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Episode 027: Joshua Caldwell

Episode 027: Joshua Caldwell

On Defining Success

I spoke to Joshua from his new home in the Hudson Valley of New York state. His office is a wood cabin, and he used the camera in his computer to show me the 360 degrees of forest that surround him on all sides. It looks like a sanctuary—especially after Joshua shared that he and his family had recently relocated from Los Angeles. 

Joshua is a director, writer, producer, and MTV movie award winner. He spent the last decade living and working in Hollywood, and I was curious to know the impetus for him to move his family across the country to a radically different landscape. Joshua reflects on a childhood of playing make-believe in the woods of Seattle and wanting to provide an environment for his children to have a similar experience. He describes his time in LA as a conscious “layover,” a place for him to find his footing in the film and television industry until he felt established enough to work remotely from an area that fed his whole being more fully. He notes:

“[My wife and I] were in this tiny two-bedroom condo [in LA]. Everything around me was people succeeding with film and doing really well, which is obviously great—but there was just something missing . . . in my soul something was missing.”

For a large portion of our conversation, Joshua and I discuss what it means to be successful. Given that our culture largely defines success by measures outside of oneself, Joshua has spent the last ten years of his career looking within to understand what success means to him. 

In 2014, Joshua had written and directed Layover, a very low budget film about a young Parisian woman who finds herself stranded in Los Angeles after her flight had been cancelled to Singapore. What entails is a 12-hour, unexpected adventure that leaves the heroine of the story contemplating who she is and how she identifies with the world around her. The film was very well-received and soon after its release Joshua was given the opportunity to direct a series for Hulu. The project already had distribution on a major digital network and Joshua was certain that the series was going to help launch him into the next, “more successful” phase of his career.

Before going into the details of the series, Joshua shares with me some of the new ways that he is starting to question what it is that’s going to make him happy and what it actually means to him to be successful. He notes, “Where is my bar going to be? If the bar is money—you’ll never have enough of it. If the bar is fame—you’ll never have enough. Is success getting to make a feature film? At one point I thought that’s what it would be and I’ve done that three times.” He continues with his reflections on The End of the Tour, a movie about the great writer David Foster Wallace. Joshua remembers a scene in which Jason Segel (who plays Wallace) notes that you can put your heart and soul into something. It comes out, it does as well as it could possibly do, and then you realize that you feel exactly the same. We want our work or our external conditions of success to make us feel different—but it’s fleeting; they never last. 

Joshua and I then discuss self-determination theory, initially developed by Edward L. Deci and Richard M. Ryan. Self-determination theory represents a broad framework for the study of human motivation and personality. It holds that human beings need three basic things in order to be content: 1) they need to feel confident in what they do; 2) they need to feel authentic in their lives; and 3) they need to feel connected to others. All of these values are considered intrinsic to human happiness and far away from extrinsic values such as beauty, money, and status. After years of living in Hollywood and recognizing that external conditions for success weren’t making him happy, Joshua has begun to reevaluate many areas and aspects of his life. 

Halfway through our conversation, Joshua shares with me the details of his Hulu project. He was hired to direct a series of episodes in Miami. The script for the series was more “soapy” than Joshua desired. Because it was his first time working with an actual budget, he was holding steadfast to the idea that with a little bit more money and greater access to high-quality equipment and staffing, he could elevate the script in a way that would give it higher production value. However, in this experience, he failed to listen to his gut instinct. He had already made a successful film on a very low budget utilizing scrappy innovation and humble tactics. In doing so, he created something with heart—something that his audience could relate to. When looking back on the Hulu project, he now recognizes that he was forcing his team and himself to create something based on ideology rather than reality. As a result, the project was unsuccessful and unrecognized. He states,

“[I] saw that [I] didn’t have the ability to get really solid supporting actors because [I] didn’t quite have the money. And there’s a way to help them be better [as a director]. But the way I shot it, the way I had determined in preproduction that I was going to do it, did not really help them in the way that it should have.”

He continues, 

“I look back on this series and I can’t lay total blame on not having enough money or not having enough time, although that was certainly an aspect of it. But I didn’t adapt to that situation in the way that I should have, in the way that I’ve learned to since then. And learned to as a result of that to help make the material better.”

This experience was a massive turning point for Joshua and how he was in relationship with his definition of success. It’s so often that the largest obstacles that we experience in life lead us on a path of self-actualization and so often that our failures force us to reevaluate our values and attempt to uncover what makes us feel happy, what brings us contentment. As Joshua and his family begin to create roots in upstate New York, I am certain he will be attempting to understand this and the meaning of many other things amidst the trees and the leaves of the forest. 


Joshua Caldwell is a director, writer, producer, and MTV movie award winner. His debut feature film Layover was made for $6000 and had its world premiere to sold out crowds at the 2014 Seattle International Film Festival where it was nominated for the prestigious FIPRESCI New American Cinema Award. In 2015, he directed the first season of Hulu’s South Beach and the Paramount Pictures feature film Be Somebody. In 2017, his latest film, the action-thriller Negative, had its world premiere at the Newport Beach Film Festival and is now available on digital HD and on-demand video.

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