I promise this isn’t a click-bait headline. This is my attempt not to bury the lead. You see, I fail every single day. From my freshman year at Carroll High School (and definitely before) and through more than 20 years since leaving (and definitely in the future), my life has consisted of a series of micro-failures, and there was a time I feared that failure.

There’s very little I’m afraid of. Heights don’t bother me. I think spiders get a bad rap. I’m more comfortable flying on a plane than I am driving to the grocery store. Slasher films, zombies, running alone through Chicago – they all provide an adrenaline rush. But after I graduated from Carroll High School, I was afraid of failure. Was I ready? Could I succeed? Will I remember the definition of ‘health’ (Yes, Mrs. Lane, I remember it’s ‘optimal personal fitness for full, fruitful, creative and spiritual living)? These same concerns have tagged along with me as I’ve worked as a marketing turn-around expert for technology and media/entertainment companies.
But my ability to embrace, learn from, and build on my failures are a result of my time at Carroll.

Fail together, in public, with confidence

If you were in English class with Miss Wourms or a Latin class with Sister Mary Alice Stein, you can probably recall the repeated rework of diagramming sentences or conjugating Latin verbs. I can remember the frustrations of Calculus and trying to follow along with Shakespeare but what stands out the most were the teachers who encouraged us to own our failures while learning these concepts. We shared them as a class, discussed the challenges, and then broke down why they occurred so we could build on those learnings. This taught me throughout my career how to develop an environment that reinforces resiliency, risk-taking, perseverance, and adaptation. I learned how to focus on solutions instead of blame and how to respond to failure.

Fail fast, and incrementally, in order to create

In business we preach, “fail and fail fast” or “create an environment where employees have the freedom to fail”. Even if the company culture truly supports that, failure doesn’t happen often. Companies hire experienced employees who have proven success in their field. Failure is rare. However, when you’re in school and learning, almost everything you first attempt fails. I believe this is why so many professionals become averse to learning. At Carroll, I failed over and over and over and over again. In my academics, athletics, and social structure, I was pushed so incredibly far outside of my comfort zone. I learned to get comfortable with being uncomfortable, and that has served me well. It has taught me that micro-failures are necessary if I’m going to continue to learn and develop.

Fail free of judgment

While at Carroll, I was surrounded by teachers and coaches that encouraged authenticity. I was taught the importance of transparency, compassion, commitment, ethics, and setting the tone. I was never fearful – well, except when walking to the lunch room and my shirttail was untucked. These teachings have allowed me to foster a culture in my teams that embraces failure, free of fear. By developing a culture of authenticity, I’ve found that I can improve manager-employee relations, respond to change, and set goals. And when you fail free of judgment, you can begin to replace blame with curiosity. Relationships are better and more interesting when working together and building. It’s too easy just to fight, but relationships with tension and conflict make life interesting because not all tension and conflict is bad. Competing and differing ideas are great things.

I’ve been incredibly fortunate to spend the better part of seventeen years working for innovative companies and iconic brands like The Second City and Oracle. I’ve worked with immense talents that push the level of creativity and challenges common convention. I’ve also learned to view everyone as a person with a special story to tell, to foster talent, and to teach. All of these learnings and all of my success can absolutely be attributed to my time at Carroll High School. But the most important lesson is to follow the fear and do what scares me the most. Carroll has taught me that if it’s uncomfortable, do it more.