Getting into Trucking

I like to be a jack of all trades and I been interested in at least trying trucking for at least a year, if I fail oh well. Regardless if I succeed or fail as a truck driver it is still something I like have to try for fun, it would still be a very fun learning experience regardless. Something always wanted to try even if I later discover I am not any good at it. Being a truck driver for two years sounds like something that would be really fun to do. I am debating about signing up for OTC driving or going to a trucking school.

I kind describe myself as a rolling stone, I like to move around into many different jobs and be a jack of all trades. My parents are fed up with me in 30's and still no idea what I want do for a living. Had no problems with employment( although it has never been any very good pay jobs) been in so many jobs in my lifetime. Have a great education. Bachelors in Computer Information Systems, Masters in Education and I have almost completed my post bachelorate certificate in Accounting. Bounced around between so many jobs, I get bored after 2-3 years in a job and decide I want to try something new for fun. Worked at Boston Market serving food: working register, cleaning dishes. Worked at Dominics Grocery stocking shelves. Worked at fitness center as an attendent and supervisor. Worked at a hospital for 5 years: transport, ultrasound, x-ray, outpatient, courier, dispatcher, etc. Worked as a web developer and computer repair technician for about a year. Worked as a substitute teacher and paraprofessional, worked as a security guard, worked in sales, etc. So many jobs. Sometimes I sign up for jobs and could care less if it is something I can do or not, I just enjoy learning and love to try something new for fun. I want to try Truck Driving for about a year. Wanted to do trucking for so many years. I think the job would teach me so much that you just can't learn in other jobs or in college.

Any advice where to start?

 

I live in Chicago Area