Creating Your Own Break | Jennifer Lieberman on Acting, Writing, and Creative Persistence

Chris sits down with actor, writer, producer, speaker, coach, and author Jennifer Lieberman to discuss creativity, storytelling, acting, publishing, rejection, persistence, mindset, and what it really takes to build a career in the creative world.

Jennifer shares her journey from growing up with a passion for performance and storytelling to building a career across theater, film, writing, producing, coaching, and education. The conversation dives deep into the realities of pursuing creative work, creating your own opportunities, and learning how to stay in the game even when doors do not immediately open.

Throughout the episode, Jennifer discusses:
 • Her passion for storytelling and performance from childhood
 • Moving from theater into writing and producing her own projects
 • Why artists often need to “make their own break”
 • The challenges of acting, auditions, agents, and rejection
 • Building a body of creative work over time
 • Producing independent theater and creative projects
 • Self publishing and overcoming setbacks in publishing
 • The evolution of her book Year of the What
 • The importance of persistence and staying creatively active
 • Why mindset and discipline matter for creatives and entrepreneurs alike

Chris and Jennifer also explore:
 • The emotional side of rejection in creative industries
 • How networking and relationships shape creative careers
 • The balance between creativity and logistics
 • Wearing different “hats” as a creator and entrepreneur
 • Why artists need both creative passion and business skills
 • The importance of focusing on what you can control
 • Helping other creatives learn to produce and launch their own work

One of the most powerful moments of the conversation comes when Jennifer explains that success in creative industries rarely follows a predictable formula. Instead of waiting for opportunities, she chose to create her own through writing, producing, teaching, and continuously building meaningful work over time.

Books discussed during the episode include:
 • Year of the What
 • Independent Theater Production for the 21st Century in Seven Simple Steps
 • Steppenwolf by Hermann Hesse
 • The Big Leap

https://www.jenniferliebermanactor.com/

If you are interested in books, acting, storytelling, entrepreneurship, creativity, personal growth, mindset, publishing, theater, leadership, or learning how to keep pursuing your goals despite rejection and uncertainty, this episode is packed with insight and inspiration.

Subscribe to Books4Guys for conversations focused on books, leadership, creativity, storytelling, entrepreneurship, mindset, wellness, personal growth, and helping people become better readers, thinkers, leaders, and professionals. 

Transcript

SPEAKER_00 0:15

So I'm in Nashville.

SPEAKER_02 0:17

But you're in Nashville. Yeah, when I send you Nashville.

SPEAKER_00 0:20

When I send an invite, it always gives Chicago the credit for the time zone, I guess.

SPEAKER_02 0:25

Okay.

SPEAKER_00 0:26

So everyone's always like, Are you in Chicago? I'm like, no, I'm in Nashville.

SPEAKER_02 0:29

Yeah, I love Nashville. I've been. It's so cool.

SPEAKER_00 0:32

Yeah, that's cool. Actually, we run into a ton of people that travel here from Toronto. I guess because there's a direct flight, and like every summer when there's concerts going on and stuff, like we always meet people who are like, Yeah, we came from Toronto.

SPEAKER_02 0:46

I was gonna say, we love our music.

SPEAKER_00 0:48

Yeah.

SPEAKER_02 0:49

We love music.

SPEAKER_00 0:50

I love that. Yeah. Well, Jennifer, super excited to have you on the podcast. And there's so many things we can talk about because I've been doing some research on you, and I'm like, Jennifer does so many different things. She's like such a creative person. She's doing like acting and coaching and speaking and book writing. And I got introduced to you from your book, Year of the What. But then I was looking and I was like, you just had another book published, like within the last week or so, right?

SPEAKER_02 1:19

Yeah, not even a week. Last Thursday, yeah.

SPEAKER_00 1:23

Very cool. And that one is geared towards, I know, like more of a theater.

SPEAKER_02 1:27

Yeah, so it's it's teaching actors how to produce.

SPEAKER_00 1:31

Very cool. Very cool. Well, Jennifer, for those that don't know who you are, if you don't mind, share your story. How did you get into, I guess, like your interest of being creative and and in plays and and writing books. Like, where did the interest start? And just kind of like bring us up to today's day and time.

