Penny Middleton Header

Penny and I first crossed paths when we both got hired to work as production assistants for a play written as entertainment for a diabetes conference. I can’t make this stuff up. Working with her was like working with an old friend. We had a great time, and over the years I remember being so impressed not only with her intellect and personality, but her follow through. Whether it was collecting clothes for underprivileged girls to go on job interviews, or packing up and moving to New York to pursue her dream of being an actress, when her mind is made up, something amazing is not far behind.

Q: Origin story time – what were you doing before and what led you to this?
A: Before I moved to New York I was living & working in Orlando, Florida. I was barely making enough money to get by (working a salary job by the way). I asked for a raise because I went from being a receptionist to a web producer. When I initially had the conversation with my boss, I didn’t plan on quitting but when I was told that I wasn’t going to receive a raise my gut instinct was to utter, “Ok. Then I have to put in my two weeks notice.” I went to my car and cried! I had no idea what I was going to do. Then, I realized that I had always wanted to move to New York, so it seemed as good as a time as ever to do that. A month later, I packed up my car and drove up. I had maybe $1000.00 in my account, no job lined up, but all the passion in the world!

Q: What resources and tools helped you grow your business/brand? (i.e. Self-learning, school, books, mentors) What would you recommend?
A: Working in production allows me to see how a project is made from start to finish. I started off as a production assistant. I know freelance as a production coordinator. So when I show up on set as an actor or if I’m self-producing the project, I already know what goes into making a production run. For any person looking to start in this or any business, I recommend learning it from all aspects. It might seem tedious, but in reality, you will have such a wealth of knowledge and appreciation for all parties involved in the execution of your business/brand, because let’s face it, you can’t do it alone!

Stop wishing start doing

Q: What are some of the hardships and realities of being a female creator/owner in your industry?
A: The reality of the situation is this; when you’re an artist on the margins (non-white/male) you have to show up. Every. Single. Time. You can’t walk into auditions with a picture; you’ve got to walk in with a Picasso. 95% of the work I do as an actor is self-produced, a fact I resented for a long time. Now, I embrace being a writer and producer. I also embrace the reality of this business, but I reject the box in which it wants to place me. I’ll audition when I can and continue to carve out a nook for myself with my self-produced work.

My hope is that through my art I can help show that it is possible to be tolerant of others beliefs without lessening or denouncing your own! I know that this is disgustingly optimistic, but I have no interest in adding to the pollution of negative talk in the world.

Q: How do you grow your network and community of clients/fans and collaborators?
A: I am the worst at networking! I’m just too awkward. I prefer to be an active participant in my community. I will see shows, workshops, openings, etc. I really like working with up-and-coming artists, writers, and directors. Also, I think it’s important to not always approach people with a “want.” In other words, having a genuine human interaction with someone is more lasting than simply trying to obtain another notch on your “who do you know” belt.

Q: Name a fear or professional challenge that keeps you up at night.
A: “Am I doing enough?” That is always on my mind. I could (and often do) work an 18-hour day and STILL wonder if I am doing enough.

All you need quote

Q: Time management – how do you fit it all in?
A: I am a person who can function on little to no sleep. I don’t recommend that! There is enough time in the day to do all that needs to be done; you just have to be smart about it. Make a plan that fits your needs. For me, I write better late at night. I find that I am more creative and less likely to self-edit at that time. So during the day, I never write. I would be wasting time. Instead, I look for auditions, go over sides, work on production documents (call sheets, schedules, promotional material, etc.)

Q: What are some key personality traits needed to do what you do?
A: Organization and the ability to multitask. I also have to work with a lot of different personalities, so the ability to operate from a neutral position is key. I can’t let others emotions or lack thereof affect my work. Cool, calm, and collected (with the occasional meltdown in the bathroom stall).

Q: In moments of self-doubt or adversity, how do you build yourself back up?
A: I always ask myself, “Is there anything else that you could be doing with your life.” The answer is always the same — no. I am an artist, and it’s the thing I think about when I wake up and the last thing I think about before I go to bed. That’s it. So when I feel like an utter failure, or I come up against adversity I know that those are fleeting moments, but my passion is forever.

Storytelling quote

Q: What was the best piece of advice you were given when you were starting out?
A: Do you. Do what you want, how you want, from where you are and with what you have. Don’t place your success in the future tense; a dream deferred stays a dream. Never allow anyone to place his or her limitations on you (which are often masked as concern.)

Q: What’s next for you?
A:  I will be performing at the Bushwick Starr as part of their BIG GREEN THEATER (BGT) project. The BGT is an annual eco-playwriting program and green theater festival celebrating environmental education, sustainability in the arts, and community enrichment. In our 7th year of BGT, our 4th and 5th-grade student playwrights are tackling the theme of climate justice. (Visit to learn more.)

Penny knew regardless of her location and circumstances, her purpose in life needed to be fulfilled. Have you found your life’s purpose yet? If so, how have you gone about sharing it with the world? If not, what steps are you taking to find it? Let us know in the comments below.

For more info on Penny, Adventures in PennyLand, and her other projects check out the following links:
Youtube: Adventures in PennyLand