I have been writing professionally since Shovel Buddies sold in 2015. Some years it pays all my bills. Other years I do a ton of side jobs to make ends meet. Still, I can call myself a writer, and I always thought that would be the dream. But I want to tell you about how I had to encounter that dream head-on recently, and what I learned from that experience.

Among my side jobs, I teach a lot of screenwriting courses. I was Skyping into a class at Boston University, my Alma Mater, and the class was winding down.

I was in the Q&A part of my lecture, and I was getting the typical questions. “How do I get an agent?”

Are screenwriting degrees worth it?”

“Will you read my spec?”

  1. Make connections that can pass your script up the ladder.

  2. Sometimes.

  3. No.

But then another hand went in the air. And the precocious guy behind it asked: “You’ve talked a lot about Hollywood and living in Los Angeles, and I just wanted to ask you...are you happy?”

For a moment I stuttered. I wasn’t sure how to answer, and wasn’t sure if I ever had to think about my life in this way. I was a working writer. I put ideas on the page that people valued.

But did it make me happy?  

In the moment I bullshitted. I talked about how I knew Hollywood was a grind, and that a lot of “breaking in” wasn’t about one success, but the struggle to keep the successes coming.

It was a good answer, if you like a surface-level analysis of happiness. But it got me thinking...

What was the real answer? Was I happy??

Later that night I washed my face and stared in the mirror.

Was I happy?

I had a script on The Black List. I had movie at SXSW.

But I also was still doing odd jobs and uncredited rewrites to pay the rent. I was still being asked to do free work by influential producers. I was still struggling to be the person on the call sheet bringing in money. I was getting better at writing, but not everything I had come up with was commercial or even viable in the marketplace.

I had to get rid of my manager. I lost my agent.

I was down on myself. My career. And my future.

In that moment... the REAL answer?

I wasn’t happy. At all.

I wish I could tell you there was a magic way I got happy, or that I sold a million dollar spec and gained some perspective on life.

But that’s not what happened.

What happened was…

My Pursuit of Happiness

I started waking up every day and thinking about happiness.

And every night, before I went to bed, I asked myself if what I did that day made me happy.

Then I got really weird, and I started writing screenplays about characters who wanted to be happy. They thought one thing would make them that way, and throughout their journeys realized that maybe life was a little more complicated with that.

This didn’t actively make my writing better, but it did make it relatable.

That relatability reinvigorated why I cared about writing. It got me a new manager and he got me a bunch of new generals.

Suddenly I had something to say, and I had characters who wanted things and weren’t afraid to be vulnerable about their failures.

Characters who weren’t afraid to admit that maybe they needed to make some changes if they were ever going to be happy. And a writer who was right there with them.

When those new scripts got me generals, I found myself not only pitching what I thought I’d write next but talking about stories in the way they’d make me happy.

And the funniest thing happened.

Instead of thinking I was crazy, the executives I talked to talked about their own struggles with happiness. With the grind of the job, with the hard parts of Hollywood, the pursuit of greatness.

And, ultimately, failures.

As my characters looked for this happiness, I learned a lot about them and their world. And as I learned about them, and the executives who liked their journeys, I learned even more about myself.

This sounds like Hollywood is full of sad people, and it might be.

But if it’s full of anything(aside from... well... you know), it’s full of a lot of people who came here because they had dreams. And at some point they woke up and realized how hard it was to achieve those dreams.

They made sacrifices.

They lost out on jobs.

They struggled.

It was that recognition that we’re all the same that made me a better writer. It made me better at crafting characters, arcs and using my own faults on the page to help other people believe in the fictitious journey of the person they were reading about.

Suddenly, my stuff was getting read more and passed around I was actually booking things.

It’s been a helluva ride, and I realized that the only way to keep moving forward, was to come to terms with the fact that I’m not going to be happy every day.

But the pursuit of happiness was a good reason to keep going. To keep writing.

So this brings me to last week.

Like Any Good Story, it Comes Full Circle

There I was, sitting in a waiting room before a huge pitch.

I hear a voice.

“Hey, Jason Hellerman, right? I’m David--I went to BU, maybe you remember me. I’m the kid who asked you if you were happy--”


I looked up and saw the face of the kid who changed my life without knowing it. The kid whose question was responsible for me becoming a better writer, and probably a more empathetic person.

And so he sat down and we talked about life. It had been two years since I Skyped into his class. He was now interning at a prestigious production house in Los Angeles. He’s doing great, started his own writing group, and suddenly facing the terrors of “making it” in Los Angeles.

So I told him the only thing I for sure know.

It’s not about making it.

It’s about being willing to work hard, take side jobs, and do whatever is necessary to confront each day, one day at a time. It’s about finding a great group of friends you can rely on, talking with your family when you hit those lows, and never being too scared to show your vulnerabilities on the page.

We hugged. He went back to work. I went into the pitch.

I guess it went well. This is Hollywood, It’s pretty hard to tell.      

But I know one thing for sure:

When I walked out of that production office I was as happy as I’ve ever been.