SPEAKER_02 1:53

Okay. Well, I'll try and make it brief. It's it's hard to condense one's whole life journey into a couple centuries.

SPEAKER_00 2:00

Born on this day.

SPEAKER_02 2:03

So, but basically, everything stemmed from my desire to perform. So, even as a kid, even as a child, I started writing when I was about eight. Not so much because I was trying to be a writer, but because I wanted to be on the TV shows that I watched. So I would like imagine, I would like dream up a scenario for myself where I could be part of the show, you know. Like nowadays, I understand that would be like a guest star role or a co-star role, you know, to kind of insert myself into the story. So it all started from wanting to act and wanting to perform. And fast forward to now, I'm an actor who basically writes and performs and produces. And I started writing and producing to give myself acting opportunities when nobody else was choosing me. So I so as much as I started writing as a child because I wanted to become an actor once I was a grown-up and became an actor once I finished university, the role, you know, the calls weren't coming in, the roles weren't coming in. So I realized that that kind of childhood fantasy land of writing myself projects is actually what I needed to do as an adult in order to stay in the game. And that's kind of how I got here.

SPEAKER_00 3:33

Yeah. That's so interesting. And you kind of like, I mean, you just carved out your own path. It was like, in a way, which is very cool. You're just like, hey, I want to go do this. I gotta like figure this out.

SPEAKER_02 3:44

Yeah. Like, don't get me wrong. I I still, you know, am hopeful that Hollywood is gonna pick up the phone one day. Hollywood, Broadway, indie films, off-Broadway. I've done um some off-Broadway before, but that's the thing. Like, I'm not opposed to working with other people and getting hired as an actor. Like, I would love that. If anyone wants to call me and hire me, but the in-between stuff, it's like the in between the gigs is the most painful and excruciating for any artist. So the more I create, the less kind of downtime and in-between time and waiting around time I have.

SPEAKER_00 4:26

Yeah. No, that's a uh, yeah, that's a good plan. Yeah, keep yourself busy and I don't want to say relevant, but like sharp, doing different things, keeping yourself in the game. And for someone who doesn't know what that world is like at all, I don't I I feel like I don't have a creative bone in my body, or like, you know, I was in choir, that was great, loved that, but like that was the extent of my performing days. Like, what is that world like as far as you obviously have big dreams, aspirations, and a lot of people do. Everyone, you know, a lot of people, that's their goal is to act, be on the screen or be on the stage. Like, how competitive is it? And like, what's the process, or or how do you go about like how do the opportunities come? Are they all organic and you just gotta be in the right place at the right time? Or is it something you've got to like put in a lot of time and and you do other things to work your way to that level? Like, what is involved with all of that?

SPEAKER_02 5:26

So, Chris, this is the million-dollar question, because if there was an actual tangible answer, like everybody would be doing that one thing. And I think the challenging thing as an artist or a creative is no two people have walked down the same path to become a success. You know, like for most vocations, it's like, okay, you want to be an accountant, you go to school, you get your degree, you have to pass, you know, your certifications, and then you go to accounting firms and apply for jobs, you know, and and then you get a job, and chances are you're there for years, if not decades, yeah, doing the same type of thing. And a lot of um, you know, a lot of more traditional jobs go down that route. But being a creative, it's like there is you can get discovered your first week in town. You can be in town for 50 years and not get the gigs that you want, you know? So there is no real kind of rhyme or reason to it. You definitely want to study your craft a little bit, but also you don't want to get stuck in the studying your craft. Like I, for example, am still doing acting classes, but not so much because I'm not confident in my ability, but because as an artist, I'm constantly hungry to explore. And as actors, we kind of call it the gym. You're not gonna go to the gym and get a trainer and get in the best shape of your life and then not go back to the gym for 10 years and still expect to be in shape. You know? So that's one aspect. The other aspect is you definitely want a team, you want an agent, you want a manager, you want a lawyer, you want people who are kind of the ones who are presenting you for the roles, the ones who are negotiating your contracts, the ones who are kind of like the buffer in between you and the people who hire you, but also those are hard to get. And you know, that's a whole other like ball game.

SPEAKER_01 7:47

Yeah.

