• Sarah Carter

Perfectly Imperfect

Who is your leadership idol? Role model? The person whose shoes you wish you stood in? When you think of them, angels sing, crowds part, a halo of light outlines their irreproachable outfit choice, and their smile rights every wrong. Okay, I may be exaggerating a little bit but hopefully it painted a cartoonist's utopian picture in your mind because that was what I was going for. That is the picture so many of us imagine when we call upon mental images of strong leaders. They have everything figured out, walked effortlessly into the success they enjoy, and can do no wrong. Odds are that none of that is true. Those people struggled just like you and me and every other person ever trusted in a leadership role. But did you ever bother to ask about the hard times?


Kristen Hadeed wrote Permission to Screw Up "to show that behind every leader is a perfectly imperfect story" pg. 244. She is the hugely successful, young CEO of Student Maid. She founded her business while still in college and initially told those who asked only the good stuff. She told the stories of successfully employing millennials, while being one herself, that she thought people wanted to hear. She feels that she did this because maybe "as a society, we've made it really uncomfortable to talk about screwing up" pg. 240. She felt she had to keep the rest under the rug lest someone see her path was not as smooth as they believed and that this would some how disappoint them.


What she discovered when she started telling the whole story was that it made her feel alive and proud. "Talking about what really happened energized [her] in a way [she'd] never felt before" pg. 240. She had 45 out of 60 employees walk out on her on job number one. Her first intern over paid the entire staff by $40,000. She spent $1,000 of her initial small business loan on sushi. She micromanaged everything. She lost the trust of one of her best employees, who later resigned, because she could not bring herself to fire another employee who was a complete mess. She did all of that while her business was still in shared office space serving one, small region. "Sometimes mistakes can be the best lessons" pg. 24.


Kristen and Student Maid recovered from all of those, and then some, and became the unicorn business model that it is today. Thinking back on my US Navy career, I do not think I ever directly asked any of my leadership role models about their failures and struggles along the way. I also do not think I had any who openly talked about them. She certainly has a point about our society making it an uncomfortable, or taboo, topic. I made many personal screw ups along the way in my career. The pilot world of the US Navy begins more as a personal journey then most of the other career paths so my dive into leading young enlisted personnel started later than most. Early in my role, I had not yet realized the power my words carried and one of my sailors suffered from my ignorance.


I had a sailor who was struggling to make weight for pre-deployment fitness test. A group of sailors, including this one, were in my office passing around a bag of marshmallows one day when I happened to comment that "if they weren't careful, they'd all end up looking like the guy on the logo." Roars of laughter ensued before I realized my struggling sailor was the one holding the bag, marshmallow mid bite, and was now who they were all laughing at. He became the butt of any fat joke made for a long time. I had no idea how to right the situation but I knew I could not swing the pendulum the other way and defend him because that would only make things worse. So I chose the next, slightly less worse thing and did nothing.


My chief, my right hand enlisted counter part, came back from vacation about a week later and I tearfully told him what had happened. In true chief fashion, he told me he would take care of it and just like that the teasing stopped. The sailor went on to make weight, pass the fitness test, and deploy with us no problem. He never did look me in the eye again though. I had betrayed his trust and failed to support him. I considered my comments carefully from that day on and mostly removed myself from office banter unless it needed reigning in. Much like Kristen I started "to understand that my responsibility as a leader wasn't to party with my people...I was there to support them every chance I got" pg. 160 especially when they struggled.


"There's no guide that explains exactly what it's like to lead and that no one gets it right the first time" pg. 242 but Permission to Screw Up comes close. I bet, if we had him here today to ask, even George Washington hit a few bumps in the road along the way. Who have you inadvertently called fat? Have people quit and walked out on you? How have you screwed it up? I would love to hear about those or any other comments you have so far on the book if you are not quite ready to share your screw ups with the digital world. Email me, comment below, reach out on social media, or send me some snail mail!


Keep reading, leading, and dreaming! Next post on Permission to Screw Up will be Aug 2nd. Head on over to Amazon to order a copy if you have not yet taken the plunge. And spread the word on how awesome this blog is so more folks join the conversation.