Asking Difficult Questions

I got back from Providence this afternoon, and it was a good trip even though I didn't feel good all or even most of the time. Academic events can be tricky to navigate and I wish I could approach them with a more positive attitude. I often find myself biting my lip and not giving an honest answer when someone asks me how I found a particular session. "It was good, but ......". At the same time, I realise that if someone was similarly critical of my work, I would be hurt too. What is it about academia that turns all of us into such fragile flowers? I asked some tough questions during audience questions and someone even complimented me later about the quality of the questions. But, I thought long and hard before asking them. Should I just ask softball questions and ask more probing questions in private? Would I be harming my career by asking difficult questions? Was I just trying to show off by asking difficult questions? Should I go back to being a journalist if I enjoy asking difficult questions? But, I decided that since this was a summer school, and as all the instructors were in secure employment and not shrinking daisies aka PhD students, they should be able to take difficult questions. Yes, you need to be strategic in any industry but you also has to ask if contorting yourself so much that you stop recognizing yourself is worth it? These might seem like a trivial question, but I have been thinking long and hard about whether I want to be in academia, and I suppose any career which doesn't allow you to be yourself (within limits) is possibly not the right career for you.