Next Act with Jeff Ornstein
A designer exploring a new path in acting and Hollywood. Join Jeff Ornstein as he shares personal experiences, lessons learned, and conversations with others making big career shifts in the entertainment industry. Practical insights, honest stories, no fluff, just the journey of breaking into a new world.
Next Act with Jeff Ornstein
Stewart Lewis – Singer-Songwriter, Novelist & Filmmaker
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What happens when one creative career evolves into another, and then another?
In this episode of Next Act with Jeff Ornstein, Jeff sits down with acclaimed singer-songwriter, bestselling novelist, filmmaker, and creative writing professor Stewart Lewis to explore a career built on curiosity, reinvention, and the courage to pursue new creative passions.
From touring with artists like Shawn Colvin and Ani DiFranco to publishing internationally acclaimed novels and bringing his stories to life on the big screen, Stewart shares how every chapter of his career prepared him for the next. Together, Jeff and Stewart discuss the differences between writing novels and screenplays, directing actors for the first time, building creative communities, and why it's never too late to start something completely new.
Whether you're an artist, entrepreneur, or someone considering a major life pivot, this conversation is a reminder that your next act can become your most meaningful one yet.
In this episode, you'll learn:
- How Stewart transitioned from music to bestselling novels and filmmaking
- Why collaboration transformed his creative process
- The biggest differences between writing books and writing screenplays
- What makes a great film director beyond technical skills
- Why embracing change leads to a more fulfilling creative life
- The mindset needed to overcome fear, rejection, and self-doubt
The best stories are often the ones we haven't written yet.
Hi everyone and welcome to Next Act with Jeff Orenstein. I am Jeff, and on this show we celebrate people on the cusp of greatness. Those building on past successes in some of the curious and inventive and sometimes unexpected ways they have achieved those, and stepping into moments that could define their legacy. We'll talk about current projects, lessons learned, and the extraordinary opportunities ahead. So the best is yet to come. Today's guest is Stuart Lewis, singer, songwriter, novelist, music supervisor, and director, whose career spans music, film, and literature. From founding the band Acoustic Junction to touring with artists like Sean Colvin and Annie DeFranco, Stuart has published multiple novels and now works across film and storytelling while teaching creative writing. Welcome, Stuart. Hey, thanks for having me. Oh, it's my pleasure. Okay, so to our listeners, this isn't a rare occasion, but for full disclosure, I know Stuart. I usually don't know our guests. So I have a history going back, I was trying to count. It's a long time, maybe 40 years or so. So I have seen him perform in venues with crowds cheering to some of his original music. I've read his novels, and I've even had the uh privilege of uh performing in his first feature and uh one of his shorts. So there's a little backstory here, but he was a great person to have for the podcast because he represents exactly what it's all about that you're never too old to jump into a new pond and build upon everything that your life's experiences have shown you and demonstrated to you and create something new. And for you, it's definitely storytelling, I think. What do you think?
Stewart LewisOh, for sure, yeah, for sure. That word gets thrown around a lot, and some people don't like using that word. Like, I'm a storyteller, but like it is what it is, like it is what we do anyway, so I don't mind it.
Jeff OrnsteinOkay. Well, your your lyrics stole told stories, and surely your your novels told stories. I mean, and you have a real following of readership, and in having read some of your scripts you you you've you know created, they're all about complex stories and the layering of characters. So I know your family was very musically involved and very inclined and skilled. Were were they the S-word? Were they storytellers?
Stewart LewisUm not necessarily. They were more telling other people's stories. We, you know, they did a lot of covers and, you know, John Prine and uh a lot of country and folk kind of stuff. So they were more performers and sort of, I guess, I guess, conduits of telling other people's songs, telling the stories of other people. Yeah. It was our generation that started writing our own material and telling our own stories.
Jeff OrnsteinRight. And your brother is uh writes his own material too, right?
Stewart LewisYeah, yeah. He's a Grammy nominated songwriter and still doing doing it. And um, yeah, he he's he's amazing.
Jeff OrnsteinWas there a particular event that prompted you to say, you know, I'm gonna put uh singing and and writing and performance on the back burner bullet because I want to focus on my writing? I mean, what was the genesis of that morphing from performer to writer?
