Deciding when to speak up is one of the things where I feel I haven’t yet figured it out at all. I don’t know when or how to do it.
In high school, a friend of mine didn’t like her boyfriend anymore. I told her that if she really feels that way then she should break up with him. The boyfriend (who was a good friend of me as well) was, understandably, quite angry at me. From that moment, I decided it wasn’t a good idea to speak up about other people’s relationships, even if I have strong opinions on it. However, recently, a friend told me he wished people would have told their true opinions about his ex-girlfriend. Mine was mildly negative, but I never said so to him. I don’t know if I should have done so.
Being a programmer, I always get a lot of business-people looking for a programmer. They tell me their idea, and in my opinion, most of the ideas suck. Whenever I think this, I’ll try to postpone judgement and get my thoughts straight. I still feel it my professional responsibility to tell them why it is a bad idea and do so eventually. But where to draw the line? Do you tell thim “your idea sucks and here’s why”? Or “this is what I don’t like about your idea”. Maybe even “I don’t think you should try to become an entrepreneur” (I’ve never said that and not planning to do so either).
One of the reasons why I find it hard to say what I’m thinking is because I have been wrong so many times. If Jack Dorsey would have pitched me Twitter, I probably would have strongly advised him not to pursue it as a business, because it doesn’t really add anything (we already had blogs, social networks, text messaging and email). Also, you need a lot of people for it to be interesting. I mean, seriously, a 140-character microblog is the best idea you can come up with? What problem does it solve anyway?