Make Your Own Break: Jennifer Lieberman

Make Your Own Break: Jennifer Lieberman on Building a Creative Career Instead of Waiting to Be Picked

When you’re trying to break into acting, writing, or producing, waiting for someone else to hand you a role can feel like a full-time job. Award-winning Canadian actor, writer, and producer Jennifer Lieberman shares why she stopped waiting, started creating her own work, and built a career around making opportunities happen.Her story is especially useful for creatives who feel stuck, underused, or invisible. Jennifer explains how one-woman shows, independent theater, and self-produced projects gave her a body of work, a stronger voice, and a path forward. She also discusses independent financing, AI in production, and why live theater may be due for a comeback.

Why waiting to be cast wasn’t a strategy

Jennifer’s creative turning point came when she realized she was spending too much time hoping to be chosen.“I’m an actor who got tired of waiting to get picked,” she says. That frustration pushed her toward writing and producing her own work, beginning with theater and eventually expanding into books, web series, short films, and feature development.For many creatives, the default path is reactive: audition, wait, and hope someone sees your value.

Jennifer’s experience shows the downside of that model. Without footage, a reel, or a body of work, people may not even know you exist.She did not begin with confidence, either. Someone encouraged her to create a one-woman show because she needed a vehicle to let people know she was there. The point was not ego—it was visibility.Making your own break does not mean doing everything alone. It means recognizing that your career cannot depend entirely on permission from other people.

The one-woman show that changed everything

Jennifer’s first major self-created project was a one-woman show, and it changed how she saw herself as an artist.She admits the process was terrifying. A close friend from Canada came to support her before the performance, and Jennifer says she might have spiraled without that encouragement. Even though it was technically a solo show, she still needed a director, lighting and sound support, and a trusted friend to keep her grounded.That is an important reminder for anyone who thinks “doing it yourself” means doing everything alone.Jennifer’s show did not attract the industry decision-makers she hoped would attend.

However, she discovered that she was more creatively fulfilled writing and developing her own material than waiting for outside approval. The experience expanded her range and proved that she could create meaningful work herself.A project can miss its original goal and still change your life.

Make Your Own Break with Jennifer Lieberman

Hollis talks with award-winning Canadian actor, writer, and producer Jennifer Lieberman about building a creative career by making your own opportunities. Jennifer shares how a one-woman show changed her path, led to her company Make Your Own Break, and inspired her book on producing independent theater.They discuss the realities of acting, independent production, funding, AI in film, and why live theater may be due for a comeback as people seek more human, in-person experiences.

Key topics

• Why Jennifer stopped waiting to be chosen and started creating her own productions.
• How a one-woman show helped transform her career.
• Overcoming self-doubt and taking on work that feels frightening.
• Why even a solo project needs a supportive team.
• How creative fulfillment can matter more than external validation.
• Building a body of work as a calling card.
• The realities of independent film and theater financing.
• Why most creative projects fail—and what failure can still teach you.
• How Make Your Own Break helps struggling creatives create opportunities.
• Jennifer’s book about producing independent theater in seven simple steps.
• Ethical AI and the continuing importance of human actors and creators.
• Why live theater may be entering a new renaissance.
• Staying grounded through exercise, yoga, and real-world connection.

00:00 – Welcome and introduction
02:16 – Why Jennifer stopped waiting to be picked
03:35 – The push that helped her create a one-woman show
06:40 – Why doing something scary matters
07:54 – The night before her first show
09:54 – When the industry audience did not show up
10:33 – Finding fulfillment in creating original work
13:03 – Moving from theater to film and web series
13:30 – The realities of indie film budgets
15:07 – How Make Your Own Break began
16:29 – Jennifer’s book on independent theater production
19:05 – The economics of acting and SAG
20:17 – Jennifer’s perspective on AI in filmmaking
21:07 – Ethical AI and keeping humans involved
26:19 – Getting out of your head through movement
27:51 – What went wrong with Dumpwater Divas
32:18 – Why theater may experience a renaissance
34:37 – Phones, screen addiction, and real-world presence

Notable quotes

“I was an actor who got tired of waiting to get picked.”Copy

“If you’re not doing something that scares you, you’re not going in the right direction.”Copy

“If you’re not having fun, you’re fired.”

