This statement can be taken in many different facets. The context in regards to this blog, however pertains to career advancement (just clarifying). It's easy to play it safe, but playing it safe 100% of the time will not yield the results you seek in your career. Don't be afraid to step outside of your comfort zone. That is a risk in and of itself. Risk being rejected, risk failure, risk the potential embarrassment of putting yourself. Whether it works or not, at least you know the answer.