SPEAKER_02 7:48

And then there's other people who focus on networking with the people who can actually hire you because an agent doesn't hire you. An agent submits you as a choice to a casting director or a director or a producer, you know, but they're not in charge of actually hiring you for the job. A casting director also is not in charge of hiring you for the job. A casting director's job is to provide choices for the director, is to narrow down from thousands of people or hundreds of people trying to get this part. They narrow, they narrow it down to 10, maybe five, maybe three, depending on the project. So, you know, every kind of leg of the journey is so involved. And for me, the reason I've been going down the path of writing and creating my own projects is because with the world of agents, managers, casting directors, and auditioning, which it's part of the business and I love it. You know, I just shot an audition today. It was so much fun. But it's also an avenue where I have very little control of the outcome. And that can get very frustrating. You know, you can do it for a couple of years and you're super passionate and super passionate, but with every no, with every rejection, with every kind of, you know, query letter that goes unanswered, it like chips away at you a little bit, a little bit, a little bit. And it doesn't matter how talented you are, you know, it does weigh on your confidence. And that's why I started creating my own projects and I started a company, Make Your Own Break, to help other actors and writers learn how to produce their own projects. And I'm not talking about on a huge scale. I'm talking about small indie projects, indie theater. It's a way to create calling cards for yourself. It's a way to work out material, it's a way to constantly be able to email casting directors and agents and managers and directors. And even if they never come, it's like the more times you're able to send them an email and be like, hey, check out my short film in this film festival. Hey, check out my play in this fringe festival, hey, check out this piece that I'm doing here, this piece that I'm, you know, eventually you're gonna find some traction somewhere. But if you keep emailing the same people and years go by and you're not building a body of work, it's like, well, you know, with each kind of contact, each point of contact, you want to show progress. So I don't know, did I answer the question?

SPEAKER_00 10:40

Yeah, you did. I'm sitting here, and again, it gave me a lot of insight because I don't know how that works, but it sounds like a lot of things are very subjective to where someone could love you, someone not so much, and that's really like you're at the mercy of someone's opinion of your performance or whatever they're looking at, but it sounds like you know, I it it seems like you've got to really love the journey of it all more so than the destination, because the destination may never come.

SPEAKER_02 11:10

Exactly.

SPEAKER_00 11:11

But if you love the process and the constant just self-evaluation, self-improvement, development, and just enjoy getting better at your craft one way or another, that seems to be the best way to have a chance of succeeding and getting to the spot that you're climbing towards.

SPEAKER_02 11:33

Yeah. And for me, it's just about I keep creating cool work that I want to work on, and I keep, you know, keep myself busy with that. And hopefully with each project, it makes me a little better, pushes me a little further. And maybe one day somebody will notice and maybe they won't. But at this point in time, I've got four short films, a web series, a one-woman show, a novel, a few how-to but you know what I mean? So, like I'm I've been building this body of work for over a decade now. And, you know, it's it's starting to speak for itself. That's the thing in life. Like, there's so many things we don't really have control over. And when you're in a career where you feel like it's so out of your control, the more control you can take, the better off you are. You know, so that's just what I focus on. It's like, it's like just life in general. Don't worry about the things you can't control. Focus on the things you can.

SPEAKER_00 12:33

Yeah. And that's a if you can figure that out, everything gets a little bit easier. We I feel like when you can get that that switch flipped to realize that and and walk in life that way. But Jennifer, talk about your book for a second. So the one I got introduced to you by was Year of the What, but it was formerly called So it was originally called Year of the Slet.

