Failing Forward: The Secret to What’s Really Holding Us Back from Achieving Our Dreams


As I was finishing my breakfast this morning, I had this flashback to when I was 7 years old. My family and I were still living in New York City and my father was teaching me how to make out addresses on an envelope. I remember him telling me that I had to make sure that I wrote my address as clearly as possible or the post office wouldn’t deliver my letter.

Not only did I have to make sure that my handwriting was legible, but the writing had to be done in a straight line. My childlike letters couldn’t start to drift off as if some wind had blown the rest of my letters on a trajectory towards the sky. I had to be neat. To ensure this my father gave me a ruler and instructed me to draw the lines neatly, with equal spacing to give me ample room to write my name and address. My father would look on approvingly as I would painstakingly draw those lines and periodically stop to examine, erase, and redraw the lines so that they were perfectly straight and aligned. And when I had finished, I loved the look of approval that my father gave when he reviewed my work and noted that I had done it correctly. Conversely, I was terrified when I felt that I had let him down.

I discovered this one day when I attempted to make out an envelope on my own; only this time, I decided to try it without the ruler. I felt pretty confident that I could do it unaided since I had done it so many times before. But when I surveyed the finished product, I remember feeling mortified because just as my father had told me, my letters had begun to drift, making the entire address section lean slightly upward. Why didn’t I just listen? I had failed.

Afraid that my father would find my mistake, I crumpled up the envelope and hid it deep within my desk drawer. I had to make sure that he would never find out that I had attempted to do something on my own without following his instructions. And I thought that I had gotten away with it until one day I came home from school and my father was standing there with the crumpled envelope in his hand demanding to know why my envelope looked that way and why I had hidden it.

I don’t remember anymore how I explained myself, but I remember how I felt. And I remember vividly the message that I had interpreted.

“Measure twice; cut once.”

This little proverb has been part of my narrative for so long I didn’t even notice the footprint that it has left on virtually every decision that I have made in my life. For me, there’s comfort in always having a plan. It’s much more empowering than winging it. And I can’t say that I disagree with or want to totally change that about myself. However, what I do want to change is that fear of failing. Because as long as I continue to harbor that fear, even my best laid plans will be sabotaged from the start, simply because I won’t have the faith and courage that I need to put them into motion for fear of not getting it right.

Dreams are wonderful, but they don’t change lives nor do they establish legacies. And I am in the legacy building business.

Are you? 

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