Meet Westley Heine

We were lucky to catch up with Westley Heine recently and have shared our conversation below.

Westley, we’re thrilled to have you sharing your thoughts and lessons with our community. So, for folks who are at a stage in their life or career where they are trying to be more resilient, can you share where you get your resilience from?

At certain periods in my life I found myself living day to day, hour to hour. Be it in jail, or living in my car cross country, or when I was a squatter in Chicago hustling as a street musician. After those experiences normal stressors like a job interview or corporate BS at work roll off my back. The world is a stage and by exposure I’ve overcome stage fright.

Thanks, so before we move on maybe you can share a bit more about yourself?

I am the author of Busking Blues: Recollections of a Street Musician and Squatter (Roadside Press 2022), and a short story collection 12 Chicago Cabbies (Newington Blue Press 2021). Most recently Roadside Press has released a poetry collection Street Corner Spirits (2023), and a new collection of short stories and poems entitled Cloud Watching in the Inferno (2025), both of which have spoken word albums available on all streaming services. I host the monthly poetry open mic at The Gallery Cabaret in Chicago. I was a featured poet at the original poetry slam at the Green Mill, Underground Lit Fest, The Vagabond Poetry Tour, and was the poet chosen to represent Illinois at the Route 66 Poetry and Arts Festival 2025.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

The three most important things that got me to where I am now as a writer is having many lived in experiences, then the actual practice of writing, and finally learning to edit and publish the work.

First, don’t allow yourself to be sheltered. Nothing new or original comes from commenting on or regurgitating what’s on a screen or in another book. Sneak out at night, travel, fall in love, get your heart broke, get drunk, get high, see a vision, or do a sport or cliff dive. Whatever turns you on do it while you’re young. You’ll have your whole life to write or reflect on it.

Writing is about knowing how to at once be out in the world gathering experience, but then pulling the window shade in a room and practicing the craft. I wrote my first book in high school in 2000. It was awful, but it let me know I had the attention span to follow through. I wrote another in college in 2003, again a practice book. I wrote short stories and poems constantly over the years. By 2015 I wrote out my whole life for catharsis, for therapy, and upon looking up the average length of a novel I saw I had five books worth of material. However, editing it all into something that would resonate was another step. I was lucky to have a professor in college James Berg who years after taking his English class continued to read my work and give me feedback. Also, in 2004 James brought me to the original poetry slam at the Green Mill in Chicago. There and at other open mics I’ve learned that exposing your work to an audience helps hone your craft, and tighten the delivery. Whenever I read a piece of writing out loud it always causes me to edit it and smooth out the language so it works on both the page and the stage.

Publishing is a separate skill. The first time I queried literary agents was back in 2016 when I was in Texas. I was going about things backwards. I had a new novel edited, but next to no publishing credits. Emailing the book to these people in the traditional industry in New York was knocking at a giant closed door. After I moved to Hollywood in 2019 I said hell with it and started sending out poems and stories everywhere. Online journals lead to print journals. A bit of bio showing others took the work led more editors to accept it. By 2020 I had been practicing writing for two decades. I had enough practice to write 12 Chicago Cabbies on the weekends the first half of 2021 while working full time, which was published as a limited run the same year. I wrote Busking Blues on the weekends the second half of 2021, which came out in 2022 through Roadside Press.

Poet and publisher Michele McDannold at Roadside Press provided a fair deal with royalties and copies of the novel for readings. This changed my creative life from a hobby to being a practicing author. Having a book out is its own currency. It has led me to readings and festivals where I can sell and share my work. I have been introduced to a whole community of readers and writers in the independent lit scene. This has been 20 years in the making. Through bad relationships, bad jobs, night shifts, being on the street, through lock down during the pandemic with the smoke from wildfires looming in the distance like mushroom clouds I kept writing.

Before we go, maybe you can tell us a bit about your parents and what you feel was the most impactful thing they did for you?

They were kind to me. Despite having to bail me out of jail countless times when I was kid they were kind to me. They didn’t see it as personal failing on their part because it wasn’t. I was young, full of energy, and hungry for experience. Somehow I was able to get decent grades while otherwise drinking to excess, having sex, doing drugs, getting into fights, and rebelling against the puritan small town values I was surrounded by. I got a lot out of my system. By the time I was an adult I was content and didn’t aggressively self-destruct any longer. My mid-life crisis has amounted to taking a leave from work to concentrate on becoming a better writer.

Contact Info:

• Website: https://roadsidefam.com
• Instagram: @westleyheine
• Facebook: https://www.facebook.com/westley.heine
• Youtube: https://www.youtube.com/channel/UCLWGl5QQGqvx6YBhp6BgLTA

Image Credits

Dmitry Samarov created the drawing