How a Book That Doesn't Fit Can Be The Perfect Fit

Chatting about Travel Artist with James Richards

Jun 12, 2026

I got into James Richards’ art for the first time about ten years ago, when I decided I wanted to learn how to draw in a sketchbook. I’d been an oil painter for many years, but weirdly, it’s possible to know how to paint without really knowing how to draw. I needed something more portable than oil painting so I could sketch when I traveled. Jim’s classes fit the bill.

I liked his style and his approach immediately. When you watch him draw, it all looks so simple and do-able. But his finished art is remarkable sophisticated—and a real crowd-pleaser. Everyone loves his spirited, carefree vibe.

Over the years, Jim and I have gotten to be friends. He’s coming to Portland for an event next month, so today I want to invite you to his event if you’re in Portland, but also to encourage you to order his book from a Portland bookstore, so Jim can sign it while he’s here and it can be shipped to you.

So first things first: Portland! Jim Richards! Architectural Heritage Center! July 7! It’s a free event, but space is limited so you do need to pre-register right here.

And if you’d like a signed copy of Jim’s book, either to pick up at the event or to have shipped to you, please order it from Broadway Books right here. Be sure to let them know when you check out whether you are picking it up at the event, picking it up from them later, or if you want it shipped to you.

Jim had a career in the world of urban design and landscape architecture, where he would draw and design public spaces. Over the last couple of decades, he’s taken his drawing skills on the road and become a popular teacher and beloved artist in the urban sketching world. His travels around the world have given him a wealth of stories and connections with people that he never would’ve had otherwise. That’s what his new full color, coffee table-sized book, Travel Artist, is all about.

I’m especially excited about this book because I played a bit part in the creation of the book. I got to see Jim’s proposal in the early stages, and we had several long, interesting conversations about how he envisioned the book and what was getting in the way of that.

I called him just now and we talked about those early days of figuring out his book. Here’s a slightly condensed version of our conversation:

AMY: When you first called me, you were kind of struggling with what kind of book you wanted to write. I remember sort of spitballing about the different kinds of books that an artist could create about their work. I think my categories were along the lines of:

A how-to book, and there are many great publishers who know exactly how to do these
A mass-market book from a major publisher for a broad audience—think Austin Kleon, for instance
An art book, which could be published by a fine art press in a limited edition
A zine or another self-published format, which is a respected and time-honored tradition for artists

What I thought you ought to consider was that with the success you’ve had, at the stage you’re at with your career and your life, you don’t have anything to prove. If you’re going to take time away from traveling around Tuscany with your watercolors, it should be for exactly the kind of book you want to write

JIM: Yeah, I knew that I didn’t want to write another how-to-draw book. I figured the world had plenty of those. I thought I wanted to tell stories. I actually had a damn good outline for all of this. Then someone offered to introduce me to their agent. I was excited to talk to a big New York agent, but it turned into a nightmare where I was really pushed to make it more of a how-to thing. It got to where none of us knew what this book was supposed to be.

When I fired the agent, I pulled out the original outline and decided to strip it down and just get it down to storytelling.

I remember in our first conversation you told me, I don’t know what the hell this is supposed to be1. The real book was in there, it was in me, and I just had to come to the realization that at my age, I don’t need to be teaching people perspective. I need to be drawing on these decades of experience and these real human connections to make the point that this isn’t about pretty pictures.

It’s about something that bridges language and culture and borders. Drawing helps us understand each other better. It can not only make the world a smaller place, but it can get you out of trouble with the customs people in Havana. That’s a great story.

That’s what I felt my contribution should be. And with my wife Patti really encouraging me, I thought, I’m going to write the book I want to write. I had to get past all my academic angst about how you write things, and once I was able to just shut out all those voices telling me how to do things and just write like I spoke, it was such a relief and it became so natural.

AMY: Yeah, I’m always telling people to write the way they talk. Write like you’re sending an email to your best friend. Record yourself talking. Really be your unscripted, messy self, at least in the first draft.

And to do that, you had to decide that it was OK to write a book that didn’t fit the very structured categories that agents and publishers like to see. They really want your book to fit into a slot that they can understand and know how to publish. Which is understandable from their perspective, but doesn’t really fit every writer and artist.

JIM: I kind of realized that the Today Show wasn’t on hold waiting for me. Nobody was going to send me a Pulitzer preemptively. There was a part of me that thought, if people really get this, it could really have legs and take off. But one of the problems was that it wasn’t just a travel book, and it wasn’t just a drawing book, both of which are established categories, but it was a travel artist memoir. I wasn’t interested in trying to make it fit too tightly into either one of those categories. I had to kind of get to that point that it was just going to be what it is.

I was willing to talk to fine art publishers, but I wasn’t willing to make the stories less than the main focus. If you don’t have the stories, there’s no point in drawing all these pictures in the first place.

Once I got to that point, I realized that the people who publish those things aren’t Penguin Random House, they’re these bespoke publishers. Oro Editions had been recommended to me by my colleagues in the architecture and urban design world. The publisher was very sympathetic to my perspective and very interested in the stories, plus he had worldwide distribution, so I decided to go that route with the understanding that it would be a book of drawings and stories with the ability to bring people together.

And it has done that! It has hit all these different parts of my life from landscape architecture, the academic world, and the urban sketchers world. It’s been so great to get out and share it with all these different groups, like what we’re doing in Portland next month. I told Patti, “I am so jazzed that we keep finding ways to lose money on this project.”

AMY: I remember we talked about the voice for this book, like how you tell these stories in a way that feels like your own voice. Your drawings are very much in your voice, and you want the prose to be that way, too. One thing I always tell writers is that it’s a good idea to find those weird books that somehow speak to you, even if they are nothing like the book you’re writing and would make no sense to anyone else. Keep them nearby for inspiration.

JIM: Yes, that was really important for me, to realize that there’s lots of different ways to tell a story. One huge influence was On the Road by Jack Kerouac. I picked it up after I watched a documentary about the Grateful Dead and I was like, holy shit, he wrote this and he got away with it? It’s like Joni Mitchell the first time she heard Bob Dylan. She said something like, we can write about this stuff? We can talk about that?

The other one was Anthony Bourdain and his books Kitchen Confidential and A Cook’s Tour. Reading those books is like you’re sitting in a bar and a guy’s telling you stories. It was just so freeing. Once I got into that, I could almost say, sentence by sentence, “Wait a minute. I wouldn’t say it like that.” I’d just write a better line right after that, kind of like restating a line in a drawing.

Here’s one last beautiful drawing from Jim, and one last reminder to join us in Portland on July 7 and/or order a signed copy of Travel Artist from Broadway Books.

Supporters are contemplating the perfect journal

Last week, we looked at what I think might be the perfect sketchbook/journal combo. Every week, we do something related to sketchbooks, journals, art supplies, and art-making. For just a few bucks, you can join us and get access to this whole archive!

137. Is This the Perfect Journal?

Amy Stewart

Jun 8

Last summer, on a trip to England, I found what I thought might be the perfect journal/sketchbook, which is to say that it is quite literally both: Half lined, half blank, on paper thick enough to handle ink and watercolor. It comes in a satisfying little chunky black hardcover with an elastic enclosure, a ribbon bookmark, and a pocket in the back for storing your treasures. I bought the A6 size, which is British for 4x6.

Read full story