Just one at a time. My first job was selling hot dogs out of a truck in a supermarket parking lot. My last job was my career as an artist and designer. In between I worked in retail and 1 office job.
I had two while in college with one being the Navy Reserve. I currently have one paid job and two aspirational jobs: want to be a baller and a shot caller.
During college summer and winter breaks, I worked an office job (served as office fill-in for people on vacation at a township office, but I actually put their whole township budget on computer for the first time (Lotus 1-2-3!). That was 9-5. Afterwards, I'd go to the local mall and work at the "Chicken Club." Seldom had any time off.
After I got married, I tried to do something similar -- worked an office job in Atlanta and then tried to work Taco Bell third shift. I couldn't keep up, and was much too tired all the time.
There have been quite a few times I've had two, either babysitting or doing retail on the side in the evenings or on the weekends. There was one stint in my 20's where I worked 7 days a week for about 10 months. It got really old, but I did get the money together to replace my car.
One full time and one as a consultant for software I developed for a previous employer. At most I worked 2-3 hours a week for the second job.
My dad always had at least three while I was growing up. Generally two full time and one part time. He worked 100+ hours a week from his early 20's until his mid 60's.
It wasn't until he "retired' that he got down to just one job.
His death was slow and gradual and gave him a lot of time to reflect on his life. His only life regret was how much he worked. Looking back he was finally able to see that the extra money was not worth the time lost.
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