How I Made a “Fool” of Myself at Work

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I set out to write a serious, reflective piece this month to mark the first anniversary of my That Nonprofiteer column—until I found out that it will be published on April 1, April Fools’ Day.

I don’t have any jokes, but I do have countless examples of me making a fool of myself in my career. Here are just couple I thought I’d share.

Story continues below.



What’s all this crap on my computer? 

embarrassedWhile I was in graduate school, I worked full-time in an academic department of a business school, providing administrative support to the professors.

One slow afternoon about a month into the job, I was eager to organize my physical and electronic files. My computer seemed to have an incredible amount of files from my predecessor, so I started deleting one file after another, making a sport of it, and enjoying the flow.

Then I came to a dark realization. These were not the former user’s files. I had never worked in a networked computing environment before, and didn’t realize I could access my colleagues’ files.  I had just trashed a huge chunk of files belong to a PhD student named Ravi. I almost threw up.

With tears rolling down my face, I told my supervisor, Carol. I still remember how she gave me a hug and sympathized with me. She brought Ravi into her office, so we could tell him the terrible news. The man’s face turned pale, but he did manage to say to me, “Don’t worry, I’m sure I can recover them,” before running out to assess the damage. Carol looked at me kindly and insisted that she should have explained better the systems we were using, and that everyone learned a good lesson, including the PhD student who should be backing up his documents anyway.

When I showed up to his desk to apologize once again, he said with a smile, “I recovered most of the important stuff. It’s not your fault.”

I need to find that man and thank him for not destroying me that day.

You seem to have sent me a boy’s sweater. 

Urkel - Did I do thatI was a relatively new program director at a young nonprofit startup.

My executive director, Rich, asked me to mail out a grant proposal to a brand new foundation prospect; he had completed the proposal himself, but could not mail out before leaving for the day.  I took it gladly and told him I would take care of it right away. While I was in mailing mode, I decided to also take care of sending back a J.Crew sweater I needed to return by mail.

You can guess what happened. I sent the burgundy sweater (I can still see it in my mind) to the foundation, and came back to my desk to see the grant application sitting there.

I called my boss in horror. He actually laughed out loud (God bless him…), and in between laughs, advised me to call the foundation and ask if I could come pick up my sweater. He also suggested I hand deliver the application packet on the same trip.

It turned out that the foundation was just few blocks away from our offices, so they received my sweater that same afternoon. A lovely woman left us a voicemail asking why we had sent them a little boy’s sweater. (For the record, it was a woman’s size XS.)

I walked those blocks with the application package in my arms, so ashamed but also grateful that it was just a sweater, not something from Victoria’a Secret.

This is really not a good time. 

Story continues below.



My first week back from my first maternity leave was spent trying to figure out when and where to pump milk. I roamed our offices with a large black shoulder bag concealing an electric pump, a cooler for milk bottles and a separate bag for my files, water and a snack.

The first day, I couldn’t find time to pump. I didn’t know how to leave a staff meeting, then a funder meeting, abruptly to do the deed. I actually got sick from not pumping regularly that day.

The second day, I had a semi medical emergency because I didn’t pump the first day. I had to stay home.

The third day, I walked around our offices and meeting space looking for an empty room. We had windows in every room, and there were no locks. I had not thought this through well.

Desperate, I grabbed giant post-its used for presentations and covered the window of a small conference room seldom used. I sat down, put a nursing cover over myself and began the deed. As soon as I started and the swooshing sound of the machine kicked in, a young, male colleague walked in. He was also a new employee. I gasped, and he apologized and walked out. But then he decided to come right back in. “Sorry to startle you. But it’s so nice to have you back in the office!”

I put on my poker face (I was “decent” but the machine is still going) and said “it’s nice to see you too,” assuming he would then leave. But he settled in, starting up a whole conversation. With the swishing sound of the pumping machine still going, I calmly stated, “This is actually not a good time.” He looked puzzled and was about to say something. Finally, I semi-ordered: “Please leave.” I am not sure he heard me but he ran out, mumbling “oh okay!” He and I have never talked about that day. (I’m sorry!)

As I read what I’ve written here, I laugh but I’m also reminded of how desperate each situation felt to me at the time. And I can’t help but wonder how different these episodes would have played out had I not been surrounded by such kind, supportive people in these vulnerable moments in my career.

What’s your workplace “fool” story? Happy April Fools’ Day!

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Caroline Kim Oh
Caroline Kim Oh is an executive coach to nonprofit leaders. She dove right into the nonprofit world after college and spent twelve years running and growing iMentor in New York City prior to coaching. Frequent speaker and advisor on a variety of nonprofit management issues, she’s also a cheerleader for all who experiment to find and tweak the optimal work-life-happiness mix. Find her on LinkedIn and on Twitter, or send her an email.