THE BLOG
08/22/2014 02:11 pm ET Updated Oct 22, 2014

Playing It Safe Is Too Often Risky

Andy Roberts via Getty Images

We don't have to experience the world in any specific way that someone else dictates. Gaining approval doesn't always make us feel like we are living with purpose. Our lives are spent pushing back on boundaries, battling the rules and trying to find a way that works for us. We can choose to follow the status quo or we can break away.

How you feel about taking risks says a lot about you. When it comes to risk, what matters is that you take the ones that matter most to you. While there are some people who naturally take risks, there are others who stand back and wonder what they are missing by playing it safe. It all comes down to how you define success and failure. If your success is determined simply by comparing yourself to everyone else, you will always be a slave to other people's standards and needs. We learn to be safe but safe can also be risky when we don't listen to our own compass.

I have spent years unlearning all the notions that were drilled into my head of how I was supposed to live my life from my career to personal life. And I have to say that unlearning has been very freeing. I was brought up with the belief that we need to be in constant motion so we don't "waste our time." I was so busy not wasting my time that I didn't know how to be still and mindful. Unlearning is hard because it is about shedding what has been expected of us and being safe. Ironically, I had to learn how to unlearn so I could shed what was expected of me and make space for a whole new world of possibilities.

What I am discovering is that it's about the journey. This is it. Right now. Right here. I don't spend my time thinking about what I am looking forward to doing. I am simply trying to make it happen in a way that works for me. I am trying. I am falling down. I am getting up and shaking the dirt off. I am trying again. And I am living. I am willing to sit on the edge, unlearn what helped guide me in the past and no longer serves me. I don't buy into other people's quick fixes and schemes. It's about doing the work to discover what works for each of us.

Life is as difficult or easy as we decide to make it. We can stay safe or we can blow things up and get rid of barriers. Whatever path you choose, do it mindfully. And know that no one has the answer for you. You can decide whether you want to follow the Dummies Manual or create a personalized plan for yourself. And you also have the ability to choose simplicity over complexity.

The real question is why can't you? It's a question that always stays with us. We can choose to give up or to keep trying. Keep hoping that it will all work out and if not, there will be an important lesson in it. At the end of the day, what you are left with is knowing that you did your best and that you'll get up in the morning and try it again. Are we ever ready? If you wait until you are ready you might be waiting forever. Trust yourself and leap into the opportunity to learn and grow.

What will you tell yourself in 20 years? We can't turn the clock back, we can only move forward. How high are you willing to fly?