Risking It All to Become an Author — My Interview with Robert Fieseler

I first met Robert Fieseler, who I know as Bobby, when he was working at an ad agency. Then, to my astonishment, I saw him make some big changes in his life. Even though he was on a great career track in advertising, he began taking classes in the evenings and weekends to get his journalism degree. Then, he quit his well-paying job in order to have the time to write a book proposal.

In our discussion today, we dig into every detail of that story, of how Bobby risked it all to make a creative shift from a full-time job to a full-time author. In the process, he redefined himself in many profound ways.

You can listen to our conversation by clicking ‘play’ below, or via iTunes.

When I invited him to do this interview, he said that this is stuff that no one else wanted to talk to him about. But this is ALL I care about because day in and day out, I work with writers and artists who want to realize their creative vision, and need to hear the stories of others who have leaned into that challenge.

In our chat, we track his career path:

  • He started out as a bookseller.
  • He then turned his experience writing poetry into a career in writing advertisements for brands such as Dominos pizza, Philip Morris and many others.
  • Why he went back to get his degree in journalism.
  • The reasons he made a huge career switch, even as he moved up the corporate ladder. He left his job to pursue an opportunity and spent his time working on a book proposal , with no guarantee that it would turn into anything. Everyone told him this was the worst thing he could possibly do from a financial or career perspective.
  • How he got his first big book deal and the process for creating that book.
    The reception to the book and the difference in his life since being a published author.
  • You can hear the moment in the interview when Bobby describes getting the offer for a book deal — he gets emotional just talking about it. That is how big that moment is for a writer. He says, “It made me feel like I was real. I had hidden my aspirations for a long time.”

He also talks about fears he has had as an author, and we end with a big discussion on impostor’s syndrome for writers.

Bobby is the author of Tinderbox: The Untold Story of the Up Stairs Lounge Fire and the Rise of Gay Liberation.

You can find him at: