What I've Learned in One Year of Freelancing



It’s hard to believe it’s really been a year since I started writing as a job. I’ve been telling stories forever, and when I published my novel in 2018, I never expected it to spark a full career. But here I am, in 2021, a full-time writer and the author of six published titles with more on the way.


How the hell did I get here? I’ve got to say, it isn’t easy. There’s no “you won’t even feel like it’s work!” feelings for me. Freelancing is definitely work — it’s grueling and annoying at times, and will occasionally make me want to scream at the sky in frustration — but oddly, despite all that, it’s turned out to be work I happen to enjoy a lot.


It feels reminiscent of how I feel when I’m acting; it’s hard work but it’s worth it, in the end, to see what I’ve created. Even when I’m writing about things I don’t have much passion for, the actual act of writing itself is fun for me. I consider myself extremely lucky to have found a career I can love like this.


Why I Chose Freelancing

Essentially, my motivation for freelancing can be boiled down to one thing — flexibility. I wanted to do all the things people generally talk about when they float the idea of becoming a freelancer; I wanted to set my own hours, be my own boss, set my own wage, and decide my own workplace. I was planning to move, and wanted a job I could bring with me. I wanted a job I could bend to my schedule rather than having to bend to someone else’s constantly.


Initially, I hadn’t considered freelancing to be a viable career path for me. Who wants to read my ramblings? I considered myself average at best. It wasn’t until I worked on an unpaid project (a fan project for a YouTuber I liked) that I discovered that, much to my surprise, people really did like my writing, and more than that, I liked the work.


I discovered that I was capable of turning out high-quality pieces that people actually liked and wanted more of, and were willing to pay for. I eventually stumbled across Upwork, I can’t remember how anymore, and from there, I was on track.


How I Use Upwork

I’ve already written about avoiding scams on Upwork, but I haven’t really talked about how I use the platform productively for work.


Building a Network

The clients I’ve worked with on Upwork are frequently more than willing to continue working with me directly after our contract is up. This has helped me build a network of clients that understand and can vouch for the value of my work.


It’s also an excellent portfolio builder; your Upwork profile is structured around proof of value in the form of previous work and client testimonials. There are sections to show off your education and other qualifications, write a short bio about yourself, and set a public per-hour work rate.


Project Management

Upwork is an excellent space for managing multiple projects at once. Its job journal is perfect for keeping track of when you’re working and how much you’re earning, as well as when your set-payment contracts are due.


It’s also got a brilliant messaging system that makes it easy to keep in touch with your clients when you need to give or get information from them quickly.


Failures and Fraud

It hasn’t all been perfect. Freelancing isn’t as easy-breezy as a lot of entrepreneurship blogs would have you believe — you’re going to fall on your face occasionally. I definitely have.


Bad Timing

Because I was applying for work all the time, I would occasionally have multiple contracts come up at once. I’ve definitely overloaded myself and caused a drop in productivity because of that many times.


I’ve had to learn to accept only the work I know I can dedicate all of my time to. While some projects might have been extremely lucrative, that doesn't mean I would have been able to give them the attention they deserve. I'd rather be turning out quality work than a huge quantity of work.


Bad Judgment

Once in a while, I still get pulled into too-good-to-be-true projects. The budgets look great, the clients are nice, I do the work, and suddenly I’m ghosted. It’s not that I’m doing anything wrong, necessarily, it’s just that, sometimes, bad judgment calls happen.


I’ve learned a lot from my encounters with faulty contracts — I’ve written about them extensively — but they still hurt when they do happen. The best I can do is get up and try again, reading the fine print a little more thoroughly the next time around.


Tips for Your First Year of Freelancing

Now we come to the part of the article everyone clicks in for. How can I do what you’re doing? How do you get into freelancing and make it work? What’s your secret?!

I don’t have one. All I’ve got for you are common sense tips to keep you from getting stuck or swept away in the overwhelming sea that is freelancing.


Stick to a Schedule

Yes, you are your own boss! You get to set your hours! Work on what you want, when you want!


You still have to work. You do still have to put in the hours. This is one of the hardest parts of freelancing to me. I’m not good at keeping a consistent schedule for myself, and that means that having a lot of projects with different deadlines working at the same time is a bit of a logistical nightmare for me.


I keep track of my work using a couple of different things.

  • First, I use my calendar app on my laptop and phone (connected through my email) to put in important dates. This includes due dates for articles, meetings, and check-ins for regular projects.

  • Second, I use the notes app on my phone to create a checklist that I can reference when I’m working. I put very specific goals under each individual project so that I have an achievable working goal for the day.

  • Third, I use physical notes. These are helpful for organizing my brain and reminding me about all of the small things I need to do in a day.

Keep a Record of Everything

And I mean everything. Every penny you spend and each one you earn, where they’re going, when they get there, who sent them, the color of your favorite pen, everything. Write it all down and make it easily accessible. Have backups of your backups’ backups.


Trust me when I say that when tax season comes around and you’re scrambling for information, having a budget document will be a lifesaver. I use the Annual Business Budget Tracker from Intuit Quickbooks to keep everything in one place.


Vary Your Work

No matter how much you love it, doing the exact same thing all day can be exhausting. It’s a good idea to have a variety of work available to you to rotate through so that you can keep your creativity going without exhausting it all in one go.


I tend to try and take on a variety of projects, from article writing to website copy to game writing and more. I also make sure to take time for my personal writing, such as on my blog and on Medium, as well as my other fiction and poetic works.


Know Your Worth

You can’t undersell your work. I know it sounds cliche but I have to reiterate — you absolutely do not have to drop your rates to rock bottom to get good projects, and you do have negotiation power, especially if you have an edge in your niche.


You are talented, and people are paying for that talent. You’re also working hard, and people are paying for that work. Don’t ever let someone devalue your time and effort because of a perceived lack of experience. Your work has worth. Period, the end.

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