Real self esteem comes from real achievement. You need to try, fail, try again, fail again and repeat and improve until you have mastered a skill or a task. It isn't about self esteem, it's about self mastery.
In today's world of tightly controlled public relations, is there any way to be other than safe? I always find myself rooting for people who stand up for what they believe in, and it always gives me a great charge to see it happen.