I know this is not not exactly a small business matter, but can and does impact small business owners.
Career regret is common among people. I have regretted decisions (and non-decisions) I have made over the years.
My biggest career regret is that I should have completed my education earlier in my life. This prevented me from obtaining positions earlier in my career or just prevented me from applying for those positions. In my mind, the lack of education was a major roadblock from advancing my career.
However, looking back, I probably was the major roadblock in my career. I have a fear of failure. I am very (overly) cautious with my career decisions. I know that my fear of failure prevents success. It is something that I work on every day.
This HBR Blog article written by Priscilla Claman discusses career regret. Good advice!
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