Interview with Ryan Dowd

Ryan Dowd posing with A Homeless Christmas Story

Ryan J. Dowd has spent most of his career as Executive Director of a large homeless shelter near Chicago. In addition, he trains organizations around the globe (including libraries, homeless shelters, and hospitals) on how to use empathy-driven enforcement with homeless individuals. He is the author of The Librarian’s Guide to Homelessness and A Homeless Christmas Story. You can find him online at and

Shauna Kosoris: What was the inspiration for writing your first book, The Librarian’s Guide to Homelessness?

Ryan Dowd: I started volunteering in a homeless shelter when I was 13. I joined the staff at 21. I’ve spent a lot of time working in homeless shelters.

Our local library asked me to help them understand their homeless patrons. I didn’t know that every library in the country was struggling with these same issues. So I started doing trainings for libraries.

I happened to be speaking at a library conference and the publishing arm of the American Library Association was there. I casually mentioned that I could maybe be coaxed into writing a book and they jumped all over it. They were a ton of fun to work with. I’m not sure I could have finished it without them. There was always one more thing I wanted to add or change and they helped me understand that at some point you have to be done.

I think that’s something that many authors and creators struggle with! You’ve just released your second book, A Homeless Christmas Story. What can you tell me about it?

It’s a story that I actually wrote as an email 15 years ago and sent out to volunteers of our shelter. I found out later that several churches read the story at their Christmas Eve services, too. I pulled that story out every Christmas. A year or two ago my wife asked, “Why don’t you make that a book?” I didn’t have a good answer!

What is particularly fun about this book is that actor Emilio Estevez (Breakfast Club, Young Guns, etc.) did a professional recording of himself reading the book. We are turning it into a video of the book with Emilio narrating. We’ll release that soon at

Emilio is a good friend. We met a few years ago when he made a movie about homelessness and libraries (The Public). We ended up doing a 30 city tour together to promote the film and raise awareness about homelessness. Emilio really cares about homelessness, so it was a great fit to bring him into the project.

That’s very fun! Your first book was geared towards adults, while A Homeless Christmas Story is written for children. Why did you decide to write for a younger audience this time around?

The Christmas book is a children’s book, but it’s also not. I tried to keep the length and language appropriate for younger audiences, but the wider message is applicable to any age.

It’s funny, though, because people will call it my “first children’s book” and I have to correct them and say “only children’s book.” I didn’t set out to write a children’s book. I set out to help middle-class folks understand individuals experiencing homelessness. In this specific case the best vehicle for that was a children’s book. I don’t know if I’ll ever write another, though. We’ll see!

Did your writing process change when going from The Librarian’s Guide to Homelessness to A Homeless Christmas Story?

Dramatically! The first book is something like 40,000 words. I locked myself in a basement for 2 weeks and wrote 18 hours a day to get the first draft done.

With the children’s book, it is less than 1,000 words and I had written the bones of it 15 years ago. The harder process for this book was making sure that every word was correct. With 40,000 words, the reader will forgive a little sloppiness. Not so with 1,000 words. The editing was really hard.

A Homeless Christmas Story is also self-published. Why did you decide to go that route?

It is incredibly time-consuming to break into the children’s literature world. A lot of people want to write children’s books. Since I only envisioned myself writing a single children’s book, I didn’t think it made sense to try to secure an agent and publisher, etc.

That’s fair. So how did you end up working with your illustrator, Bradley H. Clark?

I have zero artistic ability. I can’t even draw a stick person that looks right. I knew I needed an artist and I knew they had to be really good because the book was going to live or die by the quality of the art more than the writing.

I went out looking for someone who could paint like Norman Rockwell. Bradley sent me his portfolio and I was blown away. His style was exactly what I was looking for.

I had never met Bradley. In fact, I’ve still never met Bradley. We’ve talked on Zoom several times. It is very difficult to trust your literary baby to a stranger, but I was really, really fortunate to find someone who saw the vision and had the talent to execute it.

What are you working on now?

Most of my time is spent creating video training courses around homelessness (or working in a homeless shelter). I already know what my third book is going to be, though. It will take several years to write, so it’s too early to talk about. It’s not a children’s book, though.

I look forward to hearing more about it one day! You said earlier that you want to help people from a middle-class background better understand people experiencing homelessness. What can those from a middle-class background do for people of all ages experiencing homelessness?

The number one thing is to treat people with humanity. Make eye contact. Say ‘good morning.’ Stuff like that. The tiny little interactions are what allow a person to feel some dignity.

Donating and volunteering to your local shelter is also incredibly impactful. Most shelters are running with tiny budgets. Even small donations can make a HUGE difference.

At our shelter, 75% of the donations come between Thanksgiving and Christmas. My guess is that this is normal for shelters. Ideally the donations would be spread out a little more, but shelters learn to budget for the huge swings in donations. It is more important that people donate than that they donate at the right time.

To wrap this up, I’d like to ask you a few questions about reading. What book or author inspired you to write?

This will sound odd, but it is Jack Kerouac. Dharma Bums is my favorite book. I started reading it 25 years ago and I’m still reading it. When I get to the end, I just start back at the beginning. I read other books, too, but something always draws me back to Kerouac.

Is there a book or author that you think everyone should read?

I’ve been reading a lot of Fantasy lately. I think I’ve read everything by Brandon Sanderson. If I had to pick one book everyone should read, though, it is Nelson Mandela’s autobiography, Long Walk to Freedom. The story is so important and the writing is top-notch.

And what are you currently reading?

I tend to read several books at a time. Right now:

  1. Dharma Bums by Jack Kerouac
  2. The Only Pirate at the Party by Lindsey Stirling (the autobiography of a rock and roll violinist)
  3. Founders at Work by Jessica Livingston (She interviewed dozens of entrepreneurial founders and then transcribed the interviews exactly into the book. People were WAY more honest than they would have been with a video interview).
  4. Along the Way by Emilio Estevez and Martin Sheen (Emilio read my book, so I’m reading his!)
  5. Several others that I can’t remember… sorry…

4 thoughts on “Interview with Ryan Dowd

Add yours

  1. Great interview and post, Shauna! In fact, I was especially excited to see this author and book because I played a small role in this publication as one on a team of editors. It’s such a lovely and touching theme for a story!

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