When to Keep Going

Photo by Nick Fewings on Unsplash

"The only real 'yes' is money." The statement slapped me so hard that I had to pause the podcast just to process. I'd been in L.A. for a few years by that point, hustling between assistant jobs, putting up shows, meeting other writers, and writing—always writing. I had finished some interesting scripts and found a few amazing mentors. Each new day job had nudged me closer to a writers' room. Everyone kept telling me I was "on the right track," and I clung to their words like a kid guarding the last piece of candy.

Now this famous screenwriter, recording from the big house he bought after his many yesses, was telling me that all that encouragement might not mean anything. And the scariest part was that I knew he was right.

Not that I didn't need the encouragement. I did. Embarrassingly desperately so. There's a reason Words of Affirmation is a whole Love Language. The problem was that there was no track. Los Angeles has an abundance of wonderful, supportive people and a painful dearth of creative jobs and those who can hand them out. The more I hustled and learned about the industry, the more a writing career started to feel like a mirage shimmering just out of reach. The podcast had a point: there weren’t a lot of objective indicators that I should keep going.

A lot of dreams come with the same ruthless wilderness between passion and profession, and it's way too easy to get lost out there.

So, when I finished the podcast, I made a list—roughly in order—of the more tangible signs that I was moving in the right direction, the milestones between passion and profession, the little yesses on the way to the “real” one.

Whenever you feel stuck, take a look. If these things are happening, you're on the closest thing to a right track:

1. You are having fun.

2. You are finishing things.

3. You are proud of the results.

4. People ask to see it.

5. People give you feedback about it.

   1. That feedback is honest.

   2. That feedback is constructive.

   3. That feedback is positive and minimal.

   4. That feedback is more about what you should do with it since it's already great.

   5. That feedback is about how they can be involved in whatever comes next.

6. People ask you for feedback on their work.

7. People share your work.

   1. People share it with others who would enjoy it.

   2. People share it with others who might be able to do something bigger with it.

8. Your audience is growing.

   1. You’re reaching new people.

   2. Your existing audience is still engaged.

9. People ask to collaborate with you.

10. People recommend you for jobs.

11. People ask you to speak to/advise/mentor others starting out in a similar field.

12. People pay you a little.

13. Very Important People see your work.

14. Very Important People almost pay you.

15. Very Important People who almost paid you consider you for another opportunity.

But after a few more years and a few real yesses, I learned something: the only one that matters is #1. As long as you have that, keep going.

And you’d better hang on to it, even after you start getting paid—because you'll be going through this list again very soon.