office. The employee was then escorted back to their desk to gather their belongings, and was then escorted off the premises. It was all very clinical.

During an earlier round of layoffs, I played the role of "escort." My assignment was to walk a shy, hard-working, web designer named Kevin back to his desk to gather his belongings after his manager gave him the "it's not you, it's the company" speech. As we walked across the building, people would glance up from their computers and stare. As we passed by Kevin's friends, they would look up to give him an encouraging smile and a wave. I felt like the farmer leading a cow to slaughter.

About halfway to his desk, Kevin stopped and turned towards a group of web designers that had gathered around to obviously discuss what was going on. Not quite sure what to do, especially since it seemed so out of character, I politely said "Kevin, come on, we have to go back to your desk."

Kevin turned to look at me and said, "Just give me a minute. I'll be right back."

I let him go. There was really nothing I could do anyway. As he approached the group, the circle of designers split apart, leaving the prettiest web designer to stand face to face with Kevin. Everyone in the area had now turned around to watch. Kevin walked right up to the girl, looked her in the eyes and said, "Hey, I just got laid off, can I have your phone number?"

I didn't get it. How could someone with such uncommon courage and brilliance be asked to leave the company? I felt bad for Kevin, but I didn’t worry about his future. After he cleaned out his desk, I helped him carry his boxes to the car. When we finished packing his trunk and said our good-byes, I asked what he was going to do next.

"I don't know, but I'm not going to start looking for a job right away. My sister lives in Italy, so I'll probably hang out with her for a while and then backpack around Europe. I haven't really had time to think about it. So, the only thing I'm sure of right now is that a bunch of us that just got laid off are going to hang out at the bar across the street and toast our freedom." While I walked back to work, I watched Kevin enter the bar. I was jealous.

As I sat at my desk that day, watching the next round of layoffs begin, I became more and more anxious and dreamed about freedom. Only a few days before, I had caught wind that another round of layoffs was imminent and I knew I had to make a decision. I had thought about it for months and kept telling myself there were a thousand reasons why I shouldn't do it. But then I asked myself a question. Do I want to sit on my front porch when I'm old and gray and wonder "what if?" The answer was simple. I may not know what I want to do when I "grow up," but I sure as hell know what I don't want to do. The next day, I called a meeting with my boss.

"Jim, I heard that we're going to eliminate a lot of positions in the next week and I just want to let you know that I'm your man," I said.

Jim looked puzzled. "What do you mean, 'I'm your man?'"

"I mean, if you have to cut positions, you can cut me."

"Don't worry. Our department's not going to have any cuts."

"None?" I asked dejected.

"None, management feels our department is vital to the company's success, which means you're an important piece of that." Clearly not the answer I was hoping for. I've been around long enough to be able to translate that statement into "you're going to be doing a lot more work, with a lot more pressure, for no more money."

"Is there any possibility I could get laid off anyway?"

"What? Why do you want to get laid off?"

"Well, I'm tired of working. I've been here four years and I'm burned out. I've had seven bosses and six desks in two different buildings. I've seen our company grow from 40 people to 700 and then shrink back down to 300 people. I've worked an average of 70 hours a week for stock options that are now worthless and I haven't gotten a raise in two years. I don't believe in the direction of the company and I don't believe in the management. I want to get laid off so I can get a severance check, collect unemployment, and ride my bike across the country."

Jim paused. "I see." He paused again, this time a little longer. "A motorcycle?"

"Excuse me?"

"A motorcycle. Are you going to ride a motorcycle?"

"No, a bicycle."

"Across the country?"

"From the Pacific to the Atlantic."

"Why?"

"I need to get to Montpelier, Vermont by September 14. I'm the best man in my friend's wedding."

"You're going to ride your bike to Vermont?"

"No, Connecticut. My parents live on the coast of Connecticut. I'm going to ride to their house and then drive to the wedding."

"Why don't you just fly?"

Either people get it or they don't. It is impossible to explain "why" to people who can not conceive of doing such things themselves. During a 1922 lecture tour about his initial attempt to climb Mt. Everest, George Mallory, the famous English mountaineer, was inundated with the question "why do you want to climb Mt. Everest?" Exasperated from constantly explaining himself, he flippantly uttered the response, "because it's there."

"I don't think that's important right now. I just want to get laid off."

"Hmm. I see," again Jim paused. "Well, we'll see what we can do."

As the minutes went by, I sat and watched employee after employee get their pink slip. I became more and more nervous. I stared at my computer monitor, hoping that if I didn't look too eager, they would pick me. A half an hour passed and still no tap on the shoulder. Then, from the corner of my eye, I saw Jim exit a conference room. I tried to play it cool. Was he coming my way? Did the white envelope he was carrying contain my severance check? I stopped looking at him and again stared at my computer screen to pretend I was busy.

Then it happened. I got a tap on my shoulder. It was Jim. "Can I talk to you for a minute?" It was all I could do not to jump up and hug him.

So, there I was, sitting on my couch, staring at the wall and pondering the consequences and reality of all my life's decisions. I got up to pour myself another cup of coffee. It was 10am and I was sitting in my living room, drinking coffee in my underwear.