This is the fifth installment of the series of posts about Jerry Weinberg’s career–see the home page for Jerry’s Story for links to other installments.

Jerry says that he learned a lot from every one of the many jobs he has held. His entry into the world of work started about the year 1944, at age 10 or 11, when his family lived in Chicago. He took a job delivering a weekly newspaper that contained mostly advertising. He had a big route in the northern suburbs. To carry all of the newspapers, he tied a cardboard box to the handlebars of his bicycle using a rope. His pay came from what the recipients of these newspapers paid, but payment was voluntary. Jerry was tasked with asking the recipients to pay for it, and of course not very many people did, so it wasn’t a lucrative job for him. His clearest memory of the job was his last day. A sudden rainstorm hit while he was on his route and far from home. With no way to protect his cargo from the rain, he watched the newspapers and the box disintegrate into pulp. When the box fell on the ground along with its contents, he reflected on how much the job was worth to him. He abandoned the remains of the newspapers along with the job itself, and pedaled for home. He didn’t tell his employer he was quitting, and he doesn’t recall ever hearing from them again.

Around the same time, Jerry also started to earn money by babysitting. He liked kids, but he also liked seeing how other people lived. A voracious reader, he loved to read the books on the shelves where he was babysitting. More generally, though, he saw that families didn’t interact with each other the same way his did. Jerry was often affected by his mother’s irrational behavior—he describes her as “nutso.” He doesn’t like to discuss the details of this and perhaps other painful family interactions. Learning that the interactions he had with his mother weren’t normal was a matter of survival. Looking back on it, he said he can apply a motto he eventually adopted: “Things don’t have to be this way.”

He later had a job as a soda jerk, first at one drugstore in Chicago, then at another, over the course of two years. At one, he remembers that he was paid 30 cents an hour. The minimum wage was 40 cents an hour, and he was supposed to make up the difference in tips. But he only got a tip once, a dime, when he delivered some prescriptions to a third-floor walk-up apartment. He felt this discrepancy was easily made up for by the fact that he was allowed to eat all the ice cream he wanted.

He used his unlimited ice cream privileges to experiment with different combinations of syrups and ice cream flavors. One summer day, the store featured fresh limeade, and also peppermint ice cream, so he decided to make a milkshake out of both. He realized his mistake after the first sip, but here’s the problem–whatever treats he made for himself, he was required to drink all of it. His boss looked on as he drank the full glass of milkshake that had been curdled by the lime juice. This concoction make him feel so ill that it was a very long time before he wanted to taste any lime juice or peppermint ice cream.

In his next job, Jerry learned the grocery business as a stock boy. He filled in for absent stock boys in all departments at Hillman’s, a large grocery store for its time in Chicago. The grocery store experience came to bear years later when he wrote about “Rudy’s Rutabaga Rule” in his book The Secrets of Consulting (pp. 14-15):

“But mostly I noticed the rutabagas. I not only noticed the rutabagas, I made their acquaintance. I appreciated that each rutabaga had a distinct personality, and week after week I recognized the same rutabagas smiling at me from the same produce section. Evidently, nobody ever bought rutabagas. Rutabagas were just a permanent decoration, smiling their happy smiles at all the shoppers.

“One morning, I was standing in the produce section with Rudy, the produce manager, trying to figure out how to place the fresh vegetables in the limited counter space. Rudy had wrestled with this problem for a long time but didn’t seem to be getting anywhere. He asked if I had any bright ideas–and suddenly I was a consultant!

“‘I’ve noticed,’ I suggested, ‘that the rutabagas don’t seem very popular. In fact, they seem to be the least popular vegetable we have in the store. Would it be any great loss if we didn’t use any counter space for the rutabagas and used it maybe for something else?’

“Rudy looked at me sideways. I knew I was in serious trouble for implying that a mere, temporary stock clerk could help him solve his problems. But he had asked for help. To my surprise, he suddenly smiled and grabbed an empty banana box. Sweeping the rutabagas into he box, he said, ‘That’s a great idea, kid.’

“I beamed with a consultant’s pride. For the first time in my life, an adult had actually listened to me and taken my advice. Rudy looked at the void left by the departed rutabagas, then looked at me, then at the many vegetables that still had to be stocked, then at me again. After a long pause, he said, ‘Well, kid, that was a great idea. Now what’s the least popular vegetable?’

“Once you eliminate your number one problem, number two gets a promotion.”

After Jerry started high school, his family moved to Omaha. He had gotten his driver’s license in Chicago at age 14, but found that as a Nebraska resident, he couldn’t legally drive until age 15. This didn’t deter him from getting a job as a parking lot attendant in Omaha. He was required to keep it legal by only driving the cars on the lot.

Jerry’s father bought Wayne Auto Body in Omaha, and the rules there were more lax. Jerry helped moved cars on the lot and delivered them to their owners when the repairs were complete. This was done more for fun than as a job, but it did come with the perk of being able to borrow some of the cars. His favorites to take out on the town included a Cord luxury car, an antique Ford, and a flatbed truck that somehow got a lot of attention from the other kids.