Stewart LewisWell, I got had some success as a songwriter. I was touring with these acts that I was like, some of them were my heroes, and I loved it. And then I went to LA and I thought, oh, I'm gonna be a rock star. I ended up getting a a record deal at a smaller independent label, but it ended up being really difficult. So I thought, I'll just be a writer instead. That's a great idea because no one's trying to be a writer. But yeah, so it was sort of like a backup plan that was like, that's not really a backup plan. That's sort of another like dream. I decided to go to school for creative writing um and got my master's, and I ended up selling my first novel like right out of graduating there. So it ended up being a good career path because I got more yeses in that world than I was getting at the time as a singer.
unknownRight.
Jeff OrnsteinWell, we guys are in like validation, right? Exactly. I mean, you your novels sell, you know, they're not just produced with a limited run, and then that's the end of it. I mean, you do you have a following? Do you think you have readers that keep coming back to you? Because you you you have a theme that, you know, the which is your characters, I think.
Stewart LewisYeah. I mean, I it's a coming of age sort of theme, and it's uh more modern and not, you know, there's not zombies or apocalypses or anything like that. But yeah, I did for a while. I mean, I still do, but for a while when I was on Random House, I had a couple of books, one of which was sold to five countries. And so, you know, I always say I'm huge in France, I'm also really big in Brazil for some reason. But yeah, I I did have there was a while that I had a pretty big following um in the YA world, which is for like 12 and up. But yeah, the other books, you know, you just try to find your audiences within them. But I was able to kind of create a little bit of a career there for a while with Random House, and I'm very grateful for that.
Jeff OrnsteinDid you see a film or did a friend suggest to you and say your stories need to come to life or they should come to life and they should they should the story should become a screenplay and it should be, you know, on the silver screen. How did how did that genesis and morph into it?
Stewart LewisWell, I got a lot of a lot of initial feedback from my editors. They would use the word cinematic when describing my writing. I mean, I think it's kind of a goal of every writer to sort of see it realized on the screen. So I always had that dream of like seeing that realized. And our mutual friend, uh Linda Yellen, is a great director and producer. And I sort of like, you know, every time I put out a book, I was like, here, Linda, what about this one? Here, what about this one?
Jeff OrnsteinWhy not?
Stewart LewisAnd then, and then she finally was like, We're doing this. And I was like, Okay, I'll believe it when I actually see it. But I, as you know, got to see it. You were on the set too. And it was one of the best weeks of my life. Like uh going there and seeing the characters exactly how I pictured them, saying my lines with a crew of 50 people. You know, we were we were employing the whole town in New Jersey, you know. I mean, it was it was a special thing. And I was like, I freaking did this. Like I created it. And Linda said at one point during a staff meal with the whole crew and everything, which was really sweet, she said, you know, Stewart has the hardest job. He's the one who started with a blank piece of paper, you know, and and it's true, you know, it's true, and it is, you know, I felt very honored to to have all of these people come together to make it, including you.
Jeff OrnsteinWell, I was happy to be there. And she's right, because I mean, not only did you write the story, you created the whole world, the whole environment that took place. And to that point, also, the casting was superb. I mean, I don't know what your vision was for each character, but I you know, I can't imagine anyone else playing those characters. They just blended so well. So it was I yeah, I thought it was pretty seamless and it really came together nicely. Yeah. So I understand you're working on another feature or or more, perhaps. I don't I don't know everything.
Stewart LewisYeah, I kind of caught the bug with this one. Good or bad, I caught the bug because I got to co-produce and work on the music, which is amazing, and I decided to try and do it myself. So I made a short, which you led your talents to. And then I recently just shot a second short, which is starring Priya Ferguson from a little show you might have heard of called Stranger Things. Yeah, she's like a global star. So that was amazing to see that come together, and we're in post-production for that. And the next step will be to try and make a feature that I've been developing over about three years now, which I know you've read some drafts of and you liked. I've gotten really great feedback for it, and I feel like that's sort of like the culmination of this sort of pivoting into the film world is like being able to make my own feature. Whether or not I executive produce it or direct it, I just want to be able to say I I I wrote a feature and it it became a film.
Jeff OrnsteinSo we'll see what happens. So you spoke about how like when you write a book, and a lot of writers say their dream is to see it actualized in a film. But when you're starting writing a screenplay, I would imagine are you seeing the film in your head while you're writing? Is is the process a little bit reversed than writing a book?
Stewart LewisYeah, it's totally different. A book is sort of like diving deep into the moments. I used the metaphor of like a Google map. When you go like this and you go into the map, that's like more of where your novel is. You're seeing all the nuances, the trees, the buildings, the descriptions, blah, blah, blah. Whereas in a screenplay, you kind of have to pick the the exact the moments and have the audiences sort of fill in all of the backstory.
Jeff OrnsteinInteresting.
