The Story of My History In Business – Part 2 – My First Real Work

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-By Caleb Jones

This is the next installment in an ongoing series where I talk about my history in business, starting all the way back when I was a child to now, my mid-forties. I already wrote part “zero” right here and part one here, so you should read those first if you haven’t yet to get some context.

I was 14 years old when we last left off…



By the time I was about 14 years old, my dad had bravely quit his job from the state and started his own mental health counseling firm. After a few rough years, he was scraping by with a few employees in a small, run-down office, and I was very excited to hear that he was going to purchase a computer for his employees to use. This was a big deal back in 1985; computers were brand new and very exciting.

I begged and pleaded with him to let me go into his office to work on his computers, doing data entry or anything else he needed, and to pay me whatever he thought was fair.

He initially said no, but I keep pushing him as hard as I could, to the point where I really pissed him off. He was a stressed-out Alpha Male 1.0 with a short temper who disliked working in his business. He didn’t like to be bothered. Eventually he said yes when his office lady said that she could use the help entering all the client files into the computer.

To keep things sane, he put her in charge of me instead of himself. Her name was Rebecca and she was very nice. I forget what he paid me per hour, but it wasn’t very much. I worked a few hours per week.

His office was all the way downtown and we lived way out in the suburbs. Being only 14, I had no car and no drivers license, and there was nothing like Uber back then. My dad refused to drive me to his office and my mom was too busy with my other siblings, so I reluctantly took the bus downtown every day I worked even though it took damn near an entire hour each way. I would often walk to the bus stop right after school.

Once at the office, I would sit in a tiny desk and enter in gigantic stacks of client forms into his very cheap Dbase III database, staring at a yellow monochrome screen for hours at a time, late into the night, after all the other employees had left for the evening. (School was out at 3pm so I didn’t get into the office until 4pm at the earliest.)

It was boring, grueling work (as grueling as office work can be, that is; I realize manual labor would have been worse) but I didn’t care. I wanted to make money and I wanted to learn computers. They were super exciting and I knew they were the future. I started to learn how to type faster. I took a keyboarding class at night to learn how to touch type (type without looking at the keys, which was a very rare skill for teenagers back in the 1980s). Whenever the computer consultant came into the office to fix a computer problem, I would corner him, pelt him with questions, and take written notes. I bought several books on DOS, Quattro, Dbase, and other software programs that were common back then and devoured them.

I worked there for about two or three years, working about ten hours a week. During that time, Rebecca became so distraught at working with my dad, who was a horrible boss, that she quit one day and just walked out. Suddenly, I had no boss. My dad eventually hired another office manager, a nice woman named Dee Ann.

While working there, I made numerous stupid teenager mistakes, and my dad would get furious and fire me… three times. I say three times because once he calmed down, he would just re-hire me again a few days later once he calmed down. (Ah, the joys of having an Alpha Male 1.0 father.)

Eventually, he had enough staff to the point where he didn't need me anymore, so he "laid me off" for the final time. He did it very nicely. "I know you can make more money somewhere else anyway," he said. He was right.

Now 18 years old and a senior in high school, my class was setting up a student company and were taking interviews for the president of the company. I knew I could learn some good business skills that way, so I leapt at the chance even though I was getting Ds in most of my classes.

I made it to the three finalists; two popular kids and me. The three of us were privately interviewed by a panel of three adults. To my surprise, they selected me as president. The student company was comprised of about 25 kids, and when I walked into that room as their “president” they were all confused since most of them had no idea who I was. I wasn’t a nerd or an outcast, but I wasn’t popular. They expected one of the popular kids to be president. (So did I.)

We went on to sell plastic mugs with the high school’s logo on them. We all worked on that for about six months, and we sold a lot, but I don’t think we made a profit (but I honestly don’t remember; maybe we did). I was given several mini business manuals and kept copies of all of them for my notes in case I needed them later.

1990 rolled around, my high school time had ended, and it was time to move the hell out of my parents’ house at age 18. I got along with my parents, but I hated living with them and putting up with their rules. I needed freedom. That meant I needed money.

It was time to get a "real" full-time job.

To be continued.

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