Just over 10 years ago, I was about to turn 27 and hunting for ways to keep myself on a trajectory of upwards and onwards. Best as I could figure at the time, that meant leaving behind a very stable and very loved staff position I’d held for 6 years, to set out on a freelance career of uncertainty.

I had doubts. In fact, I was terrified. I poisoned my mind with the thought that I wouldn’t be good enough to secure enough work to make ends meet, let alone thrive. Even my parents, who’s advice I still seek and value to this day, basically advised me against it for other reasons, and I can’t say I blame them. It didn’t make a lot of sense on the surface to them. I loved my job, the work, the people, the company, and I was making great money for the season in my life. It was safe, and freelance was a risk. None the less, I charted my course, gave notice to my bosses and mentors through a very shaky voice, and to my own amazement, I took the leap.

It helped that I had a clear vision of what a successful freelance career meant to me, before I even embarked on it. I wanted to work less, earn more, make more art (as opposed to only directing it), and position myself to work remotely should I ever choose to leave the sprawl of Los Angeles behind. Those 4 ideas, each one a different form of freedom, was what I sought in freelance, and the promise of those ideas made leaving a job I loved, turn from unbearable, to obvious.

Looking back a decade into it, it’s clear my freelance career took shape differently than I imagined it would’ve, but I met the destination I set all the same. Put modestly, freelance has gone well. Put bluntly, last year alone I took months of collective time off, earned more money than ever, spent the majority of my days making art, and worked entirely from my home office. I attained the ideas I sought all those years ago, and it didn’t take 10 years. Some came immediately, and some took longer, but for the most part, reaching my definition of success in my career, is old news.

So, I’m not celebrating reaching some metaphorical mountain top in this moment, that’s already long been true. What I’m trying to do, is preserve the memory that I once did something that absolutely terrified me, and that it worked out alright. That I swam instead of sank. That I took a risk, and that I not only lived to tell the tale, but am better for it. It’s easy to forget how brave we once were, when we’re standing in the shadow of new fears. So here I am, trying to remember, because 10 years sure seems like an awful long time to have not rolled the dice.

There's More. 1981 posts across 17 years. It's a lot of content, so I put together some of my favorites all in one place. If you’re new here, it’s a great place to start.
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