
Early on in my career, I had a boss and mentor named Craig who taught me much about business, work, and life. I’m indebted to him for these reasons and certainly because he offered me a job that set the stage for much of what would take place over the coming decades of my professional life. After working in the firm for a few years, the time came for me to begin supervising others and that including making hiring choices myself. Craig empowered me to make the final selection decisions for our team but did prefer to meet finalists before completing the hiring process. I recall well the situation with Amy.
Amy’s education and experience were impressive, top notch. She impressed everyone she met at our firm, and I was convinced that she would make an excellent addition to our group. As per the norm, Craig met with her before I offered her the position and I’ll never forget the conversation we had next. After their meeting, Craig approached me and said that he thought Amy was a great candidate, but he did have one concern. He said: “She has done a lot of incredible things in her life, but I worry she has not experienced a failure and, therefore, it’s hard for me to gauge how she would respond to one.” Interesting, I thought, and I immediately remembered my own hiring process with Craig and the fact that he asked me about failures and how I had reacted to them.
Ultimately, I hired Amy and for the first year or so, all indications were that she was a great choice. But then it came – the failure. We had a particularly difficult client, one whom many members of our team had struggled to please in the past, and on one of Amy’s projects with this same client, there was a problem. A big one. And Amy was at the center of it. I tried to coach her through it, explaining that we had had similar challenges with this individual in the past, and that we would all be able to recover from this difficult moment.
But Amy took this hard. Really hard. She experienced a great deal of self-doubt, wondering if she was fit to succeed in this profession, and then that second guessing began to impact her work. Ultimately, Amy left the firm shortly after this event. Observing this situation unfold, I began to see the wisdom in Craig’s words. Sometimes we must fail in order to learn.
And furthermore, sometimes we have to experience failure, loss, great personal challenge in order to grasp some of life’s most valuable lessons. Embracing this idea has proven helpful to me whenever I experience a misstep. Instead of immediately regretting my actions and bemoaning the high cost of my mistake, I ask myself: what can I learn from this and what might I need to understand from this experience that might benefit me in some way in the future?
Of course, none of us want to fail. We would not choose to do so, but I am always struck by how often a seeming blessing eventually turns out to be anything but. By the same token, a hardship can evolve forward into some type of a gift or blessing. As Catholics, we are no strangers to this odd plot twist as one of history’s greatest signs of defeat, fear, and failure – the crucifix – adorns all of our churches and signifies redemption, love, and hope.
Sometimes, we must fail to learn.

Great insight and worth remembering!
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