Also while in high school, Jerry had a summertime night job at the Omar Baking Company. His job was to use an adding machine to calculate how much of each product to bake for the next day based on the order than came in, and he also ran the telephone switchboard for the last incoming phone calls of the day. Before he took the job, his boss had taken all night to do the calculations. Now Jerry was doing it in less than two hours. The bakers were delighted to get the numbers they needed so much earlier, but he had to convince his boss that he was actually done, by proving that his calculations were correct. There was another problem—Jerry was paid hourly, and finishing so quickly was going to drastically cut the pay he was expecting to get for working a whole shift. With the backing of the bakers, he was able to negotiate getting paid for the whole 8 hour shift even though he was finished with his work in significantly less time.

Jerry isn’t sure how he was able to complete his calculations so much faster than his boss. A few factors were probably at play. He started the calculations while still working the switchboard, but his boss had waited for all of the calls to be finished first. Also, he was doing many of the simpler calculations in his head, and his accuracy was good enough that his calculations didn’t need much verification.

A few of the bakers would drive him home in the wee hours of the morning, usually after expressing their appreciation by giving him a fresh loaf of bread. They would often stop at a bar for a drink. He wasn’t old enough to be in a bar at all, but he didn’t have any trouble coming in to enjoy a ginger ale.

An earlier installment mentioned Jerry’s summer job as a camp counselor after he graduated from high school, and some of the jobs he had while he studied at the University of Nebraska in Lincoln. There were a few other jobs that helped get him through college, like moving furniture for Eno Cabinet Works, where he learned that there was no shame in asking for help with a job, especially when that job involves moving a grand piano.

He worked at a greasy spoon restaurant that he often heard referred to as a “cancer kitchen,” based on the assumption that either the quality of food or the lack of cleanliness was likely to make the customers gravely ill. He started as a dish washer and later was a short order cook. He liked the dish washer job better, even though the pay was less. He liked being able to set the pace when he was washing dishes, and being able to see clearly when the job was done. Working as a cook, he tended to burn himself, and he didn’t like the pressure of having to get the orders out. He still enjoys washing dishes.

Jerry tried his hand at sales as a shoe salesman. He was very successful at selling men’s shoes. When helping men buy shoes, his approach was just to explain the properties of the shoes, which he felt were well-made. Then he just had to find the right size, and he had a sale. He was the top salesman for men’s shoes. But he believed the women’s shoes at the store were “cheap cardboard crap.” He explained the quality of the women’s shoes to his potential customers without sugar-coating it, and he never sold a pair. He felt he was doing the women a service. His employer, however, wanted salesmen who could sell any of the shoes they offered, so he was fired.

One summer while back home in Omaha, he had another job involving sales. He worked for a siding company, driving around rural areas of Nebraska and Kansas looking for houses where aluminum siding could be installed. He would ask the occupants questions that would qualify them as a sales prospect, and if that went well, he would try to schedule a time for a salesman to visit that evening. He would come back to introduce the salesman and then silently observe the pitch. Three weeks into the job, he saw a salesman give a high-pressure pitch to a poor farm family. He decided he didn’t want to take advantage of people like that, so he quit.

Also while working his way through his undergraduate studies, Jerry worked for a frozen food company, both in their storage locker and driving a delivery truck to make deliveries to grocery stores in Eastern Nebraska. This was when the frozen food business was in its infancy. While working at this job, he turned down an offer to take a full-time job in Florida with an orange juice company, so he could continue his studies.

Starting with his first two jobs, Jerry learned the benefits of having more than one source of income at a time. This insulated him from being influenced by threats from managers. Several times, managers have asked him to do something he didn’t feel was right to do, with the understanding that his job was on the line. He ignored the threats, being unafraid of losing the job, and he never did lose his job as a result. For all his career, he tried to avoid relying solely on one employer.

Jerry also learned that feeling exhausted from a job was a warning sign that he wasn’t doing it right. He would back off and allow the people he was working with to do more for themselves. He has applied this approach to many areas, including parenting, consulting, and training.

His most unlikely source of income while in college was from gambling. Jerry estimates that he earned half of his college expenses from gambling, which was a common pastime then. The bulk of his gambling earnings was from playing poker and hearts. He was good at it, and he would even be able to win repeatedly from the same people. Jerry said, “People always have an explanation for why they lost, and that explanation never involves their intelligence or ability.” He also played bridge. He and his bridge partner won two college bridge championships, but this wasn’t as lucrative as the other card games he played.

Jerry was awarded a National Science Foundation fellowship that supported him and his first wife through graduate school at the University of California, Berkeley, so his next job would be the the one that finally introduced him to the world of computers at IBM. We’ll explore this further as we look at Jerry’s role as a programmer.

The next installment in this series is Jerry’s Story: More Early Jobs.