I've done some serious reflecting on exactly what you've said. I'm on that "safe" route. I went through the college anxiety, the GPA worries -- all of that was my mantra. To this day, I still admit to being a "resume" builder. I want things on a paper for a sense of achievement.
This scares me, though. I'm starting to realize that is not what it's about. It's about making a difference. Sure, you can indeed make a difference doing what you and I have described. A company needs people like that. But I always wonder, could I have made an even bigger difference doing something else? I'm not even talking about my education. I've even thought about this for sports.
For instance, I grew up playing baseball religiously because I had already invested a lot of my time with it. I didn't want to adhere to anything else for the fear of wasting my time. Here I am, years later, realizing I would've been an even better tennis player had I actually been open to trying something that would've given me more success, but potentially been less safe (starting a new sport in the middle of being so devoted to one already). Here I am, hitting with racquet on every volley, wishing that I had bought into the sport earlier because I know I could've been better at it than I was baseball.