We caught up with the brilliant and insightful Rachel Westra a few weeks ago and have shared our conversation below.

Rachel , thanks for joining us, excited to have you contributing your stories and insights. What was the most important lesson/experience you had in a job that has helped you in your professional career?

The biggest lesson I learned is to never lie about what you want. To many this seems very obvious, but when you are just starting out and you need your first job to get you off the ground, it can be tempting to say what others want to hear.

As my senior year of college was coming to a close, I was panicking. I had a degree in Film and TV production a year past a worldwide shutdown and the industry that I was previously so excited to enter seemed too paralyzed by the aftermath of the Covid-19 pandemic. I started doing as many informational meetings as I could, whether through mutual connects or cold emailing people I had found on LinkedIn. I received contradicting advice because, in the end, there is no one way to make it in Entertainment. Some recommended I tell recruiters what they wanted to hear especially in the case of landing your first job in representation. “Just say you want to be a manager/agent and then when you want to leave, you can say you’ve changed your mind.”

I would agree except for the fact that the year you spend learning the basics for the rest of your career is precious. It’s a blip on your timeline but it’s the beginning of getting to know the people you one day hope to work with. For me, I already felt I wanted to be more involved in the creative process and work with writers to develop new shows. So I never lied.

I’m still relatively new in my career but because of my transparency, people that I’ve gotten to know have been more helpful than I ever could have imagined. When looking for my next job, I told anyone that would listen that I was looking for TV development jobs. In the end, it helped me cover more ground in my job hunt and led me to the right people. So while it can be tempting to say the right things to get the first job, I highly encourage those who know what they want to be honest.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m originally from Appleton, WI but would spend weeks at a time staying with my aunt and uncle in Chicago taking classes at Second City. I loved the collaborative process from pitching to writing to producing the goofball ideas you had dreamed up that morning. It’s what led me to ultimately pursuing television as a career and what continues to spark my creative drive.

Because I’ve produced my own projects outside of my 9-5, given notes to multiple writers, and received both good and bad feedback on my work, I’ve honed a way to give notes that leaves the writer excited to jump back into their drafts rather than dreading how they can “fix” their idea.

It’s a delicate balance but I’m a firm believer that first drafts should never hold the weight of what a project can become. Rarely, in my experience, is the first draft amazing, but it should give writers a jumping off point to build their masterpiece. It’s exciting to finish a draft because you’re one step closer to your final draft. At the end of the day, all that matters is “Are you still excited about this project?”

Since I started at Rhode Island Ave. Productions, I started offering script reading services on my website. My goal is to help writers feel confident about their idea and help move along their project no matter what stage it is at.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

As many people will say, entertainment is all about who you know. It’s a rather frustrating sentiment for someone whose family could not be further from the entertainment business. I often feel like a cliche, the midwesterner that showed up with a suitcase and a dream (eye roll).

However, while I do believe relationships are important, the best advocate for you is you. As I tried to leave my first job to pursue development, many of my colleagues at the time told me to ask my boss to help me look. At 10 months in, I initiated a conversation about leaving the company and was met with “What? Why would you do that? You can do all that here. You don’t know what you want anyway.” If you want to retain good relationships with your employees, telling them they don’t know what they’re doing is not a good strategy.

Understanding I was not going to get the help I was looking for, I set out on my own and met with people working in TV outside of work and applied to jobs on the side. Ultimately, I found my new role and put my two weeks in two months after my initial conversation. My boss was upset that I had done it without his help, calling my new employer to reprimand them for not asking his opinion on something that was my decision. I learned that day to not wait for permission and trust yourself. Don’t waste time waiting on someone else.

Is there mission driving your creative journey?

I hope to one day produce out of my own company. I’ve followed a thread that keeps me laughing and living in the creative. I truly believe that when you follow what brings you joy only good can come from it. It’s why I continue to work on projects with my friends because it reminds me of why I pursued entertainment in the first place.

Contact Info:

• Website: https://www.rachelwestra.com
• Linkedin: https://www.linkedin.com/in/rwestra14/

Image Credits

Paige Freeman