Sam Altman's quote is more zen. I took it to mean reach for the stars because the only thing that sucks more than failing is wondering if you would have succeed

Sam Altman's quote is more zen. I took it to mean reach for the stars because the only thing that sucks more than failing is wondering if you would have succeeded. Scott Adam's is slightly more pragmatic. I took his quote as meaning your chances of success are higher if you are a generalist than to pigeonhole yourself with only one skill set. I don't think the two quotes are conflicting pieces of advice.