I'm in....

My biggest fear of starting my new job was that people wouldn’t find me funny. I don't know if you've noticed, but I'm hilarious.  And, I don't know about you, but when one is hilarious, and comedy is lost, that, my friends, is a tragedy.  After 4 years at my previous place of employment I had built up my reputation with my ability to write emails with just the right level of sarcasm and dry wit were usually very well received generally garnering praise.  And, not gonna lie, I enjoy writing them as much as I enjoyed hearing the chuckles around the office after hitting “send.”   Now that I’m at a new place, I find myself refrained/completely censoring myself.  What if they don't think I'm funny? What if my humor is lost on them? Sarcasm is tough to pick up in email anyway, let alone in a super-professional-world-changing-overly-polite workplace. It makes me sweaty just thinking about it now.

Now, this directly coincides with my petrifying fear of my Senor Big Boss (henceforth referred to as SBB).  He actually is not big in stature but crazy wicked smart, hilarious to boot and speaks with a heavy Venezuelan accent that I have troubles deciphering sometimes (all the time).  A doctor (MD and PhD) he worked with his previous assistant for several years who he had a great relationship with (as far as I can tell) so I’m following in someone else’s habits and previous established expectations.  This is not a comfortable place for me to be. One of my neat character traits is constantly seeking/need of approval (hello other over-achievers, you can understand) so I've been working in hyper-drive to figure out how to do my job while also desperately finding a way to make SBB like me.   

So last Friday, after 2 weeks of refraining my wit and charm, I decided no time like the present. Now was my chance to win him over. I carefully crafted a very articulate but and charmingly witty email.  I got really nervous, palm sweaty, heart-pounding.  Send.   

Shortly thereafter, SBB comes out of his office and says to my admin boss, "Did you read Cara's email? It was very good, very very good." He looks at me, smiles and says, "It was very funny, very good." He then responds to my initial email with one word. "Excellent!" (His exclamation point). That was it; I had won him over. I was in.

I walked home with an extra skip in my step.