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Funny Business Lady


By Brynne Humphreys – Vice President of Client Services

At the end of 2015 I was chatting with Rachael Mason, a veteran improviser and recovering corporate workforce member, about the parallels between women in corporate America and women in comedy.  Her perspective is unique, as it pinpoints the  intersection of these worlds that make up our our company, Second City Works.

As we continue to develop new programs and evolve our POV on leadership and all the humans that are in leadership positions, we’re excited to talk with some of our strong, fancy, funny ladies and share their stories.

Ladies and Gentlemen, Rachael Mason: 

SCW:  Describe your background and the intersection of improvisation and business – how does it work for you?

Rachael:  I had worked in the finance industry for almost 20 years. I saw no glamour to starving artist so I worked every hour I wasn’t sleeping or performing in an office. I was a bank teller, bookkeeper, finance manager, HR manager, and heck I still do payroll for the department I now head up at The Second City. I like being able to subvert the corporate world with funny and in turn bring a little business slick to my comedy. It keeps me an honest person having a foot in both worlds.

SCW:  “Women aren’t funny” is such a tired statement, but one that still makes the rounds.  What was your experience of being female in a male dominated craft?

Rachael:  I was told upon arriving in Chicago that Del Close, one of the founding fathers of improvisation, hated women.

I like to say that growing up Italian/Irish prepared me for the inherent misogyny in comedy so I felt ready to deal with a dated relic who resigned women to wives and mothers on stage as the old men in my life did to the women in my real life. I learned from a very young age that if you could make the old men playing cards laugh then you did not have to go to bed. I was still downstairs doing my Mae West when my brother and sister were upstairs asleep.

So when I arrived in Chicago ready to seek my comedy fortune I had my “experience” and a quote from Steve Martin on my side, “Be so good they can’t ignore you.” I knew I was good… not better than anyone, not trying to be good, but good and trying to get great. I also assumed that If I got in a room that the people in that room were just as good as me. That’s why we were all in the room together.

SCW:  Did you ever confront Del about his misogyny?

Rachael:  I quickly began to realize that Del did not hate women. He loathed soft choices and maybe women have more trepidation about being wrong… but women drive less recklessly than men and get into fewer accidents. My father once said “people think women are terrible drivers so you will not be one.” FYI, My mother ran his trucking business.

I know that in the real world of acting I get type cast as what I look like so I know that in the world of improvisation it would be a crime if I didn’t actively play all the things I would never get to play in real life. I would never be cast as the following in real life (so I most heartily tried them on onstage): The CEO, The Coach, The Murderer, The Detective, The Bartender, The Mechanic, The Conqueror, The Monster, The God … and I had a lot of fun doing it too. Del never complained, in fact he praised me. Just like he praised Tina and Amy and Rachel and Honor and Melanie and all the other girls I saw doing great improv around me. I’m pretty sure he told Amy that she could take over the world and she basically has.

SCW:  Interesting.  So you didn’t experience Del as sexist?

Rachael:  Seemed to me like Del loved women. Like there were nothing but incredible women around me. I think there are two reasons for this: 1. Everyone in improv has to “yes, and” everyone else, man or woman. You have to say yes and explore the first idea even if it came out of the mouth of a woman and 2. A certain kind of smart person is drawn to improvisation, one who is not afraid of the nothing ahead of them but will rather throw their skill set at the void in excitement of the resulting chemical reaction. I was surrounded not only by great women but by amazing people who made and respected each other’s choices.

SCW:  How did this kind of experience mirror or contrast your corporate office experience?

Rachael:  There are a couple of HUGE similarities between being in comedy and working in an office:

A). I was usually the only women in the room.

B). I was given a tremendous amount of respect because I was good at the job.

C). Choices that are backed up and stood by are valued.

D). Failing can teach you things.

E). You will in life occasionally have to access your inner CEO, Coach, Monster, Conqueror, and Detective.

As a women in both comedy and business I have realized the greatest skill is being able to pivot and having the resources to back that up, that control, age, race, and gender are an illusion, and that talent is undeniable.

The people I have had the pleasure of dealing with in both the comedy and business world understood those things…. that’s not to say we can’t strive to make the world an even better place.

SCW:  Yes, let’s!  Any suggestions?

Rachael:  Things that would make the world an even better place:

If relics were moved to museums

If you said yes more

If you gave the respect you think you deserve

If your choices were made fearlessly

If everyone took an improv comedy class

Rachael:  Ladies, if you want it go get it. Do great work and great things will happen. I’d say the same thing to a man.


Become others-focused to see another POV,  D&I,  I don't want to make the wrong move on D&I,  talent development,  training development


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