Anna S.— First Awesome Boss (Hero #3)

My heroes are people who shine, act and broadcast clear ideals that have shaped my personality and mission in life. Heroes don’t always save babies in burning buildings. Sometimes they simply show us courageous ways to live in the world. In one way or another, all of my heroes are Not F*ing Around.


When I rolled into Seattle at the tender age of twenty four, I was struggling to pay the rent (and find a decent drummer). Through a series of incidents (which I still attribute to divine intervention) I found myself in the office of Anna S., the woman who was captaining the ship of a radio station known as The End, 107.7 FM.

Let me step back a minute. It was the mid-nineties and The End had just broken a slew of local bands onto the world stage— Nirvana, Sound Garden, Pearl Jam, etc. At the time, the station was arguably the most powerful musical tastemaker in the known universe. Our superstar DJ Marco Collins would one day be inducted into the Rock n Roll Hall of Fame. We scored a huge story in Rolling Stone. This place was the center of the cool.

Besides all of that awesome, a little thing called the internet was being born. The station had some deep pockets and some forward thinking. At the time we were the biggest music website in the world. And through the aforementioned divine intervention, I was the sole writer of all of the content on the site. Record reviews, concert review, interviews, and whatever else we could dream up. Holy shit wow! Exciting times.

So anyway, I’m sitting in Anna’s office staring out the skyscraper window (as the guy in the next room rocked the emerald city with a playlist of heavily distorted grunge tunes). I asked Anna question after question after question about the small details of my job. After all, I wanted to please her and kick ass. It was a huge opportunity and a very big deal.

She listened patiently as I rattled off the queries. Then she spoke.

“Jeff, I hired you because I think you’re smart and talented and creative. Just do whatever you think is best.”

What? Seriously?

I literally couldn’t believe what I heard. Every other boss at every other job I ever had— from flipping burgers to cleaning toilets to telemarketing home security systems— didn’t trust me (or anyone else) any more than they absolutely had to. They always micromanaged, and they always did things half assed anyway. For the first time in my life my boss empowered me to do my job. Hallelujah!

This was a revelation. And with that freedom I stepped on the gas. I made choices without asking for approval or permission. Soon the site became a huge success. Anna and the rest of the gang were thrilled with my work. F*yeah!

Anna S. is my hero because she gave me a gigantic opportunity when I wasn’t completely qualified for it. She empowered me to trust myself. And she believed in me in ways that no one else at the point ever had. To this day my memories of Anna remind me to let go, to give others a chance to shine, and to forget about trying to control every aspect of my projects.

Thanks, Anna. For the amazing opportunity. For the wisdom. And for the getting me backstage at a zillion  amazing shows.


Who was your best boss? Why?

What have your learned from you bosses?


About the Author:

Jeff Leisawitz burns with a mission—to inspire writers, artists, musicians and random creative types to amp up their creativity, heal their hearts and shine in the world. Author. Award winning musician/ producer. Internationally distributed filmmaker. College prof. Photographer. Speaker. Consultant. Not F*ing Around—The No Bullsh*t Guide for Getting Your Creative Dreams Off the Ground is Jeff’s first book.

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