SPEAKER_02 12:54

And that was my one woman show. When I first moved to LA, I had been spinning my wheels for like a year, couldn't get an agent, manager, nobody wanted to pay attention to me. But also I didn't have credits and nobody knew who I was. And networking is huge in the business. And you were saying, like, you know, you can't control how people see you. But also a lot of times it doesn't matter how talented you are. Do you fit the role? Do you fit like I have an idea of the person, what this person looks like, what they talk like, you know? So it's like, do you fit into that? It's not necessarily sure you have to be decent, but a lot of times it's like, you know, I'm trying to fill a spot and you need to fit into that spot. And also, if people don't know you and you're not on their radar, then they're never gonna call you. So anyway, I created this one woman show to invite agents, managers, directors, people who could hire me. I, I, I, you know, I kind of like, I was like, ta-da, this is me. Come to my show. And when I was kind of brainstorming ideas with the woman who suggested I do the show, everything I suggested she said was too artsy because I was coming from New York theater. I was doing off off Broadway. And she's like, no, no, no, no, no. Like, you need to get people out of the house. You need a title that's gonna like catch people right away. And that's when I was like, you're the slut, you know, like that grabs people's attention. And then I had the title first, created a crazy, outrageous, racy show around the title. And nobody really came, like in the movie La La Land, like nobody really came from the industry. I had some friends from acting class, I had my mom, I had, you know, some people were there, the seats weren't completely empty, but nobody who I wanted to come came. But that's okay. Because when I created that show, I was working at it at home in my living room. I played 10 characters, I stretched myself in ways I would have never had the opportunity to stretch. And I realized like this is the most fun and the most creatively fulfilling thing I've ever done. More so than when other people have hired me. And that's when I realized, like, oh, I'm on to something here. So I continued to create my own projects. And yes, Year of the Slut kind of took on a life of its own. It didn't get me the things that I wanted, but I kept on working on it. I got to go to a festival in New York. I won the Audience Choice Award at the Frigid Festival. And then that's when people were like, this has gotta be a book. Like in New York, people that didn't I didn't know were coming up to me after the show saying, like, this will be a great chick-lit book. The title's great. This should be a novel. Writing the novel was like a whole other journey that I don't need to get into of, you know, working really hard, getting really passionate, and then getting completely discouraged by like, you know, query letters not being responded to, not being able to find an agent, literary manager, publishing company, la la la la la. It was like, you know, the acting career all over again, just with writing.

SPEAKER_01 16:15

Yeah.

SPEAKER_02 16:16

And um, I was encouraged to self-publish it, not so much because it would be a success, but just to get it to the finish line, just for my own self-satisfaction to know like I finished it. So self-published it.

SPEAKER_01 16:32

The title was censored. Wow.

SPEAKER_02 16:39

That like drew people out of the house and got the butts in the seats at the theater was censored by all the bots online that had to approve ads for Amazon, Google, Instagram, Facebook. So then I was like dead in the water for a year with that. Somebody encouraged me to like change the title.

SPEAKER_01 17:02

And I was like, but the title was like, why was it success?

SPEAKER_02 17:07

You know, I was like, no. So I I really like lamented over that decision. Finally changed the title, and when within a year of changing that title, the book became a number one bestseller on Amazon and won five literary awards. So I guess it was the right decision.

SPEAKER_00 17:26

You're like, yeah, that's painful, but you're like, I guess everyone was on to something here.

SPEAKER_02 17:30

Yeah. Well, it's just about being able to get into the marketplace, right? Like if if the one if one word is preventing you from getting into the marketplace. And also, you know, the climate, it's different waves, right? Like that came out, that originally came out almost 10 years ago now in 2018, 2019, and it was still like the Me Too wave. Now I don't think I would have the same problems with the word.

SPEAKER_00 17:56

Yeah. I was about to say, I feel like times have changed a little bit to where and again, it's it's interesting to see the progression because I feel like today it'd be a no-brainer. Like it would probably shoot up the charts because of the title, not in defiance of it.

SPEAKER_02 18:12

Yeah. So I wrote the play before Me Too, and the title was what got it the success in New York, and um, and then published the book just after the Me Too while things were still kind of tumultuous in that whole arena. So the word, the connotation of the word was just frowned upon. And also, these bots don't really understand nuance. They could they didn't get that it was like a feminist positive empowerment piece. Um yeah, so that was a little challenging, but I pushed through and yeah, so that's how that book came about.

SPEAKER_00 18:54

Yeah, super cool. I mean, every journey is so unique. You know, we we you said it earlier, not not two people are the same or not two journeys are the same, you know, in a little bit of a different context, but it's so true. It's just one of those things like you just have to chip away daily at things and just see kind of how it plays out because you just never, you never know. And how cool of it, how cool is it though, that although you didn't really want to change the title, it still was rewarding in the end and got a lot of recognition, which I'm sure was a very fulfilling thing and something you're very proud of.

SPEAKER_02 19:32

Yeah, you know, it felt really good. Any type of recognition feels good anytime your hard work gets noticed, right? Because so much of our hard work and so many of the hours and the blood, sweat, and tears nobody sees, right? Like they say, nobody sees like the 20 years it takes to become an overnight success. So um yeah, so it always feels really good. You know, I'm I'm excited. I'm excited that the book was well received and that people enjoyed it. It's has book two in the works right now. That's gonna be coming out end of the year, beginning of next year. So that's also exciting.

SPEAKER_00 20:11

Heck yeah, you literally just answered my question because I was gonna say your books are all a little bit different from each other, especially like this last one. So I was gonna ask if you had plans to write another novel, uh sounds like you're in the process of getting through all of that. Yeah. What I guess another kind of a backup question for that. What's the main difference or challenges in writing two different types of books? Like obviously, the one you just released is about theater, how to, you know, how basically coaching helping people through, you know, that process, and then a novel is way different. How do you, I guess, do you enjoy one versus the other? Or like what are the challenges and and fun parts of each?

SPEAKER_02 20:52

That's a really great question. So I do enjoy both. Being a producer, there is a bit of creativity to it, but it's more about logistics. And I'm just lucky, I'm fortunate, I'm one of those people that I have gifts for the storytelling and the, excuse me, creating worlds, creating characters, you know, dramatic storytelling. Like I have a gift for that. But on the flip side, I'm really good with the logistics also. I'm really good with the planning, the scheduling, the budgeting, the fundraising, the managing all of the moving pieces, the managing all of the different teams, you know, kind of juggling all of those things at once. And a lot of times, people who are good producers are not necessarily creatives, or creatives are not necessarily good producers. And I just happen to be one of those people that I enjoy both. And I think that's part of it because it's hard to be really good at things you don't enjoy. You know, and I I started producing. When I was in my early 20s when I first moved to New York, and I was terrible at it. I sucked at it. But I knew if I worked at it, I could get good at this because this is like a really complicated puzzle. And I like figuring out complex problems. So, you know, I guess I, you know, I'm kind of unique in that way. But yeah, so so the book that I just released is called Independent Theater Production for the Twitter Century and Seven Simple Steps. And basically, my producing and writing my own work was like the key to my own success. And I realized like I could help because it's a real point of pain and suffering for artists when you feel like you have so much to give, you have so much creativity busting out of you, but you don't have that outlet to perform it or give it to the world. You know, like it's it's it's a serious, it's a serious problem. Like we feel like we're gonna explode. So I realized like, okay, if I can help other creatives who are struggling, who are suffering the same way that I was, you know, by teaching them a simple step-by-step method of how to get a show off the ground, you know, then that would be amazing because like I understand what position I was in. And if I could help people do the same thing, like that's awesome. So that's kind of that was the impetus. And that's how I started kind of teaching these workshops and the consulting business. And yeah, it's now it has become a book. I I was hired to teach the course at Toronto Metropolitan University. And once I was teaching the course in the university level, I was like, you know what? I wonder if there's any books about this. And I Googled it and there hadn't been a book about this written in 30 years. And I was like, maybe it's time. So, but to answer your question, I know my my answers are so involved and long-winded. I'm sorry.

SPEAKER_01 24:00

No, you're perfect.

SPEAKER_02 24:02

To answer your question, yeah, it's it's very different to write creatively than it is to write like a how-to thing, you know, and it's kind of like a step-by-step guide or manual or whatever you want to call it. They're completely different beasts. But also, writing for film or TV or theater, those are three different separate beasts. And those beasts are all different from writing an actual novel, you know? So it's just about wearing different hats at different times, right? We're not always the same person consistently every room we walk into. So it's just like, okay, today when I sit at the computer, I'm, you know, Jennifer the teacher, as opposed to Jennifer the wild storyteller. And um, you know, so you just kind of wear the different hat and kind of pivot into that mode. And um, but I think I'm lucky because, like I said, I enjoy both. I enjoy all of it. And I enjoy teaching because I feel like knowledge is power. And if I can help empower other artists to take control and take the reins with their own creative destiny, then like these are just amazing gifts that I can share with the world. You know, my creativity and my films and my acting, and you know, that's one, but it's also kind of a selfish gift because it's something that I get something out of, you know, whereas teaching people to empower themselves is like so much cooler because then it's like then they can go off and make their stuff. And like, I can't wait to see what they're gonna make, what they're gonna do.

SPEAKER_00 25:45

Yeah. Well, it's so cool because again, you're just like you're you're making a mark in several different areas and and like who knows which one's going to just like lead to you skyrocketing into a certain path. But I think people have to do that, like, and you have you have different skills, different abilities, different interests, and you're just you're pursuing each of them in a in a certain way. And I think that's smart, first of all, just because you're not limiting yourself to one path that that may face some roadblocks, but you're opening yourself up and doing a lot of different things and a lot of cool things that's you're helping others, but you're also like putting your name out there and and doing your thing and can be noticed for different different stuff. So I just think it's very unique what you're doing in all the different areas that you're touching. And I can't wait to see what what you end up doing. Like in when we look back in three to five years, you know, I'm gonna be like, wow, Jennifer's an A-list person up here. Like she was on my podcast. That's it's gonna be a really cool thing to say.

SPEAKER_02 26:43

Thank you. Thank you. Yeah, you know, like if if I if I hit it big as an actor when I first started out, I probably wouldn't have branched out into all of these other things. But I say that necessity is the mother of invention. And, you know, when you don't necessarily get what you want when you want it, you have to find ways to stay in the game. It's all about staying power.

SPEAKER_00 27:08

Yeah. And I love what you were talking about wearing different hats too. Someone came on the podcast recently and they were talking, and I forgot who it was, but they they made a great analogy. And it was like, when I see a doorframe, I think door frame, reframe, because everyone you go through is a different crowd, different people, and you gotta be a different person, you know, and be able to work the room, whether that's with family or at work or with networking, there's he's always like doorframe, reframe, and just reset with everyone you walk through. So I was thinking about that when you were talking about wearing the different hats. But Jennifer, one last question for you. This has been such a fun conversation, and I ask everyone who comes on the podcast this question just from a book standpoint. But um, I'm curious to know what is a book or two that has meant a lot to you personally or professionally, and what's a book that you like to recommend to others?

SPEAKER_02 27:59

Okay, this is this is a great question because I love I love to read. So Herman Hess's Steppenwolf is a book that I revisit frequently. And there's just it's something about, you know, kind of the struggle between like the man and the animal inside of us. And I I love Herman Hess. I think he's a wonderful writer, but Steppenwolf is pretty profound, and I've I've read it at least a dozen times at this point. So that one creatively, you know, just just as a novel, it kind of like takes your mind to another another place.

SPEAKER_01 28:39

And then I recently read it's called The Big Leap, and oh the writer escapes me right now. I think I've heard of that before.

SPEAKER_02 28:55

It's a personal development book, and I I read it a couple of months ago. And yeah, I just kind of found it really insightful and talk about reframing, right? It's about reframing and positive mindset. And you know, I know most personal development books are about mindset, you know, going back to Napoleon Hill, think and grow rich, you know, because he was kind of like the godfather of the genre. But I don't think we can hear it enough or read it enough or be reminded enough that our thoughts create our reality, our words create our world. And like we're such emotional creatures and emotional beings, and and we live in such a reactive world, especially now where we're hijacked constantly by social media and so many distractions in the world that like really becoming disciplined about our thoughts and our words is so important.

SPEAKER_00 29:56

Yeah, no, I love that. I love those recommendations. Um, Jennifer, this has been fantastic. Thank you so much for taking the time to talk with me and to share your story and your work, as I cannot wait to spotlight it and obviously can't wait to see all the cool and amazing things you accomplished. No doubt you've already done amazing things, but no doubt you're on your way to doing even more. And uh, we can't wait to see see all that transpire. And so, but thank you, Jennifer. This has been really awesome.

SPEAKER_02 30:28

Thank you, Chris. It's been so much fun chatting with you. I appreciate it.