My first day as a salesman out of the office... Felt like I was playing hookey

At 24, my entire work career, if I could call it that, was centered around a haphazard collection of temporary jobs, and the kinds of work you get when you are trying to find work on the side; waiting tables, catering jobs over the holidays, painting houses and cleaning up yards. I sometimes quit these jobs without notice because they were crummy. I struggled with getting places on time, or remembering when my shift was, and got fired a few times, too. 

I wanted to work in an office, as I had always imagined I would. I had typing skills, after all, from my work as a newspaper editor and writer in high school and college. I was looking for office work, but the jobs that I had gotten through summer work and internships came through connections I didn't want to access again. And no one wanted me; scouring through help-wanted sections and the classifieds didn't yield anything. A friend suggested a temp agency they had success with. I went in, interviewed, and the next day I was working! 

I also had AV Tech skills, and that turned into my first "real job," a great job with great benefits, but I was a chronic grass is greener type of guy, and I soon left that job for a clerical career in the mortgage business, a multifamily lender, then a residential lender as a clerk, and then a manager. There I got firsthand knowledge of the real money in business; sales! These were the guys with fancy cars and nice suits, not like me sweating behind a cubicle desk grinding for hours in a low-level glorified manager's job. 

People told me there was too much risk; I wasn't guaranteed any money in sales. But didn't worry about that. I had already gotten business that I had to turn over to another loan officer, and the sight of the commission check gave me intense inspiration. I was ready to set out. No one wanted to hire people without experience, but I traded a contract helping a company set up their closing department for a position as a loan originator. I never looked back. 1 month into the job I was near the top of production. 

That first day, stepping into the cool autumn air, I kept feeling like I should go back to the office; like I was cutting class. I literally skipped into my first appointment. A year later, headhunters were calling me offering me jobs. I had established myself. "Go ahead, fire me! I've got clients, and I can work anywhere." It wasn't even about the money. 

I'll never choose a job where I have to do exactly what someone else says and control when and how I work ever again. Even though the sky was the limit, I would rather make less money and not subject myself to the office. 

Imperfect Information - First Signs of Entrepreneurship

I can't remember if I told this story before, but in second grade, at my elementary school, I became fascinated with the school store and the supplies they sold. In the morning and at lunch there was always a line for supplies, and I was a frequent visitor because I was absent-minded and lost or forgot my pencils frequently. 

I could buy 10 pencils for $1. But they only had several hundred. I imagined that, if I bought all of the pencils, the students would have to come to me to buy pencils and I could charge a profit. I set about collecting my allowance money, spare change and savings to execute my purchase of all the pencils.

On the morning of the purchase, I expected that I would buy all the pencils and stand by the store to re-sell them to desperate students for 25 cents each. The morning store hours were less popular, so I figured I would purchase all the pencils at the close or the morning hours, that way, when the long line for pencils formed at lunch, I would tell the students that they would have to buy from me, at $0.25. 

The purchase went fine, but during my first period class I was called to the principal's office. He said, "I know what you're trying to do. It won't work. I can buy more pencils." He was kind in offering to buy back all the pencils I had bought. This is an example of imperfect information. I didn't know how easily I could be wiped out.