is for regrets: I think there are two kinds of regrets. One is regrets in hindsight--what you'd do differently if you knew how things would turn out. I'm sure most people have lots of them. I do. I think they're usually the less interesting ones, though.
More interesting are regrets about decisions you made that were wrong, and that you knew at the time were wrong, at least somewhat. I have two of them. I regret staying at my first computer programming job too long. I should have left after a couple of years, because we weren't keeping up with advances in the industry. I sort of knew this, but it was a nice place to work (a university facility)--the people were all nice, the work wasn't too demanding, we had flexible hours and no dress code (something of a rarity in the early 80's). The programmers were left alone to do our work. The pay wasn't too bad, at least after the first couple years. I was satisfied, though I knew I could do better.
Then, after I was there for about 4.5 years, there was a reorganization, and a change of management. Things were very different. We, the programmers, were no longer given carte blanche. The new management did not like our independence, though a certain amount was tolerated because they knew they couldn't do without us--they hated the flexible hours, because they couldn't keep an eye on everyone all the time. We were misled about management's intentions, even outright lied to--I was told I would be getting a raise as of a certain date, when it hadn't been approved. And my boss knew it wouldn't be approved at least a month before its supposed start date, but he didn't tell me.
I wanted to get out, but there was a big problem--I didn't have the skills that were then in demand. I managed to find something after nearly a year of looking. (I learned a lot about headhunters in the process--especially ones who would send you out on interviews for jobs you really weren't qualified for--a real waste of time.) It was working for a marketing consultant, who had a contract with a big mail order company. The guy knew nothing about programming, but wanted to make all the decisions. He didn't really lie to me about what my job would entail, but he certainly lied to the headhunter, saying it was new position, when in fact he had fired my predecessor--and then refused to give him his last paycheck. He hired two of us at the same time. I couldn't figure it out, because there really wasn't enough work for two people. He soon fired the other one, and I realized he never had any intention of keeping both of us. (He then boasted about making sure that he did this after only 29 days, because that way he wouldn't have to pay the headhunter his commission!)
He was abusive to the two other employees (one especially), though at first he let me alone. Then, a couple weeks after he fired the other guy, I made a mistake, and he let me have it. So I walked out. Literally. My old place had said I could come back, and as bad as it was, it was better than the new one. But I learned a valuable lesson: Never work for an entrepreneur--they think they know everything about their business better than anyone, even experts in the field, and they view every dime of expenses as taking food off their plates.
It took me two more years to find another new job. For the rest of my career I was well behind the curve technology-wise--though right at the end this turned out to be an advantage. By the late 90's they had stopped teaching the old technologies in computer schools, but there were still some places that used it--and we old dinosaurs found we were a bit in demand, especially during the run up to Y2K.
Oh, yes, this was about regrets. My second regret was semi-wasting my first dozen years in New York, because I was too shy and scared to take advantage of many of its attractions--rock clubs, etc. I sat at home for a lot of my mid-20's to mid-30's.
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