Your job is one of your most important assets. It gives you earning power. It can bring you personal fulfillment. But what happens when you’re stuck in a job you hate? Here’s the true story of the worst job I ever had.


I made some poor choices at the end of my college career; as a result, I graduated without a prospect for work. No matter — I lived off my credit cards for a few months, basking in the glow of adulthood. Eventually I realized that I needed to find a job.

My father, a life-long salesman, and always a sucker for other salesmen, set me up to meet with an insurance guy who had tried to sell him a policy. We met in a Denny’s on the far side of Portland early on a Saturday morning. The guy gave me long, slick pitch, touting the job’s “unlimited income potential“. He needn’t have bothered. I needed work and was dumb enough to think that this was a perfect. I signed up.

I underwent two weeks of training, during which I learned how to sell crappy insurance (though I didn’t know it was crappy insurance at the time). I spent two days learning why this was the most marvelous insurance product in the world. I spent another two days role-playing the door-to-door sales technique: I’d pretend to be the salesman and the 55-year-old chainsmoker seated next to me would be the customer. It was so easy! I sold him a policy every time.

I spent a couple more days learning “rebuttals”, the magic scripts that would turn a prospect’s objections against himself. Our goal was to sell the customer whether he needed the insurance or not. We were to create the need.

This training period was life-changing. I had awakened a giant within. I was a new man. I began to cast aside the skin of my existing life and take on that of another:

  • I broke up with my fiancee.
  • I bought a brand new car. (A car that I could not afford, obviously.)
  • I bought a new wardrobe, paying full price at trendy stores.
  • I ate out every morning, every noon, and every night.
  • I bought a brand-new Super Nintendo and a Gameboy.

In one training session, we were required to cut up magazines to make a collage depicting our goals. I cut out a big photo of a log cabin in the woods and declared, “I’m going to retire a millionaire when I’m thirty.” The older folks in the class — they were all older, and all over thirty — stared with vacant, hollow eyes as I made my presentation.

That night I went out for a fancy dinner.

After training, I spent a week shadowing my manager (the man who had hired me), watching how door-to-door insurance sales worked in the real world. We drove to rural Oregon (Enterprise, in the far northeastern corner) and set up shop in a motel. That Monday morning, we met for breakfast in a local coffee shop. I bought my manager eggs and coffee. We drove out and began knocking on doors.

At every house, we’d introduce ourselves: “Hi. I’m J.D., and I believe this will interest you also. For only fifty-eight cents a week, should any accident whatsoever require hospital confinement…” and so on. My manager was slick. He signed up three people that first day. He’d made $120!

The next day, it was my turn to try. And suddenly my enthusiasm ran smack into the reality. It wasn’t a game anymore when I was the one trying to convince the little old lady with the oxygen tank that she needed to buy my policy. “I’m on a fixed income,” she said, and I had no response. I wasn’t going to try to convince her that she needed this. She didn’t. She needed to hold on to her money. But my manager saw her weakness, and sensed my hesitation — he stepped in and smoothly countered her objections and wrote the policy for her. He let me keep the $40 for the sale. “You can’t let them make you feel sorry,” he told me. “Your goal is to get a signature and a check.

Actually, my goal was suddenly unclear. My goal had been to make a million dollars by the time I was thirty, to own log cabin in the woods. But not like this. Not selling policies to little old ladies. I went back to the hotel and called my dad. “I want to quit,” I told him.

“You can’t quit,” he said. “You’ve only been doing this two days. You don’t know what you’re talking about. Don’t be an idiot.”

I called my ex-fiancee. “I want to quit,” I told her. She wasn’t surprised. I’d just broken off our engagement, so why would I stick to a job?

I talked with my manager. “I want to quit,” I told him. He frowned, and then he smoothly countered my every argument. The one that made me change my mind was this: “Look how much you’ve spent. You bought a new car. You bought new clothes. You’re paying all this money for food and lodging. If you quit now, that money is all wasted.” I believed he was right, and so I stuck with it. I threw good money after bad.

For the next two months, I travelled with the other salesmen, spending a week at a time canvassing the small towns. “Hi. I’m J.D., and I believe this will interest you also. For only fifty-eight cents a week, should any accident whatsoever require hospital confinement…” I was a terrible salesman. I did not believe in my product. It was a crummy policy pitched in a slimy method to people who didn’t know any better. I felt dirty.

I sold some policies, it’s true, but my income was a miserable $280/week or so. My expenses were much more than that. I had reconciled with my fiancee, and so was paying rent for an apartment with her. I was also paying rent for an apartment in Portland because I was required to live close to the office. (Why? We were never there!) And I was paying for hotel rooms four or five nights a week. I was essentially paying for three sources of lodging. And for a new car. And for a shocking amount of gas. (I put 20,000 miles on that car in three months.) And for food.

It was during this period that my problems with food began. I was stressed, mentally conflicted. I began to eat poorly. In the morning, I would buy a box of old-fashioned donuts and a quart of chocolate milk, drive to some secluded spot, and down it all while thinking of my ruined dreams. I don’t even want to think of how many calories I consumed every morning. I gained twenty pounds in three months. I charged $10,000 in credit card debt. I bought a brand-new $10,000 car.

My life was a disaster and I was only twenty-two years old.

The nadir came on a drizzly Friday. I was selling policies in hilly country west of Portland. It was early morning, and I had just driven up a long gravel road to make a futile pitch to an old farmer. He was getting ready for work, and didn’t want anything to do with me. “You need to leave,” he told me, and so I did.

I drove my brand-new car further up the gravel road to a fork in the road. I could have continued straight, but I took the road less travelled by (and that made all the difference). I drove downhill and around a corner. The road narrowed and the gravel vanished. The road ended. I considered backing up, but instead decided to make a three-point turnaround. I had pulled forward into a newly-plowed field. My tires sunk in the mud. Cursing my luck, I attempted to rev myself out of the jam, but that only dug the tires in deeper.

I got out to survey the situation. The drizzle had turned to rain. I believed I could push the car back onto the road, so I rolled up my pant legs, took off my sports jacket, and tried not to worry about my muddy shoes. I went to the front of the car and pushed. The vehicle moved slightly, so I pushed some again. I rocked the car back-and-forth, and soon it rolled free. Gravity doesn’t care about bad days or crappy jobs. When the car came free, it rolled in the opposite direction from what I had intended. Because it was resting on a slope, it rolled toward me. I dove into the mud, and watched as my car rolled fifty feet downhill, where it struck a fallen tree with a crunch.

I lay still for a few moments, trying not to think about the ruined clothes and the damaged car. I was in shock. I got up and walked up the hill, back to the farmer’s house. “What do you want?” the farmer asked me. I explained my predicament. I think something about the situation must have moved him to pity, because his features softened, and his voice mellowed. “Stay here,” he told me. “I’ll get a tractor and pull you out.”

I drove home (to one of my two apartments). I took off my wet and soiled clothes and took a hot bath.

And yet I still did not quit the job.

This, my friends, was the worst period of my life in nearly every way: emotionally, physically, mentally, and financially.


There are good jobs, and there are bad jobs. And then there are shitty jobs. You should strive to work only at good jobs. Sometimes you’ll have to endure bad in order to meet a greater goal. But you should never put up with a shitty job.

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