Stewart LewisAnd you're also writing for everyone in a screenplay. I mean, people say, you know, oh, I have great dialogue. If you that's great if you have great dialogue, but that doesn't mean you can write a screenplay because you have to, you're writing for the lightning designer, you're writing for the production designer, you're writing for the actors in terms of blocking, you're writing for everyone. It's every page on a screenplay should have elements for everyone involved. So I'm learning a lot more about it. Um, and it's uh not necessarily easier, but I find it really thrilling because it's just a different, you know, it's like your podcast is all about. It's like pivoting into different things at different ages. You know, it feels fresh and new to me. It's like I I'm uh I'm a creative, like I'll always be creative, but like I've done music for so long, I've done writing books for so long. Now I'm in this whole world of film, and it just feels like a fresh, new way to be creative. And I also love the collaboration aspect of it because writing a novel is very like singular. It's like you and your laptop for like three months. The collaboration is so great. I mean, I I had a crew on this short of uh like 23 people, and they were the best crew ever. And it's nice when everyone comes together. I'm sure you're used to that in your work of collaborating. I love that aspect about it as well.
Jeff OrnsteinThat's fantastic. So you've directed three, two, three, three films? Two. Two. So that's also another tangent that you're getting into. How did you learn the skills to like jump into the directing pool? Because that is, you know, working with equipment, the camera, the lighting. I can see writing a segue into screenplay, or and certainly writing for songs, writing for novel, writing for screenplay, but directing's a whole new bag. So how'd you get the courage or the or the gumption to jump into that?
Stewart LewisYou know, it was something I kind of learned by the seat of my pants, and I was lucky. I mean, I think you, knowing you as a friend, you could also jump into something like that because I mean, 90% of it is about reading people, you know, and about being able to uh, you know, kind of massage situations or bringing out the best of people, right? And being a leader and being supportive and being, you know, someone that people can feel comfortable around. That's like 90% of it. Make people comfortable and be a great supportive leader and understand the nuances of people, right? Like we've been around all this world a long time, like we understand, you know, when something's going wrong with someone. So it's about reading the room, getting your vision across and picking the right people to help with that. I mean, the DP is a huge person, director of photography is shooting the whole film. The DP is like a huge person that has to understand your vision. And then the AD, which is the assistant director, is the one that's sort of like the sergeant, you know, that's like rallying all the troops and getting everything done. So you pick those two people, and then you're just sort of here answering all the questions and trying to be like a gracious person, you know. Like you know, you you and I know Linda, like she's one of the most gracious, authentic, amazing people. Like, I think being a director is at first and foremost, it's just being like a cool person, to put it really simply.
Jeff OrnsteinYou're the maestro for so many different artisans, and yeah, you know, I mean the best way to rally the troops, you know, the more bees with honey, right? It's it's very true. And and and with when it came to Linda was like make her proud because she was she was so encouraging from it to everyone. And I watched her, you know, communicate with lots of different people on the set, and she she was the same with everyone, you know. Yes, very supportive. So right now, I know you spend your time between Nantucket and Barcelona, but you also spend some time down in Nashville. Now that's a little off the beaten track. So was there inspiration to be found there? I mean, because the culture is very and you're and you're from Massachusetts, I should add.
Stewart LewisYes.
Jeff OrnsteinWas there a a culture shot there, or was there something about that culture that you might and you know bring into your your creative works?
Stewart LewisYeah, at first Nashville can be very overwhelming because it's literally like everyone and their mother and their cousin is like a singer-songwriter. There's I mean, literally like hundreds of thousands of singer-songwriters. But there's so much talent there. So I got to work with a bunch of people for the One Stupid Thing movie and also for my short. And it was like so easy to sort of there's such a wonderful connection of people there. It's not like Los Angeles where people, you know, where you can't get access to people. Like you can get like a meeting with Jolly Parton. You could walk in like in music row, like everything's open. You could walk into a record company and go to one of the biggest songwriters, Shay McNally, his office is like you can see him through the window. It's very accessible and people aren't like, don't touch me. You know, like it's so in that way I found it pretty amazing. And the talent, I mean, even the guy at the airport is like amazing. You walk by the airport, and there's like some guy singing and like some girls crying, like in her beer. There's so much talent everywhere there. So it can be overwhelming, but it was also really interesting to be in that world for a while. And I posted a couple of concerts on our rooftop and had some really wonderful community sort of gatherings there, and it was a good experience. My husband ran NPR there for about 10 years, and uh, we've since uh left Nashville, but I'm sure we'll go back and visit.
