My What If Year

If you were at the Coral Room with Rebecca, Laura, and Alisha, how would you answer Alisha’s question: “What would you do? If you could do anything you ever dreamed for a few months?”

On page 16, Alisha writes, “Every morning at three, I woke to my brain playing PingPong with itself. I found myself drafting imaginary emails to contacts in the art world or thinking about how I might tailor my resume for a job at a hotel. But then, in the clear light of the morning, reality would set in. Fear and reality. I had too many obligations, too many responsibilities, too many things other people needed from me; I couldn’t see any fathomable way to bridge the gulf that seemed to exist between idea and internship.” Has an impending decision ever kept you up at night? Have you ever been scared to take the next step?

When Alisha talks about leaving Broadway, she says, “As I turned to go, I couldn’t resist a peek at the bare stage. The production team had removed all vestiges of Dracula, and the Assassins setup wouldn’t start until the following day. I stood center stage and closed my eyes, imagining an audience filled with anticipation of the opening chords about to be played. It was a future that seemed like it would never happen now. I took a deep bow to the empty room, savoring my last moments as a theater intern, or maybe as an intern altogether, and then stood up and silently walked out the stage door for the last time.” Did you have moments like this in 2020? Think about turning points in your own journey.

After meeting with Harry, Alisha and Carlos go to an outdoor performance of Jesus Christ Superstar. “The cast filed onto the stage, one by one, wearing masks. At the crescendo of the overture that I’ve heard a hundred times before, they all pulled down their masks, slowly. Mine stayed on, as the rules required, but underneath, tears were streaming down my face. My first performance since leaving New York felt like coming out of hibernation: a fragile new seed, a promise that something hopeful was ahead.” Why is this moment so moving for Alisha? What do you think made her feel so hopeful?

Near the end of her internship with Harry, Alisha visits one of Edward Ruscha’s exhibits. “In a small corner of the exhibition, there was a lone business card. Apparently, no one could pronounce his name ever, so he had some printed that said: EDWARD RUSCHA (ED-WERD REWSHAY) YOUNG ARTIST. I guess I wasn’t the only one who needed some guidance. Maybe everyone in the art world had a little bit of imposter syndrome. Just like me, they were figuring it out as they went along.” Alisha was a CEO before taking on her internships. Where do you think her imposter syndrome came from? Have you ever experienced imposter syndrome?

As Alisha is getting ready for her internship at Kinloch, she writes, “even contemplating the idea of going “back to normal” incited a cold sweat. I didn’t want my old normal. I didn’t want to go back to sitting behind a desk and staring at a computer screen with an inbox of hundreds of emails, fixing the margins on slide deck after slide deck or reconciling expenses or creating proposals for new work. I wanted to be creative, challenged, pushed. I wanted to do something different than normal.” Why do you think Alisha was so set on not going “back to normal”? How can we add creativity and spontaneity to our “normal” lives?

To prepare for her interview at Kinloch, Alisha went to her twins, Theo and Lola, for support. “The twins offered to help me prepare by doing a mock interview. They sat on the sofa and peppered me with questions like ‘Why do you want to work at Kinloch?’ and ‘Do you know how to make spaghetti, and can you make some right now?’” What questions would help you prepare for doing an internship like this? Also, can you make spaghetti?

On page 238, Alisha writes, “‘Joy’ - such a simple, small word that holds so much complexity. It’s more than happiness. It’s ebullience. It’s a celebration. A party all day, every day, where everyone is invited. People think joy is elusive, and they’re right; its impermanence is what makes it all the more important to cultivate, nurture, and appreciate it whenever it comes your way.” How do you cultivate, nurture, and appreciate joy in your life? How could you be better at it?

Near the end of the book, Alisha says, “Changing your life is hard. I can see why more people don’t bother. ” What is a big change you have made in your life? Was it difficult, and would you make the same choice now? Why do you think more people don’t change their lives?

What is something you loved about My What If Year? How did it challenge you?