How I Got My First Job At Age 18

I started out at age 18 with no job, no money, no education, and sub-par people skills. By age 19 I had my own house (a condo, actually, but I owned it). By age 20 I was making the inflation equivalent of $72,000 a year, driving my cool sports car (that was completely paid off…no car payment), living in my upscale condo, with a lifestyle better than a lot of men I worked with who were decades older than me and more educated, men with debts, marriages, kids, low to average incomes, and a lot of stress.

Today I’m going to talk about how this all started.

In the summer of 1990 I finished my senior year of high school. I sat down and wrote out all of my financial goals, both one-year goals and ten-year goals. I clarified them and put deadlines on them. I knew I wanted to start my own business, but I also was able to admit to myself that I was too young, immature, and inexperienced to actually do that.

So my plan was to get a job in the tech industry (which was on the rise back then), stick with it for a few years, build my income as much as I could, save money as best I could, learn as much as I could, then quit and start my own business. I also knew I wanted to do all of this without going to college. Stories of super-successful Bill Gates-like guys were rolling around in my brain, and I was convinced I could achieve success while skipping that whole “college thing”.

This meant that mission number one was find a good tech company and get a job there. At age 18. With no college degree. And almost no experience. Hm. By that time I was living in a crappy apartment I was barely able to afford by working for a temporary agency, occasionally, doing data entry work, but that was it.

So I whipped up a resume, and it didn’t look good. During high school I had done things like volunteer for the local science center, do a little computer work for my dad’s little business, and by then I had done some temporary data entry gigs for a local hospital and insurance company. Pretty pathetic, but at least it was something to put down other than “Education: High School”. I put these  on my resume and made them sound as rich and impressive as possible (which is what everyone does on their resume).

I ran down to the local copy center and made several copies of it plus a cover letter. Then I put each resume in a nice manila envelope, and had my sister write my name on the outside of each one, since her handwriting was much better than mine.

Next, I cracked open the big fat phone book (there was no internet back then) and looked at all the big, fancy computer companies in my area. I made a list of the ones that seemed interesting and seemed like they were doing well financially from things I had heard.

Then I hopped into my piece of crap 1979 Toyota Supra that barely ran, and drove out to all of these companies. I walked into each company asking to speak to the HR manager, offering my resume for any positions they might have for a stupid, smartass 18 year-old kid with no education.

Okay, I didn’t say that last part. Instead I said something like “A smart, eager young gentleman with a diverse work experience.” I sounded so dumb I had to try not to laugh when I said it. I’m sure I looked pretty classy standing there in my crappy clothes and long 80’s-rock-star hair with the Steven Seagal ponytail. Oh yeah.

Sometimes the receptionist would actually let me talk to the HR manager, where I would smile and act impressive and hand him my resume, but usually the secretary sneered at me while holding her nose. In those cases, I just handed the resume to her with her promise that she would forward it on to the HR manager.

I did this for several months. Often I would return to the exact same office and offer my resume again.  Finally, I had two companies bite. I applied for the entry level jobs they were offering, but I was turned down. A little later, one company offered to take me on as a temporary worker for one month. I leaped at the chance…and…they hired me! Well, “hired” is a relative word when you’re a temp. I was “hired” for just a month.

The company was, at the time, one of the largest software companies in the world, selling DOS utilities. I attacked the job with gusto. As the month drew to a close, I researched all the jobs they had posted internally and applied for all of them I could even remotely qualify for. It was now 1991, a recession year, so there wasn’t much there. The month ended, and I left, hearing nothing.

A few weeks later I got a phone call saying that I was “under consideration” for one of the crappy entry-level tech jobs, specifically telephone technical support (this was well before they outsourced that kind of thing to India). They wanted me to come in and take a test on my skill with DOS. I happily agreed, even though I knew next to nothing about DOS, being a BASIC, Apple IIe, and Commodore 64 man.

I borrowed a DOS book from my uncle who worked for Hewlett Packard, read it from cover to cover over a weekend, and on Monday I took the test.

A few days later I received the phone call. They had liked me in the interview, but I had failed the test and was not going to be hired.


I knew that the tech support department was still growing though, and that they would still need more techs. So I re-read the stupid DOS book again, this time taking notes and re-reading any parts I didn’t understand, which was a lot. Then I drove out to the company several times, re-delivering my resume over and over and over again, driving the receptionist and the HR department crazy.

Finally, finally, I received another call. They were going to give me another chance. Yay! But I would still have to successfully pass the DOS test before being hired. Crap! I just said “No problem!”.

I studied again. Went in and took the test again. Then left and waited by the phone. For days. And days.

Finally, I got the call. “Well, Caleb,” the HR manager said, “It is my pleasure to offer you the position of Technical Support Specialist. You did it, kid.” I had gotten the job. While I screamed with joy and danced around the room, the HR guy gave me a warning, “Now look, Caleb. Most people we’re hiring for this position are people in their twenties and thirties with college degrees. So the fact you’ve never been to college and are still a teenager ..well, I would just keep that to yourself for the time being.” Again I gave him a “No problem!”.

At age 18, I now had a job making more money than my high school teachers. It was one of the happiest days of my life. Even better, it was an hourly position, which means I got overtime pay, which I loved. Every time they asked (or demanded) we all worked overtime, while all the married middle-age guys bitched and whined, I jumped for joy. More money! Yay!

It was all uphill from there. My goals, desire and persistence had paid off. Soon I moved to different companies and eventually started my own business by age 24. But that’s another story.

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