Jeff OrnsteinThat's nice. We have nice memories that will draw you back because you've had success in the different fields that you've done in in performance and in writing and and in screenwriting uh and and directing because Cookies was wonderful. Thank you. Which I should point out that's the first short he directed, and it has got a dream-like quality to it, and it's a story as old as time and yet fresh and new. What is some of the advice that you might give to young persons that are moving into a new creative film, whether it's any of those film, music, or writing, and what mindset will help them succeed in the battles or the challenges? Do you have any great words of wisdom for people?
Stewart LewisI read a piece recently about this woman who started figure skating at age 50. And I think it was in the New Yorker. It was so inspiring. But there's also a book uh written by the woman who wrote Eat Pray Love, Elizabeth Gilbert. I always thought it should have been eat, fuck, sleep, but that's a whole nother thing. But anyway, she wrote a book about creativity, and it's incredible, but that's a whole nother thing. But I I always go back to if I may quote Mary Oliver, she has a line that says, The world offers itself to your imagination. So it's like you get out of bed and your mind is open and you know that there is so much possibility. It's like, yes, I want to make a feature, but who knows? Maybe after that I'll go to outer space. Like life is too short and often confined by the trappings of our mind or the conventions that we think we can't do that. But the truth is, anything can happen. If you love it and you do it, other people will love it too. Right. Because that's something that they can't deny. And even if you don't, you're following your bliss. You know, like I had a friend in Nashville who always said, be nimble. You know, nimble was her favorite word. She's be nimble, you know, and then pivot was a big word for COVID. I still think it's a great word. But, you know, try something new, even if it's scary at first. And that's that's how you can build sort of a life without regrets, if that's even possible.
Jeff OrnsteinYou know, that's a common thread in these podcasts because we are talking about taking leaps and making changes. And you have to be courageous and you can't be fearful of falling or of rejection. And you have to just say, Yeah, I love this. I love being a writer, I love being an actor, I love being a director. And yeah, I'm gonna fail or I'm gonna be rejected, but I'm gonna keep doing it. Yeah. And because it's my passion. And it it's it's it's the people who say, I won't be deterred by commentary around me and the buzz around me. I'm gonna do what my heart and my brain and my soul are telling me to do. Exactly. And I think it's really important because people, you know, it's one thing in your 20s to say, I'm gonna run off to Hollywood and be a star, or I'm gonna run off to Nashville and be a star. But you know, when you're later on in years, you know, people think all my decisions are this is my golden years, and I have to, you know, be cautious and everything. And you don't. No, you can you can be as adventurous as you want. Yeah, and it's a common theme that we hear people saying, just jump into it. And and you'll also find your pillars of support, the people around you that believe in you. Yeah, so that's really important too. That you surround yourself with positivity because our industry, all of them, which we've spoken about, the non-industry folks might think is really cutthroat and competitive, is not. There's a lot of support in our within our industry.
Stewart LewisFor sure. You remind me what you you were just saying, there's one quote from Alan Ginsburg that I love, which is in order to find your voice, you have to forget about it being heard. And it's sort of like that, you know, if you're worried about what other people are gonna think, then you're not gonna be authentic in your, you know, you want to just do your art. I always tell my students, like, just do it and don't think about who's gonna read this. Like, is my neighbor gonna read this or is my is my sister gonna see this? My first novel, I was like, my mother could never, I was like, my mother's not reading this. And and my editor said that means it's good. And he she ended up reading it, and there were blowjobs and other things. But like, you know, she loved it, you know, and you read it too.
Jeff OrnsteinThere's a lot of gratuitous nudity, as I recall. You spend me spellbound to the page turner. Okay, as always, historically, we've gone over time because I'm a talker and you're a talker. And I told my production people, we're gonna go over, just don't even give me a you know, it's not gonna work. So it's I knew we would have fun. All of our guests have fun, but since we've got a history which is very unusual again, as I said, that we would have a good laugh, and you shared some really great insights because you've really, you know, you've achieved certain levels of success in a lot of different creative fields, and you're really kind of tying them all together. So it's really important. People say, hey, you know what? Stuart did it, he believed in himself. His last name isn't Goldwyn Meyer. You know, you can do it if you want to do it. So thanks for joining us. I hope to see you sometime soon, perhaps maybe in the summertime. Yes. And good luck with your your new project. Okay. Thanks, Jeff. Thanks for tuning in to Next Act with Jeff Orenstein. Follow, subscribe, and stay connected to your favorite socials at www.nextdackpodcast.com. Keep chasing your next act. The best is yet to come.