Does Playing It Safe Just Get You a Lot of Missed Opportunities?

There’s this saying, “with great risks comes even greater rewards”, and I thought about that as I was watching a news segment about Facebook COO, Sheryl Sandberg, discussing her success and her new book that is causing much controversy.  She was discussing her thoughts on women and their role as leaders in the business world and how women, albeit ambitious enough, are always playing it too safe and that is often what holds them back in their efforts to succeed.  She has taken many risks throughout her career and her several different roles as a leader and she has had many great rewards simply because she refused to play it safe.

It made me think about the fact that I am not a huge risk taker and if that is what is holding me back it would be a terrible shame.  Is that what is slowing me down on this journey to the top?  To say I am cautious would probably (if you ask my best friend Ms. L.) be putting it mildly.  I think things through, sometimes too much, and then once I decide something I rethink it through again, a couple more times.  The funny thing is that I don’t remember being this way when I was younger.  Granted when I was younger I was limited in the things I could do because I was not yet an adult and most of my childhood I was not a working individual so I relied on my mother for monetary well being, but I don’t remember being so scared to do things.

I don’t remember over analyzing things nearly as much as I do.  I mean I did to a certain extent because I had to analyze whether or not the risk I was taking was going to get me beat by my mother or in trouble in other ways, but I never thought of myself as playing it safe.  So now in a time in my life where I should be throwing caution to the wind and just going for everything and every opportunity that could possibly come my way, I am resistant, I find that I just want to be safe.  I don’t know if it was motherhood that made me that way or not but I know that I want my daughter to take risks and go after the dreams she wants without worrying what is or what is not going to go wrong.

The author of Wild, Cheryl Strayed, wrote her memoir about the journey that she took along the mountainous Pacific Crest Trail from California, all the way through Oregon and up to WashingtonState, with practically no money to her name and little idea of what it was she was really in search of.  Somehow she managed to complete her trip as well as accomplishing a level of self discovery that she didn’t even realize she was looking for.  She didn’t let the fear of not really knowing where she was going stop her, nor did she let the fact that she had barely any money stop her and she managed to get a New York Times Bestselling book out of it that landed on Oprah’s book club lists.  She didn’t play it safe and she took a huge amount of risk and she got great rewards.

Now obviously, it is not realistic for most of us to go and try that, but the point is that we shouldn’t let things hold us back and we shouldn’t play it so safe that we miss out on the adventures that we could have in our lives.  Now being overly cautious is a hard habit to break and I am not crazy enough to think that overnight I am just going to be this “throw caution to the wind” type of person but I do know that I don’t want to play it safe anymore and I can’t afford to over-think myself out of the next opportunity.  What about you, have you been playing it safe lately?


Jimmetta Carpenter


The Diary: Succession of Lies (Now Available)

Writing as “Jaycee Durant”


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