Journey to the Mountain — How My First Year in Freelancing Went

Michael Ruiz
The Startup
Published in
7 min readDec 17, 2017
Hurricane Ridge, WA

This photo was taken at the top of Hurricane Ridge.

In order to access the site, you must travel either by ferry from Seattle or head north from Olympia to the city of Port Angeles. You must then pay a fee to embark on an hour-long journey up a narrow, winding road. You’ll come to the end of this road to find a small parking lot, visitor center, and the jagged peaks of the snowcapped Olympic Mountains. And, if you take a short walk up the small hill behind you, the Puget Sound rests between you and the distant Vancouver Island.

Standing between two pine trees and in the middle of taking this photograph, I realized — no matter what happened next — that I had arrived to this place under my own volition. I had written my way to the mountaintop.

It was a long journey getting there.

I started 2017 in a rather miserable state of affairs. I felt aimless. I was working to complete a film I knew would never generate a dime. I had spent the past several months stressing over problems that did not exist and trying to help people I couldn’t reach. Most of my days were spent cooking chicken for minimum wage and my nights spent working towards my degree.

I had spent a good portion of my life thinking that I was destined to be a screenwriter. Several drafts of speculative scripts on my hard drive serve as unfortunate proof. But the older I got, the more I realized that my desires had nothing to do with the art of filmmaking, and everything to do with the art of storytelling.

I loved to tell stories. I bounced around mediums throughout high school, desperately trying to find an avenue to create in. I tried out blogging. I wrote poetry and drew comics. I composed music, and I eventually settled into screenwriting.

I chose the medium in which I found the most success. I found a project to devote my creative passions towards. I was able to work with dozens of people and learned so many things about filmmaking. But the problem was, I had finished my work on the project in the Spring of 2016. I was a storyteller out of a job — stuck between waiting years for the project to reach completion and searching for others to hand my stories off to.

The biggest frustration with screenwriting is that you’re not creating a finished project. You’re creating a blueprint. Without financiers and filmmakers, your story is intrinsically worthless on the page.

This is where freelancing comes in.

This spring, I decided to see if I could generate an income by writing online. I focused my efforts on creative writing, and set out to work on content mills.

That…was a mistake.

I soon learned that content mills were a race to the bottom rather than a pathway to success. I faced competition on a worldwide scale and was forced to compete with rates far lower than my minimum wage job. Out of frustration, I accepted a job to turn an ebook into a screenplay. The task took me a week and my final paycheck was less than a days work in the kitchen.

Through this, I learned the importance of marketing. I spread the word around about what I was able to do. I set up a website and learned how and what to charge customers. And after months of searching, I found a potential client. Three weeks and several consultation sessions later, I had booked myself out for the rest of the summer.

So, I quit.

As amazing as it feels to quit your job to follow your dreams, the reality was, I was taking on little personal risk. I was working part time and could not legally earn any less than I was already earning. I parted on amicable terms with the company and knew of three places I could be hired or rehired at if I ever needed the extra income. But most importantly, I had a strong support system and my living expenses were covered through other means.

I decided that the rest of 2017 was going to be dedicated to seeing how this grand experiment played out. I learned how to talk to clientele. I made sure I turned in the required weekly status reports and that I knew how to operate my invoicing software.

Throughout the summer, I realized the importance (and the bane) of deadlines. I began to write less when I felt like it, and more when I had to. I learned just how little the job has to do with raw talent.

Being a successful freelancer doesn’t mean you have talent. It means you work, and you work hard.

It meant turning down others when they wanted to get dinner or go to the fair. It meant informing my family ad nauseam that I was not available at their beck and call for whenever somebody wanted takeout or a free ride.

I wrote an incredible amount of material that summer — much of which without credit. But I didn’t mind. It wasn’t about credit. It was about the accomplishment.

I had succeeded in working for myself for a change. I had told a story, and I did it for money. What else could I have wanted?

To celebrate, I budgeted enough money for a small vacation. I planned to do something fun with the money to look back on as the months ahead turned back towards seeking new clientele. But I wasn’t expecting what happened.

A flash deal online dropped the price of a flight to Portland in half, giving me the opportunity to turn my extended vacation plans into a cross-country trip. The Pacific Northwest had been a travel destination of mine for years, so I couldn’t pass up the opportunity — no matter how tight the budget would be.

I flew coach in the cheapest airline imaginable. I spent half a day in layover passed out in an airport I don’t even remember.

Once I arrived in Portland, the trip turned northward. The next day was spent renting a car and driving against the setting sun to a place I knew I wanted to see.

I parked at Hurricane Ridge Visitor Center at golden hour — the last hour before sunset. The sort of opportunity photographers dream about.

I’m no photographer myself, but I did manage to snag a photo or two.

Not pictured — the incredible smell.

The experience was otherworldly for someone who hadn’t really left the American Southeast. The air smelled like pine and seawater. There was no humidity to be found. It was my first experience seeing both the snowy mountains and the pacific coastline, and it did not disappoint.

But it wasn’t the sight that was otherworldly. It was what I’d done. I’d arrived to this place because of my work ethic and my words. Isn’t that what any storyteller wants?

I have no tips to give anyone hoping for a similar experience. I’m learning every day how to work for myself, and my bank account doesn’t hold enough figures to warrant praise or adoration. Plenty of people far more talented and successful than I have great articles on the subject.

All I can offer is my experience. And here’s what I know:

  • Success is addictive. Accomplishing what you’ve set out to do is a greater high than any I’ve known. And this success will come from methodical, devoted work.
  • But you won’t always succeed in the short term. The short term is filled with stress and financial worries and missed opportunities. And success might not look like what you’ve imagined. To this day, I haven’t made a dime off of my own screenwriting. The same isn’t true for freelancing.
  • Success is self-defined, and if you define it with dollar signs, you’ll be sorely disappointed. So many of my favorite things were born from traditional failure. I’ve been more fulfilled with free work for friends than paid work from others.

Don Hertzfeldt’s World of Tomorrow has choice words concerning living in the now. And these are words I have written in the front page of my journal, greeting me every time I get ready to work:

Live well and live broadly. You are alive and living now. Now is the envy of all of the dead.

I’ve already talked about how I’ve mentally began 2018 in December. And I’ve done this because I don’t want to wait another month to get started on something new and exciting. To have to wait to find new clientele and new projects to get my hands on. That’s probably why this retrospective of 2017 comes several weeks early. Because I don’t have 2018.

I have now.

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