My interview with Writer Jon Emm
On finding characters within yourself, embracing the messy creative process, and the importance of persisting through rejection and self-doubt
While at Chateau d’Orquevaux in July 2025, I interview Jon Emm, a writer from the United States who currently lives in Chicago. I shared the Writers Salon, Esther’s Bath, with Jon and a few other writers whose interviews will be featured here soon.
Jon has been writing short stories for years and has recently transitioned to screenwriting, including screenplays and TV pilots. Jon describes his creative process as being ‘all over the place’ – sometimes starting with an idea he wants to explore, sometimes with a perspective or characters he can think of, or relationships that intrigue him.
During this interview Jon shares insights from his current screenplay project about a relationship between two men, explaining how he’s discovered that the two main characters are actually different aspects of himself – an unlikely pairing that represents his internal contradictions.
He opens up about the challenges of the creative journey, including dealing with constant rejection, self-doubt, and the overwhelming desire to quit when things get difficult. He emphasises the importance of persistence – that you have to keep going even when you’re rejected, even when you doubt yourself. His advice centres on just starting, accepting the messy nature of creativity, being persistent despite setbacks, and recognising that the characters and stories we create often reflect different parts of ourselves.
It was a joy to interview Jon and to spend time with him. I hope you enjoy this episode and don’t forget to show the love by liking, following and subscribing to the podcast on your favourite podcasting app and connecting with Jon
Interview with Jon Emm
Introduction
MD: Hi Jon. Let’s just start with introducing yourself with your name and where you’re from.
JE: Sure. My name is Jon Emm I’m from the United States, presently living in Chicago.
MD: And tell me, what do you do creatively?
JE: I am a writer. I wrote short stories for years. I am presently writing screenplays. That’s what I’m doing right now. I just recently got trained in screenplays and pilots, TV pilots. I’ve written short stories for a number of years and I’ve officially made that change now.
Creative process
MD: Can you tell me a little bit about your creative process?
JE: You know, my creative process is a bit all over the place. Sometimes I start with an idea that I think would make a great idea for a story. Other times I start from the character perspective that I can think of characters or a relationship that I think would be really wonderful to explore.
Presently, I am working on a screenplay that is, it’s more than anything else, it’s about a relationship between two men. One is a little bit off and the other is a kind of a big shot, at least he thinks he is, sort of in the same vein as Lenny and George from Of Mice and Men. That story moved me a lot and I find myself really, I find those two characters that kind of match up. They’re a really unlikely pair. I find that a lot and I’ve come to realise that that’s probably the two characters that are inside of me.
Creative inspiration
MD: Who or what or where do you get your creative inspiration from?
JE: I can honestly say I was very influenced by Rod Serling and the Twilight Zone series. That influenced me greatly from the time I was a small child, too young to be, way too young to be watching that and it kind of left an indelible scar on me. But in that scar I have grown accustomed to writing that sort of thing.
It’s taken me a while to not write like that, to be honest. All my short stories are really twisted like that. This particular story that I’m working on here at Chateau d’Orquevaux is not in that vein, but I did get a lot of inspiration from that. I get a lot of inspiration from nature and a whole lot from humans. I’ve been a bartender for a number of years, for over 25 years and I’ve got, there’s not a story I write that doesn’t have a bar in it.
MD: Yeah, that’s actually such an interesting thought that, you know, having a job like that as a writer provides you with so much.
JE: It does and I never know where it’s going to come out, but it does.
MD: Because you’re with people all the time. Have you been trying to consciously make a decision to write away from the kind of Twilight Zone kind of?
JE: Yes, I have. I’ve softened a lot as I’ve aged. I used to have quite a dark side and a lot of my writing I used to do as therapy and I don’t dwell there anymore. Now I just roll with things a lot easier and it’s kind of been a little bit confusing. It’s been a rough road to navigate, to move away from a particular style to a new style, but I’m finding great joy in this new style.
MD: I do find, you know, from the interviews, the conversations I’ve had with a lot of writers and artists that people are quite drawn for inspiration from nature. I think nature has a lot to teach us.
Creative routine
MD: Can you please tell me a little bit about your creative routine here or at home or both?
JE: Yes, if I had in my ideal world, my routine would be like this. I would get up and I would go do something that would take me in the range of an hour or so, whether it’s – like right now I live in Chicago and I live by the lake and we get up in the morning and we go down and we swim in the lake or we walk on the beach – to take about an hour or so to do that, come back to have my coffee and then sit and I would like to write until one or maybe two and then pack it in and be really, pat myself on the back and carry on with the rest of my day if I had a perfect world.
