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DREAM CAREER TOOLKIT: Pushing the Boulder Up the Hill - Getting That Dang Film Into Production

Shawn Tolleson had a spontaneous post-film screening Q&A and one big question overshadowed them all… How did you get that dang film into production?

Shawn Tolleson is a career coach working with screenwriters and other entertainment industry professionals. She gives you the practical tools you need to accomplish your dream career. Check out blogs, videos, classes and more at! Follow Shawn on Twitter: @shawntolleson

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DREAM CAREER TOOLKIT: Pushing the Boulder Up the Hill - Getting That Dang Film Into Production

Shawn Tolleson directing her feature film.

I had a spontaneous Q and A today and there were lots of questions. But, this was the biggie that overshadowed them all… How did you get that dang film into production?

This is a particularly poignant question because it took so long for me to get a film into production. I worked on my script, Saturn Returns, for five years before we rolled camera. I worked on a feature project before this one for five years. I worked on another one before that for three years. So, it’s taken a lot to get here.

As you can guess, there are several answers to this question, but let’s just start with commitment. A year ago I came to a new place of commitment. Let me tell you what it looked like: I was going to shoot Saturn Returns in June 2014 or I was going to walk away from the project, and from being a filmmaker. No joke. I didn’t come to this from a place of being mad or fed-up or desperate. This decision was passionate but very calm. I simply realized that the amount of work I’d done, the capacity I had to keep doing that amount of work, the patience of my husband and my supporters, all of this had a shelf-life, and I was near the end of it.

So, I decided to pull out all of the stops. Now, many of you know me and know that I’m a very committed, hard-working person. So, this was a whole new level of energy, time and work. I worked pretty much every night and weekend for an entire year. This is in addition to my coaching business and to being the mother of three-year-old twins. (No, I don’t have live-in help, and I have very little family support besides my husband.) It meant that every trip to Mammoth Lakes (the place the film was shot and our vacation spot) I had as many meetings as I could and sacrificed R and R. It meant I worked every day of Christmas break.

I don’t tell you this to impress you. I’m just telling you what it took.

But there’s more to it than just the hard work. Because I’m not suggesting you live your life this way, far from it.

Simply put, I got willing to leave my dream behind if we didn’t go into production. And I got clear that if I were to do that, I didn’t want to feel like I’d left anything on the sidelines. I wanted to leave it all on the court. No regrets for what I hadn’t done.

I didn’t make this decision because I thought it would be powerful, but it turned out to be extraordinarily empowering. Every time someone came up with an objection, a concern, an obstacle, I weighed it against my commitment to go into production in June, and my willingness to totally walk away from the project forever. Push another year? Sorry, no can do. Push to September? Same answer. Wait for an actor? Nothing doing.

Besides demanding that I work nearly every night and weekend for a year, this commitment had me doing things that were so far outside my comfort zone it surprised even me. It had me asking things of people—investors, team members, actors and more—that I had previously been afraid to ask for. And it had me doing it fast, with zero of the usual hand-wringing. It had me doing things at a new level of ballsy, and I am no shrinking violet.

Really facing the prospect of walking away from my dream of directing a feature film had me look at my fears in a much more profound way then I ever have before. I had to ask myself what I was willing to do for my dream. No, the answer isn’t “anything.” There are things I won’t do. I won’t lie or cheat or steal or behave without integrity. I won’t leave my husband or children for it.

But, I got willing to fail publicly. That was a very, very big one for me. And, I think it’s harder to risk failing publicly then it is to behave without integrity, frankly.

The other big answer to the question of how I got this dang film into and out of production is that I had one die-hard who was with me no matter what. He happens to be my husband, Gregory. And without him making this film wouldn’t have been possible.

It’s important to talk about this because big projects like this one don’t get done alone. They take a team, as you know. But again, it’s more nuanced then that. Before the “team” there’s the one true believer that you absolutely must have. You need one true believer who will stick by you no matter what. And let me tell you, there was a time a few weeks out from our start date when everyone else dropped like flies. We suddenly weren’t cool any more, and everyone else who’d been on for years fell like dominoes. Though Gregory had doubts and concerns, he never stopped believing in the project and in me. You gotta have someone like him. Period.

So, this is the big answer to the big question of how I pushed this boulder up the hill and finally, after more then a decade, got my first feature into the can. There’s a lot more to talk about, and I promise I will do so. Keep your eyes peeled for a blog on casting, one I’m going to call Riding the Bucking Bronco, aka Production, Coming Back to Earth (aka Transitioning Back to Your Real Life,) and more.

Hit me with questions, comments and thoughts. It’s good to share it with you. And, again, thank you so much for your support.

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© Shawn Tolleson, Strategy Coaching, Inc. 2016

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