What does "less sure about ~" mean? Then, the opposite expression is "more sure about ~"?
This is an interesting sentence. Steve Jobs has used "less sure about everything" to describe his loss of confidence as compared to the past, as indicated by the determiner word "less" here. If you want to express lower confidence or sureness (in something), you can use "less sure," and "more sure" to indicate the opposite. Ex: After successfully completing an internship, the young man was more sure in his skills. Ex: I feel less sure about myself after I experience failure.
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