But as I’ve said, I’ve been tending bar for years now and it tends to lend, it tends to take me into the evening a little bit later than I would like. So early mornings are a lot, are a little bit more difficult. So, I have that little bit of a conflict there, but I hope to not have to tend the bar anymore.
That would be really great because this routine is what, that routine is really what I want to do, that’s what I’m aspiring to do. Plus, that’s the kind of routine that Diane wants to do too and so if I can get up and she can go paint and I can go write, that would be great. I also, something that has changed is I realise I need someplace else to go.
If I try to write at home, for one thing it’s really isolating. I mean I can be easily distracted by going to a coffee shop and like hearing somebody else and get a little perturbed, but I find that I’m also perturbed when I’m all by myself. At least I have someone to blame for it when I’m in a coffee shop.
So, I really do want to find a different place that I can go and it doesn’t have to be public, it just needs to be different from my surroundings that I live in all the time.
MD: I was going to touch on the fact that you, your partner is also a creative, which I think is … a lot of people do ask me about whether having a partner was also creative would make things so much easier. And having spent nearly three weeks with you and Diane I can see there’s this beautiful routine that you both have and it looks like an incredibly supportive creative relationship that you have and you know just how do you find you feed off each other with that creativity?
JE: Well, I am huge, we are very, very supportive of each other. She has given me a lot of opportunities where I’m, you know, to go visit her. She doesn’t, she doesn’t work, she’s an artist for a living.
I’ve not been an artist for a living and so when I go to visit her it’s real, it’s a really wonderful experience to be able to do that. But we also realize that we’re both capable of working together and during COVID we created a children’s book together and that was True Colors and she, it was a big, it was a challenge. She said if you, if you write a children’s book I’ll illustrate it.
So I did it and she illustrated it and it was really wonderful and a really interesting thing happened in that process too was that when we, when I was, it was all done and you know I wrote it, she went, you know, this, this, this and then she painted it and I would go, you know, back and forth, back and forth until we got exactly what we want. Then we looked it up and realised that our book was almost two times too long from the, from the word count of what it’s supposed to be. So, then I, when I went back through, we looked at it and I said well, I don’t have to say any of this anymore because your picture says it.
So, I got to remove all that and then we don’t have to say any of this anymore because the picture shows again and again and again. When we recounted after one try it was nine words under what the word count is supposed to be, the max, and realised that the reason that she painted what she painted was because I wrote what I wrote. Whereas if I had just written what, what we edited down to, she may not have come up with those pictures.
So, it just, it really worked out. That was when I just went, all right together, we have something interesting.
MD: Yeah, you’ve got that creative side in yourselves as well as your beautiful relationship.
JE: Yeah.
Creative wisdom
MD: Tell me Jon, if you were to have conversation with someone who’s early on in their creative journey, what pearl or pearls of wisdom would you want to pass on to them?
JE: Um, I would, I would probably more than anything say that you just, there’s only one person that you, you truly need to listen to. You can, you take as many classes as you can learn as many as things as you can from, from so many different sources. Just learn all, all that you can learn so that those rules that you’re, that you’re going to come up against are yours to break as long as you know you’re breaking them.
As long as you know why you’re breaking them and you’re not breaking them for the purpose of breaking a rule. And all the answers that you actually want are, they’re, they’re right here. Like in, I mean that in every aspect of your life.
If you put your hand right here when you have a tough question, you know the answer. It’s right there. We’ve all, we, we’ve been through it already before. Like I, I totally believe we have. And you might not want to hear it. You might not answer it.
Even when you put your hand here and go, all right, I heard you. I’m still not doing that. Okay. Well then at least, at least, you know, because it’s because you do know and to just listen to yourself, take it easy. No one’s pushing you. No one’s, no one’s your, your, your own, your, your own worst enemy.
Always just let your, let your judge go away. Stop judging yourself so harshly and let yourself be.
Connect with Jon Emm
- Substack
- Buy his picture book True Colors created together with his partner Diane Rakocy
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If you haven’t discovered Creative Momentum with Meg Dunley podcast, I’d recommend having a listen. It has weekly drops of these bite sized episodes that feature creatives talking about their creative process, routine and inspiration. Each week has some great pearls of wisdom for everyone who is living or wishes they were living a creative life.