How I Learned To Stop Worrying & Love Freelance Life

Two years ago I moved from San Francisco to Hollywood to pursue a career as a screenwriter. At the time I was working as an advertising copywriter for a tech company in the city, one of the biggest brands in the world, and I was being paid more than I knew what to do with. By all accounts, I should have been happy. But I wanted something different, something new.

I wasn’t just chasing a childhood dream, though, I was hitting the reset button on my life. I had grown tired of the 9-to-5 grind. I had been logging 60+ hours a week for close to three years at a company whose values I didn’t share and whose success I was increasingly indifferent about. To put it simply, I was exhausted. I was burnt out.

But Hollywood success doesn’t happen overnight, and after getting settled in my new city, it was time to look for another job, something that would help pay the bills until I got my first break.

Right from the start my job search felt different. I didn’t know anyone in the area. I didn’t have relationships with any talent agencies. I hadn’t collaborated with anyone who could refer new clients.

My biggest obstacle, though, wasn’t finding writing positions, it was landing something full-time. I wanted another in-house writing position, one that came with a salary and a degree of security. Unfortunately, there are more writers in this town than there are opportunities, and those positions are few and far between in this new economy, especially, it seems, for creators.

Eventually, I couldn’t overthink it. I just had to take what I could get. When agencies asked if I was available for two-day gigs, I said yes. I needed the work.

One startup had me do their Brand Style Guide, which took three days. Another had me update their standard operating procedures manual so it could then be translated into Japanese by another copywriter. That lasted a week. A third had me write a bunch of marketing emails. As soon as I got comfortable with their brand voice and started to do some interesting things with it, the project ended, and I moved on to another temporary gig at another startup in another part of the city.

The instability was hard. Sometimes there were gaps between projects and I didn’t have enough money. Sometimes I had two-hour commutes (morning AND night), first taking a train, then a bus and then a long walk into an office where everyone rode scooters, everywhere. When I told them I felt liberated without a car, they thought I was crazy. Who doesn’t drive in LA?

Other times I worked from home, and the only contact I had with colleagues was through Skype, email or text. Sometimes the walls felt like they were closing in. Other times technology was an obstacle. Tone sometimes gets lost in emails, nuance missed altogether.

But at a certain point I adapted, and the more effort I put in to it, the more opportunities came my way. This wasn’t some great epiphany I had. I just stayed patient, remained good-natured and tried to do quality work. The rest just fell into place.

It’s been a few years now, and while I can’t say I love everything about it, I have now come around to freelance life. Some things I actually like better.

These days, when I wake up and the weather’s nice, maybe there’s an interesting cloud pattern or the light’s just right (this is Southern California, after all), I take a hike to Griffith Park or around Echo Park Lake with my camera. I get a little exercise, take in the mysteries of the world and snap a few photos. More than anything, I get out of my head for a little while. It’s a nice way to break up the day and approach each moment with a fresh perspective.

Of course, if I take a break, I have to stay up late. Sometimes I pull all nighters. Every once in a while a client will be slow paying an invoice and things get tight. Often I swallow my pride and accept client changes I don’t agree with. But that’s just nature of the beast.

While the long hours and solitude can be taxing, it’s also liberating once you figure out a way to manage your time efficiently. Routines are helpful. Establishing a healthy work-life balance is key. Tuning out distractions (and avoiding social media entirely) is essential. If you can find ways to manage these things, the world can be your oyster, especially if you’re good at what you do.

Ultimately, the best part about freelance work is the freedom and flexibility. You don’t have to be up so early in the morning or worry about what time you arrive at the office. There are no commutes. No traffic. No drives around the block trying to find parking. You can take meetings in your pajamas. You can spend all day at a coffee shop or work beachside. You can pivot from one thing to the next without explanation. You can take on whatever job interests you. You can do laundry and cook and still be productive all at once. You can call friends and not worry about people being nosey. You can play music as loud as you want. You don’t have to worry about meetings, declining stock prices or rumors at the water cooler. You can leave early to go to the gym or that concert you’ve been dreaming about and you don’t have to get permission beforehand.

For a third of all American workers, the freelance economy is booming today, and as technology continues to evolve, it’s going to become the norm. When you’re ready to make the leap, learn, adapt and embrace this new way of working. Just like anything, it’s a process. But you’ll figure it out. You’ll come around.

by Rob Simons