Action items

• Create a small project that functions as your calling card.
• Build at least one supportive collaborator into your process.
• Focus on practical proof of your abilities, not just potential.
• Use movement, exercise, or yoga to quiet your mind.
• Think realistically about audience, financing, and risk when producing creative work.

How creative work becomes a career asset

Self-created work is not only artistic expression—it is career infrastructure.Performers need calling cards. Writers need samples. Directors need proof that they can deliver. A body of work helps people trust you because it shows what you have already done.After her theater work, Jennifer created web series and short films and began developing her first feature film. Her progression reflects the realities of independent production.

Short films can sometimes be made through favors, in-kind donations, and small crews. Features require much larger financial structures, including incentives, soft money, and presales.Jennifer is honest about the odds. Most creative projects fail, whether they are plays, films, or books. Her takeaway is not to become cynical, but to structure projects properly and understand the risks.

Talent is not enough. You also need strategy.That is the purpose behind Make Your Own Break, Jennifer’s company for helping performers, writers, and directors create opportunities for themselves. The goal is to help creatives put tangible work into the world instead of relying only on abstract potential.The core mindset shift is simple: you are not waiting for a break. You are building one.

Why theater still matters in an AI world

Jennifer has a balanced perspective on AI. She does not see it as the end of creative work. Instead, she sees it as a tool that can lower production costs and make certain stories possible when traditional funding would be out of reach.Jennifer is involved in AI feature films with a commitment to ethical AI. That approach includes hiring actors, using motion capture and human voices, and employing designers and art directors.The question is not simply whether AI should be used.

The better question is how creative people can use new tools without erasing the humans who make the work possible.Jennifer also believes theater is poised for a resurgence. People are experiencing screen fatigue and looking for community, physical presence, and real-time connection. Theater offers an intimate, local experience where people can share a story and discuss it with strangers afterward.Live performance is not merely nostalgic. It allows for creative risk, local relevance, and artistic freedom outside a mass-market formula.

What to do when a project fails

Jennifer shares the story of Dumpwater Divas, a web series that was enjoyable to make but did not attract a large audience. The production faced challenges, including losing its cinematographer at the last minute.Even so, Jennifer says it was one of the most joyful experiences of her life.A project can be a marketplace failure and still be a personal or creative success.Her rule is simple:

if you are not having fun, reconsider the project or the team. She believes in working on things you care about and collaborating with people you enjoy. If you are not being paid the big bucks, joy matters.For creatives, this is a healthy way to think about failure. Do not ask only whether the project won. Ask what it taught you, what relationships it created, and whether it made you a stronger artist.

The biggest takeaways

Jennifer Lieberman’s career is a reminder that waiting for permission is often the slowest route to growth. She built momentum by creating her own material, learning from setbacks, and treating self-production as a way to develop both her craft and her credibility.

• If no one is casting you, consider creating your own material.
• If you are scared, you may be getting closer to meaningful work.
• If a project fails commercially, it can still be a creative win.
• If the industry changes, learn the tools and stay adaptable.
• If you want staying power, build a body of work people can trust.

For anyone in a creative field, her story is a practical blueprint: do not wait to be discovered before you make something worth discovering.

Frequently asked questions

What is Make Your Own Break?Make Your Own Break is Jennifer Lieberman’s company and creative platform for helping performers, writers, and directors create opportunities for themselves through resources, workshops, and independent theater guidance.What is Jennifer Lieberman’s book about?Her nonfiction book explains how to produce an independent play in seven simple steps.Is AI replacing actors and filmmakers?Jennifer believes AI is changing production but not eliminating the need for human creativity.

Ethical AI can still involve actors, designers, and other creatives while lowering costs.Why does Jennifer think theater may make a comeback?She believes people are tired of screen fatigue and want real-world connection. Theater offers a live, local, shared experience that cannot be replicated digitally.Where can readers find Jennifer Lieberman?Jennifer’s books are available through Amazon, Barnes & Noble in the United States, and Indigo in Canada. More resources are available at makeyourownbreak.com, and she shares updates on Instagram at @iamjenlieberman.