My favorite mistakes
When interviewing job candidates, I have a favorite question. I'll save it for the end, although I know it’s going to tell me almost everything I need to know. It goes like this:
“Tell me about the biggest mistake you’ve made, or a time things went really bad, and how did you handle it?”
They answer one of two ways.
The first is a version of: “This bad thing happened, but it was really someone else’s fault. I knew what to do, but no one would listen to me.” This candidate gets an automatic no. Doesn’t matter how qualified they are on paper. I won’t hire that person.
The second answer sounds like this: “Oh wow, this one time I screwed up so badly. Here’s what happened. I felt horrible. Here’s how I handled it. Here’s what I learned.” That person moves ahead. That person is always successful.
I ask this question knowing that we all have our wince-worthy career moments. We’ve all made mistakes, acutely and chronically. And if we’re lucky, we learn.
I have grown to love my mistakes. Thinking about them makes me nauseous, of course. But I know I needed my pressure-cooker moments to burn off my ego and teach me things no book ever could.
With that spirit, welcome to my not-quite-highlight reel. Here are three of the top mistakes I’ve made and how they “made” me:
1. Working for the title/ the office/ the pay/ the praise
When I left journalism and joined the typical office world, I became hyper aware of my status in the organization. In journalism there are reporters and there are editors, and we all generally worked together in a hectic mass of newsroom cubicles.
In this new job, I had an office. And that office was in a certain place on the hallway. Some offices had windows; others didn’t. Some offices had assistants; others didn’t. Some people were referred to by first name; others called by their title.
All of a sudden it was very important to be very important. I made decisions based on how it made me look instead of how it made me feel. I was climbing a ladder without considering if it was leaning up against the right wall.
I was humbled out of this mindset when I joined a start-up company, where the fast pace of change made titles and offices were largely irrelevant. I rediscovered the joy of meaningless little conversations that flow between cubicle partitions. The satisfaction of doing without making a show of it. The value inherent to work, without the drama, without the ego.
Titles don’t create competence, and pay doesn’t create passion. Offices certainly don’t mean anything – just ask COVID.
Nowadays I just want to do a good job at something I like doing with people I like doing it with. It really can be that simple.
2. Waiting for permission/ waiting to be “chosen”
There’s a great quote by Steve Jobs that goes: “Everything around you that you call life was made up by people no smarter than you...” It took me too long to realize this. For much of my early career, I tiptoed around, waiting to be “called on” or recognized before I stepped up to say or do something useful.
Because I largely worked in executive communications, from very early on I often found myself in rooms of executives talking about big, consequential decisions. Sitting quietly to the side (never at The Table), I often had opinions or questions or concerns about the decisions at hand, but I kept them to myself… only to quietly begrudge the decision later.
Until one day, one of my bosses turned around and did the unthinkable: She asked me what I thought. Withering under the gaze of all the Very Important People who suddenly turned to look at me, I managed to eke out a question that prompted some reflection among the group. I was shocked. I wasn’t fired, nor laughed out of the room. I may not have been “qualified” to weigh in, but I did it anyway and survived.
Too often, we wait to be recognized or given permission by people we assume have it all figured out. But nobody has it all figured out. We’re all just doing the best we have with the information available. The cost of staying silent is worse than the risk of saying something “dumb.” And the reward? You jump on a flywheel of confidence and growth that just keeps spinning faster and faster and faster.
3. Letting emotions take control and needing to be liked
A boss once called me into his office and told me he was about to give me some feedback. “OK!”I chirped, trying to sound normal as I melted into a puddle of preemptive shame.
In so many words, he told me I had a lot of potential, but I needed to check my emotionality. “BUT… BUT…. WHAT DO YOU MEAN??!” I wanted to sob, suddenly seeing his point.
Staying neutral can be your superpower, he told me. Take the emotion out of it.
This was a few years before I immersed myself into mindfulness meditation, and I didn’t appreciate the message at the time. But now I can see how tightly I clung to the need to be liked, the need to be perfect, the need to be patted on the head. There were so many things I did or said that felt like logical decisions, which I now see were just reactions to how I felt at a certain point in time.
For those of us who care a lot about our work, it’s natural to be driven by feelings. Trust how you feel, certainly, but verify.
These days I do a lot of journaling to help me stay neutral. If I’m struggling with a decision, I write a series of questions, then answer them in third person to see my options clearly – a safeguard against making decisions on emotion alone.
Our brains are wired to think in patterns. The way we “feel” may just be our brain traveling along familiar neural pathways. It has taken me a lot of self-study, therapy, meditation and ruthless questioning to peel back the layers and see what’s really there.
I heard somewhere that what humans desire most isn’t contentment, but growth. If that’s the case, keep the mistakes coming…