From Corporate America to Indie Filmmaker: Taking the Leap Toward a Creative Career

Dennis Rainaldi is a writer, director, producer and sound mixer from New York City. He recently left the corporate world where he was a technical project manager for 12 years to chase the dream of making movies. This year, he has completed his first short film as writer/director and finished his first feature film as a producer. Follow Dennis on Facebook, Instagram @dennisrainaldi and Twitter @drainaldi.

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Jessica Green in ‘The Prodigal Mother’ (Photo Credit: Soren Nielsen)

In 2006, I was robbed on a train platform while on a business trip in Rome. They got everything. Laptop. Passport. Luggage. Worst of all, my fully loaded point-and-shoot with every picture I had taken in Kenya on the first leg of my trip. I worked at the United Nations and had just spent weeks in Nairobi at the largest UN station in East Africa. Losing every photo left me devastated. A week later, while meandering around Europe on what was supposed to be a vacation, I was still sour and camera-less. I determined that a camera replacement impulse purchase was just what I needed to turn my mood around. Little did I know that the €750 camera I bought in Berlin would launch a chain of events that has led me to where I am today—the writer/director of my first short film, and producer of a feature film.

After Berlin, this new camera accompanied me around the world as I documented my travels while at the UN. It was with me the first time I summited Mt. Kilimanjaro with children from the inner cities of East and South Africa. As compliments on my photos from friends, family, and even strangers online grew in frequency, I began selling the pictures. After a year, I had made enough money selling photos to purchase a professional Canon camera. This was the first step to starting a life as a filmmaker, but I still had years to go before I could do it full time. This column is about how I made this transition happen.


Script EXTRA: Choosing a Camera for Indie Filmmaking


It wasn’t until seven years later, in 2013, that I was able to finally make this change. That also happened to be the year that I realized I was almost half dead. Sitting in my cubicle in New York City I was reading a grim article that announced the life expectancy of males in the United States had just decreased to 78 years. My 37th birthday was the following week. Dread washed over me. I was reminded of Jack Nicholson’s character in Alexander Payne’s beautiful and moving film About Schmidt. In it, a widower questions the decisions he has made throughout his life as he approaches his twilight years. The thought of having regrets on my deathbed was a terrifying prospect. Until this point, I had always been working to live rather than living to work. I was determined: this would not happen to me.

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Kieran McKenna in ‘The Prodigal Mother’ (Photo Credit: Soren Nielsen)

One thing I did have going for me is that I have always believed, even if you are in an unsatisfying job, doing as good a job as you can while constantly trying to learn will always pay-off in the long run. When I was hired at the UN in 2006, I was thrilled to be working at such a high profile job with so many perks. I took advantage of everything I could. I studied Arabic at the UN language institute for three years. I traveled around the world several times over and even got a Masters in Media in International Affairs. People always seemed to want to talk to me about the details of my job. My parents would speak of me at cocktail parties as though I was Jason Bourne. It appeared fun and exciting.

The reality of the situation, though, was that I was miserable at work. My job as a technical project manager left me unchallenged and unsatisfied. Meanwhile, my neglected creative side turned cancerous and poisoned my mental and psychical well being. Even though I continued to sell photos and get work as a videographer on nights and weekends, I was not generating much money. All the while, I was still wasting away in my cubicle. I began a more intense search for an opportunity to make this transition happen. Years of applying for jobs on-line and cold contacting production companies on Facebook and LinkedIn yielded no significant leads.

Then, a break! Two months after reading the article about life expectancy, a close friend of mine was asked to direct an indie feature named Off Season that was to be shot on Martha’s Vineyard in the Spring. It was a very low-budget independent movie. He and I had done a few small video projects together and he knew that I had extensive project management experience, was hungry for change and was trustworthy. He asked me to join the project as a producer. I agreed to do it and began to research everything I could about how to succeed as a producer.

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Chris Northrup in ‘The Prodigal Mother’ (Photo Credit: Soren Nielsen)

I had no experience on the set of a movie nor did I understand the different roles that are commonplace on film sets. It seemed to me that the production needed a project manager. Once I learned the cogs in the wheel of a film shoot (I.E.-SAG, paperwork and scheduling) I realized that everything else was no different than other projects I had managed in the corporate world. Deadlines and budgets had to be met, politics needed to be juggled and fires had to be extinguished. “I can do this,” I thought. I took all my vacation at once and traveled to Martha’s Vineyard for principal photography.

After the film wrapped, I was back in my cubicle. It was as though I was in prison, released for a month and then returned to my cell. The difference now was that I knew what was outside that cell and I knew how to get there. It was as if I was standing in the fuselage of a plane with the door open, my parachute packed, the destination in view, and all I needed were the guts to jump. But I hesitated. I had few contacts in the film world, having worked on only one major project and I knew getting a full-time job as a producer would be difficult. How could I sustain myself financially? I started to focus on the talents I did have that could get me work on film sets with the plan of meeting people and working my way up to the point where I could be producing my own creative content.


Script EXTRA: Pursuing a Screenwriting Career – Hope vs Faith


The first thing that popped into my head was to work as a sound mixer. I grew up as a musician and have an ear for music. After working on Off Season, I realized just how important sound is in film. Sound mixers are like drummers in a band. Every band needs one, and just as a poor drummer can make music unlistenable, bad sound can sink a film. Your hearing is the only one of the five senses that can’t be turned off, making everyone, whether they realize it or not, able to pick out bad sound. If there is a problem with the picture there are a thousand different tricks an editor can do to fool even the most seasoned viewer, but if the sound is strange or wrong, it’s immediately apparent to everyone watching.

A huge benefit to working in the sound department is that in order to do your job well, you also need to learn about other departments. Knowing that I did not want to work in sound forever, this is what interested me the most. You have to learn about framing, lenses and understand lighting techniques to plan for the shadows of the boom pole. Also, film sets are hierarchical and some jobs are sexy, like being a director or cinematographer, and some jobs, like being a sound mixer, are not. As I saw it, this meant that there would be more job opportunities.

Dan Bricker, Jessie Barr, Dennis Rainaldi, Clarke Mayer, Jessica Cadden Osborne, Erik Lieblein, Rob Cole - 'Off Season' (Photo Credit: Sara Nesson)

Dan Bricker, Jessie Barr, Dennis Rainaldi, Clarke Mayer, Jessica Cadden Osborne, Erik Lieblein, Rob Cole – ‘Off Season’ (Photo Credit: Sara Nesson)

The sound mixer that I hired to mix Off Season earlier that spring was now a good friend of mine and hired me as his boom operator for an indie feature he was mixing. It was a three-week feature to be shot in upstate New York. This was it. I jumped and left my cubicle forever.

The experience on that film was like a boot camp in sound for me. After, I felt ready to put my new knowledge to use.

A further benefit is when a sound mixer is hired, the production company rents their equipment, which oftentimes makes them the most well-paid member of the crew. This was going to be the first step in my plan. I read two books on sound mixing, bought a small ($2500) sound-mixing package and contacted every on-line production job board and connection I had until I found a hit, replying to an online ad for a sound-mixing job on a small feature film.

That fall, I mixed my first feature film and was paid $100 per day. I had no idea if I was going to be able to sustain myself or not. It was terrifying yet liberating. That was two years ago and every subsequent job I have gotten as a sound mixer since can be traced back to a recommendation from people I worked with on one of these jobs. In the past two years, I have mixed seven features, two television shows and more web series, shorts and commercials than I can count. Now, after having worked many different types of productions and continuing to grow my network, I felt ready for the next phase; making my own creative work.

The Prodigal Mother Poster

Poster Design: Dyanna Csaposs

In 2014, I wrote a script that I wanted to make into a short film and started passing it around to anyone I could get to read it. My goal was to shoot the script, entitled The Prodigal Mother, by the end of that year. The idea for The Prodigal Mother grew from a poem I had written as an English major in college, in which I questioned why the women and men in my life responded to obstacles and hardship so differently. Twenty years later, this question still nagged at me and I knew it would be interesting to address it in the language of cinema.


Script EXTRA: 7 Critical Tips for Short Film Ideas


After 23 drafts of the script, I felt it was ready. I contacted the best producer I had worked with and asked her if she would be interested in producing it. I was eager and tried to sell it as though this movie was going to change the fabric of cinema forever. I’m sure I sounded like an amateur. She explained that she had moved on from shorts, but offered to read it and give me feedback. After reading it, she liked the script so much that she agreed to produce it. I called in every favor I could from industry friends I had met during the past two years. In September of this past year, my first short film, The Prodigal Mother, was filmed in upstate New York.

Now, I am writing two features, have several more to pitch, and have been applying The Prodigal Mother and Off Season to the festival circuit. What I have learned trying to navigate the festival circuits will have to be saved for a future article. In short, it’s a level of headache greater than anything I have experienced so far—part-scam, part-nightmare, part-rewarding. Also, I have been asking for informational interviews with writers and directors whose work I admire and have been offering my services as a producer. Meanwhile, I am still sound mixing and am confident that soon these informational interviews will produce another break and allow me to move on from sound. Yet, I’m still challenged and inspired every day that I go to work and get paid to be a creative.

It feels incredible to sit back and think about the past several years, what I have accomplished and what my life would have been like had I continued down the path that I had been on for so long. If the past decade has taught me anything it is that life is too short to whither away in a job you don’t feel passionate about. Some clichés are just true. You never know what kind of curve balls life will throw at you. Standing on that metro platform in Rome, I remember feeling gutted from what I had lost and it seemed the stolen material items were all I could focus on. Now, I remember that day as being the moment that lead to me losing what I needed to lose the most: the feeling of being trapped in a job that was not making me happy. Today, while I still might be technically half dead, I feel more alive than ever before.

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