In Pretty Woman, a minor character shown in the background of Hollywood when Edward meets Vivian, yells: “What’s your dream?” Over and over. He’s shown in this scene, and in one of the final. “What’s your dream?”

What’s yours?

What will be your legacy?

As Mama Gump explains to Forrest on her death bed, “We all have a destiny, Forrest. I didn’t know it, but I was destined to be your Mama.” Then she rhymes the breakdown on boxes of chocolate, and the metaphor is that you have no idea the hand out life will give you, but ya gotta make the best with whatcha got.

What’s your dream?

Every time the Oscars, or the Grammys come around, I look at the glistening starlets and listen to them talk about how they were once a child in the bathroom, staring into the mirror, thanking God and their families with a makeshift microphone; usually a hairbrush. And they smile, and accept their award, and they head to the back of the stage, to be greeted with paparazzi and a barrage of questions about their next projects.

I look at them, and I ask myself, what will be your legacy?

What will you be remembered for?

What’s your dream?

“He says, ‘Bill, I believe this is killing me!’ as the smile runs away from his face. ‘Well, I’m sure that I could be a movie star, if I could get out of this place.'” sings Billy Joel, reciting a lamenting bartender in his tune, “Piano Man”.

Did I want to be a movie star?

Did I want them to chant my name when I stepped out on the stage?

I don’t know if I’m done doing what I was meant to become. They say Vera Wang designed her first dress at 40. And Oprah was fired in her 20s. And how old am I? I’m only 37. That’s it. I’m just 37.

Can you have it all? Can you have big dreams, and big wants, and big desires? Do you have to let them go, and forego the chase – the pursuit – when you get to a certain age? Do you have to resign yourself to this is all you’re going to be?

“Mr. Holland isn’t rich. And he isn’t famous,” spoke Gertrude Lang in Mr. Holland’s Opus before inviting Mr. Holland to the stage to pick up his trusty baton and lead a choir of former and current students through his first orchestral piece.

What’s your dream?

I did it backwards, you know. I had the kids, and then I chased the career. I’m raising them up to be incredible humans, and one is already out the door chasing her first apartment; the other two right behind her. And I get to watch Jan raise his own two daughters and find the joy in giving them the insight and know how to follow their own dreams; seek their own destinies and carve their own paths.

When he and I got together, I was very clear and transparent that my desires for a big future were not something I wanted to sacrifice on the altar of relationship. And he, being the man that he is, told me he loved me because I had the courage to dream, and the tenacity to try. The willingness to get out into the world, and chisel my name along the walls of the hearts of the people I’d meet.

What will be your legacy?

I want them to say that I tried.

I wanted to write, so I wrote. I wanted to write a novel, so I composed one.

I wanted to sing, and play, so we acquired a piano and I sang and performed.

I wanted to act, so I auditioned. I wanted to ride, so I busted out a skateboard and rode. I wanted to paint, and draw, and sketch, so I brought home the easel, and the supplies and I created.

I tried it all.

And if I never see the inside of the Dolby Theatre, or the Staples Centre; if I never take the elevator up Rockefeller Plaza, or sit for drinks at the Bluebird Cafe. If I never broadcast from the CN Tower, or see Sydney, or Easter Island, or Big Ben – I tried.

I tried, because I wanted my legacy to be someone who just wasn’t afraid to think big, dream big, and be bigger.

“Can a man change his stars?” asks William to his father in A Knight’s Tale.

I tattooed this sentiment to my ankle, and I seared it into my heart.

Change your stars.

What’s your dream?

— c ☆