My Biggest Career Mistake: Sailing, Secretaries and Lime Green Pants

Green Pants
I believe in the power of mistakes.

No one likes to make mistakes, of course. But that is where the learning happens. Bigger mistake, greater opportunity to learn.

What may have been my biggest career mistake happened very early on, while I was still finishing my undergraduate degree. I had my very first internship and was ready to conquer the world. Good so far. I also thought I knew exactly how to do it. Ha!

I was a lowly intern, feeling on top of the world that I had gotten “in” at a place that I very much wanted to work. The secretary in the department was very good to me, trying to help me out so I could make my way. But I didn’t take the cue.

Not only did I not yet understand that secretaries rule the roost (if not the world), but I did not appreciate that someone could make choices very different than mine and still have a lot to teach me.

Here’s the thing. This secretary (we’ll call her Nancy) wore lime green capri pants, corduroys and other outfits to work that in my naivety had judged as “not fit for the professional world”. I call myself naive not because I was wrong to recognize that Nancy would not move up the corporate ladder if she didn’t emulate the look of those at the top: dark-colored suits. She wouldn’t. Rather, I assumed that moving up within the organization was and should be Nancy and everyone else’s goal, without realizing that she had her own plan. One that was more carefully formulated than my 19-year-old point of view would allow.

Nancy wanted a place to work during the day (while she pursued her own interests on the side) that was forgiving enough so she could wear want she wanted and be whom she pleased. She was expected to conform to certain norms and left blissfully free to ignore other ones. She made calculated decisions to achieve the results she wanted. She knew exactly how to get where she wanted to go, but it wasn’t anywhere that I could have imagined.

So when Nancy pulled me aside one day to tell me that I should “follow the lead” of the head of the group (we’ll call him Troy), who wanted to talk about basketball and sailing a good part of the time, I ignored her advice. I wanted to ask Troy about things that interested me, and at the time these were not at the top of my list. While others joked and called him Captain Troy, I smiled through gritted teeth and pushed on for the certain set of experiences that I had expected out of the internship.

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After all, we were not on a yacht, we were in an office. I wanted to learn the ways of leadership and success, and they were not going to come from talking about sailing, I thought. At the time, I didn’t have a boat, or any family or friends with a boat. The one time I had taken an extended trip on a boat as a child, I had been seasick most of the week. I was bound to say something ill-informed, so wasn’t it better to steer the conversation back to what was comfortable to me?

I couldn’t look bad if I just avoided topics that were out of my league, right? Anyway, I reasoned, what did Nancy know, with her green pants and all? How could a chat about sailing be useful to me at all, other than to smile and humor my boss? Why would I encourage him to continue that conversation?

Turns out, Nancy knew a lot. In particular, she knew how to keep everyone happy while keeping herself happy. She kept these two goals in perfect balance, giving Troy and the group the support they needed while feeding her own needs. She intuitively understood that showing an interest in sailing was showing an interest in Troy. And that was the important part.

By contrast, I was being immature, overly serious and even selfish – holding on to the world as I knew it – by expecting to direct the line of conversation. And I was missing out on the chance to learn, bond, grow and have fun.

So, my biggest career mistake was actually a set of related mistakes:

Mistake #1: Discounting the message of an unexpected messenger.

Mistake #2: Closing myself off from new experiences.

Mistake #3: Making it all about me.

As I found out later, the green pants were a statement on Nancy’s part, a line in the sand that she was in a bridge job and had no pretense of “moving up” to a management position within that organization. She had her eyes on another prize – her own set of professional goals – but she also made sure to be so good at her job (orienting herself to the situation, as needed) that there was no way she would risk losing it over something as simple as wardrobe choices. In fact, as a highly creative person, she literally wore her authenticity on her sleeve. And she was respected for that by others in the group, including (in the months and years following my internship) by me.

I often think back to Nancy, the unexpected messenger, with whom I have lost touch in the over 20 years since I had that internship. I am indebted to her wisdom. I wonder if she has started her own company, maybe even a fashion line.

Nancy could have changed her style of dress any day. Changing my attitude took a lot longer.

From my biggest mistake, I learned my greatest lesson. It is not all about fitting in, it is also about being a fit.