Playing is safe is easy.
Playing it safe will get you the same results.
Playing it safe is... well, safe.
When is it time to take measured risk? When is it time to try something new? Here's a portion of a great inspirational speech to help answer these questions from Steve Jobs at the Stanford Commencement address in 2005:
You might have heard this before. I still find it powerful after years of reflection. How many days have you got up for work and felt like it was the last place you want to be. How many days have you spent "waiting for the weekend"? Life is too short. Make the most of it. Is it time to make a change?