Life Advice From Anna Wintour.

My Saturday morning alarm goes off ta 6:15am. While this may seem obscene and simply against good judgement, there is a reason why I set it for so early.

It's because I know that no matter what time it goes off at, I will fall back asleep for another hour... Before waking up naturally. And since I wanted to hit the 8am Bikram class this morning, setting it at 6:15am was strategic. 

So I rolled over and tucked myself further into my sheets, falling back asleep very quickly... And into an epic dream.

I was walking in a city. I was busy running around on errands. I grabbed some coffee at a cafe... And as I was attempting to walk through the doorway to leave, I see a woman sitting right in the doorway, on the stoop.

It was a former worker of mine from back when I worked at Martha Stewart. She was a buyer. 

"Amanda!" I said. "How are you? What are you doing here?"

She looked at me with a grumpy face. 

"Since you're here, you can take over for me," she said.

"Um," I laughed. "Take over for what?"

"You have to take care of Anna," she said, pointing to the woman sitting in at a corner table.

It was Anna Wintour.

I stared. Starting to laugh from the absurdity, I began to turn to tell Amanda there was no way I could help her out at the moment. But when I turned fully around, I noticed that Amanda had stood up and was starting to talk.

"Anna," she said, "Heather is going to take care of you from here."
And she left.

I walked over to Anna, expecting her to throw a dozen crazy requests at me for which I had no energy to execute against. 

"Hi, Anna," I said. "What can I do for you?"

She smiled. Asked me to sit. She started asking me a ton of questions about myself.

  • What did I do for work?
  • How did I feel about designers venturing into other creative endeavors outside of clothing design... Like music, photography, art, writing?
  • What did I want to be doing with my time? What kind of work did I want to be doing?
  • How did I take my coffee?

Even in the dream, I knew how absurd this all was. I stuttered through my answers to her... Explaining that I had reached a point in my career where I wasn't focused on roles for money. But I was trying to figure out how to best be useful and doing something that allowed me to feel productive.

"So right now, I am working in the field I've been in for over a decade. I am good at it. But truly, I want to have more free time than it allows for me to have. So I'm still working on envisioning what I want. But I don't think this is it. I think at some point I'll start doing something more creative."

Anna smiled. She encouraged me to explore creative opportunities, outside of my work. 

"Everyone creates in ways that are outside of the typical area in which they operate. You are more of an artist than you realize."

I thanked Anna for her advice. We sat sipping our lattes. I guessed that what she needed was just to inquire about a new person's life.

Then I woke up.

Who would have thought Anna Wintour